SECOND AMENDMENT

THIS SECOND AMENDMENT (this “ Amendment ”) is entered into as of August 3, 2015 and is effective as of January 30, 2015 (the “ Amendment Effective Date ”) by and among TIPTREE OPERATING COMPANY, LLC (the “ Borrower ”), FORTRESS CREDIT CORP. (“ Fortress ”), as Administrative Agent, Collateral Agent and Lead Arranger, and the Lenders signatory hereto.

W I T N E S S E T H:

WHEREAS, the Borrower, Fortress and the other Lenders, the Agents and the Lead Arranger are parties to that certain Credit Agreement dated as of September 18, 2013 (as amended, supplemented or otherwise modified from time to time, the “ Credit Agreement ”);

WHEREAS, the Borrower has informed Fortress that it wishes to amend the Credit Agreement to effect the modifications to the Credit Agreement set forth herein; and

WHEREAS, the Lenders party hereto are willing to agree to the Amendment on the terms and subject to the conditions set forth herein.

NOW, THEREFORE, in consideration of the mutual agreements, provisions and covenants contained herein, the parties hereto agree as follows:

1. Defined Terms . Capitalized terms used but not defined herein shall have the meanings ascribed to them in the Credit Agreement (after giving effect to this Amendment).

2.      Amendments to Credit Agreement . The Credit Agreement is hereby amended as follows:

(a)      Section 1.1 of the Credit Agreement is hereby amended by adding the following definitions in the appropriate alphabetical order:

“ “ Second Amendment ” means the Second Amendment dated as of August 3, 2015 and effective as of January 30, 2015, to Credit Agreement, by and among the Borrower, the Administrative Agent and the lenders party thereto.”

(b)      Section 2.11 of the Credit Agreement is hereby amended by replacing the last sentence thereof with the following:

“Notwithstanding the foregoing, (x) such Installments shall be reduced in connection with any voluntary or mandatory prepayments of the Term Loans in accordance with Sections 2.12 and 2.13, as applicable; (y) any Incremental Term Loan made pursuant to the First Amendment shall be disregarded and shall not be included for purposes of calculating any Installment until the Installment Date occurring on September 30, 2015 (it being understood that (i) any mandatory prepayment pursuant to Section 2.13(c) shall be applied as set forth in Section 2.14(b), and (ii) the aggregate principal amount of any Incremental Term Loans made pursuant to the First Amendment that remain outstanding as of September 30, 2015 shall be added to the original aggregate

Term Loan Commitments for purposes of calculating the amount of the Installment due on September 30, 2015 and each Installment Date thereafter); and (z) the Term Loans, together with all other amounts owed hereunder with respect thereto, shall, in any event, be paid in full no later than the Term Loan Maturity Date.”

(c)      Section 2.14(b) of the Credit Agreement is hereby amended by amended and restating the “ fifth ” clause thereof with the following:

“ fifth , in the case of (i) a voluntary prepayment, to reduce the remaining scheduled Installments of such Term Loans as specified by Borrower in such notice of prepayment, (ii) in the case of a mandatory prepayment pursuant to Section 2.13(c), to prepay the Term Loans and reduce the remaining scheduled Installments of the Term Loans pro rata, and (iii) in the case of any other mandatory prepayment, to prepay the next eight Installments of the Term Loans in direct order of maturity and then to prepay all remaining Installments of the Term Loans pro rata; and”

3.      Representations and Warranties . The Borrower hereby represents and warrants as follows:

(a)      the representations and warranties made by the Borrower contained in the Credit Documents are true and correct in all material respects (without duplication of any materiality qualifier contained therein) as of the date hereof, except to the extent such representation or warranty expressly relates to an earlier date, in which case such representation and warranty is true and correct in all material respects (without duplication of any materiality qualifier contained therein) as of such earlier date;

(b)      the Borrower is duly organized, validly existing and in good standing under the laws of the jurisdiction of its organization;

(c)      the Borrower has the power and authority to execute, deliver and perform its obligations under this Amendment;

(d)      the execution, delivery and performance by the Borrower of this Amendment have been duly authorized by all necessary action;

(e)      this Amendment constitutes the legal, valid and binding obligation of Borrower, enforceable against the Borrower in accordance with its terms, except as enforceability may be limited by applicable bankruptcy, insolvency, or similar laws affecting the enforcement of creditors’ rights generally or by equitable principles relating to enforceability; and

(f)      after giving effect to this Amendment, no Event of Default exists.

4.      Effectiveness . The effectiveness of this Amendment on the Amendment Effective Date is subject to the satisfaction of the following conditions precedent:

(a)      The Administrative Agent (or its counsel) shall have received counterparts of this Amendment that, when taken together, bear the signatures of (A) the Borrower, (C) the Requisite Lenders, and (D) the Administrative Agent.

5.      Indemnification. The terms of Section 10.3 of the Credit Agreement are incorporated herein by reference, mutatis mutandis, and the parties hereto agree to such terms.  

6.      No Modification . Except as expressly set forth herein, nothing contained herein shall be deemed to constitute a waiver of compliance with any term or condition contained in the Credit Documents or constitute a course of conduct or dealing among the parties. Fortress reserves all rights, privileges and remedies under the Credit Documents. Except as amended or otherwise modified hereby, the Credit Documents remain unmodified and in full force and effect. All references in the Credit Documents to the Credit Agreement shall be deemed to be references to the Credit Agreement as amended hereby.

7.      Counterparts . This Amendment may be executed in any number of counterparts and by different parties in separate counterparts, each of which when so executed shall be deemed to be an original and all of which taken together shall constitute one and the same agreement. Signature pages may be detached from multiple separate counterparts and attached to a single counterpart. Delivery of an executed signature page of this Amendment by facsimile transmission or other electronic transmission (including email) shall be as effective as delivery of a manually executed counterpart hereof.

8.      Successors and Assigns . The provisions of this Amendment shall be binding upon and inure to the benefit of the parties hereto and their respective successors and assigns.

9.      Further Assurances . The terms of Section 5.13 of the Credit Agreement are incorporated herein by reference, mutatis mutandis, and the parties hereto agree to such terms.  

10.      Governing Law, Submission to Jurisdiction, Waiver of Jury Trial . The terms of Sections 10.14, 10.15 and 10.16 of the Credit Agreement are incorporated herein by reference, mutatis mutandis, and the parties hereto agree to such terms.

11.      Severability . The illegality or unenforceability of any provision of this Amendment or any instrument or agreement required hereunder shall not in any way affect or impair the legality or enforceability of the remaining provisions of this Amendment or any instrument or agreement required hereunder.

12.      Reaffirmation . The Borrower as debtor, grantor, pledgor, guarantor, assignor, or in any other similar capacity in which it has granted liens or security interests in its property or otherwise acts as accommodation party or guarantor, as the case may be, hereby (i) ratifies and reaffirms all of its payment and performance obligations, contingent or otherwise, under the Credit Documents to which it is a party (after giving effect hereto), (ii) ratifies and reaffirms that the aggregate principal amount of the Term Loans outstanding is $46,500,000 and (iii) ratifies and reaffirms the grant of security interests and liens and confirms and agrees that such security interests and liens hereafter secure all of the Obligations as amended hereby. The execution of this Amendment shall not operate

as a waiver of any right, power or remedy of Fortress or the Lenders, constitute a waiver of any provision of any of the Loan Documents or serve to effect a novation of the Obligations.

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IN WITNESS WHEREOF, each of the undersigned has executed this Amendment as of the date set forth above.

BORROWER:

TIPTREE OPERATING COMPANY, LLC

By: _ /s/ Geoffrey Kauffman ___________

Name: Geoffrey Kauffman

Title: Co-Chief Executive Officer

ADMINISTRATIVE AGENT :

LENDERS :

SECOND AMENDMENT TO

SECURITIES PURCHASE AGREEMENT

BY AND AMONG

RELIANCE HOLDINGS LLC,

TIPTREE OPERATING COMPANY, LLC,

TIPTREE FINANCIAL, INC.,

RELIANCE FIRST CAPITAL, LLC,

THE MEMBERS OF RELIANCE FIRST CAPITAL, LLC,

WEXFORD CAPITAL LP, AS WEXFORD SELLERS REPRESENTATIVE

AND

MARC MILLER, AS RELIANCE SELLERS REPRESENTATIVE

Dated as of August 4, 2015

SECOND AMENDMENT TO SECURITIES PURCHASE AGREEMENT

THIS SECOND AMENDMENT TO SECURITIES PURCHASE AGREEMENT (as amended, modified or supplemented from time to time pursuant to the terms hereof, this “ Agreement ”), dated as of August 4, 2015, is entered into by and among Reliance Holdings LLC, a Delaware limited liability company (“ Buyer ”), Tiptree Operating Company, LLC, a Delaware limited liability company (“ Tiptree ”), Tiptree Financial Inc., a Maryland corporation (“ TFI ”), Reliance First Capital LLC, a Delaware limited liability company (the “ Company ”), Wexford Capital LP, a Delaware limited partnership (the “ Wexford Sellers Representative ”), Marc Miller (the “ Reliance Sellers Representative ” and together with the Wexford Sellers Representative, the “ Seller Representatives ”), and the members of the Company set forth on the signature pages of this Agreement under the caption “The Sellers” (collectively, the “ Sellers ”). The Company, Buyer, Tiptree, TFI, Seller Representatives and each Seller are referred to individually as a “ Party ” and collectively, as “ Parties. ”

RECITALS

WHEREAS, the Parties are parties to that certain Securities Purchase Agreement dated as of November 24, 2014, as amended on July 1, 2015 (the “ Securities Purchase Agreement ”); and

WHEREAS, the Parties hereto desire to amend the Securities Purchase Agreement as set forth below.

AGREEMENT

NOW, THEREFORE, in consideration of the foregoing premises and the respective representations, warranties, covenants and agreements contained herein and other good and valuable consideration the receipt and sufficiency of which are hereby acknowledged, and intending to be legally bound, the Parties hereby agree as set forth below. Capitalized terms used but not defined herein shall have the meanings ascribed to such terms in the Securities Purchase Agreement.

ARTICLE 1 AMENDMENTS

Section 1.01      Amendment . The Securities Purchase Agreement is deemed amended as follows:

The term “ Excluded Items ” shall be amended and restated in its entirety to mean “(i) all fees and expenses of the Company and the fees and expenses of Thompson & Knight LLP (provided

that such fees and expenses of Thompson & Knight LLP shall not exceed the amount set forth on Section 1.01 of the Buyer Disclosure Schedule) arising as a result or relating to the Transactions (including but not limited to any fees or expenses in connection with the calculation of any Earnout Payments and the preparation of the Earnout Statements or any dispute hereunder, the determination of Net Working Capital and the preparation of the Estimated Closing Statement, the Proposed Final Closing Statement and the Final Closing Statement or any dispute thereunder), to the extent such fees and expenses are paid by the Company or Sellers, as applicable, (ii) all discounts to fair market value in intercompany transactions, (iii) all expenses in respect of any losses as a result of changes in the balance of the liability recorded in relation to Earn-Out Payments under SFAS 141(R) - Business Combinations as of subsequent reporting periods, (iv) the Earnout Payments, (v) all administrative and regulatory costs of the Company and its subsidiaries related to being a subsidiary of a public company (including, but not limited to, all costs and expenses related to third party valuations of property and other assets and liabilities and the incremental costs of engaging and utilizing new third party auditing and auditing consulting firms), (vi) all corporate overhead (i.e., general and administrative expense) of Tiptree and its Affiliates allocated to the Company, (vii) allocation of profit, loss or expenses from Tiptree and its Affiliates to the Company and its subsidiaries relating to any Damages which give rise to an indemnity obligation pursuant to ARTICLE 9 hereof, (viii) any amounts recovered or recoverable by the Company and its subsidiaries from insurance, to the extent, and only to the extent, the Damages attributable to such insurance arose in the same period, (ix) any relocation and transition expenses of the Company and its subsidiaries resulting from the consummation of the Transactions, (x) any non-operating mortgage related non-recurring items, to include, without limitation, (a) any non-cash charges, such as goodwill write downs associated with an impairment (except non-cash charges that are reserves for future cash charges), (b) litigation expenses of the Company and its subsidiaries outside of the ordinary course, and (c) severance costs of the Company and its subsidiaries (for clarity, operating items such as (A) litigation-related expenses associated with mortgage claims, (B) all mortgage-related settlement expenses of the Company and its subsidiaries and (C) any paid claims of the Company and its subsidiaries to repurchase mortgages will be considered ordinary expense items and not Excluded Items) and (xi) any gain, loss, income or expense resulting from an adjustment or write-off to any goodwill or intangibles related to the acquisition of the Company by Buyer (including, without limitation, costs for third party fair value valuations).”

ARTICLE 2

MISCELLANEOUS

Section 2.01      Governing Law.

This Agreement will be governed by and construed in accordance with the laws of the State of New York, without giving effect to any choice or conflict of law provision or rule that would cause the application of the domestic substantive laws of any other jurisdiction.

Section 2.02      Jurisdiction.

Except as otherwise expressly provided in this Agreement, each Party, by its execution hereof, (a) hereby irrevocably submits to the exclusive jurisdiction of the courts of the

State of New York and the U.S. federal courts located in the Borough of Manhattan, New York for the purpose of any action, claim, cause of action or suit (in contract, tort or otherwise), in any way arising out of or relating to this Agreement, its negotiation or terms, or the Transactions, (b) hereby waives to the extent not prohibited by Applicable Law, and agrees not to assert by way of motion, as a defense or otherwise, in any such action, any claim that it is not subject personally to the jurisdiction of the above-named courts, that its property is exempt or immune from attachment or execution, that any such proceeding brought in one of the above-named courts is improper, that the venue is improper, or that this Agreement or the subject matter hereof may not be enforced in or by such court and (c) hereby agrees not to commence or prosecute any such action, claim, cause of action or suit other than before one of the above-named courts, nor to make any motion or take any other action seeking or intending to cause the transfer or removal of any such action, claim, cause of action or suit to any court other than one of the above-named courts, whether on the grounds of inconvenient forum or otherwise. Each Party hereby consents to service of process in any such proceeding in any manner permitted by New York law, and further consents to service of process by nationally recognized overnight courier service guaranteeing overnight delivery, or by registered or certified mail, return receipt requested, at its address specified pursuant to Section 10.01 of the Securities Purchase Agreement. Notwithstanding the foregoing in this Section 2.02 , a Party may commence any action, claim, cause of action or suit in a court other than the above-named courts solely for the purpose of enforcing an order or judgment issued by one of the above-named courts.

Section 2.03      WAIVER OF JURY TRIAL.

TO THE EXTENT NOT PROHIBITED BY APPLICABLE LAW WHICH CANNOT BE WAIVED, EACH OF THE PARTIES HERETO HEREBY WAIVES AND COVENANTS THAT IT WILL NOT ASSERT (WHETHER AS PLAINTIFF, DEFENDANT OR OTHERWISE) ANY RIGHT TO TRIAL BY JURY IN RESPECT OF ANY ISSUE, ACTION, CLAIM, CAUSE OF ACTION OR SUIT (IN CONTRACT, TORT OR OTHERWISE), IN ANY WAY ARISING OUT OF OR RELATED TO THIS AGREEMENT, ITS NEGOTIATION OR TERMS, OR THE TRANSACTIONS, IN EACH CASE WHETHER NOW EXISTING OR HEREAFTER ARISING. ANY PARTY HERETO MAY FILE AN ORIGINAL COUNTERPART OR A COPY OF THIS SECTION 2.03 WITH ANY COURT AS WRITTEN EVIDENCE OF THE CONSENT OF EACH SUCH PARTY TO THE WAIVER OF ITS RIGHT TO TRIAL BY JURY.

Section 2.04      Further Assurances.

From and after the Closing, upon the request of Buyer or the Sellers, each of the Parties will do, execute, acknowledge and deliver all such further acts, assurances, deeds, assignments, transfers, conveyances, and other instruments and papers as may be reasonably required or appropriate to carry out the Transactions.

Section 2.05      Counterparts .

This Agreement may be executed in any number of counterparts, each of which when executed will be deemed to be an original and all of which together will be deemed to be one and the same instrument binding upon all of the Parties notwithstanding the fact that all Parties are not

signatory to the original or the same counterpart. For purposes of this Agreement, facsimile and pdf signatures will be deemed originals.

Section 2.06      Third Party Beneficiaries; No Recourse Against Third Parties.

No provision of this Agreement is intended to confer upon any Person other than the Parties any rights or remedies hereunder, except as contemplated by Section 9.02 of the Securities Purchase Agreement.

Section 2.07      Severability.

If any term, provision, covenant or restriction of this Agreement is held by any Governmental Authority to be invalid, void or unenforceable, the remainder of the terms, provisions, covenants and restrictions of this Agreement will remain in full force and effect and will in no way be affected, impaired or invalidated so long as the economic or legal substance of the Transactions is not affected in any manner materially adverse to any Party. Upon such a determination, the Parties will negotiate in good faith to modify this Agreement so as to effect the original intent of the Parties as closely as possible in an acceptable manner in order that the Transactions be consummated as originally contemplated to the fullest extent possible.

Section 2.08.      Amendments, Etc .

This Agreement may not be amended or modified in any manner nor may any of its provisions be waived except by written amendment executed by the Parties. A waiver or amendment shall only be effective if (a) it is in writing and signed by the Parties, (b) it specifically refers to this Agreement and (c) it specifically states that the applicable Party is waiving or amending its rights hereunder. Any such amendment, modification or waiver shall be effective only in the specific instance and for the purpose for which it was given.

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IN WITNESS WHEREOF, each of the undersigned has executed this Second Amendment to Securities Purchase Agreement as of the date first above written.