Document:

Exhibit
10.1

 

PLAN
OF CONVERSION

 

OF

 

TOWNSQUARE MEDIA, LLC

 

This Plan of Conversion
(this “Plan of Conversion”) is adopted as of July 25, 2014, to convert Townsquare Media, LLC, a Delaware limited
liability company (the “Converting Entity”), to Townsquare Media, Inc., a Delaware corporation (the “Converted
Entity”). All capitalized terms used but not defined herein shall have the meaning ascribed to them in the Second Amended
and Restated Limited Liability Company Agreement of the Converting Entity, dated March 15, 2011, as amended (the “LLC
Agreement”).

 

RECITALS

 

WHEREAS, the Converting
Entity is a limited liability company organized under the laws of the State of Delaware;

 

WHEREAS, the Board of Managers
of the Converting Entity (the “Board”) has approved this Plan of Conversion and the transactions contemplated
hereby;

 

WHEREAS, at the Effective
Time and Date (as defined below), the Converting Entity shall be converted to the Converted Entity and become a corporation organized
under the laws of the State of Delaware (the “Conversion”); and

 

WHEREAS, the Conversion
is being effected pursuant to Section 18-216 of the Delaware Limited Liability Company Act and Section 265 of the Delaware
General Corporation Law (the “DGCL”).

 

AGREEMENT

 

1.            This
Plan of Conversion shall become effective upon the effectiveness of the filing of the duly executed Certificate of Incorporation
of the Converted Entity attached hereto as Exhibit A (the “Certificate of Incorporation”), and of the
duly executed Certification of Conversion of the Converting Entity attached hereto as Exhibit B (the “Certificate
of Conversion”), in the office of the Secretary of State of the State of Delaware (the “Effective Time and Date”).

 

2.             At
the Effective Time and Date, the By-laws of the Converted Entity attached hereto as Exhibit C (the “By-laws”)
shall become the by-laws of the Converted Entity until thereafter amended in accordance with their terms, the Certificate of Incorporation
and the DGCL.

 

3.            At
the Effective Time and Date, the name of the Converted Entity shall be Townsquare Media, Inc.

 

4.            At
the Effective Time and Date, the LLC Agreement shall be terminated and shall be of no further force and effect.

 

    	 

    	 

    

 

5.            At
the Effective Time and Date, all of the Units and Special Warrants of the Converting Entity outstanding immediately prior to the
Conversion shall, by virtue of the Conversion and without any action on the part of the Converting Entity, the Converted Entity,
or of any holder thereof, and without the payment of any additional consideration, be converted into shares of Class A Common Stock,
par value $0.01 per share, of the Converted Entity (“Class A Common Stock”), shares of Class B Common Stock,
par value $0.01 per share, of the Converted Entity (“Class B Common Stock”), shares of Class C Common Stock,
par value $0.01 per share, of the Converted Entity (“Class C Common Stock”) and/or warrants exercisable for
shares of Class A Common Stock as follows (in each case, rounded to the nearest whole share or warrant):

 

		(a)	Each strip of one Class A Preferred Unit and one Class A Common Unit of the Converting Entity held
by each holder of Units of the Converting Entity shall automatically convert into 0.29730499 shares of Class A Common Stock of
the Converted Entity; except that:

 

		(i)	each strip of one Class A Preferred Unit and one Class A Common Unit of the Converting Entity held
by OCM POF IV AIF GAP Holdings, L.P. shall automatically convert into 0.08489556 shares of Class B Common Stock of the Converted
Entity;

 

		(ii)	each strip of one Class A Preferred Unit and one Class A Common Unit of the Converting Entity held
by OCM PF/FF Radio Holdings PT, L.P. shall automatically convert into 0.14428003 shares of Class B Common Stock of the Converted
Entity;

 

		(iii)	each strip of one Class A Preferred Unit and one Class A Common Unit of the Converting Entity held
by FiveWire Media Ventures LLC or by the members of FiveWire Media Ventures LLC, all of whom are listed on Schedule A hereto
(the “FiveWire Members”), shall automatically convert into 0.29730499 shares of Class B Common Stock of the
Converted Entity; and

 

		(iv)	each strip of one Class A Preferred Unit and one Class A Common Unit of the Converting Entity held
by SOF Investments, L.P., SOF Investments, L.P. - Private V, GE Capital Equity Holdings, Inc., GE Business Financial Services Inc.
and Antares Capital Corporation shall automatically convert into 0.29730499 shares of Class C Common Stock of the Converted Entity.

 

		(b)	Each strip of one Special Warrant exercisable for Class A Preferred Units and one Special Warrant
exercisable for Class A Common Units of the Converting Entity held by each holder of Special Warrants of the Converting Entity
shall automatically convert into 0.29730499 warrants exercisable for Class A Common Stock of the Converted Entity; except that:

 

		(i)	each strip of one Special Warrant exercisable for Class A Preferred Units and one Special Warrant
exercisable for Class A Common Units of the Converting Entity held by OCM POF IV AIF GAP Holdings, L.P. shall

 

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automatically convert into 0.79387631
warrants exercisable for Class A Common Stock of the Converted Entity; and

 

		(ii)	each strip of one Special Warrant exercisable for Class A Preferred Units and one Special Warrant
exercisable for Class A Common Units of the Converting Entity held by OCM PF/FF Radio Holdings PT, L.P. shall automatically convert
into 0.40458064 warrants exercisable for Class A Common Stock of the Converted Entity.

 

		(c)	Each Class B Common Unit of the Converting Entity held by each holder of Class B Common Units of
the Converting Entity shall automatically convert into a number of shares of Class A Common Stock of the Converted Entity equal
to the result obtained by dividing (x) the Allocation Amount for such Class B Common Unit by (y) $11.00; except that:

 

		(i)	each Class B Common Unit of the Converting Entity held by a FiveWire Member shall automatically
convert into a number of shares of Class B Common Stock of the Converted Entity equal to the result obtained by dividing (x) the
Allocation Amount for such Class B Common Unit by (y) $11.00.

 

For purposes of the foregoing, the
“Allocation Amount” for each Class B Common Unit of the Converting Entity means the excess of (A) the amount
determined by dividing the Gross Class B Amount by the number of Class B Common Units, over (B) the Participation Threshold with
respect to such Class B Common Unit.

 

For purposes of the foregoing, the
“Gross Class B Amount” means the sum of (A) $5,000,000.00 and (B) the sum of the Participation Thresholds of
all Class B Common Units.

 

For purposes of the foregoing, the
“Participation Threshold” for each Class B Common Unit of the Converting Entity means the participation threshold,
if any, set forth in the unit grant agreement pursuant to which such Class B Common Unit was granted. If no participation threshold
was set forth in the unit grant agreement pursuant to which such Class B Common Unit was granted, then the Participation Threshold
for such Class B Common Unit is $0.00.

 

The shares of Class A Common Stock, Class B
Common Stock and Class C Common Stock of the Converted Entity issued by virtue of the Conversion shall be governed by, and shall
have the rights, powers and preferences (and the qualifications, limitations and restrictions thereof) as are set forth in, the
Certificate of Incorporation. The warrants exercisable for Class A Common Stock of the Converted Entity resulting from the Conversion
shall be governed by a warrant agreement among the Converted Entity and the holders of such warrants in the form attached hereto
as Exhibit D.

 

6.            Immediately
following the Conversion, but prior to the issuance of any additional equity interests of the Converted Entity, the equity ownership
of the Converted Entity shall be as set forth on Exhibit E attached hereto.

 

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7.            As
of the Effective Time and Date, the officers and members of the Board of the Converting Entity shall become the officers and directors
of the Converted Entity.

 

8.            Each
officer of the Converting Entity shall be designated as an authorized person of the Converting Entity for purposes of filing the
Certificate of Conversion and the Certificate of Incorporation and any other documents, instruments or certificates required to
be filed by or on behalf of the Converting Entity in connection with the Conversion. The duly appointed officers of the Converted
Entity shall have the authority to execute and deliver all further documents and instruments and take other further action as may
be necessary or appropriate to carry out the intent and purposes of this Plan of Conversion.

 

9.            This
Plan of Conversion shall be governed by, and construed and enforced in accordance with, the laws of the State of Delaware, without
regard to principles of conflicts of laws thereof.

 

10.          This
Plan of Conversion may be executed by facsimile and in counterparts by the parties hereto and shall become effective and binding
upon the parties at such time as signed by all of the parties hereto.

 

11.          This
Plan of Conversion, including the exhibits hereto, has been duly approved by the Board and the undersigned holders of the Required
Interest. The adoption of this Plan of Conversion by the undersigned holders of the Required Interest shall constitute an adoption
by such holders of the Conversion and the matters set forth herein, including, without limitation, the Certificate of Incorporation
and By-laws.

 

[Remainder of Page Intentionally Left Blank]

 

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IN WITNESS WHEREOF, the
undersigned has caused this Plan of Conversion to be executed as of the date first set forth above.

 

	 	CONVERTING ENTITY:
	 	 
	 	TOWNSQUARE MEDIA, LLC
	 	 
	 	By:	/s/ Stuart Rosenstein	 
	 	Name: Stuart Rosenstein
	 	Title:  Executive Vice President and Chief Financial Officer

 

[Townsquare Media, LLC - Plan of Conversion]

 

    	 

    	 

    

 

	 	HOLDERS OF THE REQUIRED INTEREST
	 	 
	 	OCM POF IV AIF GAP HOLDINGS, L.P.
	 	 
	 	By: OCM/GAP Holdings IV, Inc.
	 	Its: General Partner
	 	 
	 	By:	/s/ B. James Ford	 
	 	Name:  B. James Ford
	 	Title:  Authorized Signatory
	 	 
	 	By:	/s/ David Quick	 
	 	Name: David Quick
	 	Title: Authorized Signatory
	 	 
	 	OCM PF/FF RADIO HOLDINGS PT, L.P.
	 	 
	 	By:	Oaktree Fund AIF Series, L.P. – Series D and
	 	 	Oaktree Fund AIF Series, L.P. – Series I
	 	Its:	General Partners
	 	 
	 	By:	Oaktree Fund GP AIF, LLC
	 	Its:  	General Partner
	 	 
	 	By:	Oaktree Fund GP III, L.P.
	 	Its:	Managing Member
	 	 
	 	By: 	/s/ B. James Ford	 
	 	Name:  B. James Ford
	 	Title:  Authorized Signatory
	 	 
	 	By:	/s/ David Quick	 
	 	Name: David Quick
	 	Title: Authorized Signatory

 

[Townsquare Media, LLC - Plan of Conversion]

 

    	 

    	 

    

 

Schedule A

 

FiveWire Members

 

Steven Price

Stuart Rosenstein

Alex Berkett

Dhruv Prasad

Scott Schatz

 

    	 

    	 

    

 

Exhibit A

 

Certificate of Incorporation
of the Converted Entity

 

See attached

 

    	 

    	 

    

 

Exhibit B

 

Certificate of Conversion of the Converting
Entity

 

See attached

 

    	 

    	 

    

 

Exhibit C

 

By-laws of the Converted Entity

 

See attached

 

    	 

    	 

    

 

Exhibit D

 

Warrant Agreement

 

See attached

 

    	 

    	 

    

 

Exhibit E

 

Equity Ownership of the Converted Entity

 

See attachedExhibit 10.2

 

WARRANT AGREEMENT

 

THIS WARRANT AGREEMENT dated as of July 25,
2014 (this “Agreement”) is by and among Townsquare Media, Inc., a Delaware corporation (the “Company”),
the Persons set forth on Schedule I hereto, and any other registered holders of the Warrant Certificates (as defined below)
from time to time party hereto (each such Person or other holder, a “Holder” and, collectively, the “Holders”).

 

RECITALS:

 

WHEREAS, 9,508,878 warrants exercisable
for shares of Common Stock (as defined below) are being issued to the Persons set forth on Schedule I hereto (collectively,
the “Warrants”), with each such Person receiving the number of Warrants set forth opposite such Person’s
name on Schedule I, in connection with the conversion of Townsquare Media, LLC, a Delaware limited liability company (the
“Predecessor LLC Entity”), into the Company pursuant to the terms of the Plan of Conversion of the Predecessor
LLC Entity, dated as of July 25, 2014; and

 

WHEREAS, the Company and the Persons set forth
on Schedule I hereto desire to enter into this Agreement to set forth the terms and conditions of the Warrants and the rights
and obligations of the Company and the Holders.

 

NOW, THEREFORE, in consideration of the premises
and the mutual covenants and agreements set forth herein, and for other good and valuable consideration, the receipt and sufficiency
of which is hereby acknowledged, the Company and the Holders, intending to be legally bound, hereby agree as follows:

 

Article
I

DEFINITIONS AND INTERPRETATION

 

Section
1.1          Certain Defined Terms.
Capitalized terms used in this Agreement shall have the following respective meanings, except as otherwise provided herein or
as the context shall otherwise require:

 

“Board”
means the board of directors of the Company.

 

“Business Day”
means a day other than a Saturday, Sunday or legal holiday in the state in which the Company’s principal executive office
is located.

 

“Certificate
of Incorporation” means the Certificate of Incorporation of the Company, as amended from time to time.

 

“Common Stock”
means the Class A Common Stock, par value $0.01 per share, of the Company or any class or classes of units, stock or other equity
interests issued in respect of such Class A Common Stock as a result of any reclassification, redemption or recharacterization
thereof.

 

“Exercise Price”
means $0.0001 per one (1) share of Common Stock, which amount is not subject to adjustment.

 

    	 

    	 

    

 

“Expiration
Date” means, with respect to any Warrant, if elected by the Board, the tenth anniversary of the date hereof; otherwise,
the Warrants will not expire.

 

“FCC Restrictions”
means the FCC ownership and transfer restrictions set forth in Article Five of the Certificate of Incorporation, as determined
in the Company’s sole and absolute discretion. 

 

“Governmental
Authority” means (i) any nation or government, (ii) any federal, state, county, province, city, town, municipality,
local or other political subdivision thereof or thereto, (iii) any court, tribunal, department, commission, board, bureau, instrumentality,
agency, council, arbitrator or other entity exercising executive, legislative, judicial, regulatory or administrative functions
of or pertaining to government and (iv) any other governmental entity, agency or authority having or exercising jurisdiction over
any relevant Person, item or matter.

 

“Laws”
means all laws, statutes, rules, regulations, ordinances, orders, writs, injunctions or decrees and other pronouncements having
the effect of law of any Governmental Authority.

 

“Non-U.S. Person”
means (i) a citizen of a country other than the United States, (ii) an entity organized under the laws of a jurisdiction other
than those of the United States or any state, territory or possession of the United States, (iii) a government other than the government
of the United States or of any state, territory or possession of the United States or (iv) a representative of, or entity controlled
by, any person or entity referred to in any of the foregoing clauses (i) through (iii).

 

“Organic Change”
means any recapitalization, reorganization, reclassification, consolidation, exchange of Common Stock, merger, sale of all or substantially
all of the Company’s equity or assets or other transaction, in each case which is effected in such a way that holders of
shares of Common Stock are entitled to receive (either directly or upon subsequent liquidation) cash, interests, securities or
other assets or property with respect to or in exchange for shares of Common Stock.

 

“Person”
means any individual, limited liability company, company, partnership, joint venture, association, joint-stock company, trust,
unincorporated organization, Governmental Authority or other entity or enterprise.

 

“Registration
Agreement” means the Second Amended and Restated Registration Agreement of the Company, among the parties from time
to time party thereto, as amended from time to time.

 

“Securities
Act” means the Securities Act of 1933, as amended.

 

“Securities
Exchange Act” means the Securities Exchange Act of 1934, as amended.

 

“Transfer”
means any sale, transfer, assignment, pledge, mortgage, exchange, hypothecation, grant of a security interest or other direct or
indirect disposition or encumbrance of an interest (including without limitation by operation of law) or the acts thereof, but
explicitly excluding exchanges of a Warrant for Common Stock issuable upon the exercise of such Warrant in accordance with its
terms. The term “Transferred” shall have a correlative meaning.

 

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Section 1.2           Interpretation.
In this Agreement, unless a clear contrary intention appears:

 

(a)          the
words “hereof,” “herein” and “hereunder” and words of similar import refer to this Agreement
as a whole and not to any particular provision of this Agreement;

 

(b)          reference
to any gender includes each other gender and the neuter;

 

(c)          all
terms defined in the singular shall have the same meanings in the plural and vice versa;

 

(d)          reference
to any Person includes such Person’s heirs, executors, personal representatives, administrators, successors and assigns;
provided, however, that nothing contained in this clause (d) is intended to authorize any assignment not otherwise permitted by
this Agreement;

 

(e)          reference
to a Person in a particular capacity or capacities excludes such Person in any other capacity;

 

(f)          reference
to any contract or agreement means such contract or agreement as amended, supplemented or modified from time to time in accordance
with the terms thereof;

 

(g)          all
references to Articles and Sections shall be deemed to be references to the Articles and Sections of this Agreement;

 

(h)          all
references to Exhibits shall be deemed to be references to the Exhibits attached hereto which are made a part hereof and incorporated
herein by reference;

 

(i)          the
word “including” (and with correlative meaning “include”) means including, without limiting the generality
of any description preceding such term;

 

(j)          with
respect to the determination of any period of time, the word “from” means “from and including” and the
words “to” and “until” each means “to but excluding”;

 

(k)          the
captions and headings contained in this Agreement shall not be considered or given any effect in construing the provisions hereof
if any question of intent should arise;

 

(l)          reference
to any Law means such Law as amended, modified, codified, reenacted, supplemented or superseded in whole or in part, and in effect
from time to time;

 

(m)          where
any provision of this Agreement refers to action to be taken by any Person, which such Person is prohibited from taking, such provision
shall be applicable whether such action is taken directly or indirectly by such Person; and

 

(n)          no
provision of this Agreement shall be interpreted or construed against any party solely because that party or its legal representative
drafted such provision.

 

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Article
II

ORIGINAL ISSUE OF WARRANTS

 

Section 2.1           Form
of Warrant Certificates.

 

(a)          The
Warrants shall be evidenced by certificates substantially in the form attached hereto as Annex A (the “Warrant
Certificates” and each a “Warrant Certificate”), with each Warrant Certificate dated the
date on which such Warrant Certificate is countersigned by the Holder thereof. Each Warrant shall represent the right, subject
to the provisions of this Agreement and such Warrant Certificate, to purchase one (1) share of Common Stock (subject to adjustment
as set forth in Section 4.1) at the Exercise Price.

 

(b)          The
Warrant Certificates may have such insertions, letters, numbers or other marks of identification and such legends and endorsements
stamped, printed, lithographed or engraved thereon as may, consistently herewith, be determined to be necessary or appropriate
by the officers of the Company executing such Warrant Certificates as evidenced by their execution of the Warrant Certificates,
or as may be required to comply with any applicable Law or with any rule or regulation of any securities exchange or to conform
to usage. The definitive Warrant Certificates shall be typed, printed, lithographed or engraved or produced by any combination
of these methods or may be produced in any other manner permitted by applicable Law.

 

Section 2.2           Legends.
The Warrant Certificates originally issued to each Holder, or issued upon registration of transfer of, or upon exchange for or
in lieu of, any Warrant Certificate shall bear the following legend:

 

“THIS WARRANT, AND THE CLASS
A COMMON STOCK OF THE COMPANY WHICH MAY BE PURCHASED PURSUANT TO THE EXERCISE OF THIS WARRANT (COLLECTIVELY, THE “WARRANT
SHARES,” AND TOGETHER WITH THIS WARRANT, THE “SECURITIES”), HAVE NOT BEEN REGISTERED UNDER THE SECURITIES
ACT OF 1933, AS AMENDED, OR UNDER ANY OTHER APPLICABLE SECURITIES LAWS, AND MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF EFFECTIVE
REGISTRATION UNDER SUCH ACT AND LAWS OR EXEMPTION THEREFROM. THIS WARRANT MUST BE SURRENDERED TO THE COMPANY OR ITS TRANSFER AGENT
AS A CONDITION PRECEDENT TO THE SALE, PLEDGE OR OTHER TRANSFER OF ANY INTEREST IN ANY OF THE WARRANT SHARES REPRESENTED BY THIS
WARRANT.

 

THE WARRANT SHARES REPRESENTED BY
THIS WARRANT ARE SUBJECT TO THE POWERS, DESIGNATIONS, PREFERENCES AND RELATIVE, PARTICIPATING, OPTIONAL OR OTHER SPECIAL RIGHTS,
AND THE QUALIFICATIONS, LIMITATIONS OR RESTRICTIONS OF SUCH PREFERENCES AND/OR RIGHTS, SPECIFIED IN THE CERTIFICATE OF INCORPORATION
OF THE COMPANY, AS AMENDED FROM TIME TO TIME. A COPY OF SUCH CERTIFICATE OF

 

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INCORPORATION SHALL BE FURNISHED BY THE COMPANY TO
THE HOLDER HEREOF UPON WRITTEN REQUEST AND WITHOUT CHARGE.

 

THE SECURITIES ARE SUBJECT TO CERTAIN
RESTRICTIONS ON EXERCISE, TRANSFER, SALE, ASSIGNMENT, PLEDGE, ENCUMBRANCE OR OTHER SIMILAR TRANSFER AS SET FORTH IN A REGISTRATION
AGREEMENT AMONG THE COMPANY AND THE PERSONS PARTY THERETO, AND A WARRANT AGREEMENT AMONG THE COMPANY AND THE ORIGINAL HOLDER OF
THIS WARRANT, COPIES OF WHICH MAY BE OBTAINED AT THE PRINCIPAL OFFICE OF THE COMPANY.”

 

Each Holder further acknowledges and agrees
that the Common Stock issued upon exercise of the Warrants, if certificated, shall bear a legend substantially in the form of the
legend appearing above, and any other legends required by applicable federal and state securities laws, the Registration Agreement
or otherwise called for by this Agreement or any other agreement between the Company and such Holder.

 

Section 2.3           Certain
Transfer Restrictions.

 

(a)          Any
attempted Transfer that is prohibited by this Section 2.3 and not approved by majority vote of the Board shall be null and void
ab initio and shall not be effective to Transfer any Warrants. The Company may seek any remedy available to it at law, in equity
or otherwise, including an injunction prohibiting any such Transfer, to enforce the provisions of this Section 2.3.

 

(b)          No
Holder shall effect any Transfer of all or any portion of the Warrants held by such Holder, unless and until (i) such Holder shall
have provided executed copies of the Assignment Form and the Joinder, in each case in the form attached to the Warrant Certificates
and completed by the prospective transferee and (ii) if requested by the Company within ten (10) days of receiving the Assignment
Form and the Joinder, such Holder shall have furnished the Company with an opinion of counsel reasonably satisfactory to the Company
that such disposition will not require registration of such Warrants under the Securities Act.  

 

(c)          Subject
to Section 2.3(b), a Holder may Transfer his, her or its Warrant Certificates by written application to the Company stating the
name of the proposed transferee and otherwise complying with the terms of this Agreement and all applicable Laws. No such Transfer
shall be effected until, and such transferee shall succeed to the rights of such Holder only upon, final acceptance and registration
of the transfer by the Company in the register in accordance with this Agreement. Prior to due presentation for registration of
transfer, the Company and any agent of the Company may deem and treat the Person in whose name the Warrant Certificates are registered
as the absolute owner thereof for all purposes (notwithstanding any notation of ownership or other writing thereon made by anyone),
and the Company shall not be affected by any notice to the contrary or be bound to recognize any equitable or other claim to or
an interest in any Warrants on the part of any other Person and shall not be liable for any registration of transfer of Warrant
Certificates that are registered or to be registered in the name of a fiduciary or the nominee of a fiduciary unless made with
actual knowledge that a fiduciary or nominee is committing a breach of trust in requesting such

 

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registration of transfer or with
such knowledge of such facts that its participation therein amounts to bad faith. When Warrant Certificates are presented to the
Company with a request to register the transfer thereof or to exchange them for an equal number of Warrant Certificates of other
authorized denominations, the Company shall register the transfer or make the exchange as requested if the requirements of this
Agreement for such transaction are met, and shall execute any Warrant Certificates necessary to reflect such transfer or exchange.
No service charge shall be made for any registration of transfer or exchange of Warrant Certificates, but the Company may require
payment of a sum sufficient to cover any transfer tax or similar governmental charge payable in connection with any registration
of transfer of Warrant Certificates.

 

(d)          Except
as otherwise provided in this Section 2.3, all Warrant Certificates issued upon any registration of transfer or exchange of Warrants
shall be the valid obligations of the Company, evidencing the same obligations, and entitled to the same benefits under this Agreement,
as the Warrant Certificates surrendered for registration of transfer or exchange.

 

(e)          The
Board shall have the power to determine, in its sole and absolute discretion, all matters related to this Section 2.3, including
matters necessary or desirable to administer or to determine compliance with this Section 2.3 and, absent manifest error, the determinations
of the Board shall be final and binding on the Company and the Holder.

 

Section 2.4          Surrender
and Cancellation of Warrant Certificates. Any Warrant Certificate surrendered for registration of transfer, exchange or
exercise of the Warrants represented thereby or pursuant to Section 3.3 shall be surrendered to the Company, and all Warrant Certificates
surrendered shall be promptly canceled by the Company and shall not be reissued by the Company and, except as provided in Section
2.3 (in the case of a transfer or exchange), Section 3.2(c) (in the case of the exercise of less than all the Warrants represented
by the surrendered Warrant Certificate) or ARTICLE V (in the case of a lost, stolen, destroyed or mutilated Warrant Certificate),
no Warrant Certificate shall be issued hereunder in lieu thereof. The Company shall destroy all canceled Warrant Certificates
in accordance with its normal procedures.

 

Article
III

EXERCISE OF WARRANTS

 

Section 3.1           Exercise;
Expiration Date. Each outstanding Warrant may be exercised
on any Business Day which is on or after the date hereof and on or before the Expiration Date, but only if the exercise of such
Warrant satisfies the FCC Restrictions and is exempt from the registration requirements of the Securities Act. Any Warrants not
exercised by 5:00 p.m., Los Angeles time, on the Expiration Date shall expire and all rights thereunder and all rights in respect
thereof under this Agreement shall automatically terminate at such time.

 

Section 3.2           Method
of Exercise; Payment of Exercise Price.

 

(a)          All
or any number of Warrants represented by a Warrant Certificate may be exercised prior to the Expiration Date by the Holder thereof
by: (i) surrendering the Warrant Certificate evidencing such Warrants to the Company at its office set forth in Section 8.2 and
(ii) the Holder’s completion and execution of the Exercise Form and the Ownership Certification, in

 

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each case in the
form attached to such Warrant Certificate. The Company may, in its sole discretion, require such Holder to provide documentation
in support of the Ownership Certification and such other information necessary for the Company to make a determination that the
exercise of the Warrants by such Holder otherwise satisfies the FCC Restrictions. Upon delivery of the items set forth in subsections
(i) and (ii) above, the election to exercise such Warrants shall be irrevocable. Such documents referenced above shall be accompanied
by payment in full of the Exercise Price then in effect for each share of Common Stock for which such Warrant is exercised, together
with any documentary, stamp or transfer tax, or other applicable tax or governmental charges.

 

(b)          Except
as set forth in Section 3.3, payment of the Exercise Price shall be made by the Holder exercising his, her or its Warrants by certified
bank check or official bank check in funds payable to the order of the Company, and delivered to the Company at the address set
forth in Section 8.2.

 

(c)          Partial
Exercise; Surrender of Warrant Certificates. All or any number of whole Warrants represented by a Warrant Certificate may be
exercised by the Holder thereof. If less than all of the Warrants represented by a Warrant Certificate are exercised, such Warrant
Certificate shall be surrendered and a new Warrant Certificate executed by the Company of the same tenor and for the number of
Warrants which were not exercised shall be issued by the Company. The Company shall (i) countersign such Warrant Certificate, (ii)
register such Warrant Certificate in such name or names as may be directed in writing by such Holder and (iii) deliver the new
Warrant Certificate to the Person or Persons in whose name such new Warrant Certificate is so registered. Any Warrant Certificate
surrendered for exercise to the Company shall be promptly cancelled by the Company and shall not be reissued by the Company.

 

(d)          Issuance
of Common Stock. Upon surrender of a Warrant Certificate evidencing Warrants in conformity with the foregoing provisions and
payment of the Exercise Price in respect of the exercise of one or more Warrants evidenced thereby, the Company shall, when such
payment is received and subject to Section 8.1, as promptly as practicable, and in any event within twenty (20) Business Days after
receipt by the Company of such notice of exercise, issue the aggregate number of shares of Common Stock issuable upon such exercise
(based upon the aggregate number of Warrants so exercised), as determined in accordance with Section 3.2(f). Such shares of Common
Stock shall be registered in the name of such Holder in the Company’s stock records.

 

(e)          Time
of Exercise. Except for exercises in connection with an Optional Redemption (as defined below), any Warrant exercised hereunder
shall be deemed to have been effected immediately prior to the close of business on the day on which the Warrant Certificate representing
such Warrant shall have been surrendered for exercise as provided above, together with the notice of exercise referred to above
and payment in full of the Exercise Price and any documentary, stamp or transfer tax, or other applicable tax or governmental charges.
At such time, the shares of Common Stock issuable upon such exercise as provided in Section 3.2(d) shall be deemed to have been
issued and, for all purposes of this Agreement, the Holder exercising such Warrant shall, as between such Person and the Company,
be deemed to be and entitled to all rights of the holder of record of such shares of Common Stock.

 

    	7

    	 

    

 

(f)          Stock
Issuable. The number of shares of Common Stock “obtainable upon exercise” of Warrants at any time shall be the
number of shares of Common Stock for which such Warrants are then exercisable. The number of shares “for which each Warrant
is exercisable” shall be one (1) share of Common Stock subject to adjustment as provided in Section 4.1.

 

Section 3.3           Optional
Redemption. If the Board elects at any time, the Board may cause all Warrants issued hereunder to be deemed exercised
(an “Optional Redemption”) for Common Stock in accordance with the terms hereof and of the Warrant Certificate
(giving effect to any adjustments to the number of shares of Common Stock obtainable upon exercise of such Warrants, as the case
may be, that occur or would occur prior to such deemed exercise in accordance with the terms of this Warrant Agreement and the
Warrant Certificates). Any Optional Redemption shall include a waiver of any Exercise Price otherwise payable upon the exercise
of such Warrants. Upon making an election for an Optional Redemption, the Board shall provide the Holders with written notice
of the effectiveness of such Optional Redemption, and within twenty (20) Business Days after providing such notice, the Company
shall issue to each Holder the aggregate number of shares of Common Stock issuable upon such election to each such Holder.

 

Article
IV

ADJUSTMENTS

 

Section 4.1           Adjustments.
The number of shares of Common Stock for which each Warrant is exercisable shall be subject to adjustment from time to time as
follows:

 

(a)          Upon
Dividends, Subdivisions or Splits. If, at any time after the date hereof, the number of shares of Common Stock outstanding
is increased by a dividend or pro rata distribution, in each case payable in shares of Common Stock, or by a subdivision or split-up
of Common Stock, following the record date for the determination of holders of Common Stock entitled to receive such dividend or
distribution, or in the cases of a subdivision or split-up, on the day following the effective date thereof, the number of shares
of Common Stock obtainable upon exercise of the Warrants shall be increased in proportion to such increase in outstanding shares
of Common Stock. The adjustment made pursuant to this Section 4.1(a) shall become effective (i) in the case of any such dividend
or distribution, immediately after the close of business on the record date for the determination of holders of Common Stock entitled
to receive such dividend or distribution or (ii) in the case of such subdivision or split-up, at the time when such subdivision
or split-up becomes effective with respect to all holders of Common Stock.

 

(b)          Upon
Combinations or Reverse Splits. If, at any time after the date hereof, the number of shares of Common Stock outstanding is
decreased by a combination or reverse split of the outstanding shares of Common Stock into a smaller number of shares of Common
Stock, then the number of shares of Common Stock obtainable upon exercise of the Warrants immediately prior to the date of such
combination or reverse split shall be decreased in proportion to such decrease in outstanding shares of Common Stock. The adjustment
made pursuant to this Section 4.1(b) shall become effective at the time when such combination or reverse split becomes effective
with respect to all holders of Common Stock.

 

    	8

    	 

    

 

(c)          Organic
Change. Prior to the consummation of any Organic Change, unless the Company intends to cause an Optional Redemption in connection
with such transaction, the Company shall make appropriate provision to insure that each Holder of the Warrants shall thereafter
have the right to acquire and receive, in lieu of or addition to (as the case may be) the Common Stock immediately theretofore
acquirable and receivable upon the exercise of such Holder’s Warrants, such cash, interests, securities or other assets or
property as would have been issued or payable in such Organic Change (if the Holder had exercised such Holder’s Warrants
immediately prior to such Organic Change) with respect to or in exchange for the Common Stock immediately theretofore acquirable
and receivable upon exercise of such Holder’s Warrants had such Organic Change not taken place.

 

(d)          No
Exercise Price Adjustment. Except as the Company may determine is appropriate in connection with an adjustment pursuant to
Section 4.1(c), the Exercise Price payable upon exercise of the Warrant is not subject to adjustment in connection with the provisions
of this Section 4.1.

 

(e)          Treasury
Shares. Shares of Common Stock at any time owned by the Company or its subsidiaries shall not be deemed to be outstanding for
the purposes of any computation under this Section 4.1.

 

Section 4.2           Notice
of Adjustment. Whenever the number of shares of Common Stock or other securities
or property, as applicable, obtainable upon exercise of each Warrant is required to be adjusted pursuant to Section 4.1, the Company
shall deliver to the Holder of such Warrant a certificate setting forth (a) the number of shares of Common Stock or other securities
or property, as applicable, obtainable upon exercise of each such Warrant and the Exercise Price therefor after such adjustment,
(b) a brief statement of the facts requiring such adjustment and (c) the computation by which such adjustment was made. Such certificate
shall be conclusive evidence of the correctness of such adjustment absent manifest error.

 

Section 4.3           Statement
on Warrants.  The form of Warrant Certificate need not be changed because of
any adjustment made pursuant to Section 4.1, and Warrant Certificates issued after such adjustment may state the same number and
kind of shares of Common Stock as are stated in the Warrant Certificates initially issued pursuant to this Agreement. The Company
may, however, at any time in its sole discretion (which shall be conclusive), make any change in the form of Warrant Certificate
that it may deem appropriate to reflect any such adjustment and that does not affect the substance thereof and any Warrant Certificate
thereafter issued or countersigned, whether in exchange or substitution for an outstanding Warrant Certificate or otherwise, may
be in the form so changed.

 

Section 4.4         Notice
of Organic Change.   In the event that, at any time after the date hereof and
prior to 5:00 p.m., Los Angeles time, on the Expiration Date, (a) the Company consummates an Organic Change or (b) the Company
dissolves, liquidates or winds up its operations, and in each such case unless the Company intends to cause an Optional Redemption
in connection with such transaction, the Company shall cause to be mailed to the Holders notice of the date on which such Organic
Change, dissolution, liquidation or winding up shall or did take place, as the case may be. Such notice shall also set forth such
facts as shall indicate the effect of such action (to the extent such effect may be known at the date of such notice), if any,

 

    	9

    	 

    

 

on the kind and amount of shares of Common Stock and other securities, money and other property deliverable upon exercise of the
Warrants after giving effect to such transaction.

 

Section
4.5         Concerning All Adjustments.
 Notwithstanding anything to the contrary contained in this Agreement, if an adjustment is made under any provision of ARTICLE
IV on account of any event, transaction, circumstance, condition or happening, no additional adjustment shall be made under any
other provision of ARTICLE IV on account of such event, transaction, circumstance, condition or happening (i.e, there shall be
no “double credit” given for a single event, transaction, circumstance, condition or happening). Unless otherwise
expressly provided in this ARTICLE IV, all determinations and calculations required or permitted under this ARTICLE IV shall be
made by the Company or its Board, as appropriate, and all such calculations and determinations shall be conclusive and binding
in the absence of manifest error.

 

Article
V

LOSS, THEFT, DESTRUCTION OR MUTILATION OF WARRANT CERTIFICATES

 

Section 5.1         Loss,
Theft, Destruction or Mutilation.   Upon receipt by the Company of evidence satisfactory
to it of the ownership and the loss, theft, destruction or mutilation of any Warrant Certificate, and an indemnity bond in form
and amount and with corporate surety satisfactory to it, and (in the case of mutilation) upon surrender and cancellation thereof,
then, in the absence of notice to the Company that the Warrants represented thereby have been acquired by a bona fide purchaser,
the Company shall issue, execute and deliver to the Holder of the lost, stolen, destroyed or mutilated Warrant Certificate, in
exchange and substitution for or in lieu thereof, a new Warrant Certificate of the same tenor and representing an equivalent number
of Warrants. Upon the issuance of any new Warrant Certificate under this ARTICLE V, the Company may require the payment of a sum
sufficient to cover any tax or other governmental charge that may be imposed in relation thereto and other expenses (including
the fees and expenses of the Company) in connection therewith. The provisions of this ARTICLE V are exclusive and shall preclude
(to the extent lawful) all other rights or remedies with respect to the replacement of lost, stolen, destroyed or mutilated Warrant
Certificates.

 

Article
VI

AUTHORIZATION OF SHARES; PURCHASE OF WARRANTS

 

Section 6.1         Authorization
of Shares.   The Company covenants that all Common Stock issuable upon exercise
of the Warrants will, upon issuance, be duly and validly issued, fully paid and nonassessable and will be free from all taxes,
liens and charges in respect of the issue thereof (other than taxes in respect of any transfer occurring contemporaneously or
otherwise specified herein). The Company shall take all such actions as may be necessary to ensure that all such Common Stock
may be so issued without violation of any applicable law or governmental regulation.

 

Article
VII

WARRANT HOLDER RIGHTS

 

Section 7.1           Rights
Generally. The Holders shall be entitled to the rights applicable to the holders of Warrants, if any, set forth in the
Registration Agreement.

 

    	10

    	 

    

 

Section 7.2           Dividends
and Distributions. If the Company declares or pays a dividend or makes any other distribution upon shares of Common Stock,
except for a dividend payable in Common Stock (which will be addressed by Section 4.1) (a “Dividend”),
then the Company shall pay to each Holder at the time of the Dividend the amount which would have been paid to such Holder on
the shares of Common Stock which such Holder would have held had the Warrants held by such Holder been fully exercised immediately
prior to the date on which a record is taken for such Dividend, or, if no record is taken, the date as of which the record holders
of Common Stock entitled to such Dividend are to be determined.

 

Article
VIII

MISCELLANEOUS

 

Section 8.1          Payment
of Taxes. The Company shall pay any and all taxes (other than income taxes)
that may be payable in respect of the issue or delivery of shares of Common Stock on exercise of Warrants pursuant hereto. The
Company shall not be required, however, to pay any tax or other charge imposed in respect of any transfer involved in the issue
and delivery of any shares of Common Stock or payment of cash or other property to any recipient other than the Holder of the
Warrant Certificate surrendered upon the exercise of a Warrant, and in case of such transfer or payment, the Company shall not
be required to issue or deliver any shares or pay any cash until (a) such tax or charge has been paid or an amount sufficient
for the payment thereof has been delivered to the Company or (b) it has been established to the Company’s satisfaction that
any such tax or other charge that is or may become due has been paid.

 

Section 8.2           Notices.

 

(a)          Any
notice, request, demand or report (each, a “Communication”) required or permitted to be given or made
by this Agreement shall be in writing.

 

(b)          Any
Communication authorized by this Agreement to be given or made by the Holders to or on the Company shall be sufficiently given
or made if sent by registered or certified overnight mail or by a nationally recognized overnight delivery service for next day
delivery and shall be deemed given upon receipt, or by facsimile or electronic mail, addressed as follows:

 

Townsquare Media, Inc.

240 Greenwich Avenue

Greenwich, CT 06830

Attention: Chief Executive Officer

Facsimile: (203) 861-0920

 

(c)          Any
Communication authorized by this Agreement to be given or made by the Company to any Holder shall be sufficiently given or made
if sent by first-class mail, postage prepaid, or by facsimile or electronic mail, addressed to such Holder at the address of such
Holder as shown on the registry books of the Company.

 

    	11

    	 

    

 

Section 8.3           Submission
to Jurisdiction; Waiver of Jury Trial.

 

(a)          Submission
to Jurisdiction. Any action, suit or proceeding seeking to enforce any provision of, or based on any matter arising out of
or in connection with, this Agreement or the transactions contemplated hereby shall only be brought in any federal court located
in the State of Delaware or any Delaware state court, and each party consents to the exclusive jurisdiction and venue of such courts
(and of the appropriate appellate courts therefrom) in any such action, suit or proceeding and irrevocably waives, to the fullest
extent permitted by law, any objection that it may now or hereafter have to the laying of the venue of any such, action, suit or
proceeding in any such court or that any such action, suit or proceeding brought in any such court has been brought in an inconvenient
forum; provided, however, that any action, suit or proceeding, seeking to enforce a final judgment rendered in such court may be
brought in any court of competent jurisdiction. Process in any such action, suit or proceeding may be served on any party anywhere
in the world, whether within or without the jurisdiction of any such court. Without limiting the foregoing, service of process
on such party as provided in Section 8.2 shall be deemed effective service of process on such party.

 

(b)          Waiver
of Jury Trial. EACH PARTY ACKNOWLEDGES THAT ANY DISPUTE THAT MAY ARISE OUT OF OR RELATING TO THIS AGREEMENT IS LIKELY TO INVOLVE
COMPLICATED AND DIFFICULT ISSUES, AND THEREFORE SUCH PARTY HEREBY EXPRESSLY WAIVES ITS RIGHT TO JURY TRIAL OF ANY DISPUTE BASED
UPON OR ARISING OUT OF THIS AGREEMENT OR ANY OTHER AGREEMENTS RELATING HERETO OR ANY DEALINGS AMONG THEM RELATING TO THE TRANSACTIONS
CONTEMPLATED HEREBY. THE SCOPE OF THIS WAIVER IS INTENDED TO ENCOMPASS ANY AND ALL ACTIONS, SUITS AND PROCEEDINGS THAT RELATE TO
THE SUBJECT MATTER OF THE TRANSACTIONS CONTEMPLATED HEREBY, INCLUDING CONTRACT CLAIMS, TORT CLAIMS, BREACH OF DUTY CLAIMS, AND
ALL OTHER COMMON LAW AND STATUTORY CLAIMS. EACH PARTY REPRESENTS THAT (i) NO REPRESENTATIVE, AGENT OR ATTORNEY OF ANY OTHER PARTY
HAS REPRESENTED, EXPRESSLY OR OTHERWISE, THAT SUCH OTHER PARTY WOULD NOT IN THE EVENT OF ANY ACTION, SUIT OR PROCEEDING, SEEK TO
ENFORCE THE FOREGOING WAIVER, (ii) SUCH PARTY UNDERSTANDS AND WITH THE ADVICE OF COUNSEL HAS CONSIDERED THE IMPLICATIONS OF THIS
WAIVER, (iii) SUCH PARTY MAKES THIS WAIVER VOLUNTARILY AND (iv) SUCH PARTY HAS BEEN INDUCED TO ENTER INTO THIS AGREEMENT BY, AMONG
OTHER THINGS, THE MUTUAL WAIVERS AND REPRESENTATIONS IN THIS SECTION 8.3(b).

 

Section 8.4         Governing
Law. This Agreement will be governed by and construed in accordance
with the laws of the State of Delaware, without giving effect to any choice of law principles.

 

Section
8.5         Binding Effect.
This Agreement shall be binding upon and inure to the benefit of the Company and its successors and assigns, and the Holders from
time to time party hereto. Nothing in this Agreement is intended or shall be construed to confer upon any Person, other than the
Company and the Holders, any right, remedy or claim under or by reason of this Agreement or any part hereof.

 

    	12

    	 

    

 

Section
8.6         Counterparts.
 This Agreement may be executed manually or by facsimile in any number of counterparts, each of which shall be deemed an original,
but all of which together constitute one and the same instrument.

 

Section 8.7           Amendments.

 

(a)          The
Company may, without the consent or concurrence of the Holders, amend this Agreement for the purpose of (i) amending provisions
in regard to matters or questions arising under this Agreement which shall not materially adversely affect the interest of the
Holders or (ii) adding further covenants and agreements of the Company in this Agreement or surrendering any rights or power reserved
to or conferred upon the Company in this Agreement.

 

(b)          All
amendments or modifications other than those described in Section 8.7(a) shall require the written consent of each of the Holders
of a majority of the Warrants and the Company.

 

Section 8.8         Third
Party Beneficiaries.   This Agreement is intended for the benefit of the parties
hereto, and no other Person shall be entitled to any rights or benefits hereunder.

 

Section 8.9         Waivers.  
The failure of any party to enforce any of the provisions of this Agreement shall in no way be construed as a waiver of such provisions
and shall not affect the right of such party thereafter to enforce each and every provision of this Agreement in accordance with
its terms.

 

Section 8.10        Inspection.  
The Company shall cause a copy of this Agreement to be available at all reasonable times at the office of the Company for inspection
by the Holders. The Company may require any of the Holders to submit his, her or its Warrant Certificate for inspection by it.

 

Section 8.11        Headings.  
The descriptive headings of the several Sections of this Agreement are inserted for convenience and shall not control or affect
the meaning or construction of any of the provisions hereof.

 

Section 8.12        Construction.  
This Agreement has been freely and fairly negotiated among the parties. If an ambiguity or question of intent or interpretation
arises, this Agreement will be construed as if drafted jointly by the parties and no presumption or burden of proof will arise
favoring or disfavoring any party because of the authorship of any provision of this Agreement.

 

Section 8.13        Severability.  
In the event that any one or more of the provisions, paragraphs, words, clauses, phrases or sentences contained herein, or the
application thereof in any circumstances, is held invalid, illegal or unenforceable in any respect for any reason, the validity,
legality and enforceability of any such provision, paragraph, word, clause, phrase or sentence in every other respect and of the
other remaining provisions, paragraphs, words, clauses, phrases or sentences hereof shall not be in any way impaired, it being
intended that all rights, powers and privileges of the parties hereto shall be enforceable to the fullest extent

 

    	13

    	 

    

 

permitted by
law; provided that this Section 8.13 shall not cause this Agreement or the Warrants to differ materially from the intent of the
parties as herein expressed.

 

Section 8.14       Entire
Agreement.   This Agreement and the Warrant Certificate set forth the entire
agreement of the parties hereto as to the subject matter hereof and supersedes all previous agreements among all or some of the
parties hereto with respect thereto, whether written, oral or otherwise.

 

* * * * *

  

    	14

    	 

    

 

IN WITNESS WHEREOF, the parties hereto have
executed this Agreement as of the day and year first above written.

 

	 	TOWNSQUARE MEDIA, INC.
	 	 
	 	By: 	/s/ Stuart Rosenstein
	 	Name: 	Stuart Rosenstein
	 	Title:  	EVP / CFO

 

Signature Page - Warrant
Agreement

 

    	 

    	 

    

  

	 	HOLDERS OF THE REQUIRED INTEREST
	 	 
	 	OCM POF IV AIF GAP HOLDINGS, L.P.
	 	 
	 	By: OCM/GAP Holdings IV, Inc.
	 	Its: General Partner
	 	 
	 	By:	/s/ B. James Ford	 
	 	Name:  B. James Ford
	 	Title:  Authorized Signatory
	 	 
	 	By:	/s/ David Quick	 
	 	Name: David Quick
	 	Title: Authorized Signatory
	 	 
	 	OCM PF/FF RADIO HOLDINGS PT, L.P.
	 	 
	 	By:	Oaktree Fund AIF Series, L.P. – Series D and
	 	 	Oaktree Fund AIF Series, L.P. – Series I
	 	Its:	General Partners
	 	 
	 	By:	Oaktree Fund GP AIF, LLC
	 	Its:  	General Partner
	 	 
	 	By:	Oaktree Fund GP III, L.P.
	 	Its:	Managing Member
	 	 
	 	By: 	/s/ B. James Ford	 
	 	Name:  B. James Ford
	 	Title:  Authorized Signatory
	 	 
	 	By:	/s/ David Quick	 
	 	Name: David Quick
	 	Title: Authorized Signatory

 

Signature Page - Warrant
Agreement

 

    	 

    	 

    

 

	Bay Street Holdings, LLC Series 10-Regent Communications
	 	 
	By:	/s/ John J. Rudy	 
	Name: 	John J. Rudy	 
	Title:	President	 

  

Signature Page - Warrant
Agreement

 

    	 

    	 

    

 

BCM 2005-I ETB, Inc

BCM 2005-II ETB, Inc

BCM 2005-III ETB, Inc

BCM 2006-I ETB, Inc

BCM 2006-II ETB, Inc

BCM 2006-III ETB, Inc

BCM Mid-Market ETB, Inc

BCM Sapphire Valley ETB, Inc.

By: Babson Capital Management LLC under power of attorney

 

 

 

	By:	/s/ Thomas D. McDonnell	 
	Name: 	Thomas D. McDonnell	 
	Title:	M.D	 

  

Signature Page - Warrant
Agreement

 

    	 

    	 

    

 

Credit Suisse Securities (USA) LLC

 

	By:	/s/ Kenneth Hoffman	 
	Name: 	 Kenneth Hoffman	 
	Title:	Managing Director	 

 

Signature Page - Warrant
Agreement

 

    	 

    	 

    

  

	Series K of Special Asset Equity Holdings Series, LLC	 
		 
	 	 	 
	By:	William J. Fitzgerald	 
	Name: 	William J. Fitzgerald	 
	Title:	Senior Vice President	 

 

	By:	/s/ John S. Yusi III	 
	Name:  	John S. Yusi III	 
	Title: 	Vice President	 

 

Signature Page - Warrant
Agreement

 

    	 

    	 

    

 

Schedule I

 

Holders of Warrants

 

As of July 25, 2014

 

	 
Holder
                                         Name
	 	Warrants Exercisable for

    Class A Common Stock	 
	OCM POF IV AIF GAP Holdings, L.P.	 	 	6,052,487	 
	OCM PF/FF Radio Holdings PT, L.P	 	 	2,553,004	 
	Bay Street Holdings, LLC Series 10 - Regent Communications	 	 	531,202	 
	BCM 2005-I ETB, Inc.	 	 	43,685	 
	BCM 2005-II ETB, Inc.	 	 	23,664	 
	BCM 2005-III ETB, Inc.	 	 	4,729	 
	BCM 2006-I ETB, Inc.	 	 	7,742	 
	BCM 2006-II ETB, Inc.	 	 	72,865	 
	BCM 2007-I ETB, Inc.	 	 	7,751	 
	BCM Mid-Market ETB, Inc.	 	 	3,876	 
	BCM Sapphire Valley ETB, Inc.	 	 	45,177	 
	Credit Suisse Securities (USA) LLC	 	 	10,622	 
	Special Asset Equity Holdings Series, LLC - Series K	 	 	152,074	 
	TOTAL	 	 	9,508,878	 

 

    	 

    	 

    

 

ANNEX A

 

FORM OF WARRANT CERTIFICATE

 

TOWNSQUARE MEDIA, INC.

 

No.______

 

_________ Warrants

 

WARRANTS TO PURCHASE COMMON STOCK

 

“THIS WARRANT, AND THE CLASS
A COMMON STOCK OF THE COMPANY WHICH MAY BE PURCHASED PURSUANT TO THE EXERCISE OF THIS WARRANT (COLLECTIVELY, THE “WARRANT
SHARES,” AND TOGETHER WITH THIS WARRANT, THE “SECURITIES”), HAVE NOT BEEN REGISTERED UNDER THE SECURITIES
ACT OF 1933, AS AMENDED, OR UNDER ANY OTHER APPLICABLE SECURITIES LAWS, AND MAY NOT BE SOLD OR TRANSFERRED IN THE ABSENCE OF EFFECTIVE
REGISTRATION UNDER SUCH ACT AND LAWS OR EXEMPTION THEREFROM. THIS WARRANT MUST BE SURRENDERED TO THE COMPANY OR ITS TRANSFER AGENT
AS A CONDITION PRECEDENT TO THE SALE, PLEDGE OR OTHER TRANSFER OF ANY INTEREST IN ANY OF THE WARRANT SHARES REPRESENTED BY THIS
WARRANT.

 

THE WARRANT SHARES REPRESENTED BY
THIS WARRANT ARE SUBJECT TO THE POWERS, DESIGNATIONS, PREFERENCES AND RELATIVE, PARTICIPATING, OPTIONAL OR OTHER SPECIAL RIGHTS,
AND THE QUALIFICATIONS, LIMITATIONS OR RESTRICTIONS OF SUCH PREFERENCES AND/OR RIGHTS, SPECIFIED IN THE CERTIFICATE OF INCORPORATION
OF THE COMPANY, AS AMENDED FROM TIME TO TIME. A COPY OF SUCH CERTIFICATE OF INCORPORATION SHALL BE FURNISHED BY THE COMPANY TO
THE HOLDER HEREOF UPON WRITTEN REQUEST AND WITHOUT CHARGE.

 

THE SECURITIES ARE SUBJECT TO CERTAIN
RESTRICTIONS ON EXERCISE, TRANSFER, SALE, ASSIGNMENT, PLEDGE, ENCUMBRANCE OR OTHER SIMILAR TRANSFER AS SET FORTH IN A REGISTRATION
AGREEMENT AMONG THE COMPANY AND THE PERSONS PARTY THERETO, AND A WARRANT AGREEMENT AMONG THE COMPANY AND THE ORIGINAL HOLDER OF
THIS WARRANT, COPIES OF WHICH MAY BE OBTAINED AT THE PRINCIPAL OFFICE OF THE COMPANY.”

 

This certifies that _____________, or its registered
assigns, is the owner of the number of Warrants set forth above, each of which represents the right to purchase, commencing on
the date of execution of the Warrant Agreement hereinafter referred to, from TOWNSQUARE MEDIA, INC., a Delaware corporation (the
“Company”), one share of Class A Common Stock,

 

    	A-1

    	 

    

 

par value $0.01 per share, of the Company (the “Common
Stock”) (subject to adjustment as provided in the Warrant Agreement hereinafter referred to) at the purchase price
(the “Exercise Price”) of $0.0001 per one share of Common Stock by: (a) surrendering this Warrant Certificate
at the principal office of the Company, (b) delivering to the Company the Exercise Form attached hereto as Exhibit A-1,
(c) delivering to the Company the Ownership Certification attached hereto as Exhibit A-2 completed and duly executed
and (d) delivering to the Company payment in full of the Exercise Price by certified bank check or official bank check in funds
payable to the order of the Company, all subject to the terms and conditions hereof and of the Warrant Agreement. This Warrant
Certificate may be exercised as to all or any whole number of the Warrants evidenced hereby.

 

Each outstanding Warrant may be exercised on
any Business Day which is on or after the date of execution of the Warrant Agreement and on or before the Expiration Date, but
only if the Holder has delivered to the Company an Ownership Certification and such exercise otherwise satisfies the FCC Restrictions.
Any Warrants not exercised by 5:00 p.m., Los Angeles time, on the Expiration Date of the Warrant Agreement shall expire and all
rights thereunder and all rights in respect thereof under this Warrant and the Warrant Agreement shall automatically terminate
at such time.

 

This Warrant Certificate is issued under and
in accordance with a Warrant Agreement dated as of July 25, 2014 (as amended or modified from time to time, the “Warrant
Agreement”) by and among the Company, the original Holder of this Warrant Certificate and the other holders party
thereto and is subject to the terms and provisions contained therein, all of which terms and provisions the Holder of this Warrant
Certificate consents to by acceptance hereof. The Warrant Agreement is hereby incorporated herein by reference and made a part
hereof. Reference is hereby made to the Warrant Agreement for a full description of the rights, limitations of rights, obligations,
duties and immunities thereunder of the Company and the Holder. The summary of the terms of the Warrant Agreement contained in
this Warrant Certificate is qualified in its entirety by express reference to the Warrant Agreement. All capitalized terms used
in this Warrant Certificate that are defined in the Warrant Agreement shall have the meanings assigned to them in the Warrant Agreement.

 

Copies of the Warrant Agreement are on file
at the office of the Company and may be obtained by writing to the Company at the following address:

 

Townsquare Media, Inc.

240 Greenwich Avenue

Greenwich, CT 06830

Attention: Chief Executive Officer

Facsimile: (203) 861-0920

 

The number of shares of Common Stock obtainable
upon the exercise of each Warrant is subject to adjustment as provided in the Warrant Agreement.

 

The Company shall pay any and all taxes (other
than income taxes) that may be payable in respect of the issue or delivery of shares of Common Stock on exercise of Warrants pursuant
hereto. The Company shall not be required, however, to pay any tax or other charge imposed in

 

    	A-2

    	 

    

 

respect of any transfer involved
in the issue and delivery of any shares of Common Stock or payment of cash or other property to any recipient other than the Holder
of the Warrant Certificate surrendered upon the exercise of a Warrant, and in case of such transfer or payment, the Company shall
not be required to issue or deliver any shares or pay any cash until (a) such tax or charge has been paid or an amount sufficient
for the payment thereof has been delivered to the Company or (b) it has been established to the Company’s satisfaction that
any such tax or other charge that is or may become due has been paid.

 

Subject to Section 2.3 of the Warrant Agreement,
this Warrant Certificate and all rights hereunder are transferable by the registered Holder hereof, in any whole number of Warrants,
in accordance with the provisions of the Warrant Agreement, upon surrender of this Warrant Certificate, along with (a) an Assignment
Form in the form of Exhibit B-1 attached hereto duly executed and completed, (b) a Joinder to the Registration Agreement
in the form of Exhibit B-2 attached hereto duly executed and completed and (c) payment of any necessary transfer tax or
other governmental charge imposed upon such transfer. Upon any partial transfer, the Company will issue and deliver to such Holder
a new Warrant Certificate with respect to any portion not so transferred. Each taker and Holder of this Warrant Certificate, by
taking and holding the same, consents and agrees that prior to the registration of transfer as provided in the Warrant Agreement,
the Company may treat the Person in whose name the Warrants are registered as the absolute owner hereof for any purpose and as
the Person entitled to exercise the rights represented hereby, any notice to the contrary notwithstanding. Each taker and Holder
of a Warrant and each taker and holder of Common Stock issued pursuant to a Warrant agrees to be bound by the terms and conditions
of this Warrant and the Warrant Agreement.

 

This Warrant Certificate may be exchanged,
in accordance with the terms of the Warrant Agreement, at the Company’s offices for Warrant Certificates representing the
same aggregate number of Warrants, with each new Warrant Certificate to represent such number of Warrants as the Holder hereof
shall designate at the time of such exchange.

 

Prior to the exercise of the Warrants represented
hereby, the Holder of this Warrant Certificate shall be entitled to the rights, and subject to the obligations, set forth in
the Registration Agreement, and shall be bound by the terms of each such agreement as a party thereto. In the event the Holder
exercises any Warrant and completes and duly executes the Ownership Certification and the Exercise Form, the Company shall issue
to the Holder such shares of Common Stock as the Holder shall be entitled to under such Warrant and the Company shall record or
cause to be recorded such ownership on its books.

 

    	A-3

    	 

    

 

This Warrant Certificate shall be void and
all rights evidenced hereby shall cease on the Expiration Date. 

 

	 	TOWNSQUARE MEDIA, INC.
	 	 	 
	 	By:	 
	 	 	Name:
	 	 	Title:
	 	 	 
	 	Dated:	 

 

    	A-4

    	 

    

 

Countersigned:

 

[HOLDER]

 

	By:	 	 
	 	Name:	 
	 	Title:	 
	 	 	 
	Dated:	 	 

 

    	A-5

    	 

    

 

EXHIBIT A-1

 

EXERCISE FORM

(to be executed only upon exercise of Warrants)

 

To: TOWNSQUARE MEDIA, INC.

 

The undersigned hereby irrevocably exercises
the Warrants represented by the Warrant Certificate to obtain Class A Common Stock (subject to adjustment) of TOWNSQUARE MEDIA,
INC., a Delaware corporation (the “Company”), for each Warrant exercised, and makes payment of $______________
(such payment being by certified bank check or official bank check in funds payable to the order of the Company equal to the Exercise
Price of the Warrants being exercised), on the terms and conditions specified in the Warrant Certificate and the Warrant Agreement
therein referred to, and hereby surrenders this Warrant Certificate and all right, title and interest therein to and directs that
the Class A Common Stock due upon the exercise of such Warrants be registered or placed in the name and the address specified below.

 

HOLDER INFORMATION:

 

Name of Holder: _____________________________________

 

Signature of Holder: _____________________________________

 

Dated: _____________________________________

 

Street Address: _____________________________________

 

City, State, Zip Code:
_____________________________________

 

RECIPIENT INFORMATION:

 

Securities and/or check
to be issued to: _____________________________________

 

Signature of Recipient:
_____________________________________

 

Dated: _____________________________________

 

Recipient social security
or taxpayer ID number:____________________________

 

Street Address (if different
from above): ______________________________

 

City, State, Zip Code (if
different from above): ______________________________

 

    	A-6

    	 

    

 

EXHIBIT A-2

OWNERSHIP CERTIFICATION1

(to be executed only upon exercise of Warrants)

 

______________________________ (the “Holder”)
hereby represents and certifies that the Holder is either (a) a citizen of the United States (“U.S. Citizen”)
or (b) an entity organized under the laws of the United States (“U.S. Entity”). To the extent the Holder
is a U.S. Entity, the Holder represents and certifies that U.S. Citizens and U.S. Entities hold one hundred percent (100%) of the
direct and indirect voting interests of Holder and one hundred percent (100%) of the direct and indirect ownership interests of
Holder. The Holder further represents and certifies that, for purposes of this Ownership Certification, it has determined its level
of direct and indirect voting and ownership interests in accordance with 47 U.S.C. § 310(b)(4), as interpreted, calculated
and applied by the FCC.

 

Name of Holder: _____________________________________

 

Signature of Holder: _____________________________________

 

Dated: _____________________________________

 

 

1
The Company may, in its sole discretion, require the Holder to provide (a) documentation in support of this Ownership
Certification and (b) such other information necessary for the Company to make a determination that the exercise of the Warrants
by the Holder otherwise satisfies the FCC Restrictions. Capitalized terms not otherwise defined herein shall have the meanings
set forth in the Warrant Agreement.

 

    	A-7

    	 

    

 

EXHIBIT B-1

ASSIGNMENT FORM

(to be executed only upon assignment of Warrants)

 

FOR VALUE RECEIVED, the undersigned registered
holder of Warrant Certificate No. _____________ issued by Townsquare Media, Inc., a Delaware corporation (the “Company”),
hereby sells, assigns and transfers unto the Assignee(s) named below (including the undersigned with respect to any Warrants constituting
a part of the Warrants evidenced by the within Warrant Certificate not being assigned hereby) all of the rights of the undersigned
under the Warrant Certificate, with respect to the whole number of Warrants set forth below:

 

Name(s) of Assignee(s):

 

No. of Warrants:

 

The undersigned does hereby irrevocably constitute
and appoint the Company as the undersigned’s attorney to make such transfer on the books of the Company maintained for such
purposes, with full power of substitution in the premises.

 

Name of Assignor: _____________________________________

 

Signature of Assignor:
_____________________________________

 

Dated: _____________________________________

 

Street Address: _____________________________________

 

City, State, Zip Code:
_____________________________________

 

The Assignee has received and reviewed the
Warrant Certificate and the Warrant Agreement, and agrees for the benefit of the Company to accept the assignment of the Warrant
set forth herein and be bound by the terms and conditions thereof.

 

Name of Assignee: _____________________________________

 

Signature of Assignee:
_____________________________________

 

Dated: _____________________________________

 

Assignee social security
or taxpayer ID number:____________________________

 

Street Address: ______________________________

 

City, State, Zip Code:
______________________________

 

    	A-8

    	 

    

 

EXHIBIT B-2

JOINDER TO

REGISTRATION AGREEMENT

 

THIS JOINDER to the Second
Amended and Restated Registration Agreement, dated as of ________ __, 2014 (the “Registration Agreement”) of
Townsquare Media, Inc., a Delaware corporation (the “Company”), as amended or restated from time to time, is
made and entered into as of ________ __, _________, by and between the Company and ________________ (“Holder”).

 

WHEREAS, on the date hereof,
Holder has acquired ______ warrants exercisable for ______ shares of Class A Common Stock (the “Warrants”) and
the Registration Agreement and the Company require Holder, as a holder of the Warrants, to become a party to the Registration Agreement,
and Holder agrees to do so in accordance with the terms hereof.

 

NOW, THEREFORE, in consideration
of the mutual covenants contained herein and other good and valuable consideration, the receipt and sufficiency of which are hereby
acknowledged, the parties to this Joinder hereby agree as follows:

 

a.           Agreement
to be Bound. Holder hereby (i) acknowledges that it has received and reviewed a complete copy of the Registration Agreement
and (ii) agrees that upon execution of this Joinder it shall become a party to the Registration Agreement and shall be fully
bound by, and subject to, all of the covenants, terms and conditions of the Registration Agreement as though an original party
thereto and shall be deemed [an Other Securityholder] to the Registration Agreement for all purposes thereof and entitled to all
the rights incidental thereto.

 

b.           Members
Schedule. For purposes of the Schedule of Securityholders to the Registration Agreement, the address of the Holder is
as follows:

 

[Name]

[Address]

 

c.           Governing
Law. This Agreement and the rights of the parties hereunder shall be interpreted in accordance with the laws of the State of
Delaware, and all rights and remedies shall be governed by such laws without regard to principles of conflicts of laws.

 

d.           Counterparts.
This Joinder may be executed in separate counterparts each of which shall be an original and all of which taken together shall
constitute one and the same agreement.

 

e.           Descriptive
Headings. The descriptive headings of this Joinder are inserted for convenience only and do not constitute a part of this Joinder.

 

* * * * *

 

    	A-9

    	 

    

  

IN WITNESS WHEREOF, the parties
hereto have executed this Joinder as of the date set forth in the introductory paragraph hereof.

 

	 	TOWNSQUARE MEDIA, INC.
	 	 
	 	By:	 
	 	 	Name:
	 	 	Title:

 

	[HOLDER]	 
	 	 	 
	By:	 	 
	 	Name:	 
	 	Title:	 
	 	 	 

 

	A-10

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