Document:

EX-10.41

Exhibit 10.41

AMENDMENT

TO

2005 STOCK OPTION AGREEMENT

     This Amendment (the “Amendment”) to that certain 2005 Stock Option Agreement dated as of
December 23, 2005 (the “Option Agreement”) by and between IRWIN COMMERCIAL FINANCE CORPORATION, an
Indiana corporation (“ICF”), and Joseph R. LaLeggia (the “Option Holder”) is entered into as of
this 28th day of July, 2008, by and between ICF and Option Holder.

RECITALS

     WHEREAS, ICF’s parent company, Irwin Union Bank and Trust Company, and its subsidiaries, Irwin
Commercial Finance Canada Corporation (“ICF Canada”) and Onset Alberta Ltd., have entered into an
Asset Purchase Agreement dated as of July 23, 2008 with RoyNat, Inc., a Canada corporation
(“RoyNat”), governing the sale to RoyNat of substantially all of the assets and operations of the
Canadian small-ticket leasing business (the “APA”); and

     WHEREAS, pursuant to the APA, the Option Holder will become an employee of RoyNat effective
upon the completion of the First Closing (as defined in the APA); and

     WHEREAS, the parties wish to memorialize their mutual interest in terminating the Option
Holder’s interest in ICF by (i) having the Option Holder exercise the Option and (ii) having ICF
redeem, effective at the First Closing, all of the shares issuable upon the exercise of such
Option; and

     WHEREAS, in furtherance of the foregoing, the parties desire to amend the Option Agreement to
reflect the terms set forth in this Amendment (it being understood that capitalized terms used but
not otherwise defined herein have the meanings given to them in the Option Agreement or the related
Notice of Stock Option Grant):

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

     SECTION 1. Amendment. Section 3 of the Option Agreement is hereby amended and
restated to read in its entirety as follows:

     “3. Method of Payment. Payment of the Exercise Price may be made as follows:

	 	(a)	 	in cash or its equivalent denominated in U.S. dollars; or
	 
	 	(b)	 	in connection with any exercise occurring in anticipation of a
complete redemption by ICF of the Shares subject to the Option, by having the
notice of exercise direct that the certificate for the number of Shares
issuable upon such exercise (after having given effect to withholding tax
obligations) be delivered to the Corporate Governance Manager and Policy
Coordinator of

 

 

	 	 	 	ICF’s ultimate parent company, Irwin Financial Corporation, to be held in
trust for the benefit of the Option Holder, as shareholder, pending his
receipt of the proceeds of such redemption net of the Exercise Price,
whereupon such certificate shall be cancelled on the stock ledger of ICF and
thereafter be of no force or effect.”

     SECTION 2. Limited Effect. Except as expressly amended and modified by this Amendment,
the Option Agreement shall continue in full force and effect in accordance with its terms.
Reference to this Amendment need not be made in the Option Agreement or any other instrument or
document executed in connection therewith or herewith, any reference in any of such items to the
Option Agreement being sufficient to refer to the Option Agreement as amended hereby.

     SECTION 3. Governing Law. THIS AMENDMENT SHALL BE GOVERNED BY AND CONSTRUED IN
ACCORDANCE WITH THE LAWS OF THE STATE OF INDIANA, WITHOUT REGARD TO THE CONFLICT OF LAWS DOCTRINE
APPLIED IN SUCH STATE.

     SECTION 4. Counterparts. This Amendment may be executed by each of the parties hereto
on any number of separate counterparts, each of which shall be an original and all of which taken
together shall constitute one and the same instrument.

[signature page follows]

2

 

     IN WITNESS WHEREOF, each of the undersigned parties to the Option Agreement has caused this
Amendment to be duly executed, all as of this 28th day of July, 2008.

	 	 	 	 	 	 	 
	 	 	IRWIN COMMERCIAL FINANCE CORPORATION	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ William I. Miller	 	 
	 

	 	 	 	 

	 	 
	 

	 	Its:
	 	Chairman	 	 
	 

	 	 	 	 

	 	 
	 

	 	 	 	/s/ Joseph R. LaLeggia	 	 
	 	 	 	 	 
	 	 	JOSEPH R. LaLEGGIA	 	 

3EX-10.42

Exhibit 10.42

July 29, 2008

Joseph R. LaLeggia

Irwin Commercial Finance — Vancouver

666 Burrard Street, Suite 300 Park Place

Vancouver, B.C. V6C2X8

CANADA

     Re: Redemption Agreement

Dear Joe:

     This letter sets forth the agreement (“Agreement”) between Irwin Commercial Finance
Corporation (“ICF”) and you (the “Shareholder”) with respect to the redemption by ICF of all of
your shares of ICF common stock (“Shares”) in connection with the sale of substantially all of the
assets of Irwin Commercial Finance Canada Corporation to RoyNat, Inc. (the “RoyNat Sale”). Terms
used but not otherwise defined herein have the meanings ascribed to them in that certain First
Amended and Restated Shareholder Agreement dated May 15, 2007 (the “Shareholder Agreement”) by and
among ICF, Irwin Union Bank and Trust Company, you, and the other Option Holders named therein.

     In consideration of the mutual promises contained herein and in the Shareholder Agreement and
for other good and valuable consideration, the receipt and adequacy of which are hereby
acknowledged, the parties hereto agree as follows:

     1. Deemed Call Exercise. The parties hereby agree that the execution and delivery of
this Agreement shall constitute the delivery of a Call notice delivered by ICF under the
Shareholder Agreement.

     2. Valuation. The parties acknowledge that ICF has, at the direction of its Board of
Directors, engaged the Griffing Group as an independent appraiser to conduct, in accordance with
past practice, an appraisal of ICF as of June 30, 2008, upon which the Board’s determination of
Fair Market Value of the Shares has been based for purposes hereof. The parties agree that the
Purchase Price described in Section 4 below reflects the Fair Market Value of the Shares for
purposes hereof.

     3. Call Closing. In accordance with Section 4.4 of the Shareholder Agreement, the
parties hereby agree that the purchase and sale of the Shares shall be structured as a redemption,
to be held simultaneously with the closing of the RoyNat Sale on July 30, 2008 (the “Call
Closing”). At such Call Closing, ICF shall purchase, and the Shareholder shall sell, all of the
Shares issuable upon the Shareholder’s exercise of his option for such Shares in accordance with
the Shareholder’s Option Agreement with ICF, as amended. ICF hereby acknowledges receipt of notice
of such exercise by Shareholder.

 

 

     4. Preliminary Repurchase Price. Notwithstanding anything herein or in the
Shareholder Agreement to the contrary, the purchase price for the Shares shall be equal to
$47,000.00 per Share (the “Purchase Price”).

     5. Payment of Repurchase Price. At the Call Closing, the Purchase Price shall be paid
to Shareholder, net of the Exercise Price payable by the Shareholder upon the exercise of his
Option and applicable withholding taxes.

     6. Transfer of Shares. At the Call Closing, in exchange for the payment of the
Purchase Price, the Shareholder shall instruct the Corporate Governance Manager and Policy
Coordinator of Irwin Financial Corporation to cause the certificate for the purchased and sold
Shares to be transferred to ICF, whereupon it shall be cancelled on the stock ledger of ICF.

     7. Entire Agreement. This Agreement, together with the Shareholder Agreement referred
to herein and the Option Agreement, as amended, embodies the entire agreement and understanding
among the parties hereto with respect to the subject matter hereof and thereof, and supersedes and
preempts any and all prior and contemporaneous understandings, agreements, arrangements or
representations by or among the parties, written or oral, which may relate to the subject matter
hereof or thereof in any way.

     9. Governing Law. This Agreement shall be governed by and construed in accordance
with the laws of the State of Indiana, without regard to conflicts of laws provisions thereof.

     10. Headings. The headings of the paragraphs of this Agreement have been inserted for
convenience of reference only and shall not be deemed to be a part of this Agreement.

[signature page follows]

2

 

     By signing below, the Shareholder accepts and agrees to the terms of this Agreement as of the
date of this letter.

	 	 	 	 	 	 	 
	 	 	Sincerely,	 	 
	 
	 	 	 	 	 	 
	 	 	Irwin Commercial Finance Corporation	 	 
	 
	 	 	 	 	 	 
	 

	 	By:
	 	/s/ William I . Miller	 	 
	 

	 	Title:
	 	 

Chairman
	 	 

	 	 	 
	Accepted and agreed to:
	 	 
	 
	 	 
	/s/ Joseph R. LaLeggia
	 	 
	 

Joseph R. LaLeggia

	 	 

3EX-10.43

Exhibit 10.43

August 29, 2008

     Re: Lump Sum Payment Incentives

Dear Jocelyn,

     In consideration of your services, efforts, dedication and high quality work, and with the
understanding that your services are key to the successful completion of a series of transactions
with Roosevelt Management Company, LLC, Irwin Home Equity Corporation (“Company”) and Irwin
Financial Corporation would like to offer you the opportunity for payment of a series of Lump Sum
Payment Incentives, as described in this letter.

     In order to encourage you to remain employed with the Company through August 31, 2008, the
Company will pay you a First Lump Sum Payment in the gross amount of $25,000 (less normal
deductions required by law). This payment would be in addition to your regular compensation. In
order to earn the First Lump Sum Payment, you would have to be actively employed with the Company
on August 31. Payment would take place on the first payroll date after August 31.

     In order to encourage you to remain employed with the Company through the “Second Closing” as
defined and described in a certain Asset Purchase Agreement dated July 18, 2008 by and among
Roosevelt Management Company, LLC, Irwin Union Bank and Trust Company, and Irwin Home Equity
Corporation, the Company will pay you a Second Lump Sum Payment in the gross amount of $37,500
(less normal deductions required by law). This payment would be in addition to your regular
compensation. In order to earn the Second Lump Sum Payment, you would have to be actively employed
with the Company through the date of said Second Closing, or through October 31, 2008, whichever is
earlier. Payment would take place on the first payroll date after the Second Closing or after the
earlier payment date occurs.

     In order to encourage you to remain employed with the Company through the closing date of a
platform purchase transaction to be entered into by and among the same parties noted above, the
Company will pay you a Third Lump Sum Payment in the gross amount of $62,500 (less normal
deductions required by law). This payment would be in addition to your regular compensation. In
order to earn the Third Lump Sum Payment, you would have to be actively employed with the Company
on the date of such platform purchase transaction closing. Payment would take place on the first
payroll date after said platform transaction closes.

     Eligibility for the Lump Sum Payment Incentives is subject to your agreement to the terms
described in this letter, which will be evidenced by your signing and dating a copy of this letter
and returning it to us as described below.

 

 

     This letter agreement is intended to constitute a contract between you and the Company,
subject to the terms and conditions set forth herein. However, we do want to make it clear to you
that, in signing this letter, you are not making a legal commitment to remain employed with the
Company through the above date. We realize that you will make your own decision about that and
that your decision to remain with the Company will depend on your own personal circumstances. This
letter agreement does not alter your status as an at-will employee of the Company and it is not an
offer or a confirmation of employment for any definite period of time.
The Company, however, agrees that it will terminate your employment before payment of the
third lump sum payment only for “cause”. “Cause” is defined as: (i) conviction of a felony or any
crime involving dishonesty or violence; (ii) willful negligence in the performance of your assigned
duties or the willful commission of any act that causes substantial or material harm to the
Company; or (iii) material insubordination or refusal to comply with any reasonable request of the
Board of Directors relating to your duties.

     If at any time the Company were to terminate your employment without Cause, the Company agrees
to pay you any balance of the three lump sum payments not yet paid. The Company also agrees to pay
you, or your estate, any balance of the three lump sum payments not yet paid in the event (i) you
should begin employment with Roosevelt Management Company LLC, or you should die, prior to the
closing of the platform purchase transaction, and (ii) the transaction actually occurs. Such
payment will be made within 15 days of the closing.

     We do want to make this commitment to you in the hope that it will encourage you to remain
with the Company through the dates and events described in this letter. All terms of this letter
are subject to applicable banking laws and regulations.

     With the above in mind, our agreement is as follows:

1. The Company agrees that if you are actively employed with the Company through August 31, 2008,
you will receive a First Lump Sum Payment of $25,000 (less normal deductions required by law).
Payment will occur on the September 15 payroll date. In order to earn the First Lump Sum Payment,
you would have to be actively employed with the Company on August 31 .

2. The Company agrees that if you are actively employed with the Company on such date as coincides
with the “Second Closing” as defined and described in a certain Asset Purchase Agreement dated July
18, 2008 by and among Roosevelt Management Company, LLC, Irwin Union Bank and Trust Company, and
Irwin Home Equity Corporation, or through October 31, 2008, whichever is earlier, the Company will
pay you a Second Lump Sum Payment in the gross amount of $37,500 (less normal deductions required
by law). Payment will occur on the first regularly scheduled payroll date following the
occurrence of such Second Closing, or after the earlier payment date occurs. In order to earn the
Second Lump Sum Payment, you would have to be actively employed with the Company on such Second
Closing date or October 31 2008, whichever earlier occurs. We each acknowledge that the Second
Lump Sum Payment might be made prior to the First Lump Sum Payment.

 

 

3. The Company agrees that if you are actively employed with the Company on such date as coincides
with the closing of a platform purchase transaction whereby Roosevelt Management Company, LLC will
acquire certain assets, and hire certain employees of the Company, the Company will pay you a Third
Lump Sum Payment in the gross amount of $62,500 (less normal deductions required by law). Payment
will occur on the first regularly scheduled payroll date following the occurrence of such platform
purchase transaction closing. In order to earn the Third Lump Sum Payment, you would have to be
actively employed with the Company at the time of the platform purchase transaction closing date.

4. In consideration of the offer contained in this letter agreement, you agree that during your
remaining employment with the Company (which, as stated above, will remain at all times at-will
employment), you will work to the best of your abilities to perform your assigned duties.

5. The Company agrees that upon your acceptance of this offer, the Company will extend the
time for exercise of your stock options, awards and PUP grants, following termination of your
employment, by 24 months, on the condition that the plans adopted by the Company in regard to said
stock options, awards and PUP grants do not prohibit such extensions and on the further condition
that the Company’s Board of Directors approves said extensions.

     The Company values your contributions and hopes that you will accept the offers contained in
this letter agreement.

     This offer is available for your consideration through September 3, 2008. If you wish to
accept this offer, please sign the enclosed copy of this letter in the space indicated and return
it to Carrie Houston, First Vice President of Human Resources, in an envelope marked “Personal and
Confidential.”

	 	 	 	 	 
	 	Sincerely,

Irwin Financial Corporation

 	 
	 	By:  	/s/ Matt Souza
 	 
	 	 	 	 
	 	 	 	 
	 

I accept the offer contained in this letter agreement, in accordance with the above-stated terms and conditions:

	 	 	 	 	 	 	 	 	 
	Signed:

	 	/s/ Jocelyn Martin Leano
	 	 	 	Date:
	 	September 10, 2008
	 

	 	 

Jocelyn Martin-Leano
	 	 	 	 	 	 

Enclosure: copy of letter

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