# EDGAR Filing Document

**Accession Number:** 0001801754
**File Stem:** 0001140361-23-002161
**Filing Date:** 2023-1
**Character Count:** 336711
**Document Hash:** 88390a9e20c1d277f6896e9fd73c3fb4
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001140361-23-002161.hdr.sgml**: 20230119

**ACCESSION NUMBER**: 0001140361-23-002161

**CONFORMED SUBMISSION TYPE**: SC 13E3

**PUBLIC DOCUMENT COUNT**: 96

**FILED AS OF DATE**: 20230119

**DATE AS OF CHANGE**: 20230119

**GROUP MEMBERS**: ACP-BHC LLC

**GROUP MEMBERS**: ACP-TH LLC

**GROUP MEMBERS**: AHP CONSTELLATION GP, L.P.

**GROUP MEMBERS**: AHP III GP, L.P.

**GROUP MEMBERS**: AHP V GP, L.P.

**GROUP MEMBERS**: AHP-BHC LLC

**GROUP MEMBERS**: AHP-TH LLC

**GROUP MEMBERS**: ALTARIS CONSTELLATION PARTNERS, L.P.

**GROUP MEMBERS**: ALTARIS HEALTH PARTNERS III, L.P.

**GROUP MEMBERS**: ALTARIS HEALTH PARTNERS V, L.P.

**GROUP MEMBERS**: ALTARIS HEALTH PARTNERS V-A, L.P.

**GROUP MEMBERS**: ALTARIS PARTNERS, LLC

**GROUP MEMBERS**: DANIEL G. TULLY

**GROUP MEMBERS**: GEORGE E. AITKEN-DAVIES

**GROUP MEMBERS**: TREADSTONE AGGREGATOR L.P.

**GROUP MEMBERS**: TREADSTONE MERGER SUB INC.

**GROUP MEMBERS**: TREADSTONE PARENT INC.

**GROUP MEMBERS**: TREADSTONE UPPER PARENT INC.

**SUBJECT COMPANY**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Trean Insurance Group, Inc.
- **CENTRAL INDEX KEY:** 0001801754
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **IRS NUMBER:** 844512647
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** SC 13E3
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 005-91608
- **FILM NUMBER:** 23538280

**BUSINESS ADDRESS:**
- **STREET 1:** 150 LAKE STREET WEST
- **CITY:** WAYZATA
- **STATE:** MN
- **ZIP:** 55391
- **BUSINESS PHONE:** (952) 974-2222

**MAIL ADDRESS:**
- **STREET 1:** 150 LAKE STREET WEST
- **CITY:** WAYZATA
- **STATE:** MN
- **ZIP:** 55391
**FILED BY**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Trean Insurance Group, Inc.
- **CENTRAL INDEX KEY:** 0001801754
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **IRS NUMBER:** 844512647
- **STATE OF INCORPORATION:** DE
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** SC 13E3

**BUSINESS ADDRESS:**
- **STREET 1:** 150 LAKE STREET WEST
- **CITY:** WAYZATA
- **STATE:** MN
- **ZIP:** 55391
- **BUSINESS PHONE:** (952) 974-2222

**MAIL ADDRESS:**
- **STREET 1:** 150 LAKE STREET WEST
- **CITY:** WAYZATA
- **STATE:** MN
- **ZIP:** 55391

### SECURITIES AND EXCHANGE COMMISSION

#### WASHINGTON, D.C. 20549
_________________________

### SCHEDULE 13E-3
RULE 13E-3 TRANSACTION STATEMENT

UNDER SECTION 13(E) OF

THE SECURITIES EXCHANGE ACT OF 1934

_________________________

#### <br>

## TREAN INSURANCE GROUP, INC.
(Name of the Issuer)

_________________________

#### Trean Insurance Group, Inc.

#### Treadstone Merger Sub Inc.

#### Treadstone Parent Inc.

#### Treadstone Upper Parent Inc.

#### Treadstone Aggregator L.P.

#### Altaris Health Partners V, L.P.

#### Altaris Health Partners V-A, L.P.

#### AHP V GP, L.P.

#### AHP-TH LLC

#### AHP-BHC LLC

#### ACP-TH LLC

#### ACP-BHC LLC

#### Altaris Health Partners III, L.P.

#### AHP III GP, L.P.

#### Altaris Constellation Partners, L.P.

#### AHP Constellation GP, L.P.

#### Altaris Partners, LLC

#### George E. Aitken-Davies

#### Daniel G. Tully
(Names of Persons Filing Statement)

#### Common Stock, par value $0.01 per share
(Title of Class of Securities)

#### 89457R101
(CUSIP Number of Class of Securities)

_________________________

---

| | |
|:---|:---|
| **Trean Insurance Group, Inc.**<br> **150 Lake Street West**<br> **Wayzata, MN 55391**<br> (952) 974-2200<br> **Attn: Patricia A. Ryan**<br>| **Treadstone Merger Sub Inc.**<br> **Treadstone Parent Inc.**<br> **Treadstone Upper Parent Inc.**<br> **Treadstone Aggregator L.P.**<br> **Altaris Health Partners V, L.P.**<br> **Altaris Health Partners V-A, L.P.**<br> **AHP V GP, L.P.**<br> **AHP-TH LLC**<br> **AHP-BHC LLC**<br> **ACP-TH LLC**<br> **ACP-BHC LLC**<br> **Altaris Health Partners III, L.P.**<br> **AHP III GP, L.P.**<br> **Altaris Constellation Partners, L.P.**<br> **AHP Constellation GP, L.P.**<br> **Altaris Partners, LLC**<br> **George E. Aitken-Davies**<br> **Daniel G. Tully**<br> **c/o Altaris Partners, LLC**<br> **10 East 53rd Street, 31st Floor**<br> **New York, NY 10022**<br> (212) 931-0250<br> **Attn: Daniel G. Tully & Charles Mullens**<br>|

---

(Name, Address, and Telephone Numbers of Person Authorized to Receive Notices

and Communications on Behalf of the Persons Filing Statement)

With copies to

---

| | |
|:---|:---|
| **Bass, Berry & Sims PLC**<br> **150 Third Avenue South**<br> **Nashville, TN 37201**<br> (615) 742-6200<br> **Attn: J. Page Davidson & Scott W. Bell**<br>**Morris, Nichols, Arsht & Tunnell LLP**<br> **1201 N. Market Street**<br> **Wilmington, DE 19801**<br> (302) 351-9169<br> **Attn: Eric Klinger-Wilensky & James Honaker** | **Kirkland & Ellis LLP**<br> **601 Lexington Avenue**<br> **New York, NY 10022**<br> (212) 446-4800<br> **Attn: David B. Feirstein, P.C. & Romain Dambre**<br>|

---

_________________________

This statement is filed in connection with (check the appropriate box):

&nbsp;&nbsp;&nbsp;&nbsp;a. ☒ The filing of solicitation materials or an information statement subject to Regulation 14A, Regulation 14C or Rule 13e-3(c) under the Securities Exchange Act of 1934.

&nbsp;&nbsp;&nbsp;&nbsp;b. ☐ The filing of a registration statement under the Securities Act of 1933.

&nbsp;&nbsp;&nbsp;&nbsp;c. ☐ A tender offer.

&nbsp;&nbsp;&nbsp;&nbsp;d. ☐ None of the above.

Check the following box if the soliciting materials or information statement referred to in checking box (a) are preliminary copies: ☒

Check the following box if the filing is a final amendment reporting the results of the transaction: ☐

**Neither the Securities and Exchange Commission nor any state securities commission has approved or disapproved of this transaction, passed upon the merits or fairness of this transaction or passed upon the adequacy or accuracy of the disclosure in this transaction statement on Schedule 13E-3. Any representation to the contrary is a criminal offense.**

------

#### Introduction
This Transaction Statement on Schedule 13E-3 ("Transaction Statement") is being filed with the U.S. Securities and Exchange Commission (the "SEC") pursuant to Section 13(e) of the Securities Exchange Act of 1934, as amended (together with the rules and regulations promulgated thereunder, the "Exchange Act"), by (1) Trean Insurance Group, Inc. ("Trean" or the "Company"); (2) Treadstone Merger Sub Inc., a Delaware corporation ("Merger Sub"), (3) Treadstone Parent Inc., a Delaware corporation ("Parent"), (4) Treadstone Upper Parent Inc., a Delaware corporation ("Upper Parent"), (5) Treadstone Aggregator L.P., a Delaware limited partnership ("Aggregator"), (6) Altaris Health Partners V, L.P., a Delaware limited partnership ("Altaris Health Partners V"), (7) Altaris Health Partners V-A, L.P., a Delaware limited partnership ("Altaris Health Partners V-A"), (8) AHP V GP, L.P., a Delaware limited partnership ("AHP V GP"), (9) AHP-TH LLC, a Delaware limited liability company ("AHP-TH"), (10) AHP-BHC LLC, a Delaware limited liability company ("AHP-BHC"), (11) ACP-TH LLC, a Delaware limited liability company ("ACP-TH"), (12) ACP-BHC LLC, a Delaware limited liability company ("ACP-BHC"), (13) Altaris Health Partners III, L.P., a Delaware limited partnership ("Altaris Health Partners III"), (14) AHP III GP. L.P., a Delaware limited partnership ("AHP III GP"), (15) Altaris Constellation Partners, L.P., a Delaware limited partnership ("Altaris Constellation Partners"), (16) AHP Constellation GP, L.P., a Delaware limited partnership ("AHP Constellation GP"), (17) Altaris Partners, LLC, a Delaware limited liability company ("Altaris Partners"), (18) George E. Aitken-Davies and (19) Daniel G. Tully (each of (1) through (19) a "Filing Person," and collectively, the "Filing Persons"). Merger Sub, Parent, Upper Parent, Aggregator, Altaris Health Partners V, Altaris Health Partners V-A, AHP V GP, AHP-TH, AHP-BHC, ACP-TH, ACP-BHC, Altaris Health Partners III, AHP III GP, Altaris Constellation Partners, AHP Constellation GP, Daniel G. Tully and George E. Aitken-Davies are each affiliates of Altaris Partners, which through its affiliates, AHP-BHC, AHP-TH, ACP-BHC and ACP-TH, owns collectively 24,023,919 shares of Trean's common stock par value $0.01 per share ("Trean Common Stock"), representing approximately 47% of the voting power of the issued and outstanding shares of Trean Common Stock.

This Transaction Statement relates to the Agreement and Plan of Merger, dated as of December 15, 2022 (as it may be amended from time to time, the "Merger Agreement"), by and among Trean, Parent and Merger Sub.

If the Merger Agreement is adopted by Trean's stockholders and the other conditions under the Merger Agreement are either satisfied or waived, Merger Sub will be merged with and into Trean (which we refer to as the "Merger"), the separate corporate existence of Merger Sub will cease and Trean will continue its corporate existence under Delaware law as the surviving corporation in the Merger (the "Surviving Corporation") and as a wholly-owned subsidiary of Parent. Upon completion of the Merger, each share of Trean Common Stock issued and outstanding immediately prior to the effective time of the Merger (other than (i) any shares held in the treasury of Trean, (ii) any shares owned by Parent or any direct or indirect wholly-owned subsidiary of Parent (including Merger Sub), (iii) any shares to be treated as otherwise agreed to in writing before the Effective Time between Parent or its affiliates and the holder thereof, and (iv) any shares owned by stockholders who are entitled to and have properly exercised and perfected their demands for appraisal rights under Delaware law) will be automatically converted into the right to receive $6.15 in cash, without interest and subject to applicable withholding taxes (the "Transaction Consideration"). Following the completion of the Merger, the shares of Trean Common Stock will no longer be publicly traded, and holders of such shares of Trean Common Stock that have been converted into the right to receive the Transaction Consideration will cease to have any ownership interest in Trean.

Concurrently with the filing of this Transaction Statement, Trean is filing with the SEC a proxy statement (the "Proxy Statement") under Regulation 14A of the Exchange Act, pursuant to which Trean's board of directors (the "Board") is soliciting proxies from stockholders of Trean in connection with the Merger. As of the date hereof, the Proxy Statement is in preliminary form, and is subject to completion or amendment. Terms used but not defined in this Transaction Statement have the meanings assigned to them in the Proxy Statement. A copy of the Proxy Statement is attached hereto as Exhibit (a)(1). A copy of the Merger Agreement is attached to the Proxy Statement as Annex A thereto and is incorporated herein by reference.

On December 15, 2022, a special committee (the "Special Committee") of the Board, consisting solely of non-management members of the Board who are disinterested and independent of Altaris Partners and its affiliates, after considering various factors, including those described in the Proxy Statement, and after consultation with the Special Committee's independent legal and financial advisors, unanimously (i) determined that the terms of the Merger Agreement and the transactions contemplated thereby, including the Merger, are advisable, fair to, and in the best interests of Trean and the "Unaffiliated Stockholders" (defined as Trean's stockholders other than Altaris Partners and its affiliates, Parent, Merger Sub, any Rollover Stockholders (as defined in the Merger Agreement) or any officers of Trean whom the Board has determined are subject to the reporting requirements of Section 16 of the Exchange Act (the "Section 16 Officers") or any of their respective affiliates, associates or members of their immediate family (as such terms are defined in Rules 12b-2 and 16a-1 of the Exchange Act)), (ii) determined that it is advisable and in the best interests of Trean and the Unaffiliated Stockholders to enter into, approve, adopt and declare advisable, the Merger Agreement, (iii) recommended that the Board (A) determine that the terms of the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger, are advisable, fair to and in the best interests of, Trean and its stockholders (including the Unaffiliated Stockholders), (B) determine that it is in the best interests of Trean and its stockholders (including the Unaffiliated Stockholders) to enter into, and approve, adopt and declare advisable, the Merger Agreement, (C) approve the execution and delivery by Trean of the Merger Agreement, the performance by Trean of its covenants and agreements contained therein and the consummation of the Merger and the other transactions contemplated by the Merger Agreement upon the terms and subject to the conditions contained in the Merger Agreement, (D) direct that the adoption of the Merger Agreement and the approval of the transactions contemplated by the Merger Agreement, including the Merger, be submitted to the stockholders of Trean, and (E) recommend that the stockholders of Trean vote to adopt the Merger Agreement and approve the transactions contemplated by the Merger Agreement, including the Merger, at any meeting of the stockholders held for such purpose and any adjournment or postponement thereof.

------

The Board (other than Daniel G. Tully, who abstained from participating in the deliberations or voting on the matter due to his position as Co-Founder and Managing Director of Altaris), acting upon the unanimous recommendation of the Special Committee, unanimously (i) determined that the terms of the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger, are advisable, fair to, and in the best interests of, Trean and its stockholders (including the Unaffiliated Stockholders), (ii) determined that it is in the best interests of Trean and its stockholders (including the Unaffiliated Stockholders) to enter into, and approved, adopted and declared advisable, the Merger Agreement, (iii) approved the execution and delivery by Trean of the Merger Agreement, the performance by Trean of its covenants and agreements contained therein and the consummation of the Merger and the other transactions contemplated by the Merger Agreement, upon the terms and subject to the conditions contained in the Merger Agreement, (iv) directed that the adoption of the Merger Agreement and the approval of the transactions contemplated by the Merger Agreement, including the Merger, be submitted to the stockholders of Trean, and (v) resolved to recommend that the stockholders of Trean vote to adopt the Merger Agreement and approve the transactions contemplated by the Merger Agreement, including the Merger, at any meeting of the stockholders held for such purpose and any adjournment or postponement thereof.

The Merger cannot be completed without both (a) the affirmative vote of a majority of the aggregate voting power of the outstanding shares of Trean Common Stock beneficially owned by the Unaffiliated Stockholders entitled to vote thereon, and (b) the affirmative vote of a majority of the aggregate voting power of the outstanding shares of Trean Common Stock entitled to vote thereon.

Pursuant to General Instruction F to Schedule 13E-3, the information in the Proxy Statement, including all annexes thereto, is expressly incorporated by reference herein in its entirety, and responses to each item herein are qualified in their entirety by the information contained in the Proxy Statement and the annexes thereto. The cross-references below are being supplied pursuant to General Instruction G to Schedule 13E-3 and show the location in the Proxy Statement of the information required to be included in response to the items of Schedule 13E-3.

While each of the Filing Persons acknowledges that the Merger is a going-private transaction for purposes of Rule 13E-3 under the Exchange Act, the filing of this Transaction Statement shall not be construed as an admission by any Filing Person, or by any affiliate of a Filing Person, that Trean is "controlled" by any of the other Filing Persons and/or their respective affiliates.

The information concerning Trean contained in, or incorporated by reference into, this Transaction Statement and the Proxy Statement was supplied by Trean. Similarly, all information concerning each other Filing Person contained in, or incorporated by reference into, this Transaction Statement and the Proxy Statement was supplied by such Filing Person. No Filing Person is responsible for the accuracy of any information supplied by any other Filing Person.

**Item 1.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Summary Term Sheet**

#### Regulation M-A Item 1001
The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

**Item 2.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Subject Company Information**

#### Regulation M-A Item 1002
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)  ***Name and address*** . Trean's name, and the address and telephone number of its principal executive offices are:

Trean Insurance Group, Inc.

150 Lake Street West

Wayzata, MN 55391

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(952) 974-2200

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)  ***Securities*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers—What votes are required to approve the Special Meeting Proposals?"

"Questions and Answers—I understand that a quorum is required to conduct business at the Special Meeting. What constitutes a quorum?"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Trading market and price*** . The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"Other Important Information Regarding Trean —Market Price of Common Stock and Dividends"

------

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)  ***Dividends*** . The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"Other Important Information Regarding Trean —Market Price of Common Stock and Dividends"

"Terms of the Merger Agreement—Conduct of Business Pending the Merger"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e)  ***Prior public offerings*** . The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"Other Important Information Regarding Trean—Prior Public Offerings"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(f)  ***Prior stock purchases*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Other Important Information Regarding Trean—Certain Transactions in the Shares of Trean Common Stock"

**Item 3.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Identity and Background of Filing Person**

#### Regulation M-A Item 1003(a) through (c)

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| | |
|:---|:---|
| (a) – (b) | ***Name and Address of Each Filing Person; Business and Background of Entities***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference: |

---

"Summary Term Sheet—Parties Involved in the Merger"

"The Merger—Parties Involved in the Merger"

"Other Important Information Regarding Trean—Directors and Executive Officers of Trean"

"Other Important Information Regarding the Altaris Filing Parties"

"Where You Can Find More Information"

(c)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; ***Business and Background of Natural Persons***.

"Other Important Information Regarding Trean—Directors and Executive Officers of Trean"

"Other Important Information Regarding the Altaris Filing Parties"

"Where You Can Find More Information"

**Item 4.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Terms of the Transaction**

#### Regulation M-A Item 1004(a) and (c) through (f)
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)  ***Material terms*** .

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(1) ***Tender offer***. Not applicable.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(2) ***Merger or Similar Transactions***.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"The Merger"

"Terms of the Merger Agreement"

"Voting and Support Agreement"

Annex A—Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc.

Annex B—Opinion of Houlihan Lokey, Inc.

------

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(ii) The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers—What will I receive if the Merger is consummated?"

"Questions and Answers—What will the holders of outstanding Trean equity awards receive in the Merger?"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"The Merger—Transaction Consideration"

"Terms of the Merger Agreement—Transaction Consideration"

"Terms of the Merger Agreement—Exchange and Payment Procedures"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iii) The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Opinion of the Special Committee's Financial Advisor"

"Special Factors—Unaudited Prospective Financial Information of Trean"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

Annex B –Opinion of Houlihan Lokey, Inc.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iv) The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers—What votes are required to approve the Special Meeting Proposals?"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"The Special Meeting—Vote Required; Abstentions and Broker Non-Votes"

"The Merger—Vote Required and Board Recommendation"

"Terms of the Merger Agreement—Conditions to the Closing of the Merger"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(v) The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"Terms of the Merger Agreement—Transaction Consideration"

"Terms of the Merger Agreement—Employee Matters"

------

"Terms of the Merger Agreement—Indemnification and Insurance"

"The Voting and Support Agreement"

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(vi) The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"The Merger—Accounting Treatment"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(vii) The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"Summary Term Sheet—U.S. Federal Income Tax Consequences of the Merger"

"Questions and Answers—Will I be subject to U.S. federal income tax upon the exchange of Trean Common Stock for cash pursuant to the Merger?"

"Special Factors—U.S. Federal Income Tax Consequences of the Merger"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Different terms*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"Terms of the Merger Agreement—Transaction Consideration"

"Terms of the Merger Agreement—Employee Matters"

"Terms of the Merger Agreement—Indemnification and Insurance"

"The Voting and Support Agreement"

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)  ***Appraisal rights*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet—Appraisal Rights"

"Questions and Answers—Am I entitled to appraisal rights under the DGCL?"

"The Special Meeting—Rights of Stockholders Who Seek Appraisal"

"Appraisal Rights"

Annex C—Section 262 of the General Corporation Law of the State of Delaware

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e)  ***Provisions for unaffiliated security holders*** . The information set forth in the Proxy Statement under the following caption is incorporated herein by reference:

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Provisions for Trean's Unaffiliated Security Holders"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(f)  ***Eligibility for listing or trading*** . Not applicable.

**** 

<br> **Item 5.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Past Contacts, Transactions, Negotiations and Agreements**

#### Regulation M-A Item 1005(a) through (c) and (e)
(a)(1) – (2) ***Transactions***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Special Factors—Background of the Merger"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"The Merger—Financing of the Merger"

------

"Terms of the Merger Agreement"

"The Voting and Support Agreement"

"Other Important Information Regarding Trean—Prior Public Offerings"

"Other Important Information Regarding Trean—Certain Transactions in the Shares of Trean Common Stock"

"Where You Can Find More Information"

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| | |
|:---|:---|
| (b) – (c) | ***Significant corporate events; Negotiations or contacts***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference: |

---

"Summary Term Sheet"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"The Merger—Financing of the Merger"

"Terms of the Merger Agreement"

"The Voting and Support Agreement"

Annex A—Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc.

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

Equity Commitment Letter, dated December 15, 2022, by and between Altaris Health Partners V, L.P. and Altaris Health Partners V-A, L.P. and Treadstone Parent Inc., is attached hereto as Exhibit (d)(3) and is incorporated herein by reference.

Limited Guarantee, dated as of December 15, 2022, by and between Altaris Health Partners V, L.P., Altaris Health Partners V-A, L.P., and Trean Insurance Group, Inc., is attached hereto as Exhibit (d)(4) and is incorporated herein by reference.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e)  ***Agreements involving the subject company's securities*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Plans for Trean After the Merger"

"The Special Meeting—Vote Required; Abstentions and Broker Non-Votes"

"The Merger—Financing of the Merger"

"The Merger—Vote Required and Board Recommendation"

"Terms of the Merger Agreement"

"The Voting and Support Agreement"

"Other Important Information Regarding Trean—Prior Public Offerings"

"Other Important Information Regarding Trean—Certain Transactions in the Shares of Trean Common Stock"

Annex A—Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc.

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

------

**Item 6.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Purposes of the Transaction and Plans or Proposals**

#### Regulation M-A Item 1006(b) and (c)(1) through (8)
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)  ***Use of securities acquired*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers—What is the proposed Merger and what effects will it have on Trean?"

"Questions and Answers—What will the holders of outstanding Trean equity awards receive in the Merger?"

"Special Factors—Plans for Trean After the Merger"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

"Special Factors—Certain Effects on Trean if the Merger Is Not Consummated"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"The Merger—Certain Effects on Trean if the Merger Is Not Consummated"

"The Merger—Transaction Consideration"

"Terms of the Merger Agreement—Transaction Consideration"

"Other Important Information Regarding Trean—Market Price of Common Stock and Dividends"

(c)(1) – (8) ***Plans***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Plans for Trean After the Merger"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

"Special Factors—Certain Effects on Trean if the Merger Is Not Consummated"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"The Merger—Effects of the Merger"

"The Merger—Certain Effects on Trean if the Merger Is Not Consummated"

"The Merger—Transaction Consideration"

"The Merger—Financing of the Merger"

"The Merger Agreement—Conduct of Business Pending the Merger"

"Terms of the Merger Agreement—Transaction Consideration"

"Terms of the Merger Agreement—Directors and Officers; Certificate of Incorporation; Bylaws"

"The Voting and Support Agreement"

"Other Important Information Regarding Trean—Directors and Executive Officers of Trean"

"Other Important Information Regarding Trean—Market Price of Common Stock and Dividends"

------

Annex A—Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc.

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

**Item 7.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Purposes, Alternatives, Reasons and Effects**

#### Regulation M-A Item 1013
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)  ***Purposes*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors— Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Plans for Trean After the Merger"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

"The Merger—Effects of the Merger"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)  ***Alternatives*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Opinion of the Special Committee's Financial Advisor"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Reasons*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Plans for Trean After the Merger"

"Special Factors—Opinion of the Special Committee's Financial Advisor"

"Special Factors—Unaudited Prospective Financial Information of Trean"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

Annex B—Opinion of Houlihan Lokey, Inc.

------

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)  ***Effects*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Plans for Trean After the Merger"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Certain Effects of the Merger for the Altaris Filing Parties"

"Special Factors—Certain Effects on Trean if the Merger Is Not Consummated"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"Special Factors—U.S. Federal Income Tax Consequences of the Merger"

"Special Factors—Fees and Expenses"

"The Special Meeting—Rights of Stockholders Who Seek Appraisal"

"The Merger—Certain Effects of the Merger"

"The Merger—Certain Effects on Trean if the Merger Is Not Consummated"

"The Merger—Transaction Consideration"

"The Merger—Financing of the Merger"

"The Merger—Accounting Treatment"

"Terms of the Merger Agreement—Certain Effects of the Merger"

"Terms of the Merger Agreement—Closing and Effective Time"

"Terms of the Merger Agreement—Directors and Officers; Articles of Incorporation; Bylaws"

"Terms of the Merger Agreement—Transaction Consideration"

"The Merger Agreement—Indemnification and Insurance"

"Terms of the Merger Agreement—Employee Matters"

"Terms of the Merger Agreement—Conduct of Business Pending the Merger"

"Terms of the Merger Agreement—Fees and Expenses"

"Other Important Information Regarding Trean—Directors and Executive Officers of Trean"

"Other Important Information Regarding Trean—Market Price of Common Stock and Dividends"

"Appraisal Rights"

Annex A—Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc.

Annex B—Opinion of Houlihan Lokey, Inc.

**Item 8.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Fairness of the Transaction**

#### Regulation M-A Item 1014
(a) – (b) Fairness; Factors considered in determining fairness. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

------

"Questions and Answers—What votes are required to approve the Special Meeting Proposals?"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Opinion of the Special Committee's Financial Advisor"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Certain Effects of the Merger"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

Annex B—Opinion of Houlihan Lokey, Inc.

Discussion Materials of Houlihan Lokey, Inc. for the Special Committee, dated October 28, 2022, are attached hereto as Exhibit (c)(1) and are incorporated herein by reference.

Discussion Materials of Houlihan Lokey, Inc. for the Special Committee, dated December 15, 2022, are attached hereto as Exhibit (c)(2) and are incorporated herein by reference.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Approval of security holders*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers—What votes are required to approve the Special Meeting Proposals?"

"Special Factors— Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"The Special Meeting—Vote Required; Abstentions and Broker Non-Votes"

"The Merger—Vote Required and Board Recommendation"

"Terms of the Merger Agreement—Conditions to the Closing of the Merger"

Annex A—Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)  ***Unaffiliated representative*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Provisions for Trean's Unaffiliated Security Holders"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e)  ***Approval of directors*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

------

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Opinion of the Special Committee's Financial Advisor"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(f)  ***Other offers*** . Not applicable.

**Item 9.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Reports, Opinions, Appraisals and Negotiations**

#### Regulation M-A Item 1015

---

| | |
|:---|:---|
| (a) – (b) | ***Report, opinion or appraisal; Preparer and summary of the report, opinion or appraisal***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference: |

---

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Opinion of the Special Committee's Financial Advisor"

"Where You Can Find More Information"

Annex B—Opinion of Houlihan Lokey, Inc.

Discussion Materials of Houlihan Lokey, Inc. for the Special Committee, dated October 28, 2022, are attached hereto as Exhibit (c)(1) and are incorporated herein by reference.

Discussion Materials of Houlihan Lokey, Inc. for the Special Committee, dated December 15, 2022, are attached hereto as Exhibit (c)(2) and are incorporated herein by reference.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Availability of documents*** . The reports, opinions or appraisals referenced in this Item 9 will be made available for inspection and copying at the principal executive offices of
 Trean during its regular business hours by any interested equity security holder of Trean or representative who has been so designated in writing.

**Item 10.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Source and Amounts of Funds or Other Consideration**

#### Regulation M-A Item 1007

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| | |
|:---|:---|
| (a) – (b) | ***Source of funds; Conditions***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference: |

---

"Summary Term Sheet"

"The Merger—Parties Involved in the Merger"

"The Merger—Financing of the Merger"

"Terms of the Merger Agreement—Conditions to the Closing of the Merger"

"Terms of the Merger Agreement—Financing Efforts"

Equity Commitment Letter, dated December 15, 2022, by and between Altaris Health Partners V, L.P. and Altaris Health Partners V-A, L.P. and Treadstone Parent Inc., is attached hereto as Exhibit (d)(3) and is incorporated herein by reference.

Limited Guarantee, dated as of December 15, 2022, by and between Altaris Health Partners V, L.P., Altaris Health Partners V-A, L.P., and Trean Insurance Group, Inc., is attached hereto as Exhibit (d)(4) and is incorporated herein by reference.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Expenses*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <br>

"Summary Term Sheet"

------

"Special Factors—Fees and Expenses"

"The Merger—Financing of the Merger"

"Terms of the Merger Agreement—Damages Cap"

"Terms of the Merger Agreement—Termination Fee"

"Terms of the Merger Agreement—Fees and Expenses"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)  ***Borrowed funds*** . Not applicable.

**Item 11.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Interest in Securities of the Subject Company**

#### Regulation M-A Item 1008
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)  ***Securities ownership*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"Security Ownership of Certain Beneficial Owners and Management"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)  ***Securities transactions*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Other Important Information Regarding Trean—Certain Transactions in the Shares of Trean Common Stock"

**Item 12.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **The Solicitation or Recommendation**

#### Regulation M-A Item 1012(d) and (e)
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)  ***Intent to tender or vote in a going-private transaction*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"Special Factors—Intent to Vote in Favor of the Merger"

"Special Factors—Obligation of Altaris to Vote in Favor of the Merger"

"The Merger—Vote Required; Abstentions and Broker Non-Votes"

"The Merger—Shares Held by Trean's Directors and Executive Officers"

"The Voting and Support Agreement"

Annex D—Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e)  ***Recommendation of others*** . The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Summary Term Sheet"

"Questions and Answers"

"Special Factors—Background of the Merger"

"Special Factors—Recommendation of the Special Committee; Reasons for the Merger"

"Special Factors—Approval and Recommendations of the Board; Trean's Position as to the Fairness of the Merger to Trean's Unaffiliated Security Holders"

"Special Factors—Position of the Altaris Filing Parties as to the Fairness of the Merger"

------

"Special Factors—Purpose and Reasons of Trean for the Merger"

"Special Factors—Purpose and Reasons of the Altaris Filing Parties for the Merger"

"The Merger—Vote Required and Board Recommendation"

**Item 13.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Financial Information**

#### Regulation M-A Item 1010(a) through (b)
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)  ***Financial statements*** . The audited consolidated financial statements of Trean for the fiscal years ended December 31, 2021 and 2020 are incorporated herein by reference to Trean's
 Annual Report on Form 10-K for the fiscal year ended December 31, 2021, filed on March 16, 2022 (see "Item 8 - Financial Information" beginning on page 76) and the unaudited condensed consolidated financial statements of Trean for the
 quarterly period ended September 30, 2022, are incorporated herein by reference to Trean's Quarterly Report on Form 10-Q for the quarterly period ended September 30, 2022, filed on November 8, 2022 (see "Item 1 - Financial Statements"
 beginning on page 1).

The information set forth in the Proxy Statement under the following captions is incorporated herein by reference:

"Special Factors—Unaudited Prospective Financial Information of Trean"

"Other Important Information Regarding Trean—Book Value per Share"

"Where You Can Find More Information"

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)  ***Pro forma information*** . Not applicable.

**** 

<br> **Item 14.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Persons/Assets, Retained, Employed, Compensated or Used**

#### Regulation M-A Item 1009

---

| | |
|:---|:---|
| (a) – (b) | ***Solicitations or recommendations; Employees and corporate assets***. The information set forth in the Proxy Statement under the following captions is incorporated herein by reference: |

---

"Summary Term Sheet"

"Questions and Answers—Who will solicit votes for and bear the cost and expense of this proxy solicitation?"

"Special Factors—Fees and Expenses"

"The Special Meeting—Solicitation of Proxies"

"Special Factors—Interests of the Directors and Executive Officers of Trean in the Merger"

"Miscellaneous"

**Item 15.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Additional Information**

#### Regulation M-A Item 1011(b) and (c)
&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)  ***Golden Parachute Compensation*** . Not applicable.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)  ***Other material information*** . The information set forth in the Proxy Statement, including all annexes thereto, is incorporated herein by reference.

**Item 16.**&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; **Exhibits** 

#### Regulation M-A Item 1016(a) through (d), (f) and (g)

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| | |
|:---|:---|
| [(a)(1)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm) | Preliminary Proxy Statement of Trean Insurance Group, Inc. (the "Proxy Statement") (included in the Schedule 14A filed concurrently with the SEC and incorporated herein by reference). |

---

---

| | |
|:---|:---|
| [(a)(2)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_400-proxycards_pg1) | Form of Proxy Card (included in the Proxy Statement and incorporated herein by reference). |

---

---

| | |
|:---|:---|
| [(a)(3)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_101-letter_pg1) | Letter to Trean Insurance Group, Inc. Stockholders (included in the Proxy Statement and incorporated herein by reference). |

---

---

| | |
|:---|:---|
| [(a)(4)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_102-notice_pg1) | Notice of Special Meeting of Stockholders (included in the Proxy Statement and incorporated herein by reference). |

---

[(a)(5)](https://www.sec.gov/ix?doc=/Archives/edgar/data/1801754/000119312522306510/d399653d8k.htm) Current Report on Form 8-K, dated December 16, 2022 (included in Schedule 14A filed on December 16, 2022 and incorporated herein by reference).

[(a)(6)](https://www.sec.gov/ix?doc=/Archives/edgar/data/1801754/000119312522308421/d746935d8k.htm) Current Report on Form 8-K, dated December 19, 2022 (included in Schedule 14A filed on December 19, 2022 and incorporated herein by reference).

[(c)(1)](ny20006673x2_exc-1.htm) Discussion Materials of Houlihan Lokey, Inc. for the Special Committee, dated October 28, 2022.

[(c)(2)](ny20006673x2_exc-2.htm) Discussion Materials of Houlihan Lokey, Inc. for the Special Committee, dated December 15, 2022.

------

---

| | |
|:---|:---|
| [(c)(3)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_301-annexb_pg1) | Opinion of Houlihan Lokey, Inc., dated December 15, 2022 (incorporated herein by reference to Annex B of the Proxy Statement). |

---

---

| | |
|:---|:---|
| [(d)(1)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_300-annexa_pg1) | Agreement and Plan of Merger, dated as of December 15, 2022, by and among Trean, Treadstone Parent Inc., and Treadstone Merger Sub Inc. (incorporated herein by reference to Annex A of the Proxy Statement). |

---

---

| | |
|:---|:---|
| [(d)(2)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_303-annexd_pg1) | Voting and Support Agreement, dated as of December 15, 2022, by and among Trean Insurance Group, Inc., AHP-BHC LLC, AHP-TH LLC, ACP-BHC LLC, ACP-TH LLC and Altaris Partners, LLC (incorporated herein by reference to Annex D of the Proxy Statement). |

---

[(d)(3)](ny20006673x2_exd-3.htm) Equity Commitment Letter, dated as of December 15, 2022, by and between Altaris Health Partners V, L.P., Altaris Health Partners V-A, L.P. and Treadstone Parent Inc.

[(d)(4)](ny20006673x2_exd-4.htm) Limited Guarantee, dated as of December 15, 2022, by and between Altaris Health Partners V, L.P., Altaris Health Partners V-A, L.P., and Trean Insurance Group, Inc.

[(f)](https://www.sec.gov/Archives/edgar/data/1801754/000114036123002147/ny20006673x1_prem14a.htm#ny20006673x1_prem14a_302-annexc_pg1) Section 262 of the General Corporation Law of the State of Delaware (incorporated herein by reference to Annex C of the Proxy Statement).

[107](ny20006673x2_ex107.htm) Filing Fee Table.

------

#### SIGNATURES
After due inquiry and to the best of each of the undersigned's knowledge and belief, each of the undersigned certifies that the information set forth in this statement is true, complete and correct.

Dated: January 19, 2023

---

| | |
|:---|:---|
| **TREAN INSURANCE GROUP, INC.** | **TREAN INSURANCE GROUP, INC.** |
| By: | /s/ Julie A. Baron |
| Name: | Julie A. Baron |
| Title: | Chief Executive Officer |

---

---

| | |
|:---|:---|
| **TREADSTONE MERGER SUB INC.** | **TREADSTONE MERGER SUB INC.** |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | President |

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| | |
|:---|:---|
| **TREADSTONE PARENT INC.** | **TREADSTONE PARENT INC.** |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | President |

---

---

| | |
|:---|:---|
| **TREADSTONE UPPER PARENT INC.** | **TREADSTONE UPPER PARENT INC.** |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | President |

---

---

| | |
|:---|:---|
| **TREADSTONE AGGREGATOR L.P.** | **TREADSTONE AGGREGATOR L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **ALTARIS HEALTH PARTNERS V, L.P.** | **ALTARIS HEALTH PARTNERS V, L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **ALTARIS HEALTH PARTNERS V-A, L.P.** | **ALTARIS HEALTH PARTNERS V-A, L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **AHP V GP, L.P.** | **AHP V GP, L.P.** |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

------

---

| | |
|:---|:---|
| **AHP-TH LLC** | **AHP-TH LLC** |
| By: | Altaris Health Partners III, L.P., its sole member |
| By: | AHP III GP, L.P., its general partner |
| By: | Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **AHP-BHC LLC** | **AHP-BHC LLC** |
| By: | Altaris Health Partners III, L.P., its sole member |
| By: | AHP III GP, L.P., its general partner |
| By: | Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **ACP-TH LLC** | **ACP-TH LLC** |
| By: | Altaris Constellation Partners, L.P., its sole member |
| By: | AHP Constellation GP, L.P., its general partner |
| By: | Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **ACP-BHC LLC** | **ACP-BHC LLC** |
| By: | Altaris Constellation Partners, L.P., its sole member |
| By: | AHP Constellation GP, L.P., its general partner |
| By: | Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **ALTARIS HEALTH PARTNERS III, L.P.** | **ALTARIS HEALTH PARTNERS III, L.P.** |
| By: AHP III GP, L.P., its general partner | By: AHP III GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **AHP III GP, L.P.** | **AHP III GP, L.P.** |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

------

---

| | |
|:---|:---|
| **ALTARIS CONSTELLATION PARTNERS, L.P.** | **ALTARIS CONSTELLATION PARTNERS, L.P.** |
| By: AHP Constellation GP, L.P., its general partner | By: AHP Constellation GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **AHP CONSTELLATION GP, L.P.** | **AHP CONSTELLATION GP, L.P.** |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |

---

---

| | |
|:---|:---|
| **ALTARIS PARTNERS, LLC** | **ALTARIS PARTNERS, LLC** |
| By: | /s/ Daniel G. Tully |
| Name: | Daniel G. Tully |
| Title: | Manager |
| /s/ George E. Aitken-Davies | /s/ George E. Aitken-Davies |
| George E. Aitken-Davies | George E. Aitken-Davies |
| /s/ Daniel G. Tully | /s/ Daniel G. Tully |
| Daniel G. Tully | Daniel G. Tully |

---

------

## Ex-99.(C)(1)

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**Exhibit (c)(1)**<br>

**** <br> ![](ny20006673x2_exc-1slide1.jpg)

Project Twins PRELIMINAR Y DISCUSSION MATERIAL S FOR THE SPECIAL COMMITTEE OF THE BOARD OF DIRECT ORS OCTOBER 28, 2022 \| CONFIDENTIAL

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![](ny20006673x2_exc-1slide2.jpg)

CONFIDENTIAL **Table of Contents** 2 Page 3 5 15 26 36 37 40 43 Executive Summary Selected Company Observations Preliminary Financial Considerations Other Proposal Considerations Appendices Supplemental Financial Information Supplemental Public Company & Market Observations Supplemental Industry Observations

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![](ny20006673x2_exc-1slide3.jpg)

Page 1. Executive Summary 3 Selected Company Observations Preliminary Financial Considerations Other Proposal Considerations Appendices 5 15 26 36

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![](ny20006673x2_exc-1slide4.jpg)

Proposal Overview The Angels Parties, which beneficially own 46.9% of the Company common stock, have made a non-binding proposal (the "Proposal") to acquire all of the outstanding shares of Company common stock not owned by them (the "Unaffiliated Shares") for consideration of $6.00 per share in cash Proposed consideration reflects a premium of ~50% to 3-month VWAP, ~74% to 30-day VWAP and ~75% to the closing stock price as of 10/25/2022 Proposal conditioned on approval by a Special Committee and holders of a majority of Company common stock not held by the Angels Parties The Angels Parties have indicated that they have no interest in participating in an alternative change of control transaction involving the Company The Angels Parties have indicated that (i) diligence requirements will be limited, (ii) definitive documents will not be subject to financing conditions and (iii) at the appropriate time, they would like to discuss the possibility of certain stockholders rolling over their shares in the proposed transaction Situation Overview & Preliminary Observations The Company's expertise in workers' compensation markets and claims processing, relationships in the smaller account marketplace allowing for targeted risk selection, and AM Best "A" rating have supported a track record of consistent top-line growth and combined ratios substantially below 100% Certain transformational developments leading up to and following the July 2020 IPO have pressured return on equity metrics, including (i) shift from fee-based earnings to underwriting-based earnings, (ii) strategic acquisitions including phased Compstar purchase and (iii) unusual frequency and severity of claims in 2021 Meaningful gap exists between Twins' multiples (P/BV, P/E)1 and corresponding metrics for other industry participants due to profitability pressure/low ROE performance, lack of consistent performance and several financial guidance misses since IPO Focus on maintaining minimum capital adequacy levels and ratings limits retained premium growth, significant strategic initiatives and capital return events Mixed industry backdrop, with possible recession potentially increasing execution risk associated with strategic plan Company ran sales process in 2018-2019, declining to sell and instead pivoting to an IPO in 2020 (top bid in sale process significantly below $750mm market cap in the IPO) Limited float / trading activity, with 3-month VWAP of $4.00, 30-day VWAP of $3.45 and 10-day VWAP of $3.37 Average basis of top 25 shareholders approximates $12.00 per share, with Royce & Associates holding ~17% of the public float Potential Next Steps & Other Considerations Special Committee to determine whether and how to respond to Proposal in light of alternatives available to the Company, including maintaining the status quo If appropriate, the Special Committee and/or its advisors will need to discuss the following with Angels: (i) diligence requirements, (ii) any required third party financing and (iii) other potential participants in a transaction Materials are based on preliminary management estimates of 3Q 2022 financials, which will be finalized prior to earnings announcement on 11/2/2022 Executive Summary 4 CONFIDENTIAL 1. Refers to multiples implied by Twins stock price. VWAP refers to Volume Weighted Average Price. Sources: Proposal, Company management, public filings, Bloomberg and Capital IQ.

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![](ny20006673x2_exc-1slide5.jpg)

Page 3 1. Executive Summary 2. Selected Company Observations 5 Preliminary Financial Considerations Other Proposal Considerations Appendices 15 26 36

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![](ny20006673x2_exc-1slide6.jpg)

Selected Industry & Company Observations Source: Company management. CONFIDENTIAL 6 Multiple strategic transactions leading up to and through the July 2020 IPO, combined with mixed financial results over those periods, make it challenging to track historical performance Focus on maintaining minimum capital adequacy levels and ratings limits retained premium growth, ROEs and distributable earnings Premium flowed through the insurance company reduces free cash flow optionality given dividend-related regulatory constraints Highly dependent on pricing in a hardening reinsurance market Management projecting material improvements in ROE, profitability and combined ratio through 2025 Material public company costs and small market capitalization relative to Twins' implied IPO market capitalization and peers' market capitalizations Lack of consistent performance, recent financial guidance misses and worse than expected results have likely contributed to Twins' recent share price underperformance Increase in frequency and severity of claims outside Twins' control have impacted returns without expected benefit of future reserve releases Compstar acquisition has proven to generate meaningfully less profitability and ultimately a smaller book of business than anticipated, and material goodwill value places a drag on return on equity profitability metrics Shift from fee-based earnings to underwriting-based earnings has lowered Twins' profitability metrics as measured by return on equity Limited scale relative to certain other industry participants Industry tailwinds include the following: Unemployment continues to remain low Program business continues to grow as a percentage of the overall market Rising interest rates have the potential to increase fixed income investment yields Industry headwinds include the following: Declining regulatory workers' comp rates Potential reduction in employment payrolls Rising reinsurance costs and capacity Rising medical care costs and inflationary pressures Selected Company Attributes Selected Company Considerations Selected Company Performance & Strategy Observations Selected Industry Observations Long operating history (since 1996) and track record of consistent top- line growth with profitability, along with valuable AM Best "A" rating Entrepreneurial culture, with relationships in smaller account program marketplace allowing for targeted risk selection Expertise in traditionally challenging workers' compensation insurance Growth driven by additional commercial insurance product expansion, leveraging strong program relationships and rated fronting carrier Strong client retention and disciplined approach in choosing partners and selecting risk Comprehensive workers' compensation claims handling capabilities with strong metrics allowing for attractive underwriting performance Attractive loss, expense and combined ratios well under 100%

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![](ny20006673x2_exc-1slide7.jpg)

$43.1 $62.0 $66.6 $86.5 $108.5 $198.7 $269.2 $275.3 $285.6 $299.9 $318.5 $343.3 0.6x 1.1x 1.0x 1.0x 0.9x 0.9x 0.8x 0.8x CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Net Earned Premiums Premiums Earned/Surplus (Statutory) $144.9 $236.3 $322.1 $357.0 $411.4 $484.2 $634.2 $640.4 $749.6 $934.6 $1,011.8 $1,084.6 $1,158.8 CY 2015 CY 2016 CY 2017 Net Earned Premiums CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Selected Management Projections Highlights Premiums Gross Written Premiums (dollars in millions) (dollars in millions) 2 Projected NEP CAGR of ~5% over 2022-27 period following ~200% growth since 2019 reflects balanced focus on stable growth and preservation of strong balance sheet position and AM Best rating. Period CAGR 2015 – 2021 27.9% 2021 – 2027E 10.6% 2022E – 2027E 12.6% Period CAGR 2016 – 2021 35.7% 2021 – 2027E 9.5% 2022E – 2027E 5.0% Retention: 19.6% 20.3% 19.6% 21.7% 25.1% 34.7% 42.2% 38.7% 32.6% 30.1% 29.9% 30.3% Note: Historical financial data is not pro forma for recent acquisitions, including the Company's (i) July 6, 2021 acquisition of Western Integrated Care, LLC for ~$5.5 mm (ii) October 1, 2020 acquisition of 7710 Insurance Company (and certain affiliates) for ~$12.1 mm, (iii) April 1, 2020 acquisition of LCTA Risk Services, Inc. for ~$1.4 mm, (iv) February 19, 2019 acquisition of First Choice Casualty Insurance Company for ~$5.3 mm, (v) April 2, 2018 acquisition of Westcap Insurance Services, LLC for ~$2.5 mm, (vi) December 12, 2018 acquisition of CTS Underwriters for $0.05 mm or (viii) March 31, 2019 acquisition of a ~25% interest in American Liberty Insurance Company for ~$1.2 mm (or January 2017 purchase of a 75% interest). Historical financial data also not pro forma for the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million) 1. U.S. Bureau of Labor Statistics. CAGR refers to Compounded Annual Growth Rate; E refers to Expected; CY refers to Calendar Year. Source: Company management, except where otherwise noted and Company projections, per Company management, provided on October 20, 2022 ("Management Projections"). employment CAGR is projected to approximate 0.5% over the same period.1 1 Projected GWP CAGR of ~10%+ is expected to be driven in part through the introduction of two new programs (A&H and Excess Surplus), which will be fully reinsured. Estimated US 7 CONFIDENTIAL

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![](ny20006673x2_exc-1slide8.jpg)

(dollars in millions) $17.8 $12.6 $22.2 $33.2 $32.8 $22.1 $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Note: Historical financial data is not pro forma for recent acquisitions (refer to prior page for additional details) including the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million). (2H 2018, CY 2019 and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). CAGR refers to Compounded Annual Growth Rate. CY refers to Calendar Year. E refers to Expected. Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, 49.8% 49.2% 53.7% 51.6% 46.8% 65.8% 62.8% 62.3% 61.8% 61.3% 60.8% 60.3% 40.0% 30.4% 23.6% 24.2% 35.6% 27.5% 31.1% 29.4% 29.1% 28.7% 89.8% 79.7% 77.3% 75.8% 82.4% 93.3% 92.9% 90.7% 89.9% 89.0% CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Selected Management Projections Highlights Combined Ratio and Adjusted Net Income Combined Ratio Adjusted Net Income Projected 2022-2027 Adj. Net Income CAGR of ~18% driven by (i) underwriting income CAGR (~21%), (ii) investment income CAGR (~19%) as yields are assumed to peak in 2023 and (iii) other revenue CAGR (~6%). 4 Period CAGR 2021 – 2027E 15.5% 2022E – 2027E 18.1% 3 Projected Loss Ratio 94.7% 94.1% 31.9% 31.8% Projected Expense Ratio Combined ratios are projected to revert gradually to below 90% as loss ratios approach a normalized level following unusual frequency and severity of claims in 2021 and a build-up of reserves in subsequent years, as well as declining expense ratios due to increased operating leverage. Historical Loss Ratio Historical Expense Ratio stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments. Source: Company management and Management Projections. CONFIDENTIAL 8

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![](ny20006673x2_exc-1slide9.jpg)

5.4% 5.3% 5.9% 6.7% 8.0% 8.4% 8.9% CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Note: Historical financial data is not pro forma for recent acquisitions (refer to prior pages for additional details) including the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million). (2H 2018, CY 2019 and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). Historical financial figures are also not pro forma for the impact of the July 2020 IPO. 2019 and prior years book values do not reflect impact of AOCI related restatement. Presented on a pre-tax basis. Based on net income less gain on revaluation of 45% ownership interest in Compstar, in each case as stated in Company public filings. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from book value. Book value figures for 2019 and prior years exclude preferred stock. Adjusted ROAE refers to Adjusted Return on Average Equity (in the case of 2016 – 2020 based on Average Book Value and in the case of 2021 onwards based on Average Book Value less AOCI); $71.9 $88.2 $106.1 $136.8 $396.7 $417.5 $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Selected Management Projections Highlights Book Value and Adjusted ROAE Book Value, excluding AOCI (dollars in millions) Period CAGR 2021 – 2027E 6.5% 2022E – 2027E 6.5% Book value increased in 2020 due to (i) shares issued in initial public offering, (ii) acquisition of 55% of Compstar and (iii) revaluation of 45% stake in Compstar. 5 R 2 Adjusted ROAE3 12/13/19 Book Value (Excl. AOCI) $136.8 Shares Issued in Compstar Acquisition 99.2 OAE, which has fallen in 2021- 022 amid declines in Adj. Net Income following Compstar acquisition and IPO, is projected to increase over the projection period. Gain on Revaluation of Compstar Stake1 69.8 18.8% 22.1% 23.0% 27.0% 6 Shares Issued in IPO, Net of Discounts 93.1 Pre-IPO Distribution (18.2) Net Income (Ex-Compstar Gain)2 18.7 Other (2.9) 11.9% 12/13/20 Book Value (Excl. AOCI) $396.7 AOCI refers to Accumulated Other Comprehensive Income; CAGR refers to Compounded Annual Growth Rate; CY refers to Calendar Year. E refers to Expected. Source: Company management and Management Projections. CONFIDENTIAL 9

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![](ny20006673x2_exc-1slide10.jpg)

$71.9 $87.4 $103.1 $133.8 $180.7 $202.1 $235.7 $262.7 $293.8 $333.4 $378.6 $430.4 CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E 18.8% 22.2% 23.4% 27.7% 19.7% 11.6% 10.5% 10.8% 11.5% 12.9% 12.9% 13.0% CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Note: Historical financial data is not pro forma for recent acquisitions (refer to prior pages for additional details) including the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million). (2H 2018, CY 2019 and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). Historical financial figures are also not pro forma for the impact of the July 2020 IPO. 2019 and prior years book values do not reflect impact of AOCI related restatement. 1. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from tangible book value. Tangible book value figures for 2019 and prior years exclude preferred stock. Adjusted ROATE refers to Adjusted Return on Average Tangible Equity (in the case of 2016 – 2020 based on Average Tangible Book Value and in the case of 2021 onwards based on Average Tangible Book Value less AOCI); AOCI refers to Accumulated Other Comprehensive Income. CAGR refers to Compounded Annual Growth Rate. CY refers to Calendar Year. E refers to Expected. Selected Management Projections Highlights Tangible Book Value and Adjusted ROATE Tangible Book Value, excluding AOCI Adjusted ROATE1 (dollars in millions) Period CAGR 2021 – 2027E 13.4% 2022E – 2027E 12.8% Tangible book value increased in 2020 following the initial public offering. Projected CAGR of ~13% generally tracks Net Income growth. 7 Source: Company management and Management Projections. CONFIDENTIAL 10

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![](ny20006673x2_exc-1slide11.jpg)

Historical and Projected Financial Data Selected Metrics Note: Historical financial data is not pro forma for the Company's recent acquisitions, including its (i) July 6, 2021 acquisition of Western Integrated Care, LLC for ~$5.5 million, (ii) October 1, 2020 acquisition of 7710 Insurance Company (and certain affiliates) for ~$12.1 million, (iii) April 1, 2020 acquisition of LCTA Risk Services, Inc. for ~$1.4 million, or (iv) February 19, 2019 acquisition of First Choice Casualty Insurance Company for ~$5.3 million. Financial data reflects Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million), but 2019-2020 financial data is not pro forma for the July 15, 2020 acquisition of the remaining 55% equity interest in Compstar (2019 data and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). 2019 and 1H 2020 figures are also not pro forma for the impact of the July 2020 IPO. Book value figures for 2019 exclude preferred stock. 1. Reflects a one-time unrealized loss of $4.5 million in 2022. 2. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from book value.3. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from tangible book value. Adjusted ROAE refers to Adjusted Return on Average Equity (in the case of 2019 – 2020 based on Average Book Value and in the case of 2021 onwards based on Average Book Value less AOCI); Adjusted ROATE refers to Adjusted Return on Average Tangible Equity (in the case of 2019 – 2020 based on Average Tangible Book Value and in the case of 2021 onwards based on Average Tangible Book Value less AOCI); Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments.; AOCI refers to Accumulated Other Comprehensive Income; CAGR refers to Compound Annual Growth Rate; E refers to Estimated; LAE refers to Loss Adjustment Expenses; LTM refers to Latest 12 Months; NA refers to not available. (dollars in millions) Calendar Year Ended December 31, LTM Ended Calendar Year Ending December 31, 2019 2020 2021 9/30/2022 2022E 2023E 2024E 2025E 2026E 2027E CAGR 2021 to 2027E 2022 to 2027E Gross Written Premiums $411.4 $484.2 $634.2 $631.0 $640.4 $749.6 $934.6 $1,011.8 $1,084.6 $1,158.8 10.6% 12.6% Growth % 15.2% 17.7% 31.0% NA 1.0% 17.1% 24.7% 8.3% 7.2% 6.8% Net Earned Premiums 86.5 108.5 198.7 259.2 269.2 275.3 285.6 299.9 318.5 343.3 9.5% 5.0% Growth % 29.9% 25.4% 83.2% NA 35.5% 2.2% 3.7% 5.0% 6.2% 7.8% Retention 21.7% 25.1% 34.7% 41.0% 42.2% 38.7% 32.6% 30.1% 29.9% 30.3% Net Investment Income [1] 6.2 11.7 8.7 7.3 8.2 19.0 21.5 24.4 27.6 30.8 Gain on Revaluation of Compstar 0.0 69.8 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Net Realized Gains (Losses) 0.7 3.4 0.0 0.3 0.4 0.0 0.0 0.0 0.0 0.0 Other Revenue 9.1 12.1 10.2 8.7 8.7 9.2 9.9 10.4 11.0 11.5 Total Revenue $102.5 $205.5 $217.7 $275.5 $286.5 $303.5 $316.9 $334.7 $357.1 $385.6 10.0% 6.1% Growth % 30.6% 100.4% 6.0% NA 31.6% 5.9% 4.4% 5.6% 6.7% 8.0% Losses and LAE (44.7) (50.8) (130.8) (169.8) (169.1) (171.5) (176.5) (183.8) (193.7) (207.0) G&A Expenses (21.0) (38.7) (54.7) (76.4) (85.8) (87.6) (88.8) (88.0) (92.7) (98.7) Provision for Income Taxes (7.1) (6.2) (5.4) (7.1) (7.3) (5.9) (7.1) (9.5) (11.0) (12.9) Equity Gains (Losses) in Affiliates 3.6 2.3 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Net Income $31.3 $88.5 $19.3 $26.6 $27.6 $21.0 $25.1 $33.6 $39.2 $45.8 15.5% 10.6% Margin % 30.5% 43.1% 8.9% 9.7% 9.6% 6.9% 7.9% 10.0% 11.0% 11.9% Total Adjustments, Net of Tax Impact 1.9 (55.8) 2.8 (5.6) (4.7) 5.9 7.0 6.9 6.8 6.7 Adjusted Net Income $33.2 $32.8 $22.1 $21.1 $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 15.5% 18.1% Margin % 32.4% 16.0% 10.2% 7.6% 8.0% 8.9% 10.1% 12.1% 12.9% 13.6% Growth % 49.6% -1.4% -32.5% NA 3.5% 17.4% 19.5% 26.0% 13.6% 14.2% Book Value (excluding AOCI) $136.8 $396.7 $417.5 $443.9 $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 6.5% 6.5% Growth % 35.3% 190.0% 5.3% NA 6.6% 4.7% 5.4% 6.8% 7.5% 8.1% Tangible Book Value (excluding AOCI) $133.8 $180.7 $202.1 $233.0 $235.7 $262.7 $293.8 $333.4 $378.6 $430.4 13.4% 12.8% Growth % 29.8% 35.1% 11.8% NA 16.6% 11.5% 11.8% 13.5% 13.6% 13.7% Book Value Per Share (excl. AOCI) $8.62 Tangible Book Value Per Share (excl. AOCI) $4.53 Additional Financial Information Loss Ratio 51.6% 46.8% 65.8% 65.5% 62.8% 62.3% 61.8% 61.3% 60.8% 60.3% Expense Ratio 24.2% 35.6% 27.5% 29.5% 31.9% 31.8% 31.1% 29.4% 29.1% 28.7% Combined Ratio 75.8% 82.4% 93.3% 95.0% 94.7% 94.1% 92.9% 90.7% 89.9% 89.0% Adjusted ROAE [2] 27.0% 11.9% 5.4% 4.9% 5.3% 5.9% 6.7% 8.0% 8.4% 8.9% Adjusted ROATE [3] 27.7% 19.7% 11.6% 9.8% 10.5% 10.8% 11.5% 12.9% 12.9% 13.0% Premiums Earned/Surplus (Statutory) NA 0.6x 1.1x NA 1.0x 1.0x 0.9x 0.9x 0.8x 0.8x Source: Company management and Management Projections. CONFIDENTIAL 11

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Selected Comparison of Management Projections vs. Guidance Selected Observations Q3 management estimated results exceed guidance for gross written premiums and are near the high end of adjusted net income guidance Reflects guidance range provided by Company management as disclosed in Q2 CY 2022 earnings release dated 8/3/22. Represents average of low and high of guidance range. Per Company management. Guidance midpoint shown represents reported 1H 2022 loss ratio. Represents projected loss ratio for 2022. 2H 2022 projected loss ratio is 64.0%. Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments; CY refers to Calendar Year; E refers to Estimated; Q refers to Quarter. (dollars in millions) Q3 2022 Management Estimated Results vs. Guidance CY 2022E Management Projections vs. Guidance (dollars in millions) Selected Observations Management projections for CY 2022E contemplate top-line performance exceeding the high end of guidance Loss ratio is projected to exceed 1H 2022 results while expense ratio is projected near the low end of guidance Guidance Range [1] Low High $615.0 -- $630.0 $255.0 -- $265.0 $268.0 -- $278.0 32.0% -- 33.0% 2H 2022 Consistent with 1H 2022 Guidance Midpoint [2] $622.5 $260.0 $273.0 32.5% 61.5% Management Projections [3] $640.4 $269.2 $286.5 31.9% 62.8% Management Projections vs. Midpoint of Guidance Gross Written Premium 2.9% 3.6% 4.9% -0.6% 1.3% Net Earned Premium Total Revenue Expense Ratio Loss Ratio [4] [5] Guidance Range [1] Low High $150.0 -- $160.0 $4.3 -- $5.3 Guidance Midpoint [2] $155.0 $4.8 Management Estimates [3] $162.2 $5.2 Management Estimates vs. Midpoint of Guidance Gross Written Premium 4.6% 8.1% Adjusted Net Income Source: Company management, Management Projections and Public filings CONFIDENTIAL 12

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$0.45 $0.53 $0.49 $0.57 $1.00 $0.80 $0.60 $0.40 $0.20 $0.00 $22.9 $26.9 $24.8 $29.3 $40.0 $30.0 $20.0 $10.0 $0.0 CY 2022E CY 2023E $269.2 $259.7 $275.3 $271.4 $400.0 $300.0 $200.0 $100.0 $0.0 CY 2022E CY 2023E Selected Comparison of Management Projections vs. Wall Street Analyst Consensus Estimates Net Earned Premiums (CY 2022E to CY 2023E) Adjusted Net Income (CY 2022E to CY 2023E) (dollars in millions, except per share values) Adjusted Earnings Per Share (CY 2022E to CY 2023E) ▲ 3.7% ▲ 1.4% ▼ 7.6% ▼ 8.1% ▼ 7.7% ▼ 7.5% CY 2022E CY 2023E Management Projections1 / Q3 2022 Management Estimated Results Consensus Wall Street Estimates % Difference Net Earned Premiums (Q3 2022E) Adjusted Net Income (Q3 2022E)² Adjusted Earnings Per Share (Q3 2022E)² $71.4 $65.1 $80.0 $60.0 $40.0 $20.0 $0.0 Q3 2022E ▲ 9.6% $5.2 $4.2 $8.0 $6.0 $4.0 $2.0 $0.0 Q3 2022E ▲ 23.1% $0.10 refers to Calendar Year; E refers to Estimated; Q refers to Quarter. Sources: Bloomberg and Wall Street research as of 10/25/22, Company management and Management Projections. CONFIDENTIAL 13 $0.09 $0.00 $0.05 $0.10 $0.15 Q3 2022E ▲ 15.0% 1. Per projections prepared by Company management. 2. JMP's estimate (Adjusted Earnings Per Share of $0.05 and Adjusted Net Income of $2.7mm) was an outlier from the mean Wall Street analyst estimate. Other observed Adjusted Earnings Per Share estimates are: Evercore ($0.12), JP Morgan ($0.10) and William Blair ($0.08). Other observed Adjusted Net Income estimates are: Evercore ($6.1mm), JP Morgan ($5.0mm) and William Blair ($4.0mm). Note figures may not average due to rounding. Adjusted Earnings Per Share refers to earnings per share, adjusted for realized and unrealized gains/losses as well as certain non-recurring items; Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments; CY

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Selected Comparison of Historical Management Budget vs. Actual Performance Selected Observations Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items; CY refers to Calendar Year; YTD refers to Year-To-Date. CY 2021 YTD August 2022 (dollars in millions) (dollars in millions) Selected Observations A B Adjusted Net Income $45.1 $22.1 (50.9%) C D E Adjusted Net Income F Revenue through 8/31 was ~5% lower than originally budgeted but combined ratios were directionally in-line D F E Adjusted Net Income through 8/31 slightly exceeded budget as shortfalls in program profits were offset by higher investment income and lower taxes than budgeted A C B Source: Company management. CONFIDENTIAL 14 CY 2021 revenues were lower than budgeted but Net Earned Premiums nearly doubled relative to CY 2020 levels. Loss ratios were significantly higher than budgeted (and higher than CY 2020 levels) due to elevated loss frequency and severity across several programs with established partners Adjusted net income underperformed budget due primarily to underperformance on loss and expense ratios Budget Actual Variance Revenue Gross Written Premiums $452.0 $425.8 (5.8%) Net Earned Premiums $187.3 $178.2 (4.9%) Total Revenue $199.9 $190.0 (4.9%) Expenses Loss and Loss Adjustment Expenses $115.4 $110.3 (4.4%) General and Administrative Expenses $59.1 $55.7 (5.8%) Net Income $15.1 $21.9 45.3% $17.1 $17.5 2.5% Other Metrics Loss Ratio 61.6% 61.9% 0.3% Expense Ratio 31.5% 31.2% (0.3%) Combined Ratio 93.1% 93.2% 0.0% Retention 42.9% 42.0% (0.9%) Budget Actual Variance Revenue Gross Written Premiums $616.8 $634.2 2.8% Net Earned Premiums $215.8 $198.7 (7.9%) Total Revenue $232.9 $217.7 (6.5%) Expenses Loss and Loss Adjustment Expenses $123.0 $130.8 6.3% General and Administrative Expenses $52.3 $54.7 4.7% Net Income $40.8 $19.3 (52.7%) Other Metrics Loss Ratio 57.0% 65.8% 8.8% Expense Ratio 24.2% 27.5% 3.3% Combined Ratio 81.2% 93.3% 12.1% Retention 39.2% 34.7% (4.5%)

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Page 3 5 Executive Summary Selected Company Observations 3. Preliminary Financial Considerations 15 Other Proposal Considerations Appendices 26 36

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Flow Analysis Selected Companies Analysis MRQ (9/30/22) Book Value (Excl. AOCI): $443.9 million Selected Multiple Range: 0.40x – 0.80x MRQ (9/30/22) Tangible Book Value (Excl. AOCI): $233.0 million Selected Multiple Range: 1.00x – 1.60x CY 2022E Adjusted Net Income: $22.9 million Selected Multiple Range: 10.0x – 15.0x CY 2023E Adjusted Net Income: $26.9 million Selected Multiple Range: 8.0x – 13.0x Selected Transaction Analysis MRQ (9/30/22) Book Value (Excl. AOCI): $443.9 million Selected Multiple Range: 0.50x – 0.90x MRQ (9/30/22) Tangible Book Value (Excl. AOCI): $233.0 million Selected Multiple Range: 1.20x – 1.80x Discounted Cash Book Value (Excl. AOCI) [3] Terminal Multiple: 0.80x – 1.20x Discount Rate: 13.0% – 15.0% Tangible Book Value (Excl. AOCI) [4] Terminal Multiple: 1.20x – 1.80x Discount Rate: 13.0% – 15.0% $2 Preliminary Financial Analyses Summary Preliminary Implied Per Share Value Reference Ranges (dollars per share in actuals) .00 $3.00 $4.00 $5.00 $6.00 $7.00 $8.00 $9.00 $10.00 Note: No particular weight has been attributed to any analysis. Note: Based on (i) ~51.2 million basic shares of common stock outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 10/25/22. Does not include ~0.1 million MSUs. Based on Angels Proposal dated 9/2/22. Reflects 10-day volume-weighted average price per share of common stock as of 10/25/22. Per Company management, at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in book value, and the same discount rate range and terminal multiple range used in the preliminary discounted cash flow analysis, the implied equity value per share reference range would be $4.87 - $7.64. Per Company management, at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in tangible book value, and the same discount rate range and terminal multiple range used in the illustrative discounted cash flow analysis, the implied equity value per share reference range would be $4.98- $7.81. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items; AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public (except in the case of the Company, where it refers to the quarter ended 9/30/22); VWAP refers to Volume-Weighted Average Price. Source: Company management, Management Projections, Capital IQ, Bloomberg, public filings, and the Proposal. $4.87 $4.60 $5.43 $4.31 $4.18 $4.45 $4.53 $3.45 $8.00 $7.56 $8.14 $7.76 $6.79 $6.67 $7.24 $6.90 Proposal Price¹: $6.00 10-Day VWAP²: $3.37 17 CONFIDENTIAL lllustrative Only lllustrative Only lllustrative Only

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Preliminary Selected Companies Analysis 17 CONFIDENTIAL (dollars in millions, except per share values) Equity Market Value [1] [2] to N Workers' Comp Insurers AMERISAFE, Inc. Employers Holdings, Inc. Share Price [1] $53.47 37.52 Equity Market Value [1] [2] $1,032.1 1,034.4 Adjusted CY 2022E 18.7x 14.4x Net Income CY 2023E 20.3x 12.4x Book Value (Excl. AOCI) [3] MRQ 2.62x 0.96x Illustrative Only Tangible Book Value (Excl. AOCI) [4] MRQ 2.62x 1.01x Adjusted Return on Avg. Equity LTM 11.5% 6.6% Illustrative Only Adjusted Return on Avg. Tangible Equity LTM 11.5% 7.0% Low 14.4x 12.4x 0.96x 1.01x 6.6% 7.0% High 18.7x 20.3x 2.62x 2.62x 11.5% 11.5% Median 16.6x 16.4x 1.79x 1.82x 9.1% 9.2% Mean 16.6x 16.4x 1.79x 1.82x 9.1% 9.2% Specialty Insurers Argo Group International Holdings, Ltd. $23.49 $831.7 17.9x 6.3x 0.53x 0.59x 2.7% 3.0% James River Group Holdings, Ltd. 22.95 875.8 13.1x 9.6x 1.24x 1.78x NMF NMF Kinsale Capital Group, Inc. 268.20 6,243.8 40.2x 32.7x 8.50x 8.54x 23.9% 24.1% Palomar Holdings, Inc. 81.67 2,131.7 28.7x 21.7x 5.26x 5.38x 14.8% 15.2% ProAssurance Corporation 20.88 1,134.8 27.0x 17.0x 0.81x 0.88x 5.1% 5.6% RLI Corp. 123.05 5,659.1 31.1x 28.3x 3.45x 3.57x 15.4% 16.0% W. R. Berkley Corporation 69.07 19,396.5 16.7x 14.9x 2.51x 2.59x 16.3% 16.8% Low 13.1x 6.3x 0.53x 0.59x 2.7% 3.0% High 40.2x 32.7x 8.50x 8.54x 23.9% 24.1% Median 27.0x 17.0x 2.51x 2.59x 15.1% 15.6% Mean 25.0x 18.7x 3.18x 3.33x 13.0% 13.5% All Selected Companies Low 13.1x 6.3x 0.53x 0.59x 2.7% 3.0% High 40.2x 32.7x 8.50x 8.54x 23.9% 24.1% Median 18.7x 17.0x 2.51x 2.59x 13.2% 13.4% Mean 23.1x 18.1x 2.88x 3.00x 12.1% 12.4% Twins [6] $3.43 $176.2 7.1x 6.0x 0.40x 0.79x 5.6% [7] 11.2% Twins (Angels Proposal) [5] [6] $6.00 $308.2 12.4x 10.5x 0.71x 1.38x 5.6% [7] 11.2% [7] [7] Note: No company used in this analysis for comparative purposes is identical to the Company. Note: Bloomberg consensus used for 2022 and 2023 estimates, except for Employers Holdings and Argo Group International, which use first half 2022 actual results and Bloomberg consensus for second half 2022 due to first half 2022 reporting. Based on closing prices as of 10/25/22. Based on fully diluted shares outstanding. Calculated as shareholders' equity, less book value of preferred stock and accumulated other comprehensive income as per GAAP. Calculated as shareholders' equity, less book value of preferred stock, accumulated other comprehensive income, and goodwill and other intangibles, as per GAAP. Share price based on Angels Proposal dated 9/2/22. Based on publicly available information as of 10/25/22, including market data, financial information, and consensus estimates. Most recent publicly available financial information for Twins is for the period ended 6/30/22. Certain information for Twins may not tie to figures presented elsewhere in these materials which are based on information provided by Company management for the period ended 9/30/22. Burdening LTM Adjusted Net Income with stock-based compensation, LTM Adjusted ROAE is 5.3% and LTM Adjusted ROATE is 10.7%. Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI); Adjusted ROATE refers to Adjusted Return on Average Tangible Equity and is calculated as adjusted net income divided by average tangible book value of equity (excluding AOCI); Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items (and for certain selected companies, stock-based compensation); AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; LTM refers to the most recently completed 12-month period for which financial information has been made public; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public; NMF refers to Not Meaningful Figure. Source: Bloomberg, Capital IQ and public filings.

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Note: AMSF refers to AMERISAFE, Inc., EIG refers to Employers Holdings, Inc., ARGO refers to Argo Group International Holdings, Ltd., JRVR refers to James River Group Holdings, Ltd., KNSL refers to Kinsale Capital Group, Inc., PLMR refers to Palomar Holdings, Inc., PRA refers to ProAssurance Corporation, RLI refers to RLI Corp. and WRB refers to W. R. Berkley Corporation. 1. Calculated as shareholders' equity less book value of preferred stock and accumulated other comprehensive income as per GAAP. AOCI refers to Accumulated Other Comprehensive Income; Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI); AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; LTM refers to Latest 12 Months; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public. Illustrative ROAE and Equity Market Value / MRQ Book Value (Excl. AOCI) Observations LTM Adjusted ROAE and Equity Market Value / MRQ Book Value (Excl. AOCI)1 Multiple AMSF EIG ARGO KNSL PLMR PRA RLI WRB 0.00x 1.00x 2.00x 3.00x 4.00x 5.00x 6.00x 7.00x 8.00x 9.00x 0.0% 5.0% 10.0% 15.0% LTM Adjusted ROAE 20.0% 25.0% Equity Market Value / MRQ Book Value (excl. AOCI)1 CY 2022E Adjusted ROAE and Equity Market Value / MRQ Book Value (Excl. AOCI)1 Multiple AMSF Sources: Bloomberg, Capital IQ and public filings. CONFIDENTIAL 18 EIG JRVR KNSL PLMR PRA ARGO RLI WRB 0.00x 1.00x 2.00x 3.00x 4.00x 5.00x 6.00x 7.00x 8.00x 9.00x 0.0% 5.0% 10.0% 15.0% CY 2022E Adjusted ROAE 20.0% 25.0% Equity Market Value / MRQ Book Value (excl. AOCI)1

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Historical Trading Multiples Market Capitalization/MRQ Book Value Lookback Note: Market Capitalization/Book Value multiples less than or equal to 0.0x and greater than 10.0x deemed to be not meaningful and excluded from the displayed data. Note: For purposes of the above chart, Book Value is on an unadjusted basis and does not exclude accumulated other comprehensive income. As such, Book Value multiples shown above may differ from multiples shown elsewhere in the materials. Twins Market Capitalization/Book Value multiples shown and calculated since July 16, 2020. Assumed Book Values from July 16, 2020 to November 11, 2020 reflect Twins' March 31, 2020 Total stockholders' / members' equity on an adjusted basis after giving effect to the reorganization transactions and issuance and sale of shares in its IPO per Twins' 424B4 filing dated July 17, 2020. Calculated since July 16, 2020, Twins' IPO date. Selected Workers' Comp Insurers comprise AMERISAFE, Inc. and Employers Holdings, Inc. Data reflects median multiple. Selected Specialty Insurers comprise Argo Group International Holdings, Ltd., James River Group Holdings, Ltd., Kinsale Capital Group, Inc., Palomar Holdings, Inc., ProAssurance Corporation, RLI Corp., and W. R. Berkley Corporation. Data reflects median multiple. Reflects 10-year average. Reflects average since July 16, 2020, Twins' IPO date. One-Year Average Since Twins IPO [2] 3-Year Average 5-Year Average 10-Year Average Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] 0.8x 1.3x NA NA NA 1.7x 1.7x 1.7x 1.9x 1.7x 2.5x 2.2x 2.2x 2.0x 1.7x 1.3x 6 1.7x 5 1.7x 5 1.0x 0.8x 0.5x 0.3x 0.0x Oct-12 Apr-13 Oct-13 Apr-14 Oct-14 Apr-15 Oct-15 Apr-16 Oct-16 Apr-17 Oct-17 Apr-18 Oct-18 Apr-19 Oct-19 Apr-20 Oct-20 Apr-21 Oct-21 Apr-22 Oct-22 1.3x 1.5x 1.8x 2.5x 2.3x 2.0x 2.8x 3.0x 3.3x Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] Twins Average [1] Selected Workers' Comp Insurers Average [3] Selected Specialty Insurers Average [4] NA refers to Not Available. MRQ refers to Most Recent Quarter. Source: S&P Capital IQ as of October 25, 2022. (Multiples shown above are sourced from S&P Capital IQ; as such, certain multiples may differ slightly from the figures shown on other pages.) CONFIDENTIAL 19

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Historical Trading Multiples Market Capitalization/NTM Adjusted Net Income Lookback Note: Market Capitalization/NTM Adjusted Net Income multiples less than or equal to 0.0x and greater than 40.0x deemed to be not meaningful and excluded from the displayed data. Twins Market Capitalization/NTM Adjusted Net Income multiples shown and calculated since August 10, 2020, the first date with Twins NTM consensus Adjusted Net Income estimates available per S&P Capital IQ. Calculated since August 10, 2020, the first date with Twins NTM consensus estimates available per S&P Capital IQ. Selected Workers' Comp Insurers comprise AMERISAFE, Inc. and Employers Holdings, Inc. Data reflects median multiple. Selected Specialty Insurers comprise Argo Group International Holdings, Ltd., James River Group Holdings, Ltd., Kinsale Capital Group, Inc., Palomar Holdings, Inc., ProAssurance Corporation, RLI Corp., and W. R. Berkley Corporation. Data reflects median multiple. Reflects 10-year average. Reflects average since August 10, 2020, the first date with Twins NTM consensus estimates available per S&P Capital IQ. One-Year Average Since Twins IPO [2] 3-Year Average 5-Year Average 10-Year Average Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] 9.8x 13.4x NA NA NA 17.9x 18.9x 19.0x 18.8x 17.8x 20.7x 21.5x 21.9x 22.1x 19.2x 6 13.4x 19.2x 5 17.8x 5 0.0x Oct-12 Apr-13 Oct-13 Apr-14 Oct-14 Apr-15 Oct-15 Apr-16 Oct-16 Apr-17 Oct-17 Apr-18 Oct-18 Apr-19 Oct-19 Apr-20 Oct-20 Apr-21 Oct-21 Apr-22 Oct-22 5.0x 10.0x 15.0x 20.0x 25.0x 30.0x 35.0x Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] Twins Average [1] Selected Workers' Comp Insurers Average [3] Selected Specialty Insurers Average [4] NA refers to Not Available. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items. Source: S&P Capital IQ as of October 25, 2022. (Multiples shown above are sourced from S&P Capital IQ; as such, certain multiples may differ slightly from the figures shown on other pages.) CONFIDENTIAL 20

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Preliminary Benchmarking Data Note: No company used in this analysis for comparative purposes is identical to the Company. Based on financial information for Twins for the period ended 9/30/22 per Company management. Ratings represent the latest available (as of 10/23/2022) AM Best Financial Strength Rating for each company's largest insurance subsidiary as measured by 6/30/2022 LTM Direct Premiums Written. Represents calendar year 2021 figure, given Kinsale Capital Group, Inc. only files annual statutory statements. Calculated excluding AOCI. Burdening Adjusted Net Income with stock-based compensation, LTM ROATE is 9.2%, LTM ROAE is 4.6%, CY 2022E ROAE is 5.0%, and CY 2023E ROAE is 5.5%. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items. Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI). Adjusted ROATE refers to Adjusted Return on Average Tangible Equity and is calculated as adjusted net income divided by average tangible book value of equity (excluding AOCI). AOCI refers to Accumulated Other Comprehensive Income. CY refers to Calendar Year. E refers to Estimated. LTM refers to the most recently completed 12-month period for which financial information has been made public, other than for the Company, in which case LTM refers to Latest 12 Months. MRQ refers to Most Recent Quarter. Size & Financial Strength Leverage (LTM Net Premiums Written / Average Capital and Surplus) Workers' Comp Insurers Employers Holdings, Inc. 0.6x AMERISAFE, Inc. 0.7x Twins - FY 2022E 1.0x Specialty Insurers James River Group Holdings, Ltd. 0.6x ProAssurance Corporation 0.7x RLI Corp. 0.9x Twins - FY 2022E 1.0x Argo Group International Holdings, Ltd. 1.1x Kinsale Capital Group, Inc. [4] 1.2x W. R. Berkley Corporation 1.3x Palomar Holdings, Inc. 1.3x Financial Strength (AM Best Financial Strength Rating) [2] Workers' Comp Insurers AMERISAFE, Inc. A Twins A Employers Holdings, Inc. A- Specialty Insurers RLI Corp. A+ W. R. Berkley Corporation A+ Kinsale Capital Group, Inc. [3] A Twins A Argo Group International Holdings, Ltd. A- James River Group Holdings, Ltd. A- Palomar Holdings, Inc. A- ProAssurance Corporation A- Size (MRQ Book Value of Equity (Excl. AOCI), millions) Workers' Comp Insurers Employers Holdings, Inc. $1,072.2 Twins [1] $443.9 AMERISAFE, Inc. $393.9 Specialty Insurers W. R. Berkley Corporation $7,731.1 RLI Corp. $1,638.6 Argo Group International Holdings, Ltd. $1,572.7 ProAssurance Corporation $1,404.1 Kinsale Capital Group, Inc. $734.8 James River Group Holdings, Ltd. $709.0 Twins [1] $443.9 Palomar Holdings, Inc. $405.3 Size (MRQ Tangible Book Value of Equity (Excl. AOCI), millions) Workers' Comp Insurers Employers Holdings, Inc. $1,022.4 AMERISAFE, Inc. $393.9 Twins [1] $233.0 Specialty Insurers W. R. Berkley Corporation $7,479.8 RLI Corp. $1,585.0 Argo Group International Holdings, Ltd. $1,408.1 ProAssurance Corporation $1,284.4 Kinsale Capital Group, Inc. $731.2 James River Group Holdings, Ltd. $491.3 Palomar Holdings, Inc. $396.4 Twins [1] $233.0 Profitability (Adjusted ROAE and Adjusted ROATE) Profitability (LTM Adjusted ROATE) [4] [5] Workers' Comp Insurers AMERISAFE, Inc. 11.5% Twins [1] 9.8% Employers Holdings, Inc. 7.0% Specialty Insurers Kinsale Capital Group, Inc. 24.1% W. R. Berkley Corporation 16.8% RLI Corp. 16.0% Palomar Holdings, Inc. 15.2% Twins [1] 9.8% ProAssurance Corporation 5.6% Argo Group International Holdings, Ltd. 3.0% James River Group Holdings, Ltd. NMF Profitability (LTM Adjusted ROAE) [4] [5] Workers' Comp Insurers AMERISAFE, Inc. 11.5% Employers Holdings, Inc. 6.6% Twins [1] 4.9% Specialty Insurers Kinsale Capital Group, Inc. 23.9% W. R. Berkley Corporation 16.3% RLI Corp. 15.4% Palomar Holdings, Inc. 14.8% ProAssurance Corporation 5.1% Twins [1] 4.9% Argo Group International Holdings, Ltd. 2.7% James River Group Holdings, Ltd. NMF Profitability (CY 2022E Adjusted ROAE) [5] Workers' Comp Insurers AMERISAFE, Inc. 15.3% Employers Holdings, Inc. 6.1% Twins 5.3% Specialty Insurers Kinsale Capital Group, Inc. 22.2% RLI Corp. 19.1% Palomar Holdings, Inc. 18.6% W. R. Berkley Corporation 18.1% James River Group Holdings, Ltd. 10.5% Twins 5.3% ProAssurance Corporation 4.0% Argo Group International Holdings, Ltd. 2.7% Profitability (CY 2023E Adjusted ROAE) [5] Workers' Comp Insurers AMERISAFE, Inc. 16.1% Employers Holdings, Inc. 6.0% Twins 5.9% Specialty Insurers Kinsale Capital Group, Inc. 24.6% Palomar Holdings, Inc. 21.6% W. R. Berkley Corporation 19.1% RLI Corp. 19.1% James River Group Holdings, Ltd. 13.0% Argo Group International Holdings, Ltd. 10.8% Twins 5.9% ProAssurance Corporation 5.3% NMF refers to not meaningful figure. Source: Bloomberg, Capital IQ, Company management, Management Projections and public filings. CONFIDENTIAL 21

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Preliminary Benchmarking Data (cont.) Note: No company used in this analysis for comparative purposes is identical to the Company. 1. In 1999, company entered into a LPT Agreement with third party reinsurers. The figures above do not reflect the impact of that agreement. If those are reflected, 2019-2021 average and LTM loss ratios would be 52.2% and 56.5%, respectively and the 2019-2021 average and LTM combined ratios would be 93.2% and 95.4%, respectively. 2. Based on financial information for Twins for the period ended 9/30/22 per Company management. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items. CY refers to Calendar Year. E refers to Estimated. NA refers to not available. NMF refers to not meaningful figure. Profitability (Loss & Combined Ratios) Growth (Adjusted Net Income) Combined Ratio (CY 2019 to CY 2021 Average) Workers' Comp Insurers AMERISAFE, Inc. 79.6% Twins 83.9% Employers Holdings, Inc. [1] 95.1% Specialty Insurers Kinsale Capital Group, Inc. 82.9% Twins 83.9% RLI Corp. 90.2% Palomar Holdings, Inc. 93.4% W. R. Berkley Corporation 96.7% Argo Group International Holdings, Ltd. 106.7% ProAssurance Corporation 112.4% James River Group Holdings, Ltd. 114.6% Net Loss Ratio (CY 2019 to CY 2021 Average) Workers' Comp Insurers Employers Holdings, Inc. [1] 54.1% AMERISAFE, Inc. 54.3% Twins 54.8% Specialty Insurers Palomar Holdings, Inc. 21.6% RLI Corp. 49.0% Twins 54.8% Kinsale Capital Group, Inc. 59.8% W. R. Berkley Corporation 62.6% Argo Group International Holdings, Ltd. 69.1% ProAssurance Corporation 83.3% James River Group Holdings, Ltd. 91.5% Net Loss Ratio (LTM) Workers' Comp Insurers Employers Holdings, Inc. [1] 58.3% AMERISAFE, Inc. 61.1% Twins [2] 65.5% Specialty Insurers Palomar Holdings, Inc. 23.5% RLI Corp. 44.5% Kinsale Capital Group, Inc. 55.7% W. R. Berkley Corporation 61.3% Twins [2] 65.5% Argo Group International Holdings, Ltd. 67.9% ProAssurance Corporation 76.3% James River Group Holdings, Ltd. 90.2% Combined Ratio (LTM) Workers' Comp Insurers AMERISAFE, Inc. 87.7% Twins [2] 95.0% Employers Holdings, Inc. [1] 97.3% Specialty Insurers Kinsale Capital Group, Inc. 76.6% Palomar Holdings, Inc. 82.9% RLI Corp. 84.2% W. R. Berkley Corporation 91.9% Twins [2] 95.0% ProAssurance Corporation 103.1% Argo Group International Holdings, Ltd. 103.6% James River Group Holdings, Ltd. 112.7% Projected Growth (CY 2021 to CY 2022E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. 5.4% Twins 3.5% AMERISAFE, Inc. 0.9% Specialty Insurers Palomar Holdings, Inc. 38.8% W. R. Berkley Corporation 21.9% Kinsale Capital Group, Inc. 17.2% Argo Group International Holdings, Ltd. 11.9% Twins 3.5% RLI Corp. 2.9% ProAssurance Corporation (44.7%) James River Group Holdings, Ltd. NMF Projected Growth (CY 2021 to CY 2023E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. 10.6% Twins 10.2% AMERISAFE, Inc. (3.5%) Specialty Insurers Argo Group International Holdings, Ltd. 77.8% Palomar Holdings, Inc. 35.4% Kinsale Capital Group, Inc. 20.0% W. R. Berkley Corporation 17.0% Twins 10.2% RLI Corp. 6.3% ProAssurance Corporation (6.3%) James River Group Holdings, Ltd. NA Projected Growth (CY 2020 to CY 2022E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. (12.5%) Twins (16.4%) AMERISAFE, Inc. (18.1%) Specialty Insurers Palomar Holdings, Inc. 189.2% James River Group Holdings, Ltd. 77.2% W. R. Berkley Corporation 62.7% Kinsale Capital Group, Inc. 46.5% RLI Corp. 24.5% Twins (16.4%) Argo Group International Holdings, Ltd. NA ProAssurance Corporation NA Projected Growth (CY 2022E to CY 2023E Adjusted Net Income) Workers' Comp Insurers Twins 17.4% Employers Holdings, Inc. 16.1% AMERISAFE, Inc. (7.7%) Specialty Insurers Argo Group International Holdings, Ltd. 182.6% ProAssurance Corporation 58.9% James River Group Holdings, Ltd. 37.5% Palomar Holdings, Inc. 32.2% Kinsale Capital Group, Inc. 22.9% Twins 17.4% W. R. Berkley Corporation 12.3% RLI Corp. 9.9% LTM refers to the most recently completed 12-month period for which financial information has been made public, other than for the Company, in which case LTM refers to Latest 12 Months. Source: Bloomberg, Capital IQ, Company management, Management Projections and public filings. CONFIDENTIAL 22

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Preliminary Selected Transactions Analysis Note: No company used in this analysis for comparative purposes is identical to the Company, and no transaction used in this analysis for comparative purposes is identical to the proposed Transaction. Transaction Value refers to the implied equity value of target company, based on the announced transaction equity price and other public information available at the time of the announcement. Based on reported metric for MRQ prior to the announcement of the transaction. Computed as shareholders' equity, less accumulated other comprehensive income on GAAP basis. Based on reported metric for MRQ prior to the announcement of the transaction. Computed as shareholders' equity, less accumulated other comprehensive income and goodwill & intangibles on GAAP basis. Computed as LTM Adjusted Net Income divided by MRQ shareholders' equity less AOCI. Computed as LTM Adjusted Net Income divided by MRQ shareholders' equity less AOCI and goodwill & intangibles. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items; Adjusted ROE refers to Adjusted Return on Equity; Adjusted ROTE refers to Adjusted Return on Tangible Equity; AOCI refers to Accumulated Other Comprehensive Income; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public; NA refers to not available; NMF refers to not meaningful figure. (dollars in millions) Transaction Value [1] / Illustrative Only Transaction Book Value Tangible Book Value Adjusted Net Implied Illustrative Only Implied Announced Effective Target Acquiror Value [1] (Excl. AOCI) [2] (Excl. AOCI) [3] Income Adjusted ROE [4] Adjusted ROTE [5] 2/16/2021 6/1/2021 Protective Insurance Corporation The Progressive Corporation $337.6 0.99x 0.99x 16.9x 5.9% 5.9% 1/15/2021 8/4/2021 ProSight Global, Inc. (nka:Coaction TowerBrook Capital Partners L.P.; $585.9 1.10x 1.13x 14.6x 7.5% 7.8% 11/16/2018 9/19/2019 Global, Inc.) Further Global Capital Management, EMC Insurance Group Inc Employers Mutual Casualty Company $786.1 1.33x 1.34x 27.6x 4.8% 4.8% 8/28/2018 2/15/2019 Aspen Insurance Holdings Limited Apollo Global Management, LLC $2,600.1 0.88x 0.88x NMF NMF NMF 8/22/2018 5/23/2019 The Navigators Group, Inc The Hartford Financial Services $2,083.6 1.64x 1.68x 37.6x 4.4% 4.5% 1/9/2018 11/9/2018 Group, Inc AmTrust Financial Services, Inc. Stone Point Capital LLC ; Trident VII, $2,904.8 0.76x 1.00x 13.4x 5.7% 7.5% 12/18/2016 7/5/2017 L.P. Allied World Assurance Company Fairfax Financial Holdings Limited $4,696.2 1.29x 1.49x 20.6x 6.3% 7.2% Holdings, Ltd 7/26/2017 11/17/2017 State National Companies, Inc. Markel Corporation $922.6 2.90x 3.04x NA NA NA 5/2/2017 9/28/2017 Intact Insurance Group USA Holdings Intact Financial Corporation $1,714.8 1.65x 1.65x 24.6x 6.7% 6.7% 12/5/2016 5/1/2017 Inc. Ironshore Inc. Liberty Mutual Group, Inc. $2,935.0 1.42x 1.48x 19.0x 7.5% 7.8% 10/5/2016 3/28/2017 Endurance Specialty Holdings Ltd Sompo Holdings, Inc. $6,318.1 1.28x 1.42x 17.8x 7.2% 8.0% 3/7/2016 11/10/2016 National Interstate Corporation Great American Insurance Company, $639.1 1.77x 1.81x 27.8x 6.4% 6.5% 6/10/2015 10/28/2015 Inc. HCC Insurance Holdings Inc. Tokio Marine & Nichido Fire $7,501.8 1.99x 2.67x NA NA NA 12/30/2014 7/7/2015 Insurance Co., Ltd. Meadowbrook Insurance Group, Inc. Fosun International Limited $433.3 1.04x 1.12x NMF NMF NMF 12/17/2014 5/1/2015 (nka:AmeriTrust Group, Inc.) Catlin Group Ltd. XL Group plc $3,907.4 0.70x 0.88x 7.1x 9.8% 12.3% 1/9/2014 4/1/2014 Summit Holding Southeast Inc Great American Holding, Inc. $250.0 1.08x 1.32x 5.3x 20.3% 24.9% 1/6/2014 9/15/2014 Tower Group International, Ltd American Capital Partners Re, Ltd. $143.6 2.17x NMF NMF NMF NMF 9/24/2013 1/2/2014 Eastern Insurance Holdings, Inc. ProAssurance Corporation $205.1 1.47x 1.65x 16.2x 9.1% 10.1% Low $143.6 0.70x 0.88x 5.3x 4.4% 4.5% High $7,501.8 2.90x 3.04x 37.6x 20.3% 24.9% Median $1,318.7 1.31x 1.42x 17.8x 6.7% 7.5% Mean $2,164.7 1.42x 1.50x 19.1x 7.8% 8.8% Source: Capital IQ, public filings and press releases. CONFIDENTIAL 23

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![](ny20006673x2_exc-1slide24.jpg)

Preliminary Discounted Cash Flow Analysis Book Value Terminal Multiple (dollars in millions) Previous Year-End Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 Net Income 21.0 25.1 33.6 39.2 45.8 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Ending Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Present Value of Cash Flows (2022 - 2027) Projected Calendar Year Ending December 31, 2022E 2023E 2024E 2025E 2026E 2027E PV of Terminal Value as a Multiple of 2027 Book Value (Excl. AOCI) Discount Rate 13.00% 13.50% $0.0 $0.0 0.80x $259.4 $253.6 1.00x $324.3 $317.0 1.20x $389.2 $380.4 14.00% $0.0 + $247.9 $309.9 $371.8 = $247.9 $309.9 $371.8 14.00% $4.82 $6.02 $7.22 14.50% $0.0 $242.4 $302.9 $363.5 $242.4 $302.9 $363.5 14.50% $4.71 $5.89 $7.06 15.00% $0.0 $237.0 $296.2 $355.4 $237.0 $296.2 $355.4 15.00% $4.60 $5.75 $6.90 Impli ed Equity Value Implied Equity Value [1] Per Share 0.80x 1.00x 1.20x Discount Rate 0.80x 1.00x 1.20x $259.4 $324.3 $389.2 13.00% $5.04 $6.30 $7.56 $253.6 $317.0 $380.4 13.50% $4.93 $6.16 $7.39 Note: Present values as of 10/31/22; mid-year convention applied. Note: Present value of cash flows (2022-2027) is $0 as Management Projections do not contemplate any distributions over the projection period. Per Company management at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in book value, and the same discount rates and terminal multiple range as shown above, the implied equity value per share reference range would be $4.87-$7.64. 1. Based on (i) ~51.2 million shares outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 10/25/22. Does not include ~0.1 million MSUs. AOCI refers to Accumulated Other Comprehensive Income. E refers to Estimated. PV refers to Present Value. Source: Company management and Management Projections. CONFIDENTIAL 24

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Illustrative Only Preliminary Discounted Cash Flow Analysis Tangible Book Value Terminal Multiple (dollars in millions) Previous Year-End Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 Net Income 21.0 25.1 33.6 39.2 45.8 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Ending Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 Goodwill & Intangible Assets (209.5) (203.5) (197.5) (191.5) (185.5) (179.5) Ending Tangible Book Value (Excl. AOCI) $235.7 $262.7 $293.8 $333.4 $378.6 $430.4 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Present Value of Cash Flows (2022 - 2027) Projected Calendar Year Ending December 31, 2022E 2023E 2024E 2025E 2026E 2027E PV of Terminal Value as a Multiple of 2027 Tangible Book Value (Excl. AOCI) Discount Rate 13.00% 13.50% $0.0 $0.0 1.20x $274.6 $268.4 1.50x $343.3 $335.5 1.80x $411.9 $402.7 14.00% $0.0 + $262.4 $328.0 $393.6 = $262.4 $328.0 $393.6 14.00% $5.10 $6.37 $7.65 14.50% $0.0 $256.5 $320.7 $384.8 $256.5 $320.7 $384.8 14.50% $4.98 $6.23 $7.48 15.00% $0.0 $250.8 $313.5 $376.2 $250.8 $313.5 $376.2 15.00% $4.87 $6.09 $7.31 Impl ied Equity Value Implied Equity Value [1] Per Share 1.20x 1.50x 1.80x Discount Rate 1.20x 1.50x 1.80x $274.6 $343.3 $411.9 13.00% $5.34 $6.67 $8.00 $268.4 $335.5 $402.7 13.50% $5.21 $6.52 $7.82 Note: Present values as of 10/31/22; mid-year convention applied. Note: Present value of cash flows (2022-2027) is $0 as Management Projections do not contemplate any distributions over the projection period. Per Company management at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in tangible book value, and the same discount rates and terminal multiple range as shown above, the implied equity value per share reference range would be $4.98-$7.81. 1. Based on (i) ~51.2 million shares outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 10/25/22. Does not include ~0.1 million MSUs. AOCI refers to Accumulated Other Comprehensive Income. E refers to Estimated. PV refers to Present Value. Source: Company management and Management Projections. CONFIDENTIAL 25

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Page 3 5 15 Executive Summary Selected Company Observations Preliminary Financial Considerations 4. Other Proposal Considerations 26 5. Appendices 36

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Proposal Overview Reflects historical trading prices of Twins common stock. Based on trading prices as of 10/25/22. Based on trading prices as of 9/1/22. 52-week high closing price as of both dates reflects closing per share price as of 11/15/21. 52-week low closing price as of 9/1/22 reflects closing per share price as of 3/11/22 and 52-week low closing price as of 10/25/22 reflects closing per share price as of 10/7/22. VWAP refers to Volume-Weighted Average Price. Sources: Bloomberg and Capital IQ. On 9/2/22, the Board of Directors of Twins received the Proposal from the Angels Parties to purchase all of the outstanding shares of Twins common stock not already owned by the Angels Parties for cash consideration of $6.00 per share. Proposal consideration reflects a premium of ~75% over the closing stock price and ~74% over the 30-day VWAP as of 10/25/222 (and a premium of ~38% over the closing stock price and ~21% over the 30-day VWAP as of the date prior to the Proposal3) The Proposal is contingent on approval by the Special Committee and a majority vote of Unaffiliated Stockholders The Angels Parties have indicated that they have no interest in participating in an alternative change of control transaction involving the Company The Angels Parties have indicated that (i) diligence requirements will be limited, (ii) definitive documents will not be subject to financing conditions and (iii) at the appropriate time, they would like to discuss the possibility of certain stockholders rolling over their shares in the proposed transaction Proposal implies an aggregate equity value of ~$308 million (dollars per share in actuals) Implied Premiums / (Discounts) to Historical Trading Prices1 27 CONFIDENTIAL Price Proposal Premium Price Proposal Premium 1-Day Closing Price $4.34 38.2% $3.43 74.9% 5-Day VWAP $4.57 31.3% $3.37 77.9% 10-Day VWAP $4.60 30.4% $3.37 78.2% 20-Day VWAP $4.78 25.5% $3.38 77.6% 30-Day VWAP $4.95 21.2% $3.45 73.9% 3-Month VWAP $5.93 1.2% $4.00 50.2% 6-Month VWAP $4.86 23.6% $5.21 15.1% 1-Year VWAP $6.23 (3.7%) $5.59 7.4% 52-Week High Closing Price [4] $10.70 (43.9%) $10.70 (43.9%) 52-Week Low Closing Price [5] $3.35 79.1% $3.15 90.5% Prior to Proposal (9/1/22) Current (10/25/22)

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Preliminary Overview of Potential Alternatives 27 CONFIDENTIAL Certain potential alternatives to consider include but are not limited to the following: Status Quo A transaction with the Angels Parties Sale to a Third Party Dividend Recapitalization Share Repurchases and Dividends Preliminary considerations related to certain alternatives include, but are not limited to, the following: Angels' support will be an important consideration for the viability of certain alternatives Limited universe of potential third-party buyers given niche specialty sector focus Company has previously run a full sale process with limited success Transaction execution risk Challenging M&A and financing markets backdrop Focus on maintaining minimum capital adequacy levels and AM Best rating likely to limit potential for dividend recapitalizations or other meaningful capital returns to investors Focus on balance sheet and ratings also limit retained premium growth and/or strategic growth initiatives Meaningful gap between Twins multiples (P/BV, P/E)1 and corresponding metrics for other industry participants, with certain potential barriers to closing gap Operating risks of not delivering against standalone plan Time required to create value through execution of standalone plan 1. Refers to multiples implied by Twins stock price. Source: Company management.

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Twins vs. Selected Companies Historical Stock Performance 22.2% 21.5% 15.8% (77.9%) -- -- -- (77.9%) (66.0%) (61.3%) 226.5% 62.3% 32.0% 22.2% (15.5%) (19.8%) 203.8% 12.5% 4.7% 15.8% (2.2%) (2.1%) 211.3% 109.8% 28.7% 21.5% 0.1% (4.0%) Total Shareholder Return Ten-Year Five-Year Three-Year Since Twins IPO One-Year YTD Twins S&P 500 Index (Total Return) Selected Workers' Comp Insurers1,3 Selected Specialty Insurers2,3 75% -100% -75% -50% -25% 0% 25% 50% Jul-20 Sep-20 Nov-20 Jan-21 Mar-21 May-21 Jul-21 Sep-21 Nov-21 Jan-22 Mar-22 May-22 Jul-22 Sep-22 Twins S&P 500 Index (Total Return) Selected Workers' Comp Insurers [1] Selected Specialty Insurers [2] Selected Workers' Comp Insurers comprise AMERISAFE, Inc. and Employers Holdings, Inc.. Selected Specialty Insurers comprise Argo Group International Holdings, Ltd., James River Group Holdings, Ltd., Kinsale Capital Group, Inc., Palomar Holdings, Inc., ProAssurance Corporation, RLI Corp., and W. R. Berkley Corporation Average of Selected Workers' Comp Insurers index and Selected Specialty Insurers index. Kinsale Capital Group, Inc., Palomar Holdings, Inc. and James River Group Holdings, Ltd not included in Ten-Year return calculation. Palomar Holdings, Inc not included in Five-Year return calculation. Source: Capital IQ as of 10/25/22. CONFIDENTIAL 29

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$0.40 $0.60 $0.80 $1.00 $1.20 $1.40 Aug-20 Nov-20 Feb-21 May-21 Aug-21 Nov-21 Feb-22 May-22 Aug-22 $32.8 $22.1 $24.8 $29.3 $37.9 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E(2) Analyst Consensus EPS Estimates Trajectory Since IPO (Adjusted EPS CY 2022E) Estimated figures represent consensus estimates per Bloomberg as of 10/25/22. CY 2024E estimates based on limited number of brokers (JP Morgan and Evercore) who report 2024 estimates CY refers to Calendar Year; E refers to Expected; EPS refers to Earnings Per Share. Adjusted Net Income1 8/10/20: $1.11 10/25/22: $0.49 Twins Historical Performance & Projected Adjusted Earnings Based on Analyst Consensus Estimates $0.75 Adjusted EPS1 $0.43 $0.49 $0.57 $0.74 Sources: Bloomberg and Wall Street analyst research. CONFIDENTIAL 30

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Twins Analyst Perspectives O verall, we think the combination of Twins' history of under- delivering against market expectations and the lack of meaningful catalysts could weigh on the stock's valuation. We expect the magnitude of favorable reserve releases –which have been a major driver of underwriting income historically–to be lower, and we believe that Twins is unlikely to pursue accretive capital management initiatives despite the stock's attractive multiple." - JP Morgan, 10/03/2022 " Broker Date Recommendation Price Target Prem. / (Disc.)1 Book Value of Equity (Excl. AOCI) as of 6/30/222 Tangible Book Value of Equity (Excl. AOCI) as of 6/30/223 10/18/2022 Market Outperform $8.00 133.2% 0.94x 1.84x 10/10/2022 Neutral 6.00 74.9% 0.71x 1.38x 10/03/2022 Neutral 6.00 74.9% 0.71x 1.38x 08/04/2022 Neutral – – – – Median $6.00 74.9% 0.71x 1.38x Mean $6.67 94.4% 0.79x 1.53x Target Price / Closing share price of $3.43 as of 10/25/22. MRQ Book Value based on Book Value (Excluding AOCI) of $435.9 million per 10-Q for period ended 6/30/22 and (i) ~51.2 million shares outstanding per 10-Q for period ended 6/30/22; (ii) ~0.2 million options (to the extent in the money, per the treasury method); and (iii) ~0.1 million restricted stock units per 10-Q for period ended 6/30/22. Does not include ~0.1 million PSUs and ~0.1 million MSUs. MRQ Tangible Book Value based on Tangible Book Value (Excluding AOCI) of $223.4 million per 10-Q for period ended 6/30/22 and (i) ~51.2 million shares outstanding per 10-Q for period ended 6/30/22; (ii) ~0.2 million options (to the extent in the money, per the treasury method); and (iii) ~0.1 million restricted stock units per 10-Q for period ended 6/30/22. Does not include ~0.1 million PSUs and ~0.1 million MSUs. AOCI refers to Accumulated Other Comprehensive Income. Select Commentary Broker Outlook b - JMP, 08/03/2022 " Through a combination of existing markets, new markets, and M&A, we elieve Twins has significant runway to continue the growth it has enjoyed in recent years, albeit at a cautious pace in the near term as it remains focused on bottom line performance (we project 2022E GWP growth of -1% and 2023E of +8%). Last year's upgrade to "A" from A.M. Best has increased leads, and with the capital from 2020's IPO, Twins is well-situated to take advantage of opportunities in the market." Sources: Bloomberg, FactSet, and Equity Research as of 10/25/22. CONFIDENTIAL 31

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100.0% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% $3.00- $3.99 $4.00- $4.99 $5.00- $5.99 $6.00- $6.99 $7.00- $7.99 $8.00- $8.99 $9.00- $9.99 $10.00- $10.99 Last Twelve Months Last Six Months Last Three Months Last Month Volume1: 13.6 million (60.9% of float)2 Twins Selected Historical Trading Activity Volume1: 6.5 million (29.1% of float)2 Volume1: 34.4 million (153.4% of float)2 Volume1: 2.9 million (12.7% of float)2 Based on VWAP volume, per Bloomberg. Public float calculated as total shares less shares held by Angels and Company insiders. Based on offer price of $6.00 per share. ADTV refers to Average Daily Trading Volume. VWAP refers to Volume-Weighted Average Price. Selected VWAP Data 52-Week Range 12-Month 9-Month 6-Month 3-Month 30-Day 20-Day 10-Day 5-Day $3.15 – $10.70 $5.59 $4.80 $5.21 $4.00 $3.45 $3.38 $3.37 $3.37 Current Trading Stats: Float2: 22.4mm (43.7% of common) 90-Day ADTV: 131k 90-Day Avg. Value Traded: $0.6mm % of Volume Traded Above Offer Price3: 43% % of Volume Traded Above Offer Price3: 0% % of Volume Traded Above Offer Price3: 41% 33.1% Source: Bloomberg as of 10/25/22. CONFIDENTIAL 32 18.0% 6.3% 15.4% 9.8% 13.2% 3.3% 0.7% $3.00- $3.99 $4.00- $4.99 $5.00- $5.99 $6.00- $6.99 $7.00- $7.99 $8.00- $8.99 $9.00- $9.99 $10.00- $10.99 28.5% 14.5% 15.9% 36.6% 4.5% 0.0% 0.0% 0.0% $3.00- $3.99 $4.00- $4.99 $5.00- $5.99 $6.00- $6.99 $7.00- $7.99 $8.00- $8.99 $9.00- $9.99 $10.00- $10.99 59.5% 27.3% 13.2% 0.0% 0.0% 0.0% 0.0% 0.0% $3.00- $3.99 $4.00- $4.99 $5.00- $5.99 $6.00- $6.99 $7.00- $7.99 $8.00- $8.99 $9.00- $9.99 $10.00- $10.99

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Twins Ownership Summary Sources: Bloomberg, press releases and public filings. CONFIDENTIAL 33 (shares in millions) Reflects basic shares of common stock outstanding of 51,202,136 as of 8/4/22 per the Company's Form 10-Q for the period ended 6/30/22. Public float calculated as total shares less primarily shares held by Angels and Company insiders. Holder Shares % Outstanding Voting Interests Public Float2 Angels 24.0 46.9% -- -- Baker, Blake A. 4.3 8.5% 16.0% 19.4% Royce & Associates, LP 3.9 7.6% 14.2% 17.3% O'Brien, Andrew Michael (Executive Chairman of the Board) 3.5 6.9% 12.9% NA Vaughan Nelson Investment Management, L.P. 1.4 2.7% 5.1% 6.2% Janus Henderson Group plc 1.3 2.5% 4.8% 5.8% BlackRock, Inc. 1.2 2.3% 4.4% 5.3% Lee, Steven Barry (Senior VP & Director) 1.1 2.1% 3.9% NA The Vanguard Group, Inc. 0.9 1.7% 3.2% 3.9% William Blair Investment Management, LLC 0.7 1.3% 2.4% 3.0% Brandywine Global Investment Management, LLC 0.6 1.1% 2.2% 2.6% GW&K Investment Management, LLC 0.5 1.0% 1.9% 2.3% Other Current / Former Directors and Executive Officers 0.2 0.4% 0.7% NA Other 7.7 15.0% 28.2% 34.3% Total1 51.2 100.0% 100.0% 100.0% Voting Interest % of Non-Angels % of

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Estimated Twins Shareholder Cost Basis Current Share Price: $3.43 1. Cost basis average, per Capital IQ, based on volume weighted average price during the quarterly periods in which shares were purchased or sold Ownership 46.9% 8.5% 7.6% 6.9% 2.7% 2.5% 2.3% 2.1% 1.7% 1.3% 1.1% 1.0% 0.8% 0.8% 0.7% 0.7% 0.6% 0.6% 0.4% 0.4% 0.4% 0.4% 0.3% 0.3% 0.3% Cumulative Ownership 46.9% 55.4% 63.0% 69.8% 72.5% 75.1% 77.4% 79.5% 81.2% 82.5% 83.6% 84.6% 85.4% 86.2% 86.9% 87.6% 88.2% 88.7% 89.2% 89.6% 90.0% 90.4% 90.7% 91.0% 91.3% Ownership of Non-Angels Shares NA 16.0% 14.2% 12.9% 5.1% 4.8% 4.4% 3.9% 3.2% 2.4% 2.2% 1.9% 1.5% 1.5% 1.4% 1.3% 1.0% 1.0% 0.8% 0.8% 0.8% 0.7% 0.6% 0.6% 0.5% Average Cost Basis: $11.88 Top 25 Shareholders1 NA Source: Capital IQ as of 10/25/22 CONFIDENTIAL 34 NA $15.04 NA $16.32 $15.96 $14.31 NA $15.26 $14.70 $11.82 $5.91 $15.24 $8.59 $13.83 $6.80 $13.60 $14.93 $6.56 $13.38 $6.61 $15.02 $7.46 $7.07 $10.97 Angels Baker, Blake A. Royce & Associates, LP O'Brien, Andrew Michael Vaughan Nelson Investment Management Janus Henderson Group plc BlackRock, Inc. Lee, Steven Barry The Vanguard Group, Inc. William Blair Investment Management, LLC Brandywine Global Investment Management GW&K Investment Management, LLC Thompson, Siegel & Walmsley LLC Hotchkis and Wiley Capital Management Hotchkis and Wiley Capital Management, LLC Geode Capital Management, LLC Eaton Vance Management State Street Global Advisors, Inc. Millennium Management LLC Natixis Advisors, LLC Two Sigma Advisers, LP Northern Trust Global Investments MBA Advisors LLC Two Sigma Investments, LP Citadel Advisors LLC

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Twins Recent Shareholder Movements Top Shareholders (1%+ Ownership) (shares in millions and dollars in actuals) O'Brien, Andrew Michael 3.509 12.9% NA 0.000 0.000 (0.616) 0.000 0.025 0.000 0.000 % of Holdings Traded 0.0% 0.0% (15.0%) 0.0% 0.7% 0.0% 0.0% Vaughan Nelson Investment Management, L.P. 1.384 5.1% 6.2% 0.000 0.000 1.529 (0.028) 0.044 (0.050) (0.110) % of Holdings Traded 0.0% 0.0% New Position (1.8%) 2.9% (3.3%) (7.4%) Janus Henderson Group plc 1.301 4.8% 5.8% 0.000 0.000 1.197 0.744 0.083 (0.251) (0.471) % of Holdings Traded 0.0% 0.0% New Position 62.2% 4.3% (12.4%) (26.6%) BlackRock, Inc. 1.184 4.4% 5.3% 0.071 0.069 0.335 (0.008) 0.078 (0.016) 0.123 % of Holdings Traded 13.3% 11.5% 49.9% (0.8%) 7.8% (1.4%) 11.6% Lee, Steven Barry 1.069 3.9% NA 0.000 0.000 (0.115) 0.000 0.014 0.008 0.011 % of Holdings Traded 0.0% 0.0% (10.0%) 0.0% 1.4% 0.7% 1.1% The Vanguard Group, Inc. 0.870 3.2% 3.9% 0.155 0.181 0.187 0.005 0.014 (0.153) 0.196 % of Holdings Traded 54.3% 41.0% 30.2% 0.6% 1.7% (18.5%) 29.2% William Blair Investment Management, LLC 0.662 2.4% 3.0% 0.158 0.680 0.131 (0.234) (0.068) 0.038 (0.100) % of Holdings Traded 272.5% 315.0% 14.6% (22.8%) (8.6%) 5.3% (13.1%) Brandywine Global Investment Management, LLC 0.586 2.2% 2.6% 0.000 0.000 0.000 0.562 0.115 0.000 (0.091) % of Holdings Traded 0.0% 0.0% 0.0% New Position 20.5% 0.0% (13.4%) GW&K Investment Management, LLC 0.522 1.9% 2.3% 0.000 0.000 0.000 0.000 0.000 0.000 0.522 % of Holdings Traded 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% New Position VWAP During Quarter $13.21 $16.08 $15.94 $10.00 $8.95 $4.61 $6.02 High Closing Stock Price During Quarter $15.45 $17.50 $17.95 $15.28 $10.70 $8.86 $7.30 Low Closing Stock Price During Quarter $10.11 $13.10 $14.34 $9.00 $8.08 $3.35 $4.03 VWAP refers to Volume-Weighted Average Price. t Latest % of % of Net Shares Added / (Deduct ed) by Quar er Holder Shareholdings Non-Angels Public Float Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Angels 24.024 0.000 0.000 (4.250) 0.000 0.000 0.000 0.000 % of Holdings Traded 0.0% 0.0% (15.0%) 0.0% 0.0% 0.0% 0.0% Baker, Blake A. 4.341 16.0% 19.4% 0.000 0.000 (0.668) 0.000 (0.100) 0.000 0.000 % of Holdings Traded 0.0% 0.0% (13.1%) 0.0% (2.3%) 0.0% 0.0% Royce & Associates, LP 3.868 14.2% 17.3% 0.000 0.238 2.525 1.681 (0.379) 0.695 (0.892) % of Holdings Traded 0.0% New Position 1062.9% 60.9% (8.5%) 17.1% (18.7%) Sources: Bloomberg, Capital IQ and public filings. CONFIDENTIAL 35

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Page 3 5 15 26 Executive Summary Selected Company Observations Preliminary Financial Considerations Other Proposal Considerations 5. Appendices 36 Supplemental Financial Information Supplemental Public Company & Market Observations Supplemental Industry Observations 37 40 43

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Page 3 5 15 26 36 Executive Summary Selected Company Observations Preliminary Financial Considerations Other Proposal Considerations Appendices Supplemental Financial Information 37 Supplemental Public Company & Market Observations Supplemental Industry Observations 40 43

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Projected Adjusted Net Income Detail Selected Net Income Adjustments and ROAE Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to the next page for additional details on adjustments; Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI); E refers to Estimated. 1. Tax-effected at projected tax rate of 21.0% in 2021 and 22.0% in 2022 through 2027 per Company management. (dollars in millions) Company management's financial projections for Adjusted Net Income are consistent with public reporting of historical performance and include add- backs for expenses relating to (i) share based compensation and (ii) amortization of intangible assets. As most selected companies reviewed do not make add-back adjustments for these expenses, the below illustrates three alternative derivations of Adjusted Net Income (which may be relevant to financial analyses), as well as corresponding ROAE calculations, for the Company over the projection period: Tax Effected Share Based Compensation [1] 1.2 1.7 1.7 1.7 1.7 1.7 Adjusted Net Income: No Add-Back for Share Based Compensation $21.7 $25.2 $30.5 $38.8 $44.3 $50.8 Tax Effected Intangible Asset Amortization [1] 4.7 4.7 4.7 4.7 4.7 4.7 Adjusted Net Income: No Add-Back for Share Based Compensation and Intangible Asset Amortization $17.0 $20.5 $25.8 $34.2 $39.7 $46.2 As-Presented by Company Management No Add-Back for Share Based Compensation No Add-Back for Share Based Compensation and Intangible Asset Amortization Calendar Year Ending December 31, 2022E 2023E 2024E 2025E 2026E 2027E Implied Adjusted ROAE Based On: Adjusted Net Income: 5.3% 5.9% 6.7% 8.0% 8.4% 8.9% Adjusted Net Income: 5.0% 5.5% 6.4% 7.6% 8.1% 8.7% Adjusted Net Income: 3.9% 4.5% 5.4% 6.7% 7.3% 7.9% Adjusted Net Income: $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 As-Presented by Company Management Share Based Compensation 1.5 2.1 2.1 2.1 2.1 2.1 Intangible Asset Amortization 6.0 6.0 6.0 6.0 6.0 6.0 Source: Company management and Management Projections. CONFIDENTIAL 38

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Historical and Projected Financial Data Net Income Adjustments Note: Historical financial data is not pro forma for the Company's recent acquisitions, including its (i) July 6, 2021 acquisition of Western Integrated Care, LLC for ~$5.5 million, (ii) October 1, 2020 acquisition of 7710 Insurance Company (and certain affiliates) for ~$12.1 million, (iii) April 1, 2020 acquisition of LCTA Risk Services, Inc. for ~$1.4 million, or (iv) February 19, 2019 acquisition of First Choice Casualty Insurance Company for ~$5.3 million. Financial data reflects Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million), but 2019-2020 financial data is not pro forma for the July 15, 2020 acquisition of the remaining 55% equity interest in Compstar (2019 data and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). 2019 and 1H 2020 figures are also not pro forma for the impact of the July 2020 IPO. In 2020, negative adjustment due primarily to gain on revaluation of 45% ownership interest in Compstar, following acquisition of the remaining 55% interest. In 2020, gain on revaluation of ownership interest in Compstar had no tax impact. Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to the table above for additional details on adjustments; CAGR refers to Compound Annual Growth Rate; E refers to Estimated; LTM refers to Latest 12 Months; NA refers to not available. (dollars in millions) Calendar Year Ended December 31, LTM Ended Calendar Year Ending December 31, 2019 2020 2021 9/30/2022 2022E 2023E 2024E 2025E 2026E 2027E CAGR 2021 to 2027E 2022 to 2027E Income Statement Adjustments Net Income $31.3 $88.5 $19.3 $26.6 $27.6 $21.0 $25.1 $33.6 $39.2 $45.8 15.5% 10.6% Intangible Asset Amortization 0.0 2.6 5.8 NA 6.0 6.0 6.0 6.0 6.0 6.0 Non-Cash Share-Based Compensation 0.0 0.5 1.5 NA 1.5 2.1 2.1 2.1 2.1 2.1 Loss (Gain) on Embedded Derivatives 0.0 2.8 (4.7) NA (16.9) (0.8) 0.9 0.8 0.8 0.7 Unrealized Losses (Gains) on Equity Securities 0.0 0.0 0.0 NA 4.5 0.2 0.0 (0.1) (0.2) (0.3) Net Loss (Gain) on Purchase & Disposal of Affiliates (0.6) (3.1) 0.1 NA (1.4) 0.0 0.0 0.0 0.0 0.0 Other [1] 3.2 (55.6) 0.8 NA 0.3 0.0 0.0 0.0 0.0 0.0 Total Adjustments 2.6 (52.8) 3.6 (7.2) (6.0) 7.5 9.0 8.9 8.7 8.6 Tax Impact [2] (0.7) (3.0) (0.8) 1.7 1.3 (1.7) (2.0) (1.9) (1.9) (1.9) Adjusted Net Income $33.2 $32.8 $22.1 $21.1 $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 15.5% 18.1% Source: Company management and Management Projections. CONFIDENTIAL 38

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Page 3 5 15 26 36 37 Executive Summary Selected Company Observations Preliminary Financial Considerations Other Proposal Considerations Appendices Supplemental Financial Information Supplemental Public Company & Market Observations 40 Supplemental Industry Observations 43

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8.0 7.0 6.0 5.0 4.0 3.0 2.0 1.0 0.0 $20.00 $18.00 $16.00 $14.00 $12.00 $10.00 $8.00 $6.00 $4.00 $2.00 $0.00 Jul-20 Sep-20 Nov-21 Mar-22 May-22 Jul-22 Sep-22 Nov-20 Jan-21 Mar-21 Daily Trading Volume May-21 Twins Jul-21 Sep-21 Current Stock Price [1] Jan-22 Offer Price Closing Stock Price ($) Daily Volume (millions) Twins Stock Trading History Since Initial Public Offering Select Events 1. As of 10/25/22. Refers to per share common stock price. Adj. EPS refers to Adjusted Earnings Per Share; mm refers to million. Q refers to Quarter. YoY refers to Year-over-Year. Sources: Capital IQ and public filings. Event Date Comment Adj. EPS Earnings vs. Consensus A Reports Q2 2020 results. Gross written premiums ("GWP") increase ~5% YoY to $110mm and adjusted 8/27/20 net income ("Adj. NI") decreases ~31% YoY to $5mm. Adjusted Return on Equity ("Adj. ROE") (13.2% vs. 22.9%) and Adjusted Return on Tangible Equity ("Adj. ROTE") (13.5% vs. 23.4%) decline YoY. $0.13 Adj. NI: (10%) Adj. EPS: NA B Reports Q3 2020 results. GWP increase ~23% YoY to 11/12/20 $132mm and Adj. NI increases ~62% YoY to $10mm. Adj. ROE (15.5% vs. 20.2%) declines Y-o-Y and Adj. ROTE (25.9% vs. 20.7%) increases YoY. $0.21 Adj. NI: 34% Adj. EPS: 36% C Reports Q4 2020 results. GWP increase ~37% YoY to 3/24/21 $135mm and Adj. NI decreases ~2% YoY to $11mm. Adj. ROE (11.0% vs. 33.5%) and Adj. ROTE (23.4% vs. 34.3%) decline YoY. $0.22 Adj. NI: 35% Adj. EPS: 36% D Reports Q1 2021 results. GWP increase ~36% YoY to 5/12/21 $147mm and Adj. NI increases ~27% YoY to $8mm. Adj. ROE (7.8% vs. 17.4%) and Adj. ROTE (16.4% vs. 17.7%) decline YoY. $0.16 Adj. NI: (11%) Adj. EPS: (14%) E Reports Q2 2021 results. GWP increase ~43% YoY to 8/11/21 $157mm and Adj. NI decreases ~10% YoY to $4 mm. Adj. ROE (4.2% vs. 13.2%) and Adj. ROTE (8.6% vs. 13.6%) decline YoY. $0.08 Adj. NI: (53%) Adj. EPS: (54%) Event Date Comment Adj. EPS Earnings vs. Consensus F Reports Q3 2021 results. GWP increase ~34% YoY to 11/10/21 $178mm and Adj. NI decreases ~27% YoY to $8mm. Adj. ROE (7.3% vs. 15.5%) and Adj. ROTE (15.0% vs. 25.9%) decline YoY. $0.15 Adj. NI: (19%) Adj. EPS: (15%) G 3/9/22 Reports Q4 2021 results. GWP increase ~14% YoY to $153mm and Adj. NI decreases ~82% YoY to $2mm. Adj. ROE (1.9% vs. 11.0%) and Adj. ROTE (3.9% vs. 23.4%) decline YoY. Announces then-current President Julie Baron as new CEO. $0.04 Adj. NI: (57%) Adj. EPS: (60%) H 5/4/22 Reports Q1 2022 results. GWP increase ~10% YoY to $161mm and Adj. NI increases ~2% YoY to $8mm. Adj. ROE was flat YoY and Adj. ROTE (16.2% vs. 16.5%) declines YoY. $0.16 Adj. NI: 1% Adj. EPS: 0% I 8/3/22 Reports Q2 2022 results. GWP decrease ~1.5% YoY to $154mm and Adj. NI increases ~28% YoY to $6mm. Adj. ROE (5.4% vs. 4.2%) and Adj. ROTE (11.1% vs. 8.6%) increase YoY. $0.11 Adj. NI: 19% Adj. EPS: 22% Current Stock Price: $3.431 A B C D F G H E 5/17/21: Announces secondary offering of 5.0mm shares of common stock priced at $14 per share 8/24/22 Completes $50mm private unsecured debt offering to increase surplus of subsidiary Benchmark Insurance Company I 41 CONFIDENTIAL

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35% 35% 28% 27% 32% 36% 33% 42% 2015 2016 2017 2018 2019 2020 2021 YTD '22 Premium Paid Analysis 1. Based on data from Eikon. Criteria based on (a) Transaction Type: Merger/Acquisition, (b) Total Transaction Value is greater than $100.0 million and less than $1.0 billion, (c) Ownership Percentage Sought is greater than 50%, (d) Geographic Locations are in the United States or Bermuda, (e) 1 Day Prior Target Stock Premium is between 0% and 100%. YTD refers to year-to-date. Source: Capital IQ and public filings. Average 1-Day Prior Acquisition Premiums1 Average 1-Month Prior Acquisition Premiums1 Median 2015 – 2021: 33% 37% 40% 30% 30% 36% 42% 35% 49% 2015 2016 2017 2018 2019 2020 2021 YTD '22 Median 2015 – 2021: 36% 41 CONFIDENTIAL

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Selected Workers' Compensation Industry Observations Workers' Compensation Direct Written Premiums3 Workers' Compensation Insurance Industry Revenue4 143.3 158.1 166.5 180.0 160.0 140.0 120.0 100.0 80.0 60.0 40.0 20.0 0.0 Revenue Drivers and Metrics Total U.S. Employment1 Total U.S. Wages and Salaries2 (millions of jobs) (dollars in billions) 2011 2013 2015 2017 2019 2021 2023 2025 2027 2029 2031 U.S. Bureau of Labor Statistics. Federal Reserve Bank of St. Louis: Total wages and salaries, annual, not seasonally adjusted. SNL Financial: P&C Industry's Workers' Compensation Direct Written Premiums. IBISWorld. $2,000.0 $4,000.0 $6,000.0 $8,000.0 $10,000.0 $12,000.0 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 $20.0 $30.0 $40.0 $50.0 $60.0 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 (dollars in billions) $20.0 $30.0 $40.0 $50.0 $60.0 2021 2022 2023 2024 2025 2026 (dollars in billions) "Total employment is projected to increase from 158.1 million to 166.5 million and grow 0.5 percent annually, which is slower than the 1.0 percent annual growth recorded over the 2011 – 21 decade." 1 44 CONFIDENTIAL

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Selected Workers' Compensation Industry Observations Profitability Drivers and Metrics Workers' Compensation Net Combined Ratio1 Nonfatal Work Injuries and Illnesses Rate3 Number of Work-Related Deaths2 NCCI Holdings, Inc.; Workers' Compensation Net Combined Ratio (Private Carriers). IBISWorld. U.S. Bureau of Labor Statistics. (per 100 full-time workers) (people) 6,000 115% 109% 102% 100% 94% 94% 89% 83% 85% 87% 87% 80% 60% 40% 20% 0% 100% 120% 2011 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 0.0 0.5 1.0 1.5 2.0 2.5 3.0 3.5 2014 2015 2016 2017 2018 2019 2020 0 44 CONFIDENTIAL 1,000 2,000 3,000 4,000 5,000 2012 2014 2016 2018 2020 2022 2024 2026

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This presentation, and any supplemental information (written or oral) or other documents provided in connection therewith (collectively, the "materials"), are provided solely for the information of the Special Committee (the "Committee") of the Board of Directors (the "Board") of Twins (the "Company") by Houlihan Lokey in connection with the Committee's consideration of a potential transaction (the "Transaction") involving the Company. This presentation is incomplete without reference to, and should be considered in conjunction with, any supplemental information provided by and discussions with Houlihan Lokey in connection therewith. Any defined terms used herein shall have the meanings set forth herein, even if such defined terms have been given different meanings elsewhere in the materials. The materials are for discussion purposes only. Houlihan Lokey expressly disclaims any and all liability, whether direct or indirect, in contract or tort or otherwise, to any person in connection with the materials. The materials were prepared for specific persons familiar with the business and affairs of the Company for use in a specific context and were not prepared with a view to public disclosure or to conform with any disclosure standards under any state, federal or international securities laws or other laws, rules or regulations, and none of the Committee, the Company or Houlihan Lokey takes any responsibility for the use of the materials by persons other than the Committee. The materials are provided on a confidential basis solely for the information of the Committee and may not be disclosed, summarized, reproduced, disseminated or quoted or otherwise referred to, in whole or in part, without Houlihan Lokey's express prior written consent. Notwithstanding any other provision herein, the Company (and each employee, representative or other agent of the Company) may disclose to any and all persons without limitation of any kind, the tax treatment and tax structure of any transaction and all materials of any kind (including opinions or other tax analyses, if any) that are provided to the Company relating to such tax treatment and structure. However, any information relating to the tax treatment and tax structure shall remain confidential (and the foregoing sentence shall not apply) to the extent necessary to enable any person to comply with securities laws. For this purpose, the tax treatment of a transaction is the purported or claimed U.S. income or franchise tax treatment of the transaction and the tax structure of a transaction is any fact that may be relevant to understanding the purported or claimed U.S. income or franchise tax treatment of the transaction. If the Company plans to disclose information pursuant to the first sentence of this paragraph, the Company shall inform those to whom it discloses any such information that they may not rely upon such information for any purpose without Houlihan Lokey's prior written consent. Houlihan Lokey is not an expert on, and nothing contained in the materials should be construed as advice with regard to, legal, accounting, regulatory, insurance, tax or other specialist matters. Houlihan Lokey's role in reviewing any information was limited solely to performing such a review as it deemed necessary to support its own advice and analysis and was not on behalf of the Committee. The materials necessarily are based on financial, economic, market and other conditions as in effect on, and the information available to Houlihan Lokey as of, the date of the materials. Although subsequent developments may affect the contents of the materials, Houlihan Lokey has not undertaken, and is under no obligation, to update, revise or reaffirm the materials, except as may be expressly contemplated by Houlihan Lokey's engagement letter. The materials are not intended to provide the sole basis for evaluation of the Transaction and do not purport to contain all information that may be required. The materials do not address the underlying business decision of the Company or any other party to proceed with or effect the Transaction, or the relative merits of the Transaction as compared to any alternative business strategies or transactions that might be available for the Company or any other party. The materials do not constitute any opinion, nor do the materials constitute a recommendation to the Board, the Committee, the Company, any security holder of the Company or any other party as to how to vote or act with respect to any matter relating to the Transaction or otherwise or whether to buy or sell any assets or securities of any company. Houlihan Lokey's only opinion is the opinion, if any, that is actually delivered to the Committee. In preparing the materials Houlihan Lokey has acted as an independent contractor and nothing in the materials is intended to create or shall be construed as creating a fiduciary or other relationship between Houlihan Lokey and any party. The materials may not reflect information known to other professionals in other business areas of Houlihan Lokey and its affiliates. 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Selecting portions of the analyses, analytic methods and factors without considering all analyses and factors could create a misleading or incomplete view. The materials reflect judgments and assumptions with regard to industry performance, general business, economic, regulatory, market and financial conditions and other matters, many of which are beyond the control of the participants in the Transaction. Any estimates of value contained in the materials are not necessarily indicative of actual value or predictive of future results or values, which may be significantly more or less favorable. Any analyses relating to the value of assets, businesses or securities do not purport to be appraisals or to reflect the prices at which any assets, businesses or securities may actually be sold. The materials do not constitute a valuation opinion or credit rating. The materials do not address the consideration to be paid or received in, the terms of any arrangements, understandings, agreements or documents related to, or the form, structure or any other portion or aspect of, the Transaction or otherwise. Furthermore, the materials do not address the fairness of any portion or aspect of the Transaction to any party. In preparing the materials, Houlihan Lokey has not conducted any physical inspection or independent appraisal or evaluation of any of the assets, properties or liabilities (contingent or otherwise) of the Company or any other party and has no obligation to evaluate the solvency of the Company or any other party under any law. 44 CONFIDENTIAL Disclaimer

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All budgets, projections, estimates, financial analyses, reports and other information with respect to operations (including, without limitation, estimates of potential cost savings and synergies) reflected in the materials have been prepared by management of the relevant party or are derived from such budgets, projections, estimates, financial analyses, reports and other information or from other sources, which involve numerous and significant subjective determinations made by management of the relevant party and/or which such management has reviewed and found reasonable. The budgets, projections and estimates (including, without limitation, estimates of potential cost savings and synergies) contained in the materials may or may not be achieved and differences between projected results and those actually achieved may be material. Houlihan Lokey has relied upon representations made by management of the Company and other participants in the Transaction that such budgets, projections and estimates have been reasonably prepared in good faith on bases reflecting the best currently available estimates and judgments of such management (or, with respect to information obtained from public sources, represent reasonable estimates), and Houlihan Lokey expresses no opinion with respect to such budgets, projections or estimates or the assumptions on which they are based. Houlihan Lokey has discussed the Company's business with the Company and Houlihan Lokey does not make any representation, express or implied, as to the sufficiency or adequacy of its financial analysis or the scope thereof for any particular purpose. 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In addition, Houlihan Lokey has relied upon and assumed, without independent verification, that there has been no change in the business, assets, liabilities, financial condition, results of operations, cash flows or prospects of the Company or any other participant in the Transaction since the respective dates of the most recent financial statements and other information, financial or otherwise, provided to, discussed with or reviewed by Houlihan Lokey that would be material to its analyses, and that the final forms of any draft documents reviewed by Houlihan Lokey will not differ in any material respect from such draft documents. The materials are not an offer to sell or a solicitation of an indication of interest to purchase any security, option, commodity, future, loan or currency. 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Houlihan Lokey's personnel may make statements or provide advice that is contrary to information contained in the materials. 44 CONFIDENTIAL Disclaimer (cont.)

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CONFIDENTIAL 48 CORPORATE FINANCE FINANCIAL RESTRUCTURING FINANCIAL AND VALUATION ADVISORY HL.com

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## Ex-99.(C)(2)

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**Exhibit (c)(2)**<br> ![](ny20006673x2_exc-2slide1.jpg)

Project Twins DISCUSSION MATERIALS FOR THE SPECIAL COMMITTEE OF THE BOARD OF DIRECT ORS DECEMBER 15, 2022 \| CONFIDENTIAL

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CONFIDENTIAL **Table of Contents** 2 Page 3 5 10 20 21 23 30 33 Executive Summary Selected Updates Since Prior Discussion Materials Financial Analyses Appendices Selected Cost of Equity Considerations Supplemental Financial Information Illustrative Selected Company Multiple Trendlines Supplemental Public Company & Market Observations

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Page 1. Executive Summary 3 Selected Updates Since Prior Discussion Materials Financial Analyses Appendices 5 10 20

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Transaction Value Overview Per Draft dated [12/11/22] of the Agreement and Plan of Merger by and among [PARENT], [MERGER SUB], and Twins (the "Company") (the "Agreement"). For illustrative purposes, assumes all outstanding Company Common Stock as well as RSUs and PSUs with targets contemplated to be met over the projection period will be cashed out based on the Transaction Consideration and share counts reflect (i) ~51.2 million shares of common stock outstanding as of 12/9/22, (ii) ~0.1 million restricted stock units; and (iii) ~0.1 million performance stock units outstanding that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs and ~0.2 million options that are out-of-the-money. Per Company management and Management Projections (defined below). Closing prices per Capital IQ. VWAP based on cumulative trading activity over designated number of trading days (based on intraday trading) per Bloomberg as of 12/13/22. Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments.; AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public; VWAP refers to Volume-Weighted Average Price. Sources: Company projections, per Company management, provided on October 20, 2022 and reaffirmed as of December 11, 2022 ("Management Projections"), Company Management, the Agreement, Bloomberg, Capital IQ, and public filings. (dollars and shares in millions, except per share values) Implied Transaction Equity Value Implied Premiums to Historical Stock Trading Prices (dollars per share in actuals) Selected Transaction Information Per Share Cash Consideration (the ''Transaction Consideration'') [1] Common Shares Outstanding [2] Dilutive Shares [2] Fully-Diluted Shares $6.15 51.2 0.3 51.5 Implied Transaction Equity Value $316.8 Selected Capitalized Indications and Implied Transaction Multiples Corresponding Base Amount [3] Implied Multiple Implied Transaction Multiples Book Value (Ex. AOCI) MRQ (9/30/22) $443.9 0.71x [Illustrative Only] Tangible Book Value (Ex. AOCI) MRQ (9/30/22) $233.0 1.36x Adjusted Net Income CY 2022E $22.9 13.8x CY 2023E $26.9 11.8x Implied Premium of Per Share Consideration over Selected Metric 4 CONFIDENTIAL Trading Period As of 12/13/22 Selected Metric [4] 1-Day Closing Price $3.15 95.2% 5-Day VWAP $2.96 108.1% 10-Day VWAP $2.87 114.2% 20-Day VWAP $2.60 136.9% 30-Day VWAP $2.64 132.7% 3-Month VWAP $3.02 103.4% 6-Month VWAP $4.10 50.0% 1-Year VWAP $4.77 28.9% 52-Week High - 12/28/21 Closing $9.16 (32.9%) 52-Week Low - 11/18/22 Closing $2.18 182.1%

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Page 3 1. Executive Summary 2. Selected Updates Since Prior Discussion Materials 5 Financial Analyses Appendices 10 20

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Summary of Selected Changes to Financial Analyses fiscal period for which financial information has been made public. CONFIDENTIAL 6 Relative to Preliminary Special Committee Discussion Materials Dated 10/28/22 The following changes have been made relative to the preliminary Special Committee discussion materials dated 10/28/22: The financial analyses were updated to reflect the following updated financial information provided by Company management: LTM financial information based on actual 9/30/22 figures (compared to preliminary 9/30/22 estimated figures incorporated in the preliminary discussion materials dated 10/28/22) There was no change to 9/30/22 book value from the preliminary estimates to the actual figures Capitalization information as of 12/9/22 (compared to information as of 10/25/22 incorporated in the preliminary discussion materials dated 10/28/22) Per Company management, no changes were made to the financial projections Selected Companies Analysis The selected companies analysis was updated to reflect stock prices and other publicly available financial information as of 12/13/22 (previously, as of 10/25/22 market close) See pages 8 and 9 for further detail on observed multiple changes Based on a review of updated multiples of the selected companies: The selected multiple range applied to MRQ Book Value (excluding AOCI) was increased to 0.45x – 0.85x (previously, 0.40x – 0.80x); The illustrative only selected multiple range applied to MRQ Tangible Book Value (excluding AOCI) was increased to 1.05x – 1.65x (previously, 1.00x – 1.60x); The selected multiple range applied to CY 2022E Adjusted Net Income was increased to 11.0x – 16.0x (previously, 10.0x – 15.0x); and The selected multiple range applied to CY 2023E Adjusted Net Income was increased to 9.0x – 14.0x (previously, 8.0x – 13.0x) Selected Transactions Analysis Based on a review of recent transactions, no additional transactions were identified and no changes have been made to the selected transactions multiples Discounted Cash Flow ("DCF") Analysis Stock prices, betas, risk-free rates and other public information utilized in discount rate calculations have been updated to market close on 12/13/22 (previously, as of 10/25/22 market close) No changes have been made to the selected discount rate range (13.0% – 15.0%) The selected terminal Book Value (excluding AOCI) multiple range utilized in the DCF analysis was increased to 0.85x – 1.25x (previously, 0.80x – 1.20x); and The illustrative only selected terminal Tangible Book Value (excluding AOCI) multiple range utilized in the DCF analysis was increased to 1.25x – 1.85x (previously, 1.20x – 1.80x) Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments.; AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; LTM refers to Latest 12 Months; MRQ refers to the most recently completed quarterly

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Certain Updates to Financial Analyses Note: For Preliminary Discussion Materials dated 10/28/22, based on (i) ~51.2 million basic shares of common stock outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 10/25/22. Does not include ~0.1 million MSUs. For Current Discussion Materials, based on (i) ~51.2 million basic shares of common stock outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs. Adjusted Net Income refers to earnings, adjusted for realized and unrealized gains/losses as well as certain non-recurring items; AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; MRQ refers to MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public. Source: Financial information from Company management and Management Projections. (dollars in millions, except per share values) Selected Companies Analysis Metric Capitalized MRQ (9/30/22) Book Value (Excl. AOCI) MRQ (9/30/22) Tangible Book Value (Excl. AOCI) [Illustrative Only] CY 2022E Adjusted Net Income CY 2023E Adjusted Net Income MRQ (9/30/22) Book Value (Excl. AOCI) MRQ (9/30/22) Tangible Book Value (Excl. AOCI) [Illustrative Only] CY 2022E Adjusted Net Income CY 2023E Adjusted Net Income Base Amount $443.9 $233.0 $22.9 $26.9 $443.9 $233.0 $22.9 $26.9 Selected Multiple Range 0.40x - 0.80x 1.00x - 1.60x 10.0x - 15.0x 8.0x - 13.0x 0.45x - 0.85x 1.05x - 1.65x 11.0x - 16.0x 9.0x - 14.0x Implied Equity Value $177.6 - $355.1 $233.0 - $372.7 $229.0 - $343.5 $215.0 - $349.3 $199.8 - $377.3 $244.6 - $384.4 $251.9 - $366.4 $241.9 - $376.2 Implied Per Share Equity Value Reference Range $3.45 - $6.90 $4.53 - $7.24 $4.45 - $6.67 $4.18 - $6.79 $3.88 - $7.32 $4.75 - $7.46 $4.89 - $7.11 $4.69 - $7.30 Selected Transactions Analysis Metric Capitalized MRQ (9/30/22) Book Value (Excl. AOCI) MRQ (9/30/22) Tangible Book Value (Excl. AOCI) [Illustrative Only] MRQ (9/30/22) Book Value (Excl. AOCI) MRQ (9/30/22) Tangible Book Value (Excl. AOCI) [Illustrative Only] Base Amount $443.9 $233.0 $443.9 $233.0 Selected Multiple Range 0.50x - 0.90x 1.20x - 1.80x 0.50x - 0.90x 1.20x - 1.80x Implied Equity Value $222.0 - $399.5 $279.6 - $419.3 $222.0 - $399.5 $279.6 - $419.3 Implied Per Share Equity Value Reference Range $4.31 - $7.76 $5.43 - $8.14 $4.31 - $7.75 $5.43 - $8.14 Discounted Cash Flow Analysis Book Value (Excl. AOCI) Tangible Book Value (Excl. AOCI) [Illustrative Only] Book Value (Excl. AOCI) Tangible Book Value (Excl. AOCI) [Illustrative Only] Terminal Multiple Range 0.80x - 1.20x 1.20x - 1.80x 0.85x - 1.25x 1.25x - 1.85x Discount Rate Range 13.0% - 15.0% 13.0% - 15.0% 13.0% - 15.0% 13.0% - 15.0% Implied Equity Value $237.0 - $389.2 $250.8 - $411.9 $255.9 - $411.3 $265.6 - $429.5 Implied Per Share Equity Value Reference Range $4.60 - $7.56 $4.87 - $8.00 $4.97 - $7.98 $5.16 - $8.34 Preliminary Discussion Materials (10/28/22) Current Discussion Materials (12/15/22) 7 CONFIDENTIAL

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![](ny20006673x2_exc-2slide8.jpg)

Certain Market Changes Selected Companies – Equity Market Value to Book Value and Tangible Book Value Note: No company used in this analysis for comparative purposes is identical to the Company. Based on fully diluted shares outstanding. Calculated as shareholders' equity, less book value of preferred stock and accumulated other comprehensive income as per GAAP. Calculated as shareholders' equity, less book value of preferred stock, accumulated other comprehensive income, and goodwill and other intangibles, as per GAAP. Based on public filings, analyst estimates, market data and other public information as of applicable date. AOCI refers to Accumulated Other Comprehensive Income. Pricing as of 10/25/22 Pricing as of 12/13/22 Change Versus Prior Materials Equity Market Value [1] to Equity Market Value [1] to Equity Market Value [1] to Workers' Comp Insurers AMERISAFE, Inc. Employers Holdings, Inc. Book Value (Excl. AOCI) [2] Illustrative Only Tangible Book Value (Excl. AOCI) [3] Book Value (Excl. AOCI) [2] MRQ 2.46x 1.09x Illustrative Only Tangible Book Value (Excl. AOCI) [3] Book Value (Excl. AOCI) [2] MRQ -0.16x 0.12x Illustrative Only Tangible Book Value (Excl. AOCI) [3] MRQ MRQ MRQ MRQ 2.62x 0.96x 2.62x 1.01x 2.46x 1.14x -0.16x 0.13x Low 0.96x 1.01x 1.09x 1.14x 0.12x 0.13x High 2.62x 2.62x 2.46x 2.46x -0.16x -0.16x Median 1.79x 1.82x 1.77x 1.80x -0.02x -0.02x Mean 1.79x 1.82x 1.77x 1.80x -0.02x -0.02x Specialty Insurers Argo Group International Holdings, Ltd. 0.53x 0.59x 0.61x 0.67x 0.08x 0.08x James River Group Holdings, Ltd. 1.24x 1.78x 1.21x 1.75x -0.03x -0.03x Kinsale Capital Group, Inc. 8.50x 8.54x 8.50x 8.54x 0.00x 0.00x Palomar Holdings, Inc. 5.26x 5.38x 3.24x 3.31x -2.02x -2.07x ProAssurance Corporation 0.81x 0.88x 0.73x 0.79x -0.08x -0.09x RLI Corp. 3.45x 3.57x 3.62x 3.75x 0.17x 0.18x W. R. Berkley Corporation 2.51x 2.59x 2.65x 2.71x 0.14x 0.12x Low 0.53x 0.59x 0.61x 0.67x 0.08x 0.08x High 8.50x 8.54x 8.50x 8.54x 0.00x 0.00x Median 2.51x 2.59x 2.65x 2.71x 0.14x 0.12x Mean 3.18x 3.33x 2.94x 3.07x -0.25x -0.26x All Selected Companies Low 0.53x 0.59x 0.61x 0.67x 0.08x 0.08x High 8.50x 8.54x 8.50x 8.54x 0.00x 0.00x Median 2.51x 2.59x 2.46x 2.46x -0.05x -0.13x Mean 2.88x 3.00x 2.68x 2.79x -0.20x -0.21x Twins [4] 0.40x 0.79x 0.36x 0.69x -0.04x -0.09x MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public. Sources: Bloomberg, Capital IQ and public filings. CONFIDENTIAL 8

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Certain Market Changes (cont.) Selected Companies – Equity Market Value to Adjusted Net Income Note: No company used in this analysis for comparative purposes is identical to the Company. Based on fully diluted shares outstanding. Based on public filings, analyst estimates, market data and other public information as of applicable date. Adjusted Net Income refers to earnings, adjusted for realized and unrealized gains/losses as well as certain non-recurring items. CY refers to Calendar Year. E refers to Estimated. NA refers to not available. Pricing as of 10/25/22 Pricing as of 12/13/22 Change Versus Prior Materials Workers' Comp Insurers Equity Market Value [1] to Adjusted Net Income CY 2022E CY 2023E Equity Market Value [1] to Adjusted Net Income CY 2022E CY 2023E Equity Market Value to Adjusted Net Income CY 2022E CY 2023E AMERISAFE, Inc. 18.7x 20.3x 17.8x 19.4x -0.9x -0.8x Employers Holdings, Inc. 14.4x 12.4x 15.9x 12.4x 1.4x 0.0x Low 14.4x 12.4x 15.9x 12.4x 1.4x 0.0x High 18.7x 20.3x 17.8x 19.4x -0.9x -0.8x Median 16.6x 16.4x 16.8x 15.9x 0.3x -0.4x Mean 16.6x 16.4x 16.8x 15.9x 0.3x -0.4x Specialty Insurers Argo Group International Holdings, Ltd. 17.9x 6.3x 26.0x 7.7x 8.1x 1.4x James River Group Holdings, Ltd. 13.1x 9.6x 14.7x 9.2x 1.5x -0.4x Kinsale Capital Group, Inc. 40.2x 32.7x 40.6x 31.7x 0.3x -1.1x Palomar Holdings, Inc. 28.7x 21.7x 20.6x 14.1x -8.2x -7.7x ProAssurance Corporation 27.0x 17.0x NMF 17.5x NA 0.4x RLI Corp. 31.1x 28.3x 28.1x 28.1x -3.0x -0.2x W. R. Berkley Corporation 16.7x 14.9x 16.9x 15.1x 0.2x 0.3x Low 13.1x 6.3x 14.7x 7.7x 1.5x 1.4x High 40.2x 32.7x 40.6x 31.7x 0.3x -1.1x Median 27.0x 17.0x 23.3x 15.1x -3.7x -1.9x Mean 25.0x 18.7x 24.5x 17.6x -0.5x -1.0x All Selected Companies Low 13.1x 6.3x 14.7x 7.7x 1.5x 1.4x High 40.2x 32.7x 40.6x 31.7x 0.3x -1.1x Median 18.7x 17.0x 19.2x 15.1x 0.5x -1.9x Mean 23.1x 18.1x 22.6x 17.2x -0.5x -0.9x Twins [2] 7.1x 6.0x 7.0x 5.8x -0.1x -0.2x NMF refers to not meaningful figure. Sources: Bloomberg, Capital IQ and public filings. CONFIDENTIAL 9

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Page 3 5 Executive Summary Selected Updates Since Prior Discussion Materials 3. Financial Analyses 10 4. Appendices 20

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Flow Analysis Selected Companies Analysis MRQ (9/30/22) Book Value (Excl. AOCI): $443.9 million Selected Multiple Range: 0.45x – 0.85x MRQ (9/30/22) Tangible Book Value (Excl. AOCI): $233.0 million Selected Multiple Range: 1.05x – 1.65x CY 2022E Adjusted Net Income: $22.9 million Selected Multiple Range: 11.0x – 16.0x CY 2023E Adjusted Net Income: $26.9 million Selected Multiple Range: 9.0x – 14.0x Selected Transaction Analysis MRQ (9/30/22) Book Value (Excl. AOCI): $443.9 million Selected Multiple Range: 0.50x – 0.90x MRQ (9/30/22) Tangible Book Value (Excl. AOCI): $233.0 million Selected Multiple Range: 1.20x – 1.80x Discounted Cash Book Value (Excl. AOCI) [3] Terminal Multiple: 0.85x – 1.25x Discount Rate: 13.0% – 15.0% Tangible Book Value (Excl. AOCI) [4] Terminal Multiple: 1.25x – 1.85x Discount Rate: 13.0% – 15.0% $2 Financial Analyses Summary Implied Per Share Value Reference Ranges (dollars per share in actuals) .00 $3.00 $4.00 $5.00 $6.00 $7.00 $8.00 $9.00 $10.00 Note: No particular weight has been attributed to any analysis. Note: Based on (i) ~51.2 million basic shares of common stock outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs. Based on the Agreement. Reflects 10-day volume-weighted average price per share of common stock as of 12/13/22. Per Company management, at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in book value, and the same discount rate range and terminal multiple range used in the discounted cash flow analysis, the implied equity value per share reference range would be $5.22 - $8.04. Per Company management, at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in tangible book value, and the same discount rate range and terminal multiple range used in the illustrative discounted cash flow analysis, the implied equity value per share reference range would be $5.24 - $8.12. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items; AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public; VWAP refers to Volume-Weighted Average Price. Source: Company management, Management Projections, Capital IQ, Bloomberg, and public filings. lllustrative Only lllustrative Only lllustrative Only $5.16 $4.97 $5.43 $4.31 $4.69 $4.89 $4.75 $3.88 $8.34 $7.98 $8.14 $7.75 $7.30 $7.11 $7.46 $7.32 Transaction Consideration¹: $6.15 10-Day VWAP²: $2.87 12 CONFIDENTIAL

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![](ny20006673x2_exc-2slide12.jpg)

Historical and Projected Financial Data Selected Metrics Note: Historical financial data is not pro forma for the Company's recent acquisitions, including its (i) July 6, 2021 acquisition of Western Integrated Care, LLC for ~$5.5 million, (ii) October 1, 2020 acquisition of 7710 Insurance Company (and certain affiliates) for ~$12.1 million, (iii) April 1, 2020 acquisition of LCTA Risk Services, Inc. for ~$1.4 million, or (iv) February 19, 2019 acquisition of First Choice Casualty Insurance Company for ~$5.3 million. Financial data reflects Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million), but 2019-2020 financial data is not pro forma for the July 15, 2020 acquisition of the remaining 55% equity interest in Compstar (2019 data and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). 2019 and 1H 2020 figures are also not pro forma for the impact of the July 2020 IPO. Book value figures for 2019 exclude preferred stock. 1. Reflects a one-time unrealized loss of $4.5 million in 2022. 2. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from book value.3. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from tangible book value. Adjusted ROAE refers to Adjusted Return on Average Equity (in the case of 2019 – 2020 based on Average Book Value and in the case of 2021 onwards based on Average Book Value less AOCI); Adjusted ROATE refers to Adjusted Return on Average Tangible Equity (in the case of 2019 – 2020 based on Average Tangible Book Value and in the case of 2021 onwards based on Average Tangible Book Value less AOCI); Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments.; AOCI refers to Accumulated Other Comprehensive Income; CAGR refers to Compound Annual Growth Rate; E refers to Estimated; LAE refers to Loss Adjustment Expenses; LTM refers to Latest 12 Months; NA refers to not available. Source: Company management and Management Projections. (dollars in millions) Calendar Year Ended December 31, LTM Ended Calendar Year Ending December 31, 2019 2020 2021 9/30/2022 2022E 2023E 2024E 2025E 2026E 2027E CAGR 2021 to 2027E 2022 to 2027E Gross Written Premiums $411.4 $484.2 $634.2 $631.0 $640.4 $749.6 $934.6 $1,011.8 $1,084.6 $1,158.8 10.6% 12.6% Growth % 15.2% 17.7% 31.0% NA 1.0% 17.1% 24.7% 8.3% 7.2% 6.8% Net Earned Premiums 86.5 108.5 198.7 259.2 269.2 275.3 285.6 299.9 318.5 343.3 9.5% 5.0% Growth % 29.9% 25.4% 83.2% NA 35.5% 2.2% 3.7% 5.0% 6.2% 7.8% Retention 21.7% 25.1% 34.7% 41.0% 42.2% 38.7% 32.6% 30.1% 29.9% 30.3% Net Investment Income [1] 6.2 11.7 8.7 7.3 8.2 19.0 21.5 24.4 27.6 30.8 Gain on Revaluation of Compstar 0.0 69.8 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Net Realized Gains (Losses) 0.7 3.4 0.0 0.3 0.4 0.0 0.0 0.0 0.0 0.0 Other Revenue 9.1 12.1 10.2 8.7 8.7 9.2 9.9 10.4 11.0 11.5 Total Revenue $102.5 $205.5 $217.7 $275.5 $286.5 $303.5 $316.9 $334.7 $357.1 $385.6 10.0% 6.1% Growth % 30.6% 100.4% 6.0% NA 31.6% 5.9% 4.4% 5.6% 6.7% 8.0% Losses and LAE (44.7) (50.8) (130.8) (169.8) (169.1) (171.5) (176.5) (183.8) (193.7) (207.0) G&A Expenses (21.0) (38.7) (54.7) (77.0) (85.8) (87.6) (88.8) (88.0) (92.7) (98.7) Provision for Income Taxes (7.1) (6.2) (5.4) (7.1) (7.3) (5.9) (7.1) (9.5) (11.0) (12.9) Equity Gains (Losses) in Affiliates 3.6 2.3 0.0 0.0 0.0 0.0 0.0 0.0 0.0 0.0 Net Income $31.3 $88.5 $19.3 $26.6 $27.6 $21.0 $25.1 $33.6 $39.2 $45.8 15.5% 10.6% Margin % 30.5% 43.1% 8.9% 9.7% 9.6% 6.9% 7.9% 10.0% 11.0% 11.9% Total Adjustments, Net of Tax Impact 1.9 (55.8) 2.8 (5.3) (4.7) 5.9 7.0 6.9 6.8 6.7 Adjusted Net Income $33.2 $32.8 $22.1 $21.3 $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 15.5% 18.1% Margin % 32.4% 16.0% 10.2% 7.7% 8.0% 8.9% 10.1% 12.1% 12.9% 13.6% Growth % 49.6% -1.4% -32.5% NA 3.5% 17.4% 19.5% 26.0% 13.6% 14.2% Book Value (excluding AOCI) $136.8 $396.7 $417.5 $443.9 $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 6.5% 6.5% Growth % 35.3% 190.0% 5.3% NA 6.6% 4.7% 5.4% 6.8% 7.5% 8.1% Tangible Book Value (excluding AOCI) $133.8 $180.7 $202.1 $233.0 $235.7 $262.7 $293.8 $333.4 $378.6 $430.4 13.4% 12.8% Growth % 29.8% 35.1% 11.8% NA 16.6% 11.5% 11.8% 13.5% 13.6% 13.7% Book Value Per Share (excl. AOCI) $8.62 Tangible Book Value Per Share (excl. AOCI) $4.52 Additional Financial Information Loss Ratio 51.6% 46.8% 65.8% 65.5% 62.8% 62.3% 61.8% 61.3% 60.8% 60.3% Expense Ratio 24.2% 35.6% 27.5% 29.7% 31.9% 31.8% 31.1% 29.4% 29.1% 28.7% Combined Ratio 75.8% 82.4% 93.3% 95.2% 94.7% 94.1% 92.9% 90.7% 89.9% 89.0% Adjusted ROAE [2] 27.0% 11.9% 5.4% 5.0% 5.3% 5.9% 6.7% 8.0% 8.4% 8.9% Adjusted ROATE [3] 27.7% 19.7% 11.6% 9.9% 10.5% 10.8% 11.5% 12.9% 12.9% 13.0% Premiums Earned/Surplus (Statutory) NA 0.6x 1.1x NA 1.0x 1.0x 0.9x 0.9x 0.8x 0.8x 12 CONFIDENTIAL

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![](ny20006673x2_exc-2slide13.jpg)

Selected Companies Analysis (dollars in millions, except per share values) Equity Market Value [1] [2] to N Workers' Comp Insurers AMERISAFE, Inc. Employers Holdings, Inc. Share Price [1] $50.39 42.57 Equity Market Value [1] [2] $966.2 1,170.0 Adjusted Net Income Book Value (Excl. AOCI) [3] Illustrative Only Tangible Book Value (Excl. AOCI) [4] Adjusted Return on Avg. Equity LTM 10.1% 7.0% Illustrative Only Adjusted Return on Avg. Tangible Equity CY 2022E CY 2023E MRQ MRQ LTM 17.8x 15.9x 19.4x 12.4x 2.46x 1.09x 2.46x 1.14x 10.1% 7.3% Low 15.9x 12.4x 1.09x 1.14x 7.0% 7.3% High 17.8x 19.4x 2.46x 2.46x 10.1% 10.1% Median 16.8x 15.9x 1.77x 1.80x 8.5% 8.7% Mean 16.8x 15.9x 1.77x 1.80x 8.5% 8.7% Specialty Insurers Argo Group International Holdings, Ltd. $26.14 $926.2 26.0x 7.7x 0.61x 0.67x 1.7% 1.9% James River Group Holdings, Ltd. 22.20 847.5 14.7x 9.2x 1.21x 1.75x NMF NMF Kinsale Capital Group, Inc. 279.87 6,514.7 40.6x 31.7x 8.50x 8.54x 23.0% 23.1% Palomar Holdings, Inc. 51.54 1,331.0 20.6x 14.1x 3.24x 3.31x 16.1% 16.5% ProAssurance Corporation 18.57 1,009.3 NMF 17.5x 0.73x 0.79x 3.9% 4.3% RLI Corp. 128.97 5,938.7 28.1x 28.1x 3.62x 3.75x 15.4% 16.0% W. R. Berkley Corporation 73.08 20,498.8 16.9x 15.1x 2.65x 2.71x 16.3% 16.7% Low 14.7x 7.7x 0.61x 0.67x 1.7% 1.9% High 40.6x 31.7x 8.50x 8.54x 23.0% 23.1% Median 23.3x 15.1x 2.65x 2.71x 15.8% 16.3% Mean 24.5x 17.6x 2.94x 3.07x 12.7% 13.1% All Selected Companies Low 14.7x 7.7x 0.61x 0.67x 1.7% 1.9% High 40.6x 31.7x 8.50x 8.54x 23.0% 23.1% Median 19.2x 15.1x 2.46x 2.46x 12.7% 13.0% Mean 22.6x 17.2x 2.68x 2.79x 11.7% 12.0% Twins [6] $3.15 $161.8 7.0x 5.8x 0.36x 0.69x 5.0% [7] 9.9% Twins (Transaction) [5] [6] $6.15 $316.8 13.8x 11.4x 0.71x 1.36x 5.0% [7] 9.9% [7] [7] Note: No company used in this analysis for comparative purposes is identical to the Company. Note: Bloomberg consensus used for 2022 and 2023 estimates, except for Employers Holdings and Argo Group International, which use first three quarters 2022 actual results and Bloomberg consensus for fourth quarter 2022 due to first three quarters 2022 reporting. Based on closing prices as of 12/13/22. Based on fully diluted shares outstanding. Calculated as shareholders' equity, less book value of preferred stock and accumulated other comprehensive income as per GAAP. Calculated as shareholders' equity, less book value of preferred stock, accumulated other comprehensive income, and goodwill and other intangibles, as per GAAP. Share price based on the Agreement. Based on publicly available information as of 12/13/22, including market data, financial information, and consensus estimates. Most recent publicly available financial information for Twins is for the period ended 9/30/22. Burdening LTM Adjusted Net Income with stock-based compensation, LTM Adjusted ROAE is 4.7% and LTM Adjusted ROATE is 9.3%. Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI); Adjusted ROATE refers to Adjusted Return on Average Tangible Equity and is calculated as adjusted net income divided by average tangible book value of equity (excluding AOCI); Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items (and for certain selected companies, stock-based compensation); AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; LTM refers to the most recently completed 12-month period for which financial information has been made public; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public; NMF refers to Not Meaningful Figure. Source: Bloomberg, Capital IQ and public filings. CONFIDENTIAL 13

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![](ny20006673x2_exc-2slide14.jpg)

Note: AMSF refers to AMERISAFE, Inc., EIG refers to Employers Holdings, Inc., ARGO refers to Argo Group International Holdings, Ltd., JRVR refers to James River Group Holdings, Ltd., KNSL refers to Kinsale Capital Group, Inc., PLMR refers to Palomar Holdings, Inc., PRA refers to ProAssurance Corporation, RLI refers to RLI Corp. and WRB refers to W. R. Berkley Corporation. 1. Calculated as shareholders' equity less book value of preferred stock and accumulated other comprehensive income as per GAAP. AOCI refers to Accumulated Other Comprehensive Income; Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI); AOCI refers to Accumulated Other Comprehensive Income; CY refers to Calendar Year; E refers to Estimated; LTM refers to the most recently completed 12-month period for which financial information has been made public; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public. Illustrative ROAE and Equity Market Value / MRQ Book Value (Excl. AOCI) Observations for Selected Companies LTM Adjusted ROAE and Equity Market Value / MRQ Book Value (Excl. AOCI)1 Multiple CY 2022E Adjusted ROAE and Equity Market Value / MRQ Book Value (Excl. AOCI)1 Multiple AMSF EIG KNSL ARGO PRA RLI PLMR WRB 0.00x 1.00x 2.00x 3.00x 4.00x 5.00x 6.00x 7.00x 8.00x 9.00x 0.0% 5.0% 10.0% 15.0% LTM Adjusted ROAE 20.0% 25.0% Equity Market Value / MRQ Book Value (excl. AOCI)¹ AMSF Sources: Bloomberg, Capital IQ and public filings. CONFIDENTIAL 14 EIG JRVR KNSL PLMR PRA ARGO RLI WRB 0.00x 1.00x 2.00x 3.00x 4.00x 5.00x 6.00x 7.00x 8.00x 9.00x 0.0% 5.0% 10.0% 15.0% CY 2022E Adjusted ROAE 20.0% 25.0% Equity Market Value / MRQ Book Value (excl. AOCI)¹

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![](ny20006673x2_exc-2slide15.jpg)

Benchmarking Data Note: No company used in this analysis for comparative purposes is identical to the Company. Based on financial information for Twins for the period ended 9/30/22 per Company management. Ratings represent the latest available (as of 12/13/2022) AM Best Financial Strength Rating for each company's largest insurance subsidiary as measured by 9/30/2022 LTM Direct Premiums Written. Represents calendar year 2021 figure, given Kinsale Capital Group, Inc. only files annual statutory statements. Calculated excluding AOCI. Burdening Adjusted Net Income with stock-based compensation, Twins LTM Adj. ROATE is 9.3%, LTM Adj. ROAE is 4.7%, CY 2022E Adj. ROAE is 5.0%, and CY 2023E Adj. ROAE is 5.5%. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items. Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI). Adjusted ROATE refers to Adjusted Return on Average Tangible Equity and is calculated as adjusted net income divided by average tangible book value of equity (excluding AOCI). AOCI refers to Accumulated Other Comprehensive Income. CY refers to Calendar Year. E refers to Estimated. LTM refers to the most recently completed 12-month period for which financial information has been made public. MRQ refers to the most recently completed fiscal quarter for which financial information has been made public. Size & Financial Strength Profitability (Adjusted ROAE and Adjusted ROATE) Leverage (LTM Net Premiums Written / Average Capital and Surplus) Workers' Comp Insurers Employers Holdings, Inc. 0.7x AMERISAFE, Inc. 1.0x Twins - FY 2022E 1.0x Specialty Insurers ProAssurance Corporation 0.7x RLI Corp. 1.0x Twins - FY 2022E 1.0x Argo Group International Holdings, Ltd. 1.1x Kinsale Capital Group, Inc. [3] 1.2x Palomar Holdings, Inc. 1.2x W. R. Berkley Corporation 1.3x James River Group Holdings, Ltd. 2.1x Financial Strength (AM Best Financial Strength Rating) [2] Workers' Comp Insurers AMERISAFE, Inc. A Twins A Employers Holdings, Inc. A- Specialty Insurers RLI Corp. A+ W. R. Berkley Corporation A+ Kinsale Capital Group, Inc. A Twins A Argo Group International Holdings, Ltd. A- James River Group Holdings, Ltd. A- Palomar Holdings, Inc. A- ProAssurance Corporation A- Size (MRQ Book Value of Equity (Excl. AOCI), millions) Workers' Comp Insurers Employers Holdings, Inc. $1,077.9 Twins [1] $443.9 AMERISAFE, Inc. $393.0 Specialty Insurers W. R. Berkley Corporation $7,731.9 RLI Corp. $1,638.6 Argo Group International Holdings, Ltd. $1,513.8 ProAssurance Corporation $1,390.2 Kinsale Capital Group, Inc. $766.8 James River Group Holdings, Ltd. $702.1 Twins [1] $443.9 Palomar Holdings, Inc. $410.5 Size (MRQ Tangible Book Value of Equity (Excl. AOCI), millions) Workers' Comp Insurers Employers Holdings, Inc. $1,028.1 AMERISAFE, Inc. $393.0 Twins [1] $233.0 Specialty Insurers W. R. Berkley Corporation $7,562.2 RLI Corp. $1,585.0 Argo Group International Holdings, Ltd. $1,377.7 ProAssurance Corporation $1,272.2 Kinsale Capital Group, Inc. $763.3 James River Group Holdings, Ltd. $484.5 Palomar Holdings, Inc. $401.9 Twins [1] $233.0 Profitability (LTM Adjusted ROATE) [4] [5] Workers' Comp Insurers AMERISAFE, Inc. 10.1% Twins [1] 9.9% Employers Holdings, Inc. 7.3% Specialty Insurers Kinsale Capital Group, Inc. 23.1% W. R. Berkley Corporation 16.7% Palomar Holdings, Inc. 16.5% RLI Corp. 16.0% Twins [1] 9.9% ProAssurance Corporation 4.3% Argo Group International Holdings, Ltd. 1.9% James River Group Holdings, Ltd. NMF Profitability (LTM Adjusted ROAE) [4] [5] Workers' Comp Insurers AMERISAFE, Inc. 10.1% Employers Holdings, Inc. 7.0% Twins [1] 5.0% Specialty Insurers Kinsale Capital Group, Inc. 23.0% W. R. Berkley Corporation 16.3% Palomar Holdings, Inc. 16.1% RLI Corp. 15.4% Twins [1] 5.0% ProAssurance Corporation 3.9% Argo Group International Holdings, Ltd. 1.7% James River Group Holdings, Ltd. NMF Profitability (CY 2022E Adjusted ROAE) [5] Workers' Comp Insurers AMERISAFE, Inc. 16.0% Employers Holdings, Inc. 6.4% Twins 5.3% Specialty Insurers Kinsale Capital Group, Inc. 23.2% W. R. Berkley Corporation 18.9% RLI Corp. 17.0% Palomar Holdings, Inc. 13.9% James River Group Holdings, Ltd. 10.7% Twins 5.3% Argo Group International Holdings, Ltd. 3.2% ProAssurance Corporation 2.3% Profitability (CY 2023E Adjusted ROAE) [5] Workers' Comp Insurers AMERISAFE, Inc. 17.4% Employers Holdings, Inc. 7.6% Twins 5.9% Specialty Insurers Kinsale Capital Group, Inc. 25.9% Palomar Holdings, Inc. 20.8% W. R. Berkley Corporation 19.9% RLI Corp. 14.5% James River Group Holdings, Ltd. 14.1% Argo Group International Holdings, Ltd. 10.3% Twins 5.9% ProAssurance Corporation 5.5% NMF refers to not meaningful figure. Source: Bloomberg, Capital IQ, Company management, Management Projections and public filings. CONFIDENTIAL 15

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Benchmarking Data (cont.) Note: No company used in this analysis for comparative purposes is identical to the Company. 1. In 1999, company entered into a LPT Agreement with third party reinsurers. The figures above do not reflect the impact of that agreement. If those are reflected, 2019-2021 average and LTM loss ratios would be 52.2% and 56.9%, respectively and the 2019-2021 average and LTM combined ratios would be 93.2% and 95.5%, respectively. 2. Based on financial information for Twins for the period ended 9/30/22 per Company management. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items. CY refers to Calendar Year. E refers to Estimated. NA refers to not available. NMF refers to not meaningful figure. Profitability (Loss & Combined Ratios) Growth (Adjusted Net Income) Projected Growth (CY 2022E to CY 2023E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. 27.6% Twins 17.4% AMERISAFE, Inc. (8.2%) Specialty Insurers James River Group Holdings, Ltd. 60.5% Palomar Holdings, Inc. 46.3% Kinsale Capital Group, Inc. 28.0% Twins 17.4% W. R. Berkley Corporation 11.7% RLI Corp. (0.0%) Argo Group International Holdings, Ltd. NMF ProAssurance Corporation NMF Projected Growth (CY 2021 to CY 2022E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. 8.7% Twins 3.5% AMERISAFE, Inc. (1.0%) Specialty Insurers W. R. Berkley Corporation 27.4% Kinsale Capital Group, Inc. 21.3% Palomar Holdings, Inc. 21.0% RLI Corp. 19.4% Twins 3.5% Argo Group International Holdings, Ltd. (14.2%) ProAssurance Corporation (87.5%) James River Group Holdings, Ltd. NMF Projected Growth (CY 2021 to CY 2023E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. 17.8% Twins 10.2% AMERISAFE, Inc. (4.6%) Specialty Insurers Argo Group International Holdings, Ltd. 70.4% Palomar Holdings, Inc. 33.1% Kinsale Capital Group, Inc. 24.6% W. R. Berkley Corporation 19.3% Twins 10.2% RLI Corp. 9.2% ProAssurance Corporation (12.7%) James River Group Holdings, Ltd. NA Projected Growth (CY 2020 to CY 2022E Adjusted Net Income) Workers' Comp Insurers Employers Holdings, Inc. (11.2%) Twins (16.4%) AMERISAFE, Inc. (18.9%) Specialty Insurers Palomar Holdings, Inc. 170.0% W. R. Berkley Corporation 66.3% James River Group Holdings, Ltd. 64.9% Kinsale Capital Group, Inc. 49.0% RLI Corp. 34.1% Twins (16.4%) Argo Group International Holdings, Ltd. NA ProAssurance Corporation NA Combined Ratio (CY 2019 to CY 2021 Average) Workers' Comp Insurers AMERISAFE, Inc. 79.6% Twins 83.9% Employers Holdings, Inc. [1] 95.1% Specialty Insurers Kinsale Capital Group, Inc. 82.9% Twins 83.9% RLI Corp. 90.2% Palomar Holdings, Inc. 93.4% W. R. Berkley Corporation 96.7% Argo Group International Holdings, Ltd. 106.7% ProAssurance Corporation 112.4% James River Group Holdings, Ltd. 114.6% Net Loss Ratio (CY 2019 to CY 2021 Average) Workers' Comp Insurers Employers Holdings, Inc. [1] 54.1% AMERISAFE, Inc. 54.3% Twins 54.8% Specialty Insurers Palomar Holdings, Inc. 21.6% RLI Corp. 49.0% Twins 54.8% Kinsale Capital Group, Inc. 59.8% W. R. Berkley Corporation 62.6% Argo Group International Holdings, Ltd. 69.1% ProAssurance Corporation 83.3% James River Group Holdings, Ltd. 91.5% Net Loss Ratio (LTM) Workers' Comp Insurers Employers Holdings, Inc. [1] 58.7% AMERISAFE, Inc. 64.0% Twins [2] 65.5% Specialty Insurers Palomar Holdings, Inc. 23.3% RLI Corp. 44.5% Kinsale Capital Group, Inc. 58.1% W. R. Berkley Corporation 61.3% Twins [2] 65.5% Argo Group International Holdings, Ltd. 68.3% ProAssurance Corporation 74.9% James River Group Holdings, Ltd. 86.1% Combined Ratio (LTM) Workers' Comp Insurers AMERISAFE, Inc. 91.2% Twins [2] 95.2% Employers Holdings, Inc. [1] 97.3% Specialty Insurers Kinsale Capital Group, Inc. 78.7% Palomar Holdings, Inc. 81.8% RLI Corp. 84.2% W. R. Berkley Corporation 91.9% Twins [2] 95.2% ProAssurance Corporation 103.4% Argo Group International Holdings, Ltd. 103.9% James River Group Holdings, Ltd. 108.6% LTM refers to the most recently completed 12-month period for which financial information has been made public. Source: Bloomberg, Capital IQ, Company management, Management Projections and public filings. CONFIDENTIAL 16

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Selected Transactions Analysis Source: Capital IQ, public filings and press releases. CONFIDENTIAL 17 Note: No company used in this analysis for comparative purposes is identical to the Company, and no transaction used in this analysis for comparative purposes is identical to the proposed Transaction. Transaction Value refers to the implied equity value of target company, based on the announced transaction equity price and other public information available at the time of the announcement. Based on reported metric for MRQ prior to the announcement of the transaction. Computed as shareholders' equity, less accumulated other comprehensive income on GAAP basis. Based on reported metric for MRQ prior to the announcement of the transaction. Computed as shareholders' equity, less accumulated other comprehensive income and goodwill & intangibles on GAAP basis. Computed as LTM Adjusted Net Income divided by MRQ shareholders' equity less AOCI. Computed as LTM Adjusted Net Income divided by MRQ shareholders' equity less AOCI and goodwill & intangibles. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items; Adjusted ROE refers to Adjusted Return on Equity; Adjusted ROTE refers to Adjusted Return on Tangible Equity; AOCI refers to Accumulated Other Comprehensive Income; MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public; NA refers to not available; NMF refers to not meaningful figure. (dollars in millions) Transaction Value [1] / Illustrative Only Transaction Book Value Tangible Book Value Implied Illustrative Only Implied Announced Effective Target Acquiror Value [1] (Excl. AOCI) [2] (Excl. AOCI) [3] Adjusted ROE [4] Adjusted ROTE [5] 2/16/2021 6/1/2021 Protective Insurance Corporation The Progressive Corporation $337.6 0.99x 0.99x 5.9% 5.9% 1/15/2021 8/4/2021 ProSight Global, Inc. (nka:Coaction Global, Inc.) TowerBrook Capital Partners L.P.; Further Global Capital Management, $585.9 1.10x 1.13x 7.5% 7.8% 11/16/2018 9/19/2019 EMC Insurance Group Inc Employers Mutual Casualty Company $786.1 1.33x 1.34x 4.8% 4.8% 8/28/2018 2/15/2019 Aspen Insurance Holdings Limited Apollo Global Management, LLC $2,600.1 0.88x 0.88x NMF NMF 8/22/2018 5/23/2019 The Navigators Group, Inc The Hartford Financial Services Group, Inc $2,083.6 1.64x 1.68x 4.4% 4.5% 1/9/2018 11/9/2018 AmTrust Financial Services, Inc. Stone Point Capital LLC ; Trident VII, L.P. $2,904.8 0.76x 1.00x 5.7% 7.5% 12/18/2016 7/26/2017 7/5/2017 11/17/2017 Allied World Assurance Company Holdings, Ltd State National Companies, Inc. Fairfax Financial Holdings Limited Markel Corporation $4,696.2 $922.6 1.29x 2.90x 1.49x 3.04x 6.3% NA 7.2% NA 5/2/2017 9/28/2017 Intact Insurance Group USA Holdings Inc. Intact Financial Corporation $1,714.8 1.65x 1.65x 6.7% 6.7% 12/5/2016 5/1/2017 Ironshore Inc. Liberty Mutual Group, Inc. $2,935.0 1.42x 1.48x 7.5% 7.8% 10/5/2016 3/28/2017 Endurance Specialty Holdings Ltd Sompo Holdings, Inc. $6,318.1 1.28x 1.42x 7.2% 8.0% 3/7/2016 11/10/2016 National Interstate Corporation Great American Insurance Company, Inc. $639.1 1.77x 1.81x 6.4% 6.5% 6/10/2015 10/28/2015 HCC Insurance Holdings Inc. Tokio Marine & Nichido Fire Insurance Co., Ltd. $7,501.8 1.99x 2.67x NA NA 12/30/2014 7/7/2015 Meadowbrook Insurance Group, Inc. (nka:AmeriTrust Group, Inc.) Fosun International Limited $433.3 1.04x 1.12x NMF NMF 12/17/2014 5/1/2015 Catlin Group Ltd. XL Group plc $3,907.4 0.70x 0.88x 9.8% 12.3% 1/9/2014 4/1/2014 Summit Holding Southeast Inc Great American Holding, Inc. $250.0 1.08x 1.32x 20.3% 24.9% 1/6/2014 9/15/2014 Tower Group International, Ltd American Capital Partners Re, Ltd. $143.6 2.17x NMF NMF NMF 9/24/2013 1/2/2014 Eastern Insurance Holdings, Inc. ProAssurance Corporation $205.1 1.47x 1.65x 9.1% 10.1% Low $143.6 0.70x 0.88x 4.4% 4.5% High $7,501.8 2.90x 3.04x 20.3% 24.9% Median $1,318.7 1.31x 1.42x 6.7% 7.5% Mean $2,164.7 1.42x 1.50x 7.8% 8.8%

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![](ny20006673x2_exc-2slide18.jpg)

Discounted Cash Flow Analysis Book Value Terminal Multiple (dollars in millions) Previous Year-End Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 Net Income 21.0 25.1 33.6 39.2 45.8 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Ending Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Present Value of Cash Flows (2022 - 2027) Projected Calendar Year Ending December 31, 2022E 2023E 2024E 2025E 2026E 2027E PV of Terminal Value as a Multiple of 2027 Book Value (Excl. AOCI) Implied Equity Value Discount Rate 13.00% 13.50% 14.00% 14.50% 15.00% 0.85x $279.7 $273.5 $267.5 $261.6 $255.9 1.05x $345.5 $337.8 $330.4 $323.2 $316.2 1.25x $411.3 $402.2 $393.4 $384.8 $376.4 0.85x $279.7 $273.5 $267.5 $261.6 $255.9 1.05x $345.5 $337.8 $330.4 $323.2 $316.2 1.25x $411.3 $402.2 $393.4 $384.8 $376.4 Discount Rate 13.00% 13.50% 14.00% 14.50% 15.00% 0.85x $5.43 $5.31 $5.19 $5.08 $4.97 1.05x $6.71 $6.56 $6.41 $6.27 $6.14 1.25x $7.98 $7.81 $7.63 $7.47 $7.31 $0.0 $0.0 $0.0 $0.0 $0.0 + = Implied Equity Value Per Share [1] Note: Present values as of 12/13/22; mid-year convention applied. Note: Present value of cash flows (2022-2027) is $0 as Management Projections do not contemplate any distributions over the projection period. Per Company management at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in book value, and the same discount rates and terminal multiple range as shown above, the implied equity value per share reference range would be $5.22-$8.04. 1. Based on (i) ~51.2 million shares of common stock outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs. AOCI refers to Accumulated Other Comprehensive Income. E refers to Estimated. PV refers to Present Value. Source: Company management and Management Projections. CONFIDENTIAL 18

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![](ny20006673x2_exc-2slide19.jpg)

Illustrative Only Discounted Cash Flow Analysis Tangible Book Value Terminal Multiple (dollars in millions) Previous Year-End Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 Net Income 21.0 25.1 33.6 39.2 45.8 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Ending Book Value (Excl. AOCI) $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 Goodwill & Intangible Assets (209.5) (203.5) (197.5) (191.5) (185.5) (179.5) Ending Tangible Book Value (Excl. AOCI) $235.7 $262.7 $293.8 $333.4 $378.6 $430.4 Dividends $0.0 $0.0 $0.0 $0.0 $0.0 $0.0 Present Value of Cash Flows (2022 - 2027) Projected Calendar Year Ending December 31, 2022E 2023E 2024E 2025E 2026E 2027E PV of Terminal Value as a Multiple of 2027 Tangible Book Value (Excl. AOCI) Implied Equity Value Discount Rate 13.00% 13.50% 14.00% 14.50% 15.00% 1.25x $290.2 $283.8 $277.6 $271.5 $265.6 1.55x $359.9 $351.9 $344.2 $336.7 $329.4 1.85x $429.5 $420.1 $410.8 $401.9 $393.1 1.25x $290.2 $283.8 $277.6 $271.5 $265.6 1.55x $359.9 $351.9 $344.2 $336.7 $329.4 1.85x $429.5 $420.1 $410.8 $401.9 $393.1 Discount Rate 13.00% 13.50% 14.00% 14.50% 15.00% 1.25x $5.63 $5.51 $5.39 $5.27 $5.16 1.55x $6.99 $6.83 $6.68 $6.54 $6.39 1.85x $8.34 $8.15 $7.97 $7.80 $7.63 $0.0 $0.0 $0.0 $0.0 $0.0 + = Implied Equity Value Per Share [1] Note: Present values as of 12/13/22; mid-year convention applied. Note: Present value of cash flows (2022-2027) is $0 as Management Projections do not contemplate any distributions over the projection period. Per Company management at this time the Company is not contemplating making cash distributions over the projection period. For illustrative purposes only and based on discussions with Company management, assuming distributions of 75% of distributable cash at Twins Corporation of $4.2 million in 2022, $5.9 million in 2023, $6.5 million in 2024, $8.2 million in 2025, $9.1 million in 2026 and $10.5 million in 2027, corresponding reduction in tangible book value, and the same discount rates and terminal multiple range as shown above, the implied equity value per share reference range would be $5.24-$8.12. 1. Based on (i) ~51.2 million shares of common stock outstanding; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million performance stock units outstanding that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs. AOCI refers to Accumulated Other Comprehensive Income. E refers to Estimated. PV refers to Present Value. Source: Company management and Management Projections. CONFIDENTIAL 19

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Page 3 5 10 Executive Summary Selected Updates Since Prior Discussion Materials Financial Analyses 4. Appendices 20 Selected Cost of Equity Considerations Supplemental Financial Information Illustrative Selected Company Multiple Trendlines Supplemental Public Company & Market Observations 21 23 30 33

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Page 3 5 10 20 Executive Summary Selected Updates Since Prior Discussion Materials Financial Analyses Appendices Selected Cost of Equity Considerations 21 Supplemental Financial Information Illustrative Selected Company Multiple Trendlines Supplemental Public Company & Market Observations 23 30 33

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![](ny20006673x2_exc-2slide22.jpg)

Cost of Equity Calculation Note: No company used in this analysis for comparative purposes is identical to the Company. Based on actual levered beta per Bloomberg 5-year weekly as of 12/13/22. Based on review of studies measuring the historical returns between stocks and bonds, theoretical models such as supply-side and demand-side models and other materials. Duff & Phelps Cost of Capital Navigator ("Navigator"). Cost of Equity = Risk-Free Rate of Return + (Levered Beta \* Equity Risk Premium) + Size Premium. Risk-Free Rate of Return as of 12/13/22, based on 20-year U.S. Treasury Bond Yield. Based on publicly available information, analyst estimates and market data as of 12/13/2022. Risk-Free Rate of Return 12/13/2022, based on 20-year U.S. Treasury Bond Yield. Based on review of selected companies' levered betas. Source: Bloomberg and Capital IQ. Workers' Comp Insurers Levered Beta [1] Equity Risk Premium [2] Size Premium [3] Cost of Equity [4] AMERISAFE, Inc. 0.64 6.00% 1.21% 8.8% Employers Holdings, Inc. 0.56 6.00% 1.21% 8.3% Median 0.60 8.6% Mean 0.60 8.6% Specialty Insurers Argo Group International Holdings, Ltd. 0.83 6.00% 1.21% 9.9% Risk-Free Rate of Return [6] Equity Risk Premium [2] Size Premium [3] 3.74% 6.00% 4.80% James River Group Holdings, Ltd. 0.93 6.00% 1.21% 10.6% Kinsale Capital Group, Inc. 0.99 6.00% 0.54% 10.2% Computed Cost of Equity Palomar Holdings, Inc. 0.99 6.00% 1.34% 11.0% Selected Companies' Levered Beta ProAssurance Corporation 0.50 6.00% 1.21% 8.0% Selected Companies Levered Beta [7] 0.83 RLI Corp. 0.74 6.00% 0.54% 8.7% Cost of Equity [4] 13.5% W. R. Berkley Corporation 0.86 6.00% 0.43% 9.3% Median 0.86 9.9% Computed Cost of Equity Mean 0.84 9.7% Twins' Observed Levered Beta Twins' Observed Levered Beta 1.17 All Selected Companies Cost of Equity [4] 15.5% Median 0.83 9.3% Mean 0.78 9.4% Twins [5] 1.17 6.00% 4.80% 15.5% Selected Cost of Equity Range 13.0% -- 15.0% Market Assumptions 22 CONFIDENTIAL

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Page 3 5 10 20 21 Executive Summary Selected Updates Since Prior Discussion Materials Financial Analyses Appendices Selected Cost of Equity Considerations Supplemental Financial Information 23 Illustrative Selected Company Multiple Trendlines Supplemental Public Company & Market Observations 30 33

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![](ny20006673x2_exc-2slide24.jpg)

$43.1 $62.0 $66.6 $86.5 $108.5 $198.7 $269.2 $275.3 $285.6 $299.9 $318.5 $343.3 0.6x 1.1x 1.0x 1.0x 0.9x 0.9x 0.8x 0.8x CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Net Earned Premiums Premiums Earned/Surplus (Statutory) $144.9 $236.3 $322.1 $357.0 $411.4 $484.2 $634.2 $640.4 $749.6 $934.6 $1,011.8 $1,084.6 $1,158.8 CY 2015 CY 2016 CY 2017 Net Earned Premiums CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Selected Management Projections Highlights Premiums Gross Written Premiums (dollars in millions) (dollars in millions) 2 Projected NEP CAGR of ~5% over 2022-27 period following ~200% growth since 2019 reflects balanced focus on stable growth and preservation of strong balance sheet position and AM Best rating. Period CAGR 2015 – 2021 27.9% 2021 – 2027E 10.6% 2022E – 2027E 12.6% Period CAGR 2016 – 2021 35.7% 2021 – 2027E 9.5% 2022E – 2027E 5.0% Retention: 19.6% 20.3% 19.6% 21.7% 25.1% 34.7% 42.2% 38.7% 32.6% 30.1% 29.9% 30.3% Note: Historical financial data is not pro forma for recent acquisitions, including the Company's (i) July 6, 2021 acquisition of Western Integrated Care, LLC for ~$5.5 mm (ii) October 1, 2020 acquisition of 7710 Insurance Company (and certain affiliates) for ~$12.1 mm, (iii) April 1, 2020 acquisition of LCTA Risk Services, Inc. for ~$1.4 mm, (iv) February 19, 2019 acquisition of First Choice Casualty Insurance Company for ~$5.3 mm, (v) April 2, 2018 acquisition of Westcap Insurance Services, LLC for ~$2.5 mm, (vi) December 12, 2018 acquisition of CTS Underwriters for $0.05 mm or (viii) March 31, 2019 acquisition of a ~25% interest in American Liberty Insurance Company for ~$1.2 mm (or January 2017 purchase of a 75% interest). Historical financial data also not pro forma for the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million) 1. U.S. Bureau of Labor Statistics. CAGR refers to Compounded Annual Growth Rate; E refers to Expected; CY refers to Calendar Year. Source: Company management, except where otherwise noted and Management Projections. employment CAGR is projected to approximate 0.5% over the same period.1 1 Projected GWP CAGR of ~10%+ is expected to be driven in part through the introduction of two new programs (A&H and Excess Surplus), which will be fully reinsured. Estimated US 24 CONFIDENTIAL

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![](ny20006673x2_exc-2slide25.jpg)

(dollars in millions) $17.8 $12.6 $22.2 $33.2 $32.8 $22.1 $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Note: Historical financial data is not pro forma for recent acquisitions (refer to prior page for additional details) including the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million). (2H 2018, CY 2019 and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). CAGR refers to Compounded Annual Growth Rate. CY refers to Calendar Year. E refers to Expected. Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, 49.8% 49.2% 53.7% 51.6% 46.8% 65.8% 62.8% 62.3% 61.8% 61.3% 60.8% 60.3% 40.0% 30.4% 23.6% 24.2% 35.6% 27.5% 31.1% 29.4% 29.1% 28.7% 89.8% 79.7% 77.3% 75.8% 82.4% 93.3% 92.9% 90.7% 89.9% 89.0% CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Selected Management Projections Highlights Combined Ratio and Adjusted Net Income Combined Ratio Adjusted Net Income Projected 2022-2027 Adj. Net Income CAGR of ~18% driven by (i) underwriting income CAGR (~21%), (ii) investment income CAGR (~19%) as yields are assumed to peak in 2023 and (iii) other revenue CAGR (~6%). 4 Period CAGR 2021 – 2027E 15.5% 2022E – 2027E 18.1% 3 Projected Loss Ratio 94.7% 94.1% 31.9% 31.8% Projected Expense Ratio Combined ratios are projected to revert gradually to below 90% as loss ratios approach a normalized level following unusual frequency and severity of claims in 2021 and a build-up of reserves in subsequent years, as well as declining expense ratios due to increased operating leverage. Historical Loss Ratio Historical Expense Ratio stock-based compensation and certain unusual or non-recurring items. Refer to Appendix for additional details on adjustments. Source: Company management and Management Projections. CONFIDENTIAL 25

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![](ny20006673x2_exc-2slide26.jpg)

5.4% 5.3% 5.9% 6.7% 8.0% 8.4% 8.9% CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Note: Historical financial data is not pro forma for recent acquisitions (refer to prior pages for additional details) including the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million). (2H 2018, CY 2019 and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). Historical financial figures are also not pro forma for the impact of the July 2020 IPO. 2019 and prior years book values do not reflect impact of AOCI related restatement. Presented on a pre-tax basis. Based on net income less gain on revaluation of 45% ownership interest in Compstar, in each case as stated in Company public filings. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from book value. Book value figures for 2019 and prior years exclude preferred stock. Adjusted ROAE refers to Adjusted Return on Average Equity (in the case of 2016 – 2020 based on Average Book Value and in the case of 2021 onwards based on Average Book Value less AOCI); $71.9 $88.2 $106.1 $136.8 $396.7 $417.5 $445.2 $466.2 $491.3 $524.9 $564.0 $609.8 CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Selected Management Projections Highlights Book Value and Adjusted ROAE Book Value, excluding AOCI (dollars in millions) Period CAGR 2021 – 2027E 6.5% 2022E – 2027E 6.5% Book value increased in 2020 due to (i) shares issued in initial public offering, (ii) acquisition of 55% of Compstar and (iii) revaluation of 45% stake in Compstar. 5 R 2 Adjusted ROAE3 12/13/19 Book Value (Excl. AOCI) $136.8 Shares Issued in Compstar Acquisition 99.2 OAE, which has fallen in 2021- 022 amid declines in Adj. Net Income following Compstar acquisition and IPO, is projected to increase over the projection period. Gain on Revaluation of Compstar Stake1 69.8 18.8% 22.1% 23.0% 27.0% 6 Shares Issued in IPO, Net of Discounts 93.1 Pre-IPO Distribution (18.2) Net Income (Ex-Compstar Gain)2 18.7 Other (2.9) 11.9% 12/13/20 Book Value (Excl. AOCI) $396.7 AOCI refers to Accumulated Other Comprehensive Income; CAGR refers to Compounded Annual Growth Rate; CY refers to Calendar Year. E refers to Expected. Source: Company management and Management Projections. CONFIDENTIAL 26

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![](ny20006673x2_exc-2slide27.jpg)

$71.9 $87.4 $103.1 $133.8 $180.7 $202.1 $235.7 $262.7 $293.8 $333.4 $378.6 $430.4 CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E 18.8% 22.2% 23.4% 27.7% 19.7% 11.6% 10.5% 10.8% 11.5% 12.9% 12.9% 13.0% CY 2016 CY 2017 CY 2018 CY 2019 CY 2020 CY 2021 CY 2022E CY 2023E CY 2024E CY 2025E CY 2026E CY 2027E Note: Historical financial data is not pro forma for recent acquisitions (refer to prior pages for additional details) including the Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million). (2H 2018, CY 2019 and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). Historical financial figures are also not pro forma for the impact of the July 2020 IPO. 2019 and prior years book values do not reflect impact of AOCI related restatement. 1. For calendar years prior to 2021, metric is based on figures provided by Company management, derived from tangible book value. Tangible book value figures for 2019 and prior years exclude preferred stock. Adjusted ROATE refers to Adjusted Return on Average Tangible Equity (in the case of 2016 – 2020 based on Average Tangible Book Value and in the case of 2021 onwards based on Average Tangible Book Value less Selected Management Projections Highlights Tangible Book Value and Adjusted ROATE Tangible Book Value, excluding AOCI Adjusted ROATE1 (dollars in millions) Period CAGR 2021 – 2027E 13.4% 2022E – 2027E 12.8% Tangible book value increased in 2020 following the initial public offering. Projected CAGR of ~13% generally tracks Net Income growth. 7 AOCI); AOCI refers to Accumulated Other Comprehensive Income. CAGR refers to Compounded Annual Growth Rate. CY refers to Calendar Year. E refers to Expected. Source: Company management and Management Projections. CONFIDENTIAL 27

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![](ny20006673x2_exc-2slide28.jpg)

Projected Adjusted Net Income Detail Selected Net Income Adjustments and ROAE Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to the next page for additional details on adjustments; Adjusted ROAE refers to Adjusted Return on Average Equity and is calculated as adjusted net income divided by average book value of equity (excluding AOCI); E refers to Estimated. (dollars in millions) Company management's financial projections for Adjusted Net Income are consistent with public reporting of historical performance and include add- backs for expenses relating to (i) share based compensation and (ii) amortization of intangible assets. As most selected companies reviewed do not make add-back adjustments for these expenses, the below illustrates three alternative derivations of Adjusted Net Income (which may be relevant to financial analyses), as well as corresponding ROAE calculations, for the Company over the projection period: Tax Effected Share Based Compensation [1] 1.2 1.7 1.7 1.7 1.7 1.7 Adjusted Net Income: No Add-Back for Share Based Compensation $21.7 $25.2 $30.5 $38.8 $44.3 $50.8 Tax Effected Intangible Asset Amortization [1] 4.7 4.7 4.7 4.7 4.7 4.7 Adjusted Net Income: No Add-Back for Share Based Compensation and Intangible Asset Amortization $17.0 $20.5 $25.8 $34.2 $39.7 $46.2 As-Presented by Company Management No Add-Back for Share Based Compensation No Add-Back for Share Based Compensation and Intangible Asset Amortization Calendar Year Ending December 31, 2022E 2023E 2024E 2025E 2026E 2027E Implied Adjusted ROAE Based On: Adjusted Net Income: 5.3% 5.9% 6.7% 8.0% 8.4% 8.9% Adjusted Net Income: 5.0% 5.5% 6.4% 7.6% 8.1% 8.7% Adjusted Net Income: 3.9% 4.5% 5.4% 6.7% 7.3% 7.9% Adjusted Net Income: $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 As-Presented by Company Management Share Based Compensation 1.5 2.1 2.1 2.1 2.1 2.1 Intangible Asset Amortization 6.0 6.0 6.0 6.0 6.0 6.0 1. Tax-effected at projected tax rate of 21.0% in 2021 and 22.0% in 2022 through 2027 per Company management. Source: Company management and Management Projections. CONFIDENTIAL 28

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Historical and Projected Financial Data Net Income Adjustments Note: Historical financial data is not pro forma for the Company's recent acquisitions, including its (i) July 6, 2021 acquisition of Western Integrated Care, LLC for ~$5.5 million, (ii) October 1, 2020 acquisition of 7710 Insurance Company (and certain affiliates) for ~$12.1 million, (iii) April 1, 2020 acquisition of LCTA Risk Services, Inc. for ~$1.4 million, or (iv) February 19, 2019 acquisition of First Choice Casualty Insurance Company for ~$5.3 million. Financial data reflects Company's April 2018 ~$18 million purchase of a 45% equity interest in Compstar Holding Company LLC and subsequent purchase of the remaining 55% equity interest on July 15, 2020 through the issuance of ~6.6 million shares of Company common stock based on the stock price of $15 per share (reflecting a purchase price of $99 million), but 2019-2020 financial data is not pro forma for the July 15, 2020 acquisition of the remaining 55% equity interest in Compstar (2019 data and 1H 2020 data reflects the impact of a ~45% equity interest in Compstar using the equity method). 2019 and 1H 2020 figures are also not pro forma for the impact of the July 2020 IPO. In 2020, negative adjustment due primarily to gain on revaluation of 45% ownership interest in Compstar, following acquisition of the remaining 55% interest. In 2020, gain on revaluation of ownership interest in Compstar had no tax impact. Adjusted Net Income refers to earnings, adjusted for unrealized gains/losses, intangible asset amortization, stock-based compensation and certain unusual or non-recurring items. Refer to the table above for additional (dollars in millions) Calendar Year Ended December 31, LTM Ended Calendar Year Ending December 31, CAGR 2019 2020 2021 9/30/2022 2022E 2023E 2024E 2025E 2026E 2027E 2021 to 2027E 2022 to 2027E Income Statement Adjustments Net Income $31.3 $88.5 $19.3 $26.6 $27.6 $21.0 $25.1 $33.6 $39.2 $45.8 15.5% 10.6% Intangible Asset Amortization 0.0 2.6 5.8 6.0 6.0 6.0 6.0 6.0 6.0 6.0 Non-Cash Share-Based Compensation 0.0 0.5 1.5 1.4 1.5 2.1 2.1 2.1 2.1 2.1 Loss (Gain) on Embedded Derivatives 0.0 2.8 (4.7) (17.8) (16.9) (0.8) 0.9 0.8 0.8 0.7 Unrealized Losses (Gains) on Equity Securities 0.0 0.0 0.0 4.5 4.5 0.2 0.0 (0.1) (0.2) (0.3) Net Loss (Gain) on Purchase & Disposal of Affiliates (0.6) (3.1) 0.1 0.1 (1.4) 0.0 0.0 0.0 0.0 0.0 Other [1] 3.2 (55.6) 0.8 (1.2) 0.3 0.0 0.0 0.0 0.0 0.0 Total Adjustments 2.6 (52.8) 3.6 (6.9) (6.0) 7.5 9.0 8.9 8.7 8.6 Tax Impact [2] (0.7) (3.0) (0.8) 1.6 1.3 (1.7) (2.0) (1.9) (1.9) (1.9) Adjusted Net Income $33.2 $32.8 $22.1 $21.3 $22.9 $26.9 $32.1 $40.5 $46.0 $52.5 15.5% 18.1% details on adjustments; CAGR refers to Compound Annual Growth Rate; E refers to Estimated; LTM refers to Latest 12 Months; NA refers to not available. Source: Company management and Management Projections. CONFIDENTIAL 29

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1.7x 1.7x 1.0x 0.8x 0.5x 0.3x 0.0x 1.3x 1.5x 1.8x 2.5x 2.3x 2.0x 2.8x 3.0x 3.3x Dec-12 Jun-13 Dec-13 Jun-14 Dec-14 Jun-15 Dec-15 Jun-16 Dec-16 Jun-17 Dec-17 Jun-18 Dec-21 Jun-22 Dec-22 Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] Dec-18 Jun-19 Dec-19 Jun-20 Dec-20 Jun-21 Twins Average [1] Selected Workers' Comp Insurers Average [3] Selected Specialty Insurers Average [4] Source: S&P Capital IQ as of December 13, 2022. (Multiples shown above are sourced from S&P Capital IQ; as such, certain multiples may differ slightly from the figures shown on other pages.) CONFIDENTIAL 31 Historical Trading Multiples Market Capitalization/MRQ Book Value Lookback Note: Market Capitalization/Book Value multiples less than or equal to 0.0x and greater than 10.0x deemed to be not meaningful and excluded from the displayed data. Note: For purposes of the above chart, Book Value is on an unadjusted basis and does not exclude accumulated other comprehensive income. As such, Book Value multiples shown above may differ from multiples shown elsewhere in the materials. Twins Market Capitalization/Book Value multiples shown and calculated since July 16, 2020. Assumed Book Values from July 16, 2020 to November 11, 2020 reflect Twins' March 31, 2020 Total stockholders' / members' equity on an adjusted basis after giving effect to the reorganization transactions and issuance and sale of shares in its IPO per Twins' 424B4 filing dated July 17, 2020. Calculated since July 16, 2020, Twins' IPO date. Selected Workers' Comp Insurers comprise AMERISAFE, Inc. and Employers Holdings, Inc. Data reflects median multiple. Selected Specialty Insurers comprise Argo Group International Holdings, Ltd., James River Group Holdings, Ltd., Kinsale Capital Group, Inc., Palomar Holdings, Inc., ProAssurance Corporation, RLI Corp., and W. R. Berkley Corporation. Data reflects median multiple. Reflects 10-year average. Reflects average since July 16, 2020, Twins' IPO date. NA refers to Not Available. MRQ refers to the most recently completed quarterly fiscal period for which financial information has been made public. One-Year Average Since Twins IPO [2] 3-Year Average 5-Year Average 10-Year Average Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] 0.7x 1.3x NA NA NA 1.7x 1.7x 1.7x 1.9x 1.7x 2.5x 2.2x 2.2x 2.0x 1.7x 6 1.3x 5 5

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Historical Trading Multiples Market Capitalization/NTM Adjusted Net Income Lookback Note: Market Capitalization/NTM Adjusted Net Income multiples less than or equal to 0.0x and greater than 40.0x deemed to be not meaningful and excluded from the displayed data. Twins Market Capitalization/NTM Adjusted Net Income multiples shown and calculated since August 10, 2020, the first date with Twins NTM consensus Adjusted Net Income estimates available per S&P Capital IQ. Calculated since August 10, 2020, the first date with Twins NTM consensus estimates available per S&P Capital IQ. Selected Workers' Comp Insurers comprise AMERISAFE, Inc. and Employers Holdings, Inc. Data reflects median multiple. Selected Specialty Insurers comprise Argo Group International Holdings, Ltd., James River Group Holdings, Ltd., Kinsale Capital Group, Inc., Palomar Holdings, Inc., ProAssurance Corporation, RLI Corp., and W. R. Berkley Corporation. Data reflects median multiple. Reflects 10-year average. Reflects average since August 10, 2020, the first date with Twins NTM consensus estimates available per S&P Capital IQ. NA refers to Not Available. Adjusted Net Income refers to earnings, adjusted, among other things, for unrealized gains/losses and certain unusual or non-recurring items. 6 13.0x 5 19.3x 17.9x 5 0.0x Dec-12 Jun-13 Dec-13 Jun-14 Dec-14 Jun-15 Dec-15 Jun-16 Dec-16 Jun-17 Dec-17 Jun-18 Dec-18 Jun-19 Dec-19 Jun-20 Dec-20 Jun-21 Dec-21 Jun-22 Dec-22 5.0x 10.0x 15.0x 20.0x 25.0x 30.0x 35.0x Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] Twins Average [1] Selected Workers' Comp Insurers Average [3] Selected Specialty Insurers Average [4] One-Year Average Source: S&P Capital IQ as of December 13, 2022. (Multiples shown above are sourced from S&P Capital IQ; as such, certain multiples may differ slightly from the figures shown on other pages.) CONFIDENTIAL 31 Since Twins IPO [2] 3-Year Average 5-Year Average 10-Year Average Twins [1] Selected Workers' Comp Insurers [3] Selected Specialty Insurers [4] 8.9x 13.0x NA NA NA 17.9x 18.9x 19.0x 18.7x 17.9x 19.7x 21.4x 21.6x 22.0x 19.3x

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Twins vs. Selected Companies Historical Stock Performance (79.7%) 29.8% 27.9% 20.0% -- -- -- (79.7%) (61.6%) (64.4%) 243.5% 64.9% 33.2% 29.8% (12.5%) (14.9%) 224.5% 14.9% 4.7% 27.9% 10.9% 8.2% 237.8% 120.4% 23.3% 20.0% (2.1%) (5.2%) Since IPO Total Shareholder Return Ten-Year Five-Year Three-Year Since Twins IPO One-Year YTD Twins S&P 500 Index (Total Return) Selected Workers' Comp Insurers1,3 Selected Specialty Insurers2,3 75% -100% -75% -50% -25% 0% 25% 50% Jul-20 Sep-20 Nov-20 Jan-21 Mar-21 May-21 Jul-21 Sep-21 Nov-21 Jan-22 Mar-22 May-22 Jul-22 Sep-22 Nov-22 Twins S&P 500 Index (Total Return) Selected Workers' Comp Insurers [1] Selected Specialty Insurers [2] Selected Workers' Comp Insurers comprise AMERISAFE, Inc. and Employers Holdings, Inc. Selected Specialty Insurers comprise Argo Group International Holdings, Ltd., James River Group Holdings, Ltd., Kinsale Capital Group, Inc., Palomar Holdings, Inc., ProAssurance Corporation, RLI Corp., and W. R. Berkley Corporation. Average of Selected Workers' Comp Insurers index and Selected Specialty Insurers index. Kinsale Capital Group, Inc., Palomar Holdings, Inc. and James River Group Holdings, Ltd. not included in Ten-Year return calculation. Palomar Holdings, Inc. not included in Five-Year return calculation. Source: Capital IQ as of 12/13/22. 34 CONFIDENTIAL

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Twins Analyst Perspectives M t anagement has not provided any commentary for 2023 but we think here is likely to be more downside than upside in our PYD assumption. Following 3Q22, we are reducing EPS estimates and our price target for Twins; our Neutral rating is unchanged. While Twins trades at a below- average multiple, our view is that risk-reward in the stock is not compelling due to the lack of meaningful catalysts as well as the potential for negative EPS revisions. - JP Morgan, 11/03/2022 " Target Price / Broker Date Recommendation Price Target Prem. / (Disc.)1 Book Value of Equity (Excl. AOCI) as of 9/30/222 Tangible Book Value of Equity (Excl. AOCI) as of 9/30/223 11/08/2022 Market Outperform 8.00 154.0% 0.93x 1.77x 11/07/2022 Neutral – – – – 11/03/2022 Neutral 5.50 74.6% 0.64x 1.22x 11/03/2022 Neutral 5.50 74.6% 0.64x 1.22x Median $5.50 74.6% 0.64x 1.22x Mean $6.33 101.1% 0.74x 1.40x Closing share price of $3.15 as of 12/13/22. MRQ Book Value based on Book Value (Excluding AOCI) of $443.9 million per 10-Q for period ended 9/30/22 and (i) ~51.2 million shares outstanding as of 12/9/22; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million PSUs that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs. MRQ Tangible Book Value based on Tangible Book Value (Excluding AOCI) of $233.0 million per 10-Q for period ended 9/30/22 and (i) ~51.2 million shares outstanding as of 12/9/22; (ii) ~0.2 million options (to the extent in the money, per the treasury method); (iii) ~0.1 million restricted stock units; and (iv) ~0.1 million PSUs that are projected to vest, as of 12/9/22. Does not include ~0.1 million MSUs. AOCI refers to Accumulated Other Comprehensive Income. Sources: Bloomberg, FactSet, Equity Research and public filings as of 12/13/22. Select Commentary Broker Outlook m We expect earnings to remain constrained in the near term as Twins akes the shift to a higher-retention business model in a highly competitive environment. Premium growth levels are unlikely to meaningfully reaccelerate despite higher retentions as competition is not showing signs of letting up. And increased expense levels resulting from higher retention should keep margins [below] historical levels. We therefore expect 2023 operating EPS of $0.54 versus a historical average in the $0.70 to $0.75 range. - William Blair, 11/07/2022 " 34 CONFIDENTIAL Evercore and JP Morgan reduced their price targets from $6.00 to $5.50 since preliminary discussion materials dated 10/28/22

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Last Twelve Months Last Six Months Last Three Months Since Release of 3Q Earnings (11/2/22 After Hours) Volume1: 15.2 million (67.8% of float)2 Twins Selected Historical Trading Activity Volume1: 9.0 million (40.0% of float)2 Volume1: 35.1 million (156.7% of float)2 Volume1: 4.7 million (20.8% of float)2 Based on VWAP volume, per Bloomberg. Public float calculated as total shares less primarily shares held by Angels and Company insiders. ADTV refers to Average Daily Trading Volume. VWAP refers to Volume-Weighted Average Price. Selected VWAP Data 52-Week Range 12-Month 9-Month 6-Month 3-Month 30-Day 20-Day 10-Day 5-Day $2.18 – $9.16 $4.77 $4.42 $4.10 $3.02 $2.64 $2.60 $2.87 $2.96 Current Trading Stats: Float2: 22.4mm (43.8% of common) 90-Day ADTV: 138k 90-Day Avg. Value Traded: $0.5mm 12.6% 34.3% 17.6% 6.2% 15.1% 7.8% 6.2% 0.2% $2.00- $3.00- $4.00- $5.00- $6.00- $7.00- $8.00- $9.00- $2.00- $3.00- $4.00- $5.00- $6.00- $7.00- $8.00- $9.00- $2.99 $3.99 $4.99 $5.99 $6.99 $7.99 $8.99 $9.99 $2.99 $3.99 $4.99 $5.99 $6.99 $7.99 $8.99 $9.99 29.1% 29.9% 11.7% 10.2% 19.1% 0.0% 0.0% 0.0% 49.3% 50.7% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% $2.00- $2.99 $3.00- $3.99 $4.00- $4.99 $5.00- $5.99 $6.00- $6.99 $7.00- $7.99 $8.00- $8.99 $9.00- $9.99 95.0% Source: Bloomberg as of 12/13/22. CONFIDENTIAL 36 5.0% 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% $2.00- $2.99 $3.00- $3.99 $4.00- $4.99 $5.00- $5.99 $6.00- $6.99 $7.00- $7.99 $8.00- $8.99 $9.00- $9.99

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Twins Ownership Summary (shares in millions) Reflects basic shares of common stock outstanding of 51,220,485 as of 11/4/22 per the Company's Form 10-Q for the period ended 9/30/22. Public float calculated as total shares less primarily shares held by Angels and Company insiders. Holder Shares % Outstanding Voting Interests Public Float2 Angels 24.0 46.9% -- -- Baker, Blake A. 4.3 8.5% 16.0% 19.4% Royce & Associates, LP 3.9 7.6% 14.3% 17.4% O'Brien, Andrew Michael (Executive Chairman of the Board) 3.5 6.9% 12.9% NA Vaughan Nelson Investment Management, L.P. 1.4 2.7% 5.1% 6.2% BlackRock, Inc. 1.2 2.3% 4.3% 5.2% Lee, Steven Barry (Senior VP & Director) 1.1 2.1% 3.9% NA The Vanguard Group, Inc. 0.9 1.7% 3.2% 3.9% William Blair Investment Management, LLC 0.6 1.2% 2.2% 2.7% Hotchkis and Wiley Capital Management, LLC 0.5 1.0% 1.9% 2.3% GW&K Investment Management, LLC 0.5 1.0% 1.8% 2.2% Other Current / Former Directors and Executive Officers 0.2 0.4% 0.7% NA Other 9.1 17.9% 33.6% 40.8% Total1 51.2 100.0% 100.0% 100.0% Voting Interest Sources: Bloomberg, press releases and public filings. CONFIDENTIAL 37 % of Non-Angels % of

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Estimated Twins Shareholder Cost Basis Current Share Price: $3.15 1. Cost basis average, per Capital IQ, based on volume weighted average price during the quarterly periods in which shares were purchased or sold Source: Capital IQ as of 12/13/22 Ownership 46.9% 8.5% 7.6% 6.9% 2.7% 2.3% 2.1% 1.7% 1.2% 1.0% 1.0% 0.8% 0.8% 0.8% 0.7% 0.7% 0.6% 0.6% 0.5% 0.4% 0.4% 0.4% 0.4% 0.4% 0.3% Cumulative Ownership 46.9% 55.4% 63.0% 69.8% 72.5% 74.8% 76.9% 78.6% 79.8% 80.8% 81.7% 82.5% 83.3% 84.1% 84.8% 85.6% 86.2% 86.8% 87.3% 87.7% 88.1% 88.5% 88.8% 89.2% 89.5% Ownership of Non-Angels Shares NA 16.0% 14.3% 12.9% 5.1% 4.3% 3.9% 3.2% 2.2% 1.9% 1.8% 1.5% 1.5% 1.5% 1.4% 1.3% 1.2% 1.1% 1.0% 0.7% 0.7% 0.7% 0.7% 0.7% 0.6% Average Cost Basis: $10.59 Top 25 Shareholders1 NA 38 CONFIDENTIAL NA $15.02 NA $16.32 $15.24 $14.51 NA $15.20 $7.63 $5.91 $5.91 $5.78 $15.24 $11.93 $13.82 $16.32 $13.33 $4.75 $5.07 $4.75 $6.66 $14.81 $6.73 $7.38 Angels Baker, Blake A. Royce & Associates, LP O'Brien, Andrew Michael Vaughan Nelson Investment Management, L.P. BlackRock, Inc. Lee, Steven Barry The Vanguard Group, Inc. William Blair Investment Management, LLC Hotchkis and Wiley Capital Management, LLC GW&K Investment Management, LLC Thompson, Siegel & Walmsley LLC Millennium Management LLC Principal Global Investors, LLC Brandywine Global Investment Management, LLC Geode Capital Management, LLC Janus Henderson Group plc State Street Global Advisors, Inc. Federated Hermes, Inc. Assenagon Asset Management S.A. Jacobs Levy Equity Management Inc Two Sigma Investments, LP Northern Trust Global Investments Two Sigma Advisers, LP MBA Advisors LLC

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Twins Recent Shareholder Movements Top Shareholders (1%+ Ownership) (shares in millions and dollars in actuals) Latest % of % of Angels 24.024 0.000 0.000 (4.250) 0.000 0.000 0.000 0.000 0.000 % of Holdings Traded 0.0% 0.0% (15.0%) 0.0% 0.0% 0.0% 0.0% 0.0% Baker, Blake A. 4.341 16.0% 19.4% 0.000 0.000 (0.668) 0.000 (0.100) 0.000 0.000 0.000 % of Holdings Traded 0.0% 0.0% (13.1%) 0.0% (2.3%) 0.0% 0.0% 0.0% Royce & Associates, LP 3.891 14.3% 17.4% 0.000 0.238 2.525 1.681 (0.379) 0.695 (0.892) 0.023 % of Holdings Traded 0.0% New Position 1062.9% 60.9% (8.5%) 17.1% (18.7%) 0.6% O'Brien, Andrew Michael 3.509 12.9% NA 0.000 0.000 (0.616) 0.000 0.025 0.000 0.000 0.000 % of Holdings Traded 0.0% 0.0% (15.0%) 0.0% 0.7% 0.0% 0.0% 0.0% Vaughan Nelson Investment Management, L.P. 1.383 5.1% 6.2% 0.000 0.000 1.529 (0.028) 0.044 (0.050) (0.110) (0.001) % of Holdings Traded 0.0% 0.0% New Position (1.8%) 2.9% (3.3%) (7.4%) (0.1%) BlackRock, Inc. 1.156 4.3% 5.2% 0.071 0.069 0.335 (0.008) 0.078 (0.016) 0.123 (0.028) % of Holdings Traded 13.3% 11.5% 49.9% (0.8%) 7.8% (1.4%) 11.6% (2.3%) Lee, Steven Barry 1.069 3.9% NA 0.000 0.000 (0.115) 0.000 0.014 0.008 0.011 0.000 % of Holdings Traded 0.0% 0.0% (10.0%) 0.0% 1.4% 0.7% 1.1% 0.0% The Vanguard Group, Inc. 0.879 3.2% 3.9% 0.155 0.181 0.187 0.005 0.014 (0.153) 0.196 0.009 % of Holdings Traded 54.3% 41.0% 30.2% 0.6% 1.7% (18.5%) 29.2% 1.1% William Blair Investment Management, LLC 0.608 2.2% 2.7% 0.158 0.680 0.131 (0.234) (0.068) 0.038 (0.100) (0.055) % of Holdings Traded 272.5% 315.0% 14.6% (22.8%) (8.6%) 5.3% (13.1%) (8.3%) Hotchkis and Wiley Capital Management, LLC 0.509 1.9% 2.3% 0.000 0.000 0.000 0.000 0.284 0.045 0.053 0.127 % of Holdings Traded 0.0% 0.0% 0.0% 0.0% New Position 15.7% 16.1% 33.3% GW&K Investment Management, LLC 0.501 1.8% 2.2% 0.000 0.000 0.000 0.000 0.000 0.000 0.522 (0.021) % of Holdings Traded 0.0% 0.0% 0.0% 0.0% 0.0% 0.0% New Position (4.0%) VWAP During Quarter $13.21 $16.08 $15.94 $10.00 $8.95 $4.61 $6.02 $4.50 High Closing Stock Price During Quarter $15.45 $17.50 $17.95 $15.28 $10.70 $8.86 $7.30 $6.40 Low Closing Stock Price During Quarter $10.11 $13.10 $14.34 $9.00 $8.08 $3.35 $4.03 $3.34 VWAP refers to Volume-Weighted Average Price. Sources: Bloomberg, Capital IQ and public filings. 39 CONFIDENTIAL Net Shares Added / (Deducted) by Quarter Holder Shareholdings Non-Angels Public Float Q4 2020 Q1 2021 Q2 2021 Q3 2021 Q4 2021 Q1 2022 Q2 2022 Q3 2022

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This presentation, and any supplemental information (written or oral) or other documents provided in connection therewith (collectively, the "materials"), are provided solely for the information of the Special Committee (the "Committee") of the Board of Directors (the "Board") of Twins (the "Company") by Houlihan Lokey in connection with the Committee's consideration of a potential transaction (the "Transaction") involving the Company. This presentation is incomplete without reference to, and should be considered in conjunction with, any supplemental information provided by and discussions with Houlihan Lokey in connection therewith. Any defined terms used herein shall have the meanings set forth herein, even if such defined terms have been given different meanings elsewhere in the materials. The materials are for discussion purposes only. Houlihan Lokey expressly disclaims any and all liability, whether direct or indirect, in contract or tort or otherwise, to any person in connection with the materials. The materials were prepared for specific persons familiar with the business and affairs of the Company for use in a specific context and were not prepared with a view to public disclosure or to conform with any disclosure standards under any state, federal or international securities laws or other laws, rules or regulations, and none of the Committee, the Company or Houlihan Lokey takes any responsibility for the use of the materials by persons other than the Committee. The materials are provided on a confidential basis solely for the information of the Committee and may not be disclosed, summarized, reproduced, disseminated or quoted or otherwise referred to, in whole or in part, without Houlihan Lokey's express prior written consent. Notwithstanding any other provision herein, the Company (and each employee, representative or other agent of the Company) may disclose to any and all persons without limitation of any kind, the tax treatment and tax structure of any transaction and all materials of any kind (including opinions or other tax analyses, if any) that are provided to the Company relating to such tax treatment and structure. However, any information relating to the tax treatment and tax structure shall remain confidential (and the foregoing sentence shall not apply) to the extent necessary to enable any person to comply with securities laws. For this purpose, the tax treatment of a transaction is the purported or claimed U.S. income or franchise tax treatment of the transaction and the tax structure of a transaction is any fact that may be relevant to understanding the purported or claimed U.S. income or franchise tax treatment of the transaction. If the Company plans to disclose information pursuant to the first sentence of this paragraph, the Company shall inform those to whom it discloses any such information that they may not rely upon such information for any purpose without Houlihan Lokey's prior written consent. Houlihan Lokey is not an expert on, and nothing contained in the materials should be construed as advice with regard to, legal, accounting, regulatory, insurance, tax or other specialist matters. Houlihan Lokey's role in reviewing any information was limited solely to performing such a review as it deemed necessary to support its own advice and analysis and was not on behalf of the Committee. The materials necessarily are based on financial, economic, market and other conditions as in effect on, and the information available to Houlihan Lokey as of, the date of the materials. Although subsequent developments may affect the contents of the materials, Houlihan Lokey has not undertaken, and is under no obligation, to update, revise or reaffirm the materials, except as may be expressly contemplated by Houlihan Lokey's engagement letter. The materials are not intended to provide the sole basis for evaluation of the Transaction and do not purport to contain all information that may be required. The materials do not address the underlying business decision of the Company or any other party to proceed with or effect the Transaction, or the relative merits of the Transaction as compared to any alternative business strategies or transactions that might be available for the Company or any other party. The materials do not constitute any opinion, nor do the materials constitute a recommendation to the Board, the Committee, the Company, any security holder of the Company or any other party as to how to vote or act with respect to any matter relating to the Transaction or otherwise or whether to buy or sell any assets or securities of any company. Houlihan Lokey's only opinion is the opinion, if any, that is actually delivered to the Committee. In preparing the materials Houlihan Lokey has acted as an independent contractor and nothing in the materials is intended to create or shall be construed as creating a fiduciary or other relationship between Houlihan Lokey and any party. The materials may not reflect information known to other professionals in other business areas of Houlihan Lokey and its affiliates. The preparation of the materials was a complex process involving quantitative and qualitative judgments and determinations with respect to the financial, comparative and other analytic methods employed and the adaption and application of these methods to the unique facts and circumstances presented and, therefore, is not readily susceptible to partial analysis or summary description. Furthermore, Houlihan Lokey did not attribute any particular weight to any analysis or factor considered by it, but rather made qualitative judgments as to the significance and relevance of each analysis and factor. Each analytical technique has inherent strengths and weaknesses, and the nature of the available information may further affect the value of particular techniques. Accordingly, the analyses contained in the materials must be considered as a whole. Selecting portions of the analyses, analytic methods and factors without considering all analyses and factors could create a misleading or incomplete view. The materials reflect judgments and assumptions with regard to industry performance, general business, economic, regulatory, market and financial conditions and other matters, many of which are beyond the control of the participants in the Transaction. Any estimates of value contained in the materials are not necessarily indicative of actual value or predictive of future results or values, which may be significantly more or less favorable. Any analyses relating to the value of assets, businesses or securities do not purport to be appraisals or to reflect the prices at which any assets, businesses or securities may actually be sold. The materials do not constitute a valuation opinion or credit rating. The materials do not address the consideration to be paid or received in, the terms of any arrangements, understandings, agreements or documents related to, or the form, structure or any other portion or aspect of, the Transaction or otherwise. Furthermore, the materials do not address the fairness of any portion or aspect of the Transaction to any party. In preparing the materials, Houlihan Lokey has not conducted any physical inspection or independent appraisal or evaluation of any of the assets, properties or liabilities (contingent or otherwise) of the Company or any other party and has no obligation to evaluate the solvency of the Company or any other party under any law. 39 CONFIDENTIAL Disclaimer

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All budgets, projections, estimates, financial analyses, reports and other information with respect to operations reflected in the materials have been prepared by management of the relevant party or are derived from such budgets, projections, estimates, financial analyses, reports and other information or from other sources, which involve numerous and significant subjective determinations made by management of the relevant party and/or which such management has reviewed and found reasonable. The budgets, projections and estimates contained in the materials may or may not be achieved and differences between projected results and those actually achieved may be material. Houlihan Lokey has relied upon representations made by management of the Company and other participants in the Transaction that such budgets, projections and estimates have been reasonably prepared in good faith on bases reflecting the best currently available estimates and judgments of such management (or, with respect to information obtained from public sources, represent reasonable estimates), and Houlihan Lokey expresses no opinion with respect to such budgets, projections or estimates or the assumptions on which they are based. Houlihan Lokey has discussed the Company's business with the management of the Company and Houlihan Lokey does not make any representation, express or implied, as to the sufficiency or adequacy of its financial analysis or the scope thereof for any particular purpose. Houlihan Lokey has assumed and relied upon the accuracy and completeness of the financial and other information provided to, discussed with or reviewed by it without (and without assuming responsibility for) independent verification of such information, makes no representation or warranty (express or implied) in respect of the accuracy or completeness of such information and has further relied upon the assurances of the Company and other participants in the Transaction that they are not aware of any facts or circumstances that would make such information inaccurate or misleading. In addition, Houlihan Lokey has relied upon and assumed, without independent verification, that there has been no change in the business, assets, liabilities, financial condition, results of operations, cash flows or prospects of the Company or any other participant in the Transaction since the respective dates of the most recent financial statements and other information, financial or otherwise, provided to, discussed with or reviewed by Houlihan Lokey that would be material to its analyses, and that the final forms of any draft documents reviewed by Houlihan Lokey will not differ in any material respect from such draft documents. The materials are not an offer to sell or a solicitation of an indication of interest to purchase any security, option, commodity, future, loan or currency. The materials do not constitute a commitment by Houlihan Lokey or any of its affiliates to underwrite, subscribe for or place any securities, to extend or arrange credit, or to provide any other services. In the ordinary course of business, certain of Houlihan Lokey's affiliates and employees, as well as investment funds in which they may have financial interests or with which they may co-invest, may acquire, hold or sell, long or short positions, or trade or otherwise effect transactions, in debt, equity, and other securities and financial instruments (including loans and other obligations) of, or investments in, the Company, any Transaction counterparty, any other Transaction participant, any other financially interested party with respect to any transaction, other entities or parties that are mentioned in the materials, or any of the foregoing entities' or parties' respective affiliates, subsidiaries, investment funds, portfolio companies and representatives (collectively, the "Interested Parties"), or any currency or commodity that may be involved in the Transaction. Houlihan Lokey provides mergers and acquisitions, restructuring and other advisory and consulting services to clients, which may have in the past included, or may currently or in the future include, one or more Interested Parties, for which services Houlihan Lokey has received, and may receive, compensation. Although Houlihan Lokey in the course of such activities and relationships or otherwise may have acquired, or may in the future acquire, information about one or more Interested Parties or the Transaction, or that otherwise may be of interest to the Board, the Committee, or the Company, Houlihan Lokey shall have no obligation to, and may not be contractually permitted to, disclose such information, or the fact that Houlihan Lokey is in possession of such information, to the Board, the Committee, or the Company or to use such information on behalf of the Board, the Committee, or the Company. Houlihan Lokey's personnel may make statements or provide advice that is contrary to information contained in the materials. 39 CONFIDENTIAL Disclaimer (cont.)

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![](ny20006673x2_exc-2slide42.jpg)

CONFIDENTIAL 42 CORPORATE FINANCE FINANCIAL RESTRUCTURING FINANCIAL AND VALUATION ADVISORY HL.com

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## Ex-99.(D)(3)

#### Exhibit (d)(3)

#### Altaris Health Partners V, L.P.

#### Altaris Health Partners V-A, L.P.

#### 10 E. 53<sup>rd</sup> Street, 31<sup>st</sup> Floor

#### New York, NY 10022

December 15, 2022

Treadstone Parent Inc.

c/o Altaris, LLC

10 East 53<sup>rd</sup> Street, 31st Floor

New York, NY 10022

Re:&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Equity Commitment</u>

Ladies and Gentlemen:

Altaris Health Partners V, L.P., a Delaware limited partnership and Altaris Health Partners V-A, L.P., a Delaware limited partnership (the foregoing together, the "<u>Investors</u>", and each of the Investors individually, an "<u>Investor</u>"), are pleased to offer, subject to and on the terms and conditions hereof, the Commitment (as defined below) to Treadstone Parent Inc., a Delaware corporation ("<u>Parent</u>"), which has been formed in connection with the entry into that certain Agreement and Plan of Merger, dated as of the date hereof (as it may be amended, supplemented or modified from time to time, the "<u>Merger Agreement</u>"), by and among Parent, Treadstone Merger Sub Inc., a Delaware corporation and wholly-owned subsidiary of Parent ("<u>Merger Sub</u>"), and Trean Insurance Group, Inc., a Delaware corporation (the "<u>Company</u>"). Capitalized terms used but not defined in this letter agreement shall have the meanings ascribed to such terms in the Merger Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1. Each Investor, severally (and not jointly or jointly and severally) hereby agrees that, subject to and on the terms and conditions set forth in this letter agreement,
 such Investor shall, or shall cause one or more of its assignees permitted by the terms and conditions of this letter agreement to, contribute to Parent the amount set forth beside such Investor's name on <u>Schedule A</u> hereto (for each Investor, such Investor's " <u>Commitment</u> "), solely for the
 purpose of allowing Parent and/or Merger Sub to fund, along with the Company Cash on Hand, (i) the payment of the aggregate Transaction Consideration for the acquisition or conversion of all shares of Company Common Stock (other than the
 Cancelled Shares) pursuant to the Merger (assuming no Dissenting Shares) and all consideration payable pursuant to the Merger Agreement in respect of Company Stock Awards, in each case, to the extent required to be paid pursuant to Sections
 2.1 and 2.3 of the Merger Agreement (as applicable) and (ii) the payment of all fees and expenses required to be paid by Parent or Merger Sub at the Closing in connection with the transactions contemplated by the Merger Agreement (clauses (i)
 and (ii), collectively, the " <u>Transaction Payments</u> "). Each Investor may effect its contribution of the Commitment to Parent directly or indirectly
 through one or more affiliated entities, and any Investor may allocate a portion of the Commitment to co-investors, including such Investor's Affiliates, <u>provided</u> that such allocation shall not relieve such Investor of its obligations hereunder and such Investor shall remain liable for any portion of
 its Commitment not actually funded by such co-investor. No Investor shall, under any circumstances, be obligated to contribute to Parent more than such Investor's respective Commitment (and only on and subject to the terms and conditions
 contained herein), and the cumulative liability of each Investor under this letter agreement shall not exceed such Investor's respective Commitment. The amount of the Commitment to be funded by each Investor under this letter agreement at or
 immediately prior to the Closing may be reduced pro rata on a dollar-for-dollar basis (a) for the amount of purchases, directly or indirectly, by co-investors (including Affiliates of each Investor), of equity securities of Parent solely for
 the purpose of funding a portion of the Transaction Payments and (b) as agreed to by the Investors in the event that Parent does not require such amount to fund a portion of the Transaction Payments; <u>provided</u>, in each case, that any such reduction shall occur solely in connection with the Closing and the simultaneous payment of all Transaction Payments required to be paid by
 Parent and/or Merger Sub. In no event shall any Investor or its permitted assignees have any obligation to contribute or otherwise provide any funds to Parent, the Company or any other Person, except as provided in this letter agreement or
 in the Limited Guarantee, subject to the terms, conditions and limitations set forth herein and therein, as applicable.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2. Each Investor's several (and not joint or joint and several) obligation under this letter agreement to, or to cause one or more of its assignees permitted by the terms
 and conditions of this letter agreement to, fund its respective Commitment is subject to (a) the execution and delivery of the Merger Agreement by the parties thereto, (b) the satisfaction or waiver (to the extent permitted by the Merger
 Agreement) of each of the conditions to Parent and Merger Sub's obligations to consummate the transactions contemplated by the Merger Agreement set forth in Sections 6.1 and 6.2 thereof (other than those conditions that by their nature are to
 be satisfied at or immediately prior to the Closing, but subject to the satisfaction or waiver of such conditions), and (c) the substantially concurrent consummation of the Closing in accordance with the terms of the Merger Agreement. For
 the avoidance of doubt, the obligations of Parent under the Merger Agreement shall be determined in accordance with the terms thereof, and nothing in this letter agreement shall amend, modify, or waive any of the terms of the Merger Agreement
 or any defenses that Parent may have to any assertion of liability or obligation against it under the Merger Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;3. Each Investor's obligation under this letter agreement to, or to cause one or more of its assignees permitted by the terms and conditions of this letter agreement to,
 fund its respective Commitment shall automatically and immediately terminate upon the earliest to occur of (a) the consummation of the Closing and the payment of the Transaction Payments in accordance with the Merger Agreement (at which time
 the obligation shall be discharged in full), (b) the valid termination of the Merger Agreement in accordance with its terms, (c) the valid termination of the Limited Guarantee in accordance with its terms, (d) a Chosen Court (as defined
 below) having declined in a final and non-appealable decision to specifically enforce the obligations of Parent and/or Merger Sub to cause the Commitment to be funded or to effect the Closing pursuant to a claim of specific performance or
 other equitable relief brought against Parent and/or Merger Sub pursuant to Section 8.5 of the Merger Agreement or (d) the Company or any of its Affiliates, Subsidiaries, officers or Non-Recused Directors, or any other Person acting on behalf
 or at the request of the Company or any of its Affiliates, Subsidiaries, officers or Non-Recused Directors, filing any claim or action against any Investor or any Investor Affiliate (as defined below) in connection with the Merger Agreement,
 this letter agreement, the Limited Guarantee or any transaction contemplated hereby or thereby, other than as expressly permitted by <u>Section 6</u> of this
 letter agreement, Sections 3(b) and 8 of the Limited Guarantee, Section 2 or 18 of the Support Agreement, and the Confidentiality Agreement. For purposes of this Agreement, " <u>Affiliates</u> " of the Company shall not include the Sponsor, the Specified Stockholders and their respective controlled Affiliates (other than the Company and its Subsidiaries).

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4. Neither the rights nor the obligations of the Company, any Investor or Parent under this letter agreement may be assigned, transferred or delegated, in whole or in
 part, directly or indirectly, by operation of Law or otherwise, without the prior written consent of the Company (as a third-party beneficiary hereof), each Investor and Parent, except as provided in the following sentence, and any attempted
 assignment, transfer or delegation thereof shall be null and void and of no force or effect. Notwithstanding the foregoing, the obligation of any Investor under this letter agreement to fund one or more portions of its respective Commitment
 may be assigned by such Investor to any equity co-investor and/or its Affiliates and affiliated funds; <u>provided</u> that any such assignment shall not relieve such Investor of its obligations under this letter agreement and such Investor shall remain liable for any portion of its
 Commitment not actually funded by such co-investor or Affiliate. This letter agreement (including any document or instrument delivered in connection herewith), together with the Limited Guarantee, the Merger Agreement, the Support Agreement,
 and the Confidentiality Agreement constitute the entire agreement among the parties hereto and supersede any prior understandings, agreements or representations by or among the parties hereto, written or oral, with respect to the subject
 matter hereof, and the parties hereto specifically disclaim reliance on any such prior understandings, agreements or representations to the extent not embodied in this letter agreement or any of the foregoing specifically identified
 documents.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;5. Notwithstanding anything to the contrary that may be expressed or implied in this letter agreement or any document or instrument delivered in connection herewith, each
 party hereto, by its acceptance of the benefits hereof, covenants, agrees and acknowledges that no Person, other than the Investors and their respective permitted assigns, has liabilities, commitments or other obligations hereunder and that,
 notwithstanding that each Investor is a limited partnership, no Person has any remedy, recourse or right of recovery hereunder (or any document or instrument delivered in connection herewith or in connection with the Merger Agreement) or in
 respect of any oral or written representation made or alleged to be made in connection herewith (or therewith) against, or contribution hereunder from, any Investor Affiliate (as defined below), through any Investor, Parent, Merger Sub or
 otherwise, whether by or through attempted piercing of the corporate (or limited liability company or partnership) veil or similar action, by the enforcement of any assessment or by any legal or equitable proceeding, by virtue of any statute,
 regulation or applicable Law, by or through a claim by or on behalf of any Investor, Parent or Merger Sub against any Investor or any Investor Affiliate, or otherwise. For purposes of this letter agreement, the term " <u>Investor Affiliate</u> " means any past, present or future director, officer, employee, incorporator, member, general or limited partner, manager, direct or indirect
 equityholder, management company, controlling Person, Affiliate, agent, attorney, or representative of, and any financial advisor or lender to, any Investor or of any of the foregoing (it being understood that the term Investor Affiliate
 shall not include any Investor, Parent or Merger Sub or any of their respective permitted assigns (in their capacity as such)). For the avoidance of doubt, neither Investor nor any Investor Affiliate is a party to, or has any obligations
 under, the Merger Agreement. Without limiting the generality of this <u>Section 5</u>, Parent shall not have any remedies against any Investor or any
 Investor Affiliate for any loss, damage or recovery of any kind (including consequential, indirect or punitive damages, and whether at Law, in equity, based on contract, tort or otherwise) arising under or in connection with any breach of the
 Merger Agreement or the failure of the transactions contemplated thereby to be consummated or otherwise in connection with the transactions contemplated thereby or in respect of any oral representations made or alleged to be made in
 connection therewith; provided, however, that the foregoing shall not limit Parent's or the Company's rights and remedies (i) to enforce the express terms of this letter agreement against the Investors pursuant to and to the extent permitted
 by <u>Section 6</u> or (ii) against any Investor pursuant to the Limited Guarantee.

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6. <br>

a) Except as otherwise set forth in <u>Section 6(b)</u>, (i) the Permitted Claims (as defined in the Limited Guarantee), and (ii) the remedies of the Company under the Confidentiality Agreement and the Support Agreement against the counterparties thereto, shall be the sole and exclusive remedies available to the Company and all of its Affiliates and equityholders against any Investor or any Investor Affiliate in respect of any liabilities or obligations arising under, or in connection with, the Merger Agreement, or the transactions contemplated thereby, whether or not Parent's breach is caused by any Investor's breach of its obligations under this letter agreement. Except as otherwise set forth in <u>Section 6(b)</u>, this letter agreement is solely for the benefit of Parent and is not intended to, nor does it, confer any benefits on, or create any rights or remedies in favor of, any Person other than Parent. Except as set forth in <u>Section 6(b)</u>, this letter agreement may only be enforced by Parent. In no event shall any of Parent's creditors have any right to enforce this letter agreement or to cause Parent to enforce this letter agreement.

b) The Company is hereby made a third party beneficiary of this letter agreement solely for the purpose and to the extent of the Company seeking specific performance of the rights granted to Parent hereby to cause each Investor to fund its respective Commitment to the extent that the conditions to the funding of such Commitment set forth in <u>Section 1</u> hereof are satisfied and the Company is expressly permitted to do so by Section 8.5 of the Merger Agreement and for no other purpose whatsoever (including, without limitation, any claim for monetary damages hereunder or under the Merger Agreement or any other document or instrument delivered in connection therewith or based on any theory, whether in law, equity, contract or tort), provided, that the Company may not directly enforce the Investors' obligations to fund their respective Commitments unless the Company has been granted from a court of competent jurisdiction a final and non-appealable order of specific performance or similar injunctive relief against Parent or Merger Sub pursuant to, and in accordance with, Section 8.5 of the Merger Agreement, requiring Parent to cause the Investors to fund their respective Commitments.

c) The exercise by Parent or the Company of any right to enforce this letter agreement pursuant to this <u>Section 6</u> does not give rise to any other remedies, monetary or otherwise, such remedies being limited, as described in this letter agreement, to those provided under the Merger Agreement and this letter agreement.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;7. Other than as required by Law or the rules of any national securities exchange or in connection with the enforcement of, or any claims or causes of action related to or
 arising in connection with, this letter agreement in accordance with the terms hereof or the Merger Agreement, each of the parties hereto agrees that it will not, nor will it permit its respective advisors or Affiliates to, disclose to any
 Person the contents of this letter agreement, other than to the respective advisors or Affiliates of the parties hereto (including, as regards any Investor, such Investor's Investor Affiliates), which advisors or Affiliates (or, as regards
 any Investor, such Investor's Investor Affiliates) shall be required to maintain the confidentiality of this letter agreement in accordance herewith. Without limiting the foregoing, each Investor and Investor Affiliate shall have the right
 to make such disclosures as are required by any Governmental Entity having jurisdiction over such Investor or its Investor Affiliates, and such Investor or Investor Affiliate shall not be required to provide any notice of such disclosure.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;8. Each Investor hereby represents and warrants to Parent severally (and not jointly or jointly and severally) as to itself that: (a) such Investor is a limited
 partnership duly organized, validly existing and in good standing under the Laws of the State of Delaware, and such Investor has all requisite organizational power and authority to execute, deliver and perform this letter agreement, (b) the
 execution, delivery and performance of this letter agreement have been duly and validly authorized by all necessary action and do not contravene any provision of such Investor's partnership agreement or similar organizational documents or any
 Law or contractual restriction binding on such Investor or its assets, (c) except for such consents, approvals, authorizations, permits of, filings with and notifications to, any Governmental Entity contemplated by the Merger Agreement to be
 obtained or made after the date hereof, all consents, approvals, authorizations, permits of, filings with and notifications to, any Governmental Entity necessary for the due execution, delivery and performance of this letter agreement by such
 Investor have been obtained or made and all conditions thereof have been duly complied with, and no other action by, and no notice to or filing with, any Governmental Entity is required in connection with the execution, delivery or
 performance of this letter agreement, (d) this letter agreement constitutes a legal, valid and binding obligation of such Investor enforceable against such Investor in accordance with its terms, subject to the Bankruptcy and Equity Exception,
 (e) such Investor has, and will continue to have for so long as this letter agreement shall remain in effect, sufficient liquid and unencumbered assets and the financial capacity to pay and perform its obligations under this letter agreement,
 and (f) such Investor's Commitment is less than the maximum amount that such Investor is permitted to invest in any one portfolio investment pursuant to the terms of its constituent documents or otherwise.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;9. This letter agreement, and all claims or causes of action (whether at Law, in contract or in tort or otherwise) that may be based upon, arise out of or relate to this
 letter agreement or the negotiation, execution or performance hereof, shall be governed by and construed in accordance with the Laws of the State of Delaware, without giving effect to any choice or conflict of law provision or rule (whether
 of the State of Delaware or any other jurisdiction) that would cause the application of the Laws of any jurisdiction other than the State of Delaware.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;10. Each of the parties hereto irrevocably agrees that any legal suit, action or proceeding with respect to this letter agreement and the rights and obligations arising
 hereunder, or for recognition and enforcement of any judgment in respect of this letter agreement and the rights and obligations arising hereunder brought by the other party hereto or its successors or assigns, shall be brought and determined
 exclusively in the Delaware Court of Chancery and any state appellate court therefrom within the State of Delaware (or, if the Delaware Court of Chancery declines to accept jurisdiction over a particular matter, any state or federal court
 within the State of Delaware) (collectively, the " <u>Chosen Courts</u> "). Each of the parties hereto hereby irrevocably submits with regard to any such suit,
 action or proceeding for itself and in respect of its property, generally and unconditionally, to the personal jurisdiction of the Chosen Courts and agrees that it will not bring any action relating to this letter agreement or the
 transactions contemplated thereby in any court other than the Chosen Courts. Each of the parties hereto hereby irrevocably waives, and agrees not to assert, by way of motion, as a defense, counterclaim or otherwise, in any suit, action or
 proceeding with respect to this letter agreement, (i) any claim that it is not personally subject to the jurisdiction of the Chosen Courts, (ii) any claim that it or its property is exempt or immune from jurisdiction of any such Chosen Court
 or from any legal process commenced in such Chosen Courts (whether through service of notice, attachment prior to judgment, attachment in aid of execution of judgment, execution of judgment or otherwise) and (iii) to the fullest extent
 permitted by applicable Law, any claim that (A) the suit, action or proceeding in such Chosen Court is brought in an inconvenient forum, (B) the venue of such suit, action or proceeding is improper or (C) this letter agreement, or the subject
 matter hereof, may not be enforced in or by such Chosen Courts. To the fullest extent permitted by applicable Law, each of the parties hereto hereby consents to process being served by any party hereto in any suit, action or proceeding by
 delivery of a copy thereof in accordance with the provisions of Section 8.7 of the Merger Agreement (and the address for delivery to each Investor shall be the address for Parent as set forth in Section 8.7 of the Merger Agreement).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;11. EACH OF THE PARTIES HERETO IRREVOCABLY WAIVES ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS LETTER AGREEMENT OR THE
 TRANSACTIONS CONTEMPLATED HEREBY. EACH OF THE PARTIES HERETO CERTIFIES AND ACKNOWLEDGES THAT (A) NO REPRESENTATIVE, AGENT OR ATTORNEY OF THE OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT
 OF LITIGATION, SEEK TO ENFORCE THE FOREGOING WAIVER, (B) EACH SUCH PARTY UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (C) EACH SUCH PARTY MAKES THIS WAIVER VOLUNTARILY AND (D) EACH SUCH PARTY HAS BEEN INDUCED TO ENTER INTO
 THIS LETTER AGREEMENT BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS <u>SECTION 11</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;12. This letter agreement may not be amended, and no provision of this letter agreement may be waived or modified, without the prior written consent of each party hereto
 and the Company (as a third-party beneficiary hereof), and any attempted amendment, waiver or modification hereof without such prior written consent shall be null and void and of no force or effect.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;13. This letter agreement may be executed in one or more counterparts, each of which shall be deemed to be an original, with the same effect as if the signatures thereto
 and hereto were upon the same instrument, and shall become effective when one or more counterparts have been signed by each of the parties hereto and delivered (by telecopy, electronic delivery or otherwise) to the other parties. Signatures
 to this letter agreement transmitted by facsimile transmission, by electronic mail in "portable document format" (".pdf") form, or by any other electronic means intended to preserve the original graphic and pictorial appearance of a document,
 will have the same effect as physical delivery of the paper document bearing the original signature.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;14. For all purposes hereunder, the Company (prior to the Effective Time) and the Company Board of Directors, as applicable, shall act, including with respect to the
 granting of any consent, permission or waiver or the making of any determination, only as directed in writing by the Special Committee or its designees.

[*signature page follows*]

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If this letter agreement is agreeable to you, please so indicate by signing in the space indicated below.

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| | |
|:---|:---|
| Very truly yours, | Very truly yours, |
| **<u>INVESTORS:</u>** | **<u>INVESTORS:</u>** |
| **ALTARIS HEALTH PARTNERS V, L.P.** | **ALTARIS HEALTH PARTNERS V, L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/George Aitken-Davies |
| Name: | George Aitken-Davies |
| Title: | Authorized Signatory |
| **ALTARIS HEALTH PARTNERS V-A, L.P.** | **ALTARIS HEALTH PARTNERS V-A, L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/George Aitken-Davies |
| Name: | George Aitken-Davies |
| Title: | Authorized Signatory |

---

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Accepted and agreed as of

the date first written above:

#### PARENT :

#### TREADSTONE PARENT INC.

---

| | | |
|:---|:---|:---|
| By: | /s/ Daniel Tully | /s/ Daniel Tully |
|  | Name: | Daniel Tully |
|  | Title: | Authorized Signatory |

---

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#### Schedule A

---

| | |
|:---|:---|
| **<u>Investor</u>** | **<u>Commitment</u>** |
| Altaris Health Partners V, L.P. | $119315000 |
| Altaris Health Partners V-A, L.P. | $55685000 |
| **Total:** | $175000000 |

---

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## Ex-99.(D)(4)

#### Exhibit (d)(4)

#### Limited Guarantee

This Limited Guarantee, dated as of December 15, 2022 (this "<u>Limited</u>**<u> </u>**<u>Guarantee</u>"), is made by each of Altaris Health Partners V, L.P., a Delaware limited partnership, and Altaris Health Partners V-A, L.P., a Delaware limited partnership (each a "<u>Guarantor</u>" and together the "<u>Guarantors</u>"), in favor of Trean Insurance Group, Inc., a Delaware corporation (the "<u>Guaranteed Party</u>"). Capitalized terms used but not otherwise defined herein shall have the respective meanings given to them in the Merger Agreement (as defined below).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Limited Guarantee</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; To induce the Guaranteed Party to enter into that certain Agreement and Plan of Merger, dated as of the date hereof (as it may be amended, supplemented or modified from time to time, the "<u>Merger Agreement</u>"), by and among the Guaranteed Party, Treadstone Parent Inc., a Delaware corporation ("<u>Parent</u>"), and Treadstone Merger Sub Inc., a Delaware corporation and wholly-owned subsidiary of Parent ("<u>Merger Sub</u>"), each of the Guarantors hereby absolutely, unconditionally and irrevocably guarantees, severally (and not jointly or jointly and severally) subject to the limitations contained herein, the due, punctual and complete payment of any monetary damages payable by Parent, Merger Sub or any of their Affiliates to the Company pursuant to, and subject to the terms and conditions set forth in, Section 7.2(a) of the Merger Agreement, solely to the extent a court of competent jurisdiction shall have entered a final and non-appealable judgment that such monetary damages are due and payable by Parent, Merger Sub or any of their Affiliates pursuant to Section 7.2(a) of the Merger Agreement, in a maximum aggregate amount equal to the Damages Cap (collectively, the "<u>Obligation</u>"); <u>provided</u>, that in no event shall any Guarantor's liability with respect to any Obligation exceed such Guarantor's Maximum Guarantor Percentage of the Obligation. For purposes of this Limited Guarantee, "<u>Maximum Guarantor Percentage</u>" means, with respect to each Guarantor, the percentage set forth opposite such Guarantor's name on <u>Schedule A</u> hereto. If Parent or Merger Sub fails to pay and discharge all or any portion of the Obligation when due and payable (as determined by a final and non-appealable judgment of a court of competent jurisdiction), upon the Guaranteed Party's demand each Guarantor shall immediately pay, or cause to be paid, to the Guaranteed Party its Maximum Guarantor Percentage of such Obligation. The Guaranteed Party may not bring a claim against any Guarantor under or in respect of this Limited Guarantee unless and until the Merger Agreement has been validly terminated in accordance with Section 7.1 thereof. For the avoidance of doubt, in no event shall the Guarantors be obligated to pay or contribute (as applicable) any amount in respect of both the Obligation and the Commitment (as defined in the Equity Commitment Letter).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Notwithstanding anything to the contrary in this Limited Guarantee, the Merger Agreement or otherwise, the Guaranteed Party hereby agrees that the liability of each Guarantor hereunder shall be several (and not joint or joint and several) based upon its respective Maximum Guarantor Percentage. The parties hereto agree that this Limited Guarantee may not be enforced without giving effect to each Guarantor's Maximum Guarantor Percentage. The Guaranteed Party may, in its sole discretion, bring and prosecute a separate action against any Guarantor for such Guarantor's Maximum Guarantor Percentage of any Obligation, regardless of whether action is brought against Parent, Merger Sub or any other Guarantor or whether Parent, Merger Sub or any other Guarantor is joined in any such action or actions. The Guaranteed Party agrees, on behalf of itself, its Affiliates and its and their respective Representatives, that none of them shall assert any claim of any kind, directly or indirectly, in any Proceeding, that any Guarantor is liable hereunder for the Obligation in an aggregate amount in excess of such Guarantor's Maximum Guarantor Percentage of such Obligation. All payments hereunder shall be made in lawful money of the United States, in immediately available funds.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Nature of Guarantee</u>. The Guaranteed Party shall not be obligated to file any claim relating to the Obligation in the event that Parent or Merger Sub becomes subject to a bankruptcy, reorganization or similar proceeding, and the failure of the Guaranteed Party to so file shall not affect the Guarantors' obligations hereunder. This Limited Guarantee is an unconditional guarantee of payment in accordance with <u>Section 1</u> hereof and not of collection, and a separate proceeding or proceedings may be brought and prosecuted against any of the Guarantors to enforce this Limited Guarantee, irrespective of whether any proceeding is brought against Parent, Merger Sub or any other Guarantor or whether Parent, Merger Sub or any other Guarantor are joined in any such proceeding or proceedings; <u>provided</u>, <u>however</u>, that in the event that multiple proceedings are brought, the aggregate recovery in respect of the Obligation in all such proceedings shall not exceed with respect to any Guarantor such Guarantor's Maximum Guarantor Percentage of such Obligation. Subject to the other provisions of this Limited Guarantee, the Guaranteed Party hereby agrees that each Guarantor may assert, as a defense to, or release or discharge of, such payment by such Guarantor under this Limited Guarantee, against an affirmative claim by the Guaranteed Party, or any of its Affiliates and Representatives, or any other Person claiming by, through or on behalf of any of them, any claim, release, rights, remedies, set-offs and defenses that Parent or Merger Sub could assert with respect to the Obligation pursuant to the terms of the Merger Agreement or pursuant to any applicable Law in connection therewith (other than any such rights, remedies, set-offs and defenses arising out of, due to, or as a result of, the insolvency, bankruptcy, reorganization or other similar proceeding affecting Parent).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;3.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Changes in Obligations; Certain Waivers</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; The Guarantors agree that the Guaranteed Party may at any time and from time to time, without notice to or further consent of any Guarantor, extend the time of payment of the Obligation, and may also enter into any agreement with Parent and/or Merger Sub for the extension, renewal, payment, compromise, discharge or release thereof, in whole or in part, or for any modification of the Merger Agreement or the Equity Commitment Letter or of any agreement between the Guaranteed Party, Parent and/or Merger Sub or any Person interested in the transactions contemplated by the Merger Agreement without in any way impairing or affecting the Guarantor's obligations under this Limited Guarantee, in each case, subject to the limitations contained herein. The Guarantors agree that the obligations of the Guarantors hereunder are absolute, unconditional and irrevocable, subject to the limitations contained in this Limited Guarantee, and shall not be released or discharged, in whole or in part, or otherwise affected by (i) the failure of the Guaranteed Party to assert any claim or demand or to enforce any right or remedy against Parent, Merger Sub, the Guarantors or any other Person with respect to the Obligation; (ii) any change in the time, place or manner of payment of the Obligation or any rescission, waiver, compromise, consolidation or other amendment or modification of any of the terms or provisions of the Merger Agreement made in accordance with the terms thereof, except to the extent Parent or Merger Sub has a defense to the payment of the Obligation under such rescission, waiver, compromise, consolidation or other amendment or modification; (iii) any insolvency, bankruptcy, reorganization or other similar proceeding with respect to Parent or Merger Sub or any other Person interested in the transactions contemplated by the Merger Agreement or any of their respective assets or any other Person now or hereafter liable with respect to the Obligation; (iv) the availability of any other means the Guaranteed Party may have of obtaining payment of the Obligation; (v) any change in the corporate existence, structure or ownership of Parent, Merger Sub, any Guarantor, or any other Person interested in the transactions contemplated by the Merger Agreement or any other Person now or hereafter liable with respect to the Obligation; (vi) the addition, substitution or release of any Person now or hereafter liable with respect to the Obligation or otherwise interested in the transactions contemplated by the Merger Agreement; or (vii) the value, genuineness, validity, regularity, illegality or enforceability of the Merger Agreement in accordance with its terms. To the fullest extent permitted by applicable Law, each Guarantor hereby expressly waives any and all rights or defenses arising by reason of any applicable Law which would otherwise require any election of remedies by the Guaranteed Party. Each Guarantor hereby expressly waives promptness, diligence, notice of the acceptance of this Limited Guarantee and of the Obligation, presentment, demand for payment, notice of non-performance, default, dishonor and protest, notice of the Obligation incurred and all other notices of any kind (except for notices to be provided pursuant to this Limited Guarantee or to Parent or Merger Sub and their counsel in accordance with the Merger Agreement), all defenses which may be available by virtue of any valuation, stay, moratorium or other similar applicable Law now or hereafter in effect, any right to require the marshalling of assets of Parent, Merger Sub or any other Person interested in the transactions contemplated by the Merger Agreement, and all suretyship defenses generally, other than defenses that are available to any Guarantor, Parent or Merger Sub, as applicable: (x) under the Merger Agreement or (y) in respect of a breach by the Guaranteed Party of this Limited Guarantee. Each Guarantor acknowledges that it will receive substantial direct and indirect benefits from the transactions contemplated by the Merger Agreement and that the waivers set forth in this Limited Guarantee are knowingly made in contemplation of such benefits. Notwithstanding anything to the contrary contained in this Limited Guarantee, the Guaranteed Party hereby agrees that to the extent that Parent and Merger Sub are relieved of any portion of the Obligation under the Merger Agreement by satisfaction or waiver thereof on the terms and subject to the conditions set forth in the Merger Agreement, the Guarantors shall be similarly relieved of such Obligation to such extent under this Limited Guarantee. Notwithstanding anything to the contrary contained herein, any payment made by or on behalf of Parent or Merger Sub to the Guaranteed Party with respect to an Obligation shall reduce the total Obligation of the Guarantors under this Limited Guarantee accordingly on a pro rata basis, based on the percentages set forth on <u>Schedule A</u>.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; The Guaranteed Party hereby covenants and agrees that it shall not institute or assert, and shall cause its Affiliates and its and their respective directors, officers, employees, members, managers, advisors, agents or other representatives (collectively, "<u>Representatives</u>") not to institute or assert, any proceeding or bring any claim of any kind whatsoever in any Proceeding, whether at Law or in equity, and whether sounding in contract, tort, statute or otherwise (including, without limitation, any Claim (as defined in <u>Section 9</u>)) arising under or in connection with this Limited Guarantee, the Equity Commitment Letter or the Merger Agreement or any other agreement or instrument delivered in connection therewith, the negotiation, execution, performance or breach hereof or thereof, or the transactions contemplated hereby or thereby against the Guarantors or any of their Non-Parties, except for claims (i) in connection with a valid termination (including pursuant to the final sentence of Section 8.5 of the Merger Agreement) of the Merger Agreement in accordance with the terms thereof, by the Guaranteed Party against any Guarantor under and pursuant to this Limited Guarantee (as limited by its terms, including, without limitation, the provisions of <u>Section 1</u>), (ii) by the Guaranteed Party as a third-party beneficiary of the Equity Commitment Letter pursuant to and upon the terms and conditions set forth therein, (iii) by the Guaranteed Party against Parent or Merger Sub pursuant to and upon the terms and conditions set forth in the Merger Agreement, (iv) by the Guaranteed Party pursuant to and upon the terms and conditions set forth in the Support Agreement against the counterparties thereto, or (v) by the Guaranteed Party against Altaris, LLC pursuant to and upon the terms and conditions set forth in the Confidentiality Agreement (the claims referred to in the foregoing clauses (i)-(v) of this <u>Section 3(b)</u>, collectively, the "<u>Permitted Claims</u>").

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Except as expressly set forth herein, each Guarantor hereby unconditionally and irrevocably waives, and agrees not to exercise, any rights that it may now have or hereafter acquire against Parent or Merger Sub that arise from the existence, payment, performance or enforcement of a Guarantor's Obligation under or in respect of this Limited Guarantee, including, without limitation, any right of subrogation, reimbursement, exoneration, contribution or indemnification and any right to participate in any claim or remedy of the Guaranteed Party against Parent or Merger Sub, whether or not such claim, remedy or right arises in equity or under contract, statute or common law, including, without limitation, the right to take or receive from Parent or Merger Sub, directly or indirectly, in cash or other property or by set-off or in any other manner, payment or security on account of such claim, remedy or right, unless and until the Obligation shall have been paid to the Guaranteed Party in full in immediately available funds. If any amount shall be paid to any Guarantor in violation of the immediately preceding sentence at any time prior to the payment in full of the Obligation, such amount shall be received and held in trust for the benefit of the Guaranteed Party, shall be segregated from other property and funds of such Guarantor and shall forthwith be paid or delivered by such Guarantor to the Guaranteed Party in the same form as so received (with any necessary endorsement or assignment) to be credited and applied to the Obligation in accordance with the terms of the Merger Agreement, whether matured or unmatured, or to be held as collateral for the Obligation thereafter existing.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Effect on Certain Rights</u>. No failure on the part of the Guaranteed Party to exercise, and no delay in exercising, any right, remedy or power hereunder shall operate as a waiver thereof, nor shall any single or partial exercise by the Guaranteed Party of any right, remedy or power hereunder preclude any other or future exercise of any right, remedy or power hereunder except as explicitly set forth herein (including, without limitation, <u>Section 9</u> hereof). Subject to the terms, conditions and limitations hereof and of the Merger Agreement and the Equity Commitment Letter, each and every right, remedy and power hereby granted to the Guaranteed Party or allowed to it by applicable Law shall be cumulative and not exclusive of any other, and may be exercised by the Guaranteed Party at any time or from time to time. The Guaranteed Party shall not have any obligation to proceed at any time or in any manner against, or exhaust any or all of the Guaranteed Party's rights against, Parent, Merger Sub or any other Person liable for any portion of the Obligation prior to proceeding against any Guarantor hereunder.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;5.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Representations and Warranties</u>. Each Guarantor hereby represents and warrants to the Guaranteed Party severally (and not jointly or jointly and severally) as to itself that:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; such Guarantor is a limited partnership duly organized, validly existing and in good standing under the laws of the jurisdiction of its formation and such Guarantor has all requisite organizational power and authority to execute, deliver and perform this Limited Guarantee;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; the execution, delivery and performance of this Limited Guarantee have been duly and validly authorized by all necessary action and do not contravene any provision of such Guarantor's partnership agreement or similar organizational documents or any applicable Law or material contract binding on such Guarantor or its assets;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; all consents, approvals, authorizations, permits of, filings with and notifications to, any Governmental Entity necessary for the due execution, delivery and performance of this Limited Guarantee by such Guarantor have been obtained or made and all conditions thereof have been duly complied with, and no other action by, and no notice to or filing with, any Governmental Entity is required in connection with the execution, delivery or performance of this Limited Guarantee by such Guarantor;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; this Limited Guarantee constitutes a legal, valid and binding obligation of such Guarantor enforceable against such Guarantor in accordance with its terms, subject, as to enforcement, to the Bankruptcy and Equity Exception; and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e)&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; such Guarantor has, and will continue to have for so long as this Limited Guarantee shall remain in effect, sufficient liquid and unencumbered assets and the financial capacity to pay and perform its obligations under this Limited Guarantee.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;6.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Assignment</u>. This Limited Guarantee may not be assigned (including, without limitation, assignment by operation of Law) by the Guaranteed Party without the prior written consent of each Guarantor, or by a Guarantor without the prior written consent of the Guaranteed Party; <u>provided</u> that each Guarantor may assign all or any portion of its obligations with respect to the Obligation under this Limited Guarantee to any equity co-investor and/or any of its Affiliates and affiliated funds without the prior written consent of the Guaranteed Party; provided, however, that (a) all representations, warranties and covenants herein shall be deemed to be those of the assigning Guarantor and such assignee, and (b) no such assignment shall relieve such Guarantor of any portion of its obligations hereunder. Any attempted assignment in violation of this <u>Section 6</u> shall be null and void and of no force or effect.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;7.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Notices</u>. All notices and other communications under this Limited Guarantee shall be given by the means specified in the Merger Agreement, *mutatis mutandis* (and shall be deemed given as specified therein), as follows:

If to the Guaranteed Party, to:

Trean Insurance Group, Inc.

150 Lake Street West

Wayzata, MN 55391

Attention: Patricia Ryan, Chief Legal Officer

E-mail: Patricia.Ryan@Trean.com

With a copy to (which shall not constitute notice):

Bass, Berry & Sims PLC

150 Third Avenue South, Suite 2800

Nashville, Tennessee 37201

Attention: J. Page Davidson

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Scott W. Bell

E-mail: pdavidson@bassberry.com

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; sbell@bassberry.com

and

Morris Nichols Arsht & Tunnell LLP

101 N Market St #1600

Wilmington, DE 19801

Attention: James D. Honaker

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Eric S. Klinger-Wilensky

Email: JHonaker@morrisnichols.com

&nbsp;&nbsp;&nbsp;&nbsp; &nbsp;&nbsp;&nbsp;&nbsp; EKWilensky@morrisnichols.com

If to the Guarantors, to:

Altaris Health Partners V, L.P.

Altaris Health Partners V-A, L.P.

c/o Altaris, LLC

10 E. 53rd Street, 31st Floor

New York, NY 10022

Attention: Charles Mullens

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Nicholas Fulco

Email: [Redacted]

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; [Redacted]

With a copy to (which shall not constitute notice):

Kirkland & Ellis LLP

601 Lexington Avenue

New York, NY 10022

Attention: David B. Feirstein, P.C.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; Romain Dambre

Email: david.feirstein@kirkland.com

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; romain.dambre@kirkland.com

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;8.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Continuing Guarantee; Termination</u>. Unless terminated pursuant to this <u>Section 8</u>, this Limited Guarantee shall remain in full force and effect and shall be binding on each Guarantor, its successors and permitted assigns until all of the Obligation has been indefeasibly paid in full (subject to the Damages Cap and each Guarantor's Maximum Guarantor Percentage). Notwithstanding the foregoing or anything to the contrary expressed in or implied by this Limited Guarantee or otherwise, this Limited Guarantee shall terminate automatically and immediately (other than this <u>Section 8</u> and <u>Sections 9</u> through <u>19</u>, all of which shall survive the termination of this Limited Guarantee) and the Guarantors shall have no further liability or obligations under or with respect to this Limited Guarantee as of the earliest to occur of (a) the consummation of the Closing and the payment of all amounts required to be paid by Parent and/or Merger Sub under the Merger Agreement in connection with the Closing, (b) sixty (60) days following the date the Merger Agreement is validly terminated in accordance with its terms (the date of such sixty (60) day anniversary, the "<u>Final Date</u>"), unless the Guaranteed Party commences any Proceeding for payment against any Guarantor in a Chosen Court prior to the Final Date (which, for the avoidance of doubt, may be brought regardless of whether any judgment for monetary damages against Parent, Merger Sub or any of their Affiliates has been obtained, but only to the extent a Proceeding has been commenced in a Chosen Court against Parent, Merger Sub or any of their Affiliates seeking monetary damages pursuant to Section 7.2(a) of the Merger Agreement), in which case this Limited Guarantee shall terminate immediately and with no further liability or obligations of any Guarantor upon the final resolution of such Proceeding and the indefeasible payment to the Guaranteed Party of all amounts (if any) finally determined (and not subject to any appeal) by the Chosen Court or agreed in writing by the parties hereto to be owing thereunder by or on behalf of all Guarantors, (c) the payment and performance in full of all of the Obligation (or with respect to any Guarantor, the date the Obligation in an amount equal to such Guarantor's Maximum Guarantor Percentage has been paid in full by it), and (d) at the Guarantors' election, at any time when the Guaranteed Party or any of its Affiliates or any of its or their respective Representatives asserts a claim in any Proceeding (i) that the provisions of <u>Section 1</u> with respect to each Guarantor's Maximum Guarantor Percentage, or the provisions of this <u>Section 8</u> or <u>Section 9</u> are illegal, invalid or unenforceable in whole or in part, (ii) against the Guarantors or any of their Non-Parties asserting a theory of liability against the Guarantors or any of their Non-Parties with respect to this Limited Guarantee, the Equity Commitment Letter or the Merger Agreement, except for Permitted Claims, (iii) that any Guarantor is liable hereunder in excess of its Maximum Guarantor Percentage of any Obligations or that the Guarantors or any of their Non-Parties are collectively liable in excess of the Damages Cap (other than in a Proceeding by the Guaranteed Party as a third-party beneficiary of the Equity Commitment Letter pursuant to and upon the terms and conditions set forth therein), or (iv) in respect of a Permitted Claim in any court other than a Chosen Court. In the event of a valid termination by the Guarantors pursuant to the above clause (d), then (x) the obligations of the Guarantors under this Limited Guarantee shall terminate *ab initio* and be null and void, (y) if any Guarantor shall have previously made any payments under this Limited Guarantee, it shall be entitled to recover and retain any and all such payments and (z) none of the Guarantors, Parent, Merger Sub or any Non-Party shall have any liability to the Guaranteed Party, its equityholders or any of their respective Representatives under this Limited Guarantee or with respect to the Merger Agreement, the Equity Commitment Letter or the transactions contemplated hereby or thereby.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;9.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>No Recourse</u>. The Guaranteed Party acknowledges and agrees, on behalf of itself, its Affiliates and its and their respective Representatives, that Parent does not have any assets other than its rights under the Merger Agreement and the Equity Commitment Letter, and that no funds are expected to be contributed to Parent unless and until the Closing occurs and that, except for its rights under Section 6 of the Equity Commitment Letter and Section 8.5 of the Merger Agreement, and subject to all of the terms, conditions and limitations therein, the Guaranteed Party shall not have any right to cause any assets to be contributed to Parent by the Guarantor, any Affiliate thereof or any other Person. The Guaranteed Party acknowledges, covenants and agrees, on behalf of itself, its Affiliates and its and their respective Representatives, that all claims, obligations, liabilities, causes of action, actions or other proceedings (in each case, whether at Law or in equity, and whether sounding in contract, tort, statute or otherwise) that may be based upon, in respect of, arise under, out or by reason of, be connected with, or relate in any manner to this Limited Guarantee, or the negotiation, execution, performance, or breach (whether willful, intentional, unintentional or otherwise) of this Limited Guarantee, including, without limitation, any representation or warranty made or alleged to be made in, in connection with, or as an inducement to, this Limited Guarantee (each of such above-described legal, equitable or other theories or sources of liability, a "<u>Claim</u>") may be made or asserted only against (and are expressly limited to) the Guarantors as expressly identified in the preamble to and signature page(s) of this Limited Guarantee (as limited by its terms, including, without limitation, the provisions of <u>Section 1</u>) or their permitted assigns and that, other than a Guarantor, no Person (including, without limitation, any of the Non-Parties of a Guarantor) shall have any liability or obligation whatsoever for, in respect of, based upon or arising out of or relating to any Claims.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;10.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Governing Law; Jurisdiction; Waiver of Jury Trial</u>. This Limited Guarantee, and all claims or causes of action (whether at Law, in contract or in tort or otherwise) that may be based upon, arise out of or relate to this Limited Guarantee or the negotiation, execution or performance hereof, shall be governed by and construed in accordance with the Laws of the State of Delaware, without giving effect to any choice or conflict of law provision or rule (whether of the State of Delaware or any other jurisdiction) that would cause the application of the Laws of any jurisdiction other than the State of Delaware. Each of the parties hereto irrevocably agrees that any legal suit, action or proceeding with respect to this Limited Guarantee and the rights and obligations arising hereunder, or for recognition and enforcement of any judgment in respect of this Limited Guarantee and the rights and obligations arising hereunder brought by the other party hereto or its successors or assigns, shall be brought and determined exclusively in the Delaware Court of Chancery and any state appellate court therefrom within the State of Delaware (or, if the Delaware Court of Chancery declines to accept jurisdiction over a particular matter, any state or federal court within the State of Delaware) (collectively, the "<u>Chosen Courts</u>"). Each of the parties hereto hereby irrevocably submits with regard to any such suit, action or proceeding for itself and in respect of its property, generally and unconditionally, to the personal jurisdiction of the Chosen Courts and agrees that it will not bring any action relating to this Limited Guarantee or the transactions contemplated hereby in any court other than the Chosen Courts. Each of the parties hereto hereby irrevocably waives, and agrees not to assert, by way of motion, as a defense, counterclaim or otherwise, in any suit, action or proceeding with respect to this Limited Guarantee, (i) any claim that it is not personally subject to the jurisdiction of the Chosen Courts, (ii) any claim that it or its property is exempt or immune from jurisdiction of any such Chosen Court or from any legal process commenced in such Chosen Courts (whether through service of notice, attachment prior to judgment, attachment in aid of execution of judgment, execution of judgment or otherwise) and (iii) to the fullest extent permitted by applicable Law, any claim that (A) the suit, action or proceeding in such Chosen Court is brought in an inconvenient forum, (B) the venue of such suit, action or proceeding is improper or (C) this Limited Guarantee, or the subject matter hereof, may not be enforced in or by such Chosen Courts. To the fullest extent permitted by applicable Law, each of the parties hereto hereby consents to process being served by any party hereto in any suit, action or proceeding by delivery of a copy thereof in accordance with the provisions of Section 8.7 of the Merger Agreement and <u>Section 7</u> of this Limited Guarantee. EACH OF THE PARTIES HERETO IRREVOCABLY WAIVES ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING ARISING OUT OF OR RELATING TO THIS LIMITED GUARANTEE OR THE TRANSACTIONS CONTEMPLATED HEREBY. EACH OF THE PARTIES HERETO CERTIFIES AND ACKNOWLEDGES THAT (A) NO REPRESENTATIVE, AGENT OR ATTORNEY OF THE OTHER PARTY HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT, IN THE EVENT OF LITIGATION, SEEK TO ENFORCE THE FOREGOING WAIVER, (B) EACH SUCH PARTY HERETO UNDERSTANDS AND HAS CONSIDERED THE IMPLICATIONS OF THIS WAIVER, (C) EACH SUCH PARTY MAKES THIS WAIVER VOLUNTARILY AND (D) EACH SUCH PARTY HAS BEEN INDUCED TO ENTER INTO THIS LIMITED GUARANTEE BY, AMONG OTHER THINGS, THE MUTUAL WAIVERS AND CERTIFICATIONS IN THIS <u>SECTION 10</u>.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;11.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Entire Agreement</u>. This Limited Guarantee (including the Schedule hereto and the documents and instruments referred to herein), together with the Equity Commitment Letter, the Support Agreement the Confidentiality Agreement and the Merger Agreement, constitutes the entire agreement among the parties hereto and supersedes any prior understandings, agreements or representations by or among the parties hereto, written or oral, with respect to the subject matter hereof, and the parties hereto specifically disclaim reliance on any such prior understandings, agreements or representations to the extent not embodied in this Limited Guarantee or any of the foregoing specifically identified documents.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;12.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Amendments</u>. This Limited Guarantee may not be amended except by an instrument in writing signed on behalf of each of the parties hereto.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;13.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Extension; Waiver</u>. To the extent legally allowed, the Guaranteed Party may (a) extend the time for the performance of any of the obligations or other acts of the other parties hereto, (b) waive any inaccuracies in the representations and warranties of the Guarantors contained herein or in any document delivered pursuant hereto and (c) waive compliance by the Guarantors with any of the agreements or conditions contained herein. To the extent legally allowed, each Guarantor may (i) extend the time for performance of any of the obligations or other acts of the Guaranteed Party, (ii) waive any inaccuracies in the representations and warranties of the Guaranteed Party contained herein or in any document delivered pursuant hereto and (iii) waive compliance by the Guaranteed Party with any of the agreements or conditions contained herein. Any agreement on the part of a party hereto to any extension or waiver of the terms hereof shall be valid only if set forth in a written instrument signed on behalf of such party. Such extension or waiver shall not apply to any time for performance, inaccuracy in any representation or warranty, or noncompliance with any agreement or condition, as the case may be, other than that which is specified in the extension or waiver. The delay or failure of any party hereto to assert any of its rights under this Limited Guarantee or otherwise shall not constitute a waiver of such rights.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;14.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Severability</u>. Any term or provision (or part thereof) of this Limited Guarantee that is invalid or unenforceable in any situation in any jurisdiction shall not affect the validity or enforceability of the remaining terms and provisions (or parts thereof) hereof or the validity or enforceability of the offending term or provision (or part thereof) in any other situation or in any other jurisdiction. If the final judgment of a court of competent jurisdiction declares that any term or provision (or part thereof) hereof is invalid or unenforceable, the parties hereto shall replace such invalid or unenforceable term or provision (or part thereof) with a valid and enforceable term or provision (or part thereof) that will achieve, to the extent possible, the economic, business and other purposes of such invalid or unenforceable term (or part thereof). Notwithstanding the foregoing, this Limited Guarantee may not be enforced without giving full force and effect to each Guarantor's Maximum Guarantor Percentage, and the other limitations set forth in <u>Section 1</u>, <u>Section 8</u> and <u>Section 9</u>.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;15.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Counterparts and Signature</u>. This Limited Guarantee may be executed in one or more counterparts, each of which shall be deemed to be an original and all of which, when taken together, one and the same agreement or document. A signed copy of this Limited Guarantee, with the same effect as if the signatures thereto and hereto were upon the same instrument, shall become effective when one or more counterparts have been signed by each of the parties hereto and delivered (by telecopy, electronic delivery or otherwise) to the other parties. Signatures to this Limited Guarantee transmitted by facsimile transmission, by electronic mail in "portable document format" (".pdf") form, or by any other electronic means intended to preserve the original graphic and pictorial appearance of a document, will have the same effect as physical delivery of the paper document bearing the original signature.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;16.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>No Third Party Beneficiaries</u>. The parties hereto hereby agree that their respective representations, warranties and covenants set forth herein are solely for the benefit in accordance with and subject to the terms of this Limited Guarantee, and this Limited Guarantee is not intended to, and shall not, confer upon any Person other than the parties hereto and their respective successors and permitted assigns any rights or remedies hereunder; <u>provided</u>, <u>however</u>, that the Non-Parties of each Guarantor are intended third-party beneficiaries of <u>Section 9</u>, and any and all such Non-Parties may enforce such rights directly.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;17.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Confidentiality</u>. This Limited Guarantee shall be treated as strictly confidential and is being provided to the Guaranteed Party solely in connection with the Merger Agreement and the transactions contemplated by the Merger Agreement. This Limited Guarantee may not be used, circulated, quoted or otherwise referred to in any document (other than the Merger Agreement and the Equity Commitment Letter) or otherwise distributed to any Person, except with the prior written consent of each Guarantor and the Guaranteed Party. Notwithstanding the foregoing, (a) this <u>Section 17</u> shall not prevent the use of this Limited Guarantee in connection with any proceeding to enforce the terms of this Limited Guarantee, (b) this Limited Guarantee may be provided to those of the Guarantors' and the Guaranteed Party's advisors who have been directed to treat this Limited Guarantee as confidential on terms substantially identical to the terms contained in this <u>Section 17</u>, and (c) this Limited Guarantee may be disclosed by a party to the extent compelled by a Governmental Entity or required by Law or legal process or pursuant to the applicable rules of any national securities exchange.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;18.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Covenants</u>. So long as this Limited Guarantee is in effect pursuant to its terms, each party hereto hereby covenants and agrees that it shall not institute or assert, and shall cause each of its Affiliated Persons not to institute or assert, directly or indirectly, any proceeding or bring any other claim, asserting that this Limited Guarantee or any part hereof is illegal, invalid or unenforceable in accordance with its terms.

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&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;19.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Certain Terms</u>. As used herein:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;a. "<u>Non-Parties</u>" means, with respect to any Person, (i) any past, present or future general or limited partners, director, officer, employee, incorporator, member, partner, manager, direct or indirect equityholder, management company, Affiliate, agent, attorney, or representative of, and any financial advisor or lender to (all above-described Persons in this subclause (i), collectively, "<u>Affiliated Persons</u>") such Person, and (ii) any Affiliated Persons of such Affiliated Persons, in each case together with the respective successors, assigns, heirs, executors or administrators of the Persons in subclauses (i) and (ii); <u>provided</u> that none of any Guarantor, Parent, Merger Sub or any Investor (as defined in the Equity Commitment Letter), or any of their respective permitted assigns, shall be a Non-Party of any Guarantor;

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;b. "<u>Affiliates</u>" and "<u>Affiliated Persons</u>" of the Company shall not include the Sponsor, the Specified Stockholders and their respective controlled Affiliates (other than the Company and its Subsidiaries); and

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;c. "<u>directors</u>" of the Company shall include only the Non-Recused Directors.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;20.&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp; <u>Special Committee</u>. For all purposes hereunder, the Company (prior to the Effective Time) and the Company Board of Directors, as applicable, shall act, including with respect to the granting of any consent, permission or waiver or the making of any determination, only as directed in writing by the Special Committee or its designees.

[Remainder of Page Intentionally Left Blank – Signature Pages Follow]

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IN WITNESS WHEREOF, the parties have duly executed and delivered this Limited Guarantee as of the date first above written.

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| | |
|:---|:---|
| <u>**GUARANTORS**:</u> | <u>**GUARANTORS**:</u> |
| **ALTARIS HEALTH PARTNERS V, L.P.** | **ALTARIS HEALTH PARTNERS V, L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ George Aitken-Davies |
| Name: | George Aitken-Davies |
| Title: | Authorized Signatory |
| **ALTARIS HEALTH PARTNERS V-A, L.P.** | **ALTARIS HEALTH PARTNERS V-A, L.P.** |
| By: AHP V GP, L.P., its general partner | By: AHP V GP, L.P., its general partner |
| By: Altaris Partners, LLC, its general partner | By: Altaris Partners, LLC, its general partner |
| By: | /s/ George Aitken-Davies |
| Name: | George Aitken-Davies |
| Title: | Authorized Signatory |

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[Signature Page to Limited Guarantee]

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---

| | |
|:---|:---|
| **<u>GUARANTEED PARTY:</u>** | **<u>GUARANTEED PARTY:</u>** |
| **TREAN INSURANCE GROUP, INC.** | **TREAN INSURANCE GROUP, INC.** |
| By: | /s/ Julie A. Baron |
| Name: | Julie A. Baron |
| Title: | Chief Executive Officer and President |

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[Signature Page to Limited Guarantee]

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<u>Schedule A</u>

#### Guarantors

---

| | |
|:---|:---|
| **<u>Guarantor</u>** | **<u>Maximum Guarantor</u>**<br> **<u>Percentage</u>** |
| &nbsp;&nbsp; **ALTARIS HEALTH PARTNERS V, L.P.** | **68.18%** |
| &nbsp;&nbsp; **ALTARIS HEALTH PARTNERS V-A, L.P.** | **31.82%** |
| **Total** | **100%** |

---

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## Ex-Filing

#### Exhibit 107

#### <br>

#### CALCULATION OF FILING FEE TABLES

#### <br>

#### Schedule 13E-3
(Form Type)

#### Trean Insurance Group, Inc.

#### Treadstone Merger Sub Inc.

#### Treadstone Parent Inc.

#### Treadstone Upper Parent Inc.

#### Treadstone Aggregator L.P.

#### Altaris Health Partners V, L.P.

#### Altaris Health Partners V-A, L.P.

#### AHP V GP, L.P.

#### AHP-TH LLC

#### AHP-BHC LLC

#### ACP-TH LLC

#### ACP-BHC LLC

#### Altaris Health Partners III, L.P.

#### AHP III GP, L.P.

#### Altaris Constellation Partners, L.P.

#### AHP Constellation GP, L.P.

#### Altaris Partners, LLC

#### George E. Aitken-Davies

#### Daniel G. Tully
(Exact Name of Registrant and Name of Persons Filing Statement)

<u>Table 1: Transaction Valuation</u>

 

<br> ---

| | | | |
|:---|:---|:---|:---|
|  | Proposed Maximum<br> Aggregate Value of<br> Transaction | Fee rate | Amount of<br> Filing Fee |
|  Fees to be Paid | $349045162.65<br><sup>(1)(2)</sup> | .00011020 | $38464.78<br><sup>(3)</sup> |
|  Fees Previously Paid | $0 |  | $38464.78 |
| &nbsp;&nbsp;&nbsp; **Total Transaction Valuation** | $349045162.65 |  |  |
| &nbsp;&nbsp;&nbsp; **Total Fees Due for Filing** |  |  | $0 |
| &nbsp;&nbsp;&nbsp; **Total Fees Previously Paid** |  |  | $38464.78 |
| &nbsp;&nbsp;&nbsp; **Total Fee Offsets** |  |  | $38464.78<br><sup>(4)</sup><br>|
| &nbsp;&nbsp;&nbsp; **Net Fee Due** |  |  | $0 |

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<br> <u>Table 2: Fee Offset Claims and Sources</u>

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| | | | | | | | |
|:---|:---|:---|:---|:---|:---|:---|:---|
|  | Registrant or Filer Name | Form of Filing Type | File Number | Initial Filing Date | Filing Date | Fee Offset <br> Claimed | Fee Paid with Fee Offset Source |
|  Fees Offset Claims |  | PREM 14A | 001-39392 | January 19, 2023 |  | $38464.78 |  |
|  Fees Offset Sources | Trean Insurance Group, Inc. | PREM 14A | 001-39392 |  | January 19, 2023 |  | $38464.78 |

---

&nbsp;&nbsp;&nbsp;&nbsp;(1) Aggregate number of securities to which transaction applies:

As of January 13, 2023, the maximum number of shares of common stock, par value $0.01 per share ("Common Stock"), of Trean Insurance Group, Inc. ("Trean") to which this transaction applies is estimated to be 56,920,034, which consists of (a) 51,222,485 shares of Common Stock entitled to receive the per share transaction consideration of $6.15; (b) 164,723 shares of Common Stock underlying outstanding stock options, which are entitled to receive the per share merger consideration of $6.15 minus any applicable exercise price; (c) 147,552 shares of Common Stock underlying outstanding restricted stock units, which may be entitled to receive the per share transaction consideration of $6.15; (d) 211,424 shares of Common Stock underlying outstanding performance stock units subject to performance-based vesting (assuming the 105,712 target shares pay out at the maximum 200% of target), which may be entitled to receive the per share transaction consideration of $6.15; (e) 211,432 shares of Common Stock underlying outstanding market stock units subject to performance-based vesting (assuming the 105,716 target shares pay out at the maximum 200% of target), which may be entitled to receive the per share transaction consideration of $6.15; and (f) 4,962,418 shares of common stock reserved for issuance pursuant to Trean's 2020 Omnibus Incentive Plan.

&nbsp;&nbsp;&nbsp;&nbsp;(2) Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and
 state how it was determined):

Estimated solely for the purposes of calculating the filing fee, the underlying value of the transaction was calculated based on the sum of (a) the product of 51,222,485 shares of Common Stock and the per share transaction consideration of $6.15; (b) the product of 147,552 shares of Common Stock underlying outstanding restricted stock units and the per share transaction consideration of $6.15; (c) the product of 211,424 shares of Common Stock underlying outstanding performance stock units and the per share transaction consideration of $6.15; (d) 211,432 shares of Common Stock underlying outstanding market stock units and the per share transaction consideration of $6.15; and (e) the product of 4,962,418 shares of common stock reserved for issuance pursuant to Trean's 2020 Omnibus Incentive Plan and the per share transaction consideration of $6.15. Pursuant to the terms of that certain Agreement and Plan of Merger, by and among Trean, Treadstone Parent Inc. and Treadstone Merger Sub Inc., all options with an exercise price per share greater than the per share merger consideration of $6.15 will be canceled for no consideration at the effective time of the merger. As of January 19, 2023, all outstanding options had an exercise price per share greater than the per share merger consideration of $6.15.

&nbsp;&nbsp;&nbsp;&nbsp;(3) In accordance with Section 14(g) of the Securities Exchange Act of 1934, as amended, the filing fee was determined by multiplying the sum calculated in the preceding sentence by
 0.00011020.

&nbsp;&nbsp;&nbsp;&nbsp;(4) The Company previously paid $38,464.78 upon the filing of its Preliminary Proxy Statement on Schedule 14A on January 19, 2023 in connection with the transaction reported hereby.

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