Document:

EX-10.1

 Exhibit 10.1 

AMENDED AND RESTATED INVESTMENT MANAGEMENT AGREEMENT 

AMENDED AND RESTATED INVESTMENT MANAGEMENT AGREEMENT (this “Agreement”), dated as of January 16, 2018, between BlackRock
Capital Investment Corporation, a Delaware corporation (the “BDC”), and BlackRock Capital Investment Advisors, LLC, a Delaware limited liability company (the “Advisor”). 

WHEREAS, the BDC and BlackRock Advisors, LLC (the “Previous Advisor”) were parties to that certain Investment Management Agreement,
dated March 6, 2015 (the “Previous Agreement”), pursuant to which the Previous Advisor provided investment management services to the BDC; and 

WHEREAS, the Previous Advisor and the Advisor, a wholly-owned subsidiary of the Previous Advisor, entered into that certain Assignment and
Assumption Agreement, dated January 16, 2018, to assign the Previous Agreement to the Advisor under state law and in a manner that is not an “assignment” for purposes of the Investment Company Act of 1940 (the “1940 Act”) in
reliance on Rule 2a-6 thereunder; and 
 WHEREAS, the BDC and the Advisor desire to amend and
restate the Previous Agreement in its entirety to acknowledge such assignment and to delete those portions of the Previous Agreement that are no longer operative in accordance with their terms; and 

WHEREAS, the Advisor has agreed to furnish investment advisory services to the BDC, a closed-end
management company that has elected to be regulated as a business development company under the 1940 Act; and 
 WHEREAS, this Agreement has
been approved in accordance with the provisions of the 1940 Act, and the Advisor is willing to furnish such services upon the terms and conditions herein set forth. 

NOW, THEREFORE, in consideration of the mutual premises and covenants herein contained and other good and valuable consideration, the receipt
of which is hereby acknowledged, it is agreed by and between the parties hereto as follows: 
 1. In General. The Advisor agrees, all
as more fully set forth herein, to act as investment advisor to the BDC with respect to the investment of the BDC’s assets and to supervise and arrange for the
day-to-day operations of the BDC and the purchase of securities for and the sale of securities held in the investment portfolio of the BDC. 

 2. Duties and Obligations of the Advisor with Respect to Investment of Assets of the BDC.

 (a) Subject to the succeeding provisions of this paragraph and subject to the direction and control of the BDC’s Board of Directors,
the Advisor shall (i) act as investment advisor for and supervise and manage the investment and reinvestment of the BDC’s assets and in connection therewith have complete discretion in purchasing and selling securities and other assets for
the BDC and in voting, exercising consents and exercising all other rights appertaining to such securities and other assets on behalf of the BDC; (ii) supervise continuously the investment program of the BDC and the composition of its
investment portfolio; (iii) arrange, subject to the provisions of Section 3(b) hereof, for the purchase and sale of securities and other assets held in the investment portfolio of the BDC; and (iv) oversee the administration of all
aspects of the BDC’s business and affairs and provide, or arrange for others whom it believes to be competent to provide, certain services as specified in paragraph (b) below. Nothing contained herein shall be construed to restrict the
BDC’s right to hire its own employees or to contract for administrative services to be performed by third parties, including but not limited to, the calculation of the net asset value of the BDC’s shares. 

(b) Except to the extent provided for directly by the BDC, the specific services to be provided or arranged for by the Advisor for the BDC
pursuant to paragraph (a)(iv) above are (i) maintaining the BDC’s books and records, to the extent not maintained by the BDC’s custodian, transfer agent and dividend disbursing agent in accordance with applicable laws and regulations;
(ii) initiating all money transfers to the BDC’s custodian and from the BDC’s custodian for the payment of the BDC’s expenses, investments and dividends; (iii) reconciling account information and balances among the
BDC’s custodian, transfer agent and dividend disbursing agent; (iv) preparing all governmental filings by the BDC and all reports by the BDC to its shareholders; (v) supervising the calculation of the net asset value of the BDC’s
shares; and (vi) preparing notices and agendas for meetings of the BDC’s shareholders and the BDC’s Board of Directors as well as minutes of such meetings in all matters required by applicable law to be acted upon by the Board of
Directors. 
 (c) In the performance of its duties under this Agreement, the Advisor shall at all times use all reasonable efforts to
conform to, and act in accordance with, any requirements imposed by (i) the provisions of the 1940 Act, and of any rules or regulations in force thereunder; (ii) any other applicable provision of law; (iii) the provisions of the
Certificate of Incorporation and the By-Laws of the BDC, as such documents are amended from time to time; (iv) the investment objectives, policies and restrictions applicable to the BDC as set forth in
the BDC’s Registration Statement on Form N-2 (the “Registration Statement”); and (v) any policies and determinations of the Board of Directors of the BDC. 

(d) The Advisor will seek to provide qualified personnel to fulfill its duties hereunder and, except as set forth in the following sentence,
will bear all costs and expenses incurred in connection with its investment advisory duties thereunder. The BDC shall reimburse the Advisor for all direct and indirect cost and expenses incurred by the Advisor (i) for office space rental,
office equipment and utilities allocable to performance of investment advisory and non investment advisory administrative or operating services hereunder by the Advisor and (ii) allocable to any
non-investment 

 
advisory administrative or operating services provided by the Advisor hereunder, including salaries, bonuses, health insurance, retirement benefits and all similar employment costs, such as
office equipment and other overhead items. All allocations made pursuant to this paragraph (d) shall be made pursuant to allocation guidelines approved from time to time by the Board of Directors. The BDC shall also be responsible for the
payment of all the BDC’s other expenses, including (i) payment of the fees payable to the Advisor under Section 8 hereof; (ii) organizational expenses; (iii) brokerage fees and commissions; (iv) taxes; (v) interest
charges on borrowings; (vi) the cost of liability insurance or fidelity bond coverage for the BDC’s officers and employees, and directors’ and officers’ errors and omissions insurance coverage; (vii) legal, auditing and
accounting fees and expenses; (viii) charges of the BDC’s administrator (if any), custodian, transfer agent and dividend disbursing agent and any other service providers; (ix) the BDC’s dues, fees and charges of any trade
association of which the BDC is a member; (x) the expenses of printing, preparing and mailing proxies, stock certificates, reports, prospectuses, registration statements and other documents used by the BDC; (xi) expenses of registering and
offering securities of the BDC under applicable law; (xii) the expenses of holding shareholder meetings; (xiii) the compensation, including fees, of any of the BDC’s directors, officers or employees who are not affiliated persons of
the Advisor; (xiv) all expenses of computing the BDC’s net asset value per share; (xv) litigation and indemnification and other extraordinary or non recurring expenses; and (xvi) all other non investment advisory expenses of the
BDC. 
 (e) The Advisor shall give the BDC the benefit of its professional judgment and effort in rendering services hereunder, but neither
the Advisor nor any of its officers, directors, employees, agents or controlling persons shall be liable for any act or omission or for any loss sustained by the BDC in connection with the matters to which this Agreement relates, except a loss
resulting from willful misfeasance, bad faith or gross negligence in the performance of its duties, or by reason of its reckless disregard of its obligations and duties under this Agreement; provided, however, that the foregoing shall not constitute
a waiver of any rights which the BDC may have which may not be waived under applicable law. 
 3. Covenants. (a) In the
performance of its duties under this Agreement, the Advisor shall at all times conform to, and act in accordance with, any requirements imposed by: (i) the provisions of the 1940 Act and the Investment Advisers Act of 1940, as amended (the
“Advisers Act”), and all applicable Rules and Regulations of the Securities and Exchange Commission (the “SEC”); (ii) any other applicable provision of law; (iii) the provisions of the Certificate of Incorporation and By-Laws of the BDC, as such documents are amended from time to time; (iv) the investment objectives and policies of the BDC as set forth in its Registration Statement; and (v) any policies and
determinations of the Board of Directors of the BDC. 
 (b) In addition, the Advisor will: 

(i) place orders either directly with the issuer or with any broker or dealer. Subject to the other provisions of this
paragraph, in placing orders with brokers and dealers, the Advisor will attempt to obtain the best price 

 
and the most favorable execution of its orders. In placing orders, the Advisor will consider the experience and skill of the firm’s securities traders as well as the firm’s financial
responsibility and administrative efficiency. Consistent with this obligation, the Advisor may select brokers on the basis of the research, statistical and pricing services they provide to the BDC and other clients of the Advisor. Information and
research received from such brokers will be in addition to, and not in lieu of, the services required to be performed by the Advisor hereunder. A commission paid to such brokers may be higher than that which another qualified broker would have
charged for effecting the same transaction, provided that the Advisor determines in good faith that such commission is reasonable in terms either of the transaction or the overall responsibility of the Advisor to the BDC and its other clients and
that the total commissions paid by the BDC will be reasonable in relation to the benefits to the BDC over the long term. In addition, the Advisor is authorized to take into account the sale of shares of the BDC in allocating purchase and sale orders
for portfolio securities to brokers or dealers (including brokers and dealers that are affiliated with the Advisor), provided that the Advisor believes that the quality of the transaction and the commission are comparable to what they would be with
other qualified firms. In no instance, however, will the BDC’s securities be purchased from or sold to the Advisor, or any affiliated person thereof, except to the extent permitted by the SEC or by applicable law; 

(ii) maintain a policy and practice of conducting its investment advisory services hereunder independently of the commercial
banking operations of its affiliates. When the Advisor makes investment recommendations for the BDC, its investment advisory personnel will not inquire or take into consideration whether the issuer of securities proposed for purchase or sale for the
BDC’s account are customers of the commercial department of its affiliates; and 
 (iii) treat confidentially and as
proprietary information of the BDC all records and other information relative to the BDC, and the BDC’s prior, current or potential shareholders, and will not use such records and information for any purpose other than performance of its
responsibilities and duties hereunder, except after prior notification to and approval in writing by the BDC, which approval shall not be unreasonably withheld and may not be withheld where the Advisor may be exposed to civil or criminal contempt
proceedings for failure to comply, when requested to divulge such information by duly constituted authorities, or when so requested by the BDC. 

4. Services Not Exclusive. Nothing in this Agreement shall prevent the Advisor or any officer, employee or other affiliate thereof from
acting as investment advisor for any other person, firm or corporation, or from engaging in any other lawful activity, and shall not in any way limit or restrict the Advisor or any of its officers, employees or agents from buying, selling or trading
any securities for its or their own accounts or for the accounts of others for whom it or they may be acting; provided, however, that the Advisor will undertake, and will cause its employees to undertake, no activities which, in its
judgment, will adversely affect the performance of the Advisor’s obligations under this Agreement. 

 5. Books and Records. In compliance with the requirements of Rule 31a-3 under the 1940 Act, the Advisor hereby agrees that all records which it maintains for the BDC are the property of the BDC and further agrees to surrender promptly to the BDC any such records upon the
BDC’s request. The Advisor further agrees to preserve for the periods prescribed by Rule 31a-2 under the 1940 Act the records required to be maintained by Rule
31a-1 under the 1940 Act. 
 6. Agency Cross Transactions. From time to time, the Advisor or
brokers or dealers affiliated with it may find themselves in a position to buy for certain of their brokerage clients (each an “Account”) securities which the Advisor’s investment advisory clients wish to sell, and to sell for certain
of their brokerage clients securities which advisory clients wish to buy. Where one of the parties is an advisory client, the Advisor or the affiliated broker or dealer cannot participate in this type of transaction (known as a cross transaction) on
behalf of an advisory client and retain commissions from one or both parties to the transaction without the advisory client’s consent. This is because in a situation where the Advisor is making the investment decision (as opposed to a brokerage
client who makes his own investment decisions), and the Advisor or an affiliate is receiving commissions from both sides of the transaction, there is a potential conflicting division of loyalties and responsibilities on the Advisor’s part
regarding the advisory client. The SEC has adopted a rule under the Advisers Act, which permits the Advisor or its affiliates to participate on behalf of an Account in agency cross transactions if the advisory client has given written consent in
advance. By execution of this Agreement, the BDC authorizes the Advisor or its affiliates to participate in agency cross transactions involving an Account. The BDC may revoke its consent at any time by written notice to the Advisor. 

7. Expenses. During the term of this Agreement, the Advisor will bear all costs and expenses of its employees and any overhead incurred
in connection with its duties hereunder and shall bear the costs of any salaries or Directors’ fees of any officers or Directors of the BDC who are affiliated persons (as defined in the 1940 Act) of the Advisor; provided that the Board of
Directors of the BDC may approve reimbursement to the Advisor of the pro rata portion of the salaries, bonuses, health insurance, retirement benefits and all similar employment costs for the time spent on BDC operations (other than the provision of
investment advice and administrative services required to be provided hereunder) of all personnel employed by the Advisor who devote substantial time to BDC operations or the operations of other investment companies advised by the Advisor. 

8. Compensation. 
 (a)
The provisions of this Section 8 shall apply with respect to the compensation of the Advisor. 

 (b) The Advisor, for its services to the BDC, will be entitled to receive a Management Fee from
the BDC. The Management Fee will be calculated at an annual rate of 1.75% of total assets, excluding cash. The Management Fee will be paid quarterly in arrears based on the asset valuation as of the end of the prior quarter and will be prorated for
any period of less than a quarter. 
 (c) For purposes of this Agreement, the assets and net assets of the BDC shall be calculated pursuant
to the procedures adopted by resolutions of the Directors of the BDC for calculating the value of the BDC’s assets or delegating such calculations to third parties. 

(d) The Advisor will be entitled to receive the Incentive Fee during each calendar quarter (which will apply only to the portion of the
Incentive Fee based on income) and each Annual Period (which will apply only to the portion of the Incentive Fee based on capital gains), as follows: 

(i) Incentive Fee Based on Income. 

(A) The portion of the Incentive Fee based on income other than capital gains will be calculated separately for each calendar
quarter and will be paid on a quarterly basis. The BDC will pay the Advisor the portion of the Incentive Fee based on income for each period as follows: 
  

	 	(i)	No Incentive Fee based on income other than capital gains for any calendar quarter in which the BDC’s Pre-Incentive Fee Net Investment Income does not exceed 1.75% (7.00%
annualized) of the BDC’s net assets attributable to common stock at the beginning of such quarter. 

  

	 	(ii)	100% of the BDC’s Pre-Incentive Fee Net Investment Income in any calendar quarter with respect to that portion of such Pre-Incentive
Fee Net Investment Income, if any, for such calendar quarter, that exceeds 1.75% (7.00% annualized) of the BDC’s net assets attributable to common stock at the beginning of such quarter but is less than 2.1875% (8.75% annualized).

  

	 	(iii)	20% of the BDC’s Pre-Incentive Fee Net Investment Income, if any, for any calendar quarter, that exceeds 2.1875% (8.75% annualized) of the BDC’s net assets attributable
to common stock at the beginning of such quarter. 

 (B) The calculations described above in sub-paragraph (A) will be appropriately pro rated for any period of less than a quarter and adjusted for the net proceeds from any common stock issuances and the cost of any common stock repurchases during such
quarter. The payment of any such Incentive Fee based on income otherwise earned by the Advisor shall be deferred if, for the most recent four full calendar quarter period ending on or prior to the date such payment is to be made, the Annualized Rate
of Return is less than 7.0% 

 
of the BDC’s net assets attributable to common stock at the beginning of such four quarter period as adjusted for the net proceeds from any common stock issuances and the cost of any common
stock repurchases during such four full calendar quarter period, with any deferred Incentive Fees to be carried over for payment in subsequent quarterly calculation periods to the extent such payment can then be made in accordance with this
Agreement. 
 (ii) Incentive Fee Based on Capital Gains. 

(A) The portion of the Incentive Fee based on capital gains will be calculated separately for each Annual Period. The Advisor
will be entitled to receive an Incentive Fee based on capital gains for each Annual Period in an amount equal to 20% of the amount by which (1) the BDC’s net realized capital gains occurring during the period, if any, exceeds (2) its
unrealized capital depreciation, if any, occurring during the period. 
 (B) In calculating the portion of the Incentive Fee
based on capital gains payable for any period, the BDC’s investments shall be accounted for on a security-by-security basis. In addition, the portion of the
Incentive Fee based on capital gains will be determined using the “period-to-period” method pursuant to which the portion of the Incentive Fee based on capital
gains for any period will be based on realized capital gains for the period reduced by realized capital losses for the period and unrealized capital depreciation for the period. 

(iii) The calculation of the Incentive Fee described above in this Section 8(d) is illustrated in the examples attached
to this Agreement in Annex A. In the event of a conflict between the language above and the examples, the examples shall prevail. 

(iv) Notwithstanding anything else set forth herein, the Incentive Fee shall not include any amounts of capital gain that
would violate Section 205(b)(3) of the Advisers Act as interpreted from time to time by the SEC or its staff. 
 (e) For purposes of
Section 8(d), the following terms shall have the meanings ascribed to them below: 
 (i) “Annual Period”
means the period beginning on July 1 of each calendar year and ending on June 30 of the next calendar year; 

(ii) “Annualized Rate of Return” is computed by reference to the sum of (i) the aggregate distributions to the
BDC’s common stockholders for the period in question and (ii) the change in the BDC’s net assets attributable to common stock (before taking into account any Incentive Fees otherwise payable during such period); 

 (iii) “net assets attributable to common stock” means the BDC’s
total assets less indebtedness and preferred stock; and 
 (iv) “Pre-Incentive
Fee Net Investment Income” means net investment income (as determined in accordance with United States generally accepted accounting principles) accrued by the BDC during the calendar quarter excluding any accruals for or payments in respect of
the Incentive Fee. 
 9. Indemnity. (a) The BDC may, in the discretion of the Board of Directors of the BDC, indemnify the
Advisor, and each of the Advisor’s directors, officers, employees, agents, associates and controlling persons and the directors, partners, members, officers, employees and agents thereof (including any individual who serves at the
Advisor’s request as director, officer, partner, member or the like of another entity) (each such person being an “Indemnitee”) against any liabilities and expenses, including amounts paid in satisfaction of judgments, in compromise
or as fines and penalties, and counsel fees (all as provided in accordance with applicable state law) reasonably incurred by such Indemnitee in connection with the defense or disposition of any action, suit or other proceeding, whether civil or
criminal, before any court or administrative or investigative body in which such Indemnitee may be or may have been involved as a party or otherwise or with which such Indemnitee may be or may have been threatened, while acting in any capacity set
forth herein or thereafter by reason of such Indemnitee having acted in any such capacity, except with respect to any matter as to which such Indemnitee shall have been adjudicated not to have acted in good faith in the reasonable belief that such
Indemnitee’s action was in the best interest of the BDC and furthermore, in the case of any criminal proceeding, so long as such Indemnitee had no reasonable cause to believe that the conduct was unlawful; provided, however, that (1) no
Indemnitee shall be indemnified hereunder against any liability to the BDC or its shareholders or any expense of such Indemnitee arising by reason of (i) willful misfeasance, (ii) bad faith, (iii) gross negligence or
(iv) reckless disregard of the duties involved in the conduct of such Indemnitee’s position (the conduct referred to in such clauses (i) through (iv) being sometimes referred to herein as “disabling conduct”), (2) as to any
matter disposed of by settlement or a compromise payment by such Indemnitee, pursuant to a consent decree or otherwise, no indemnification either for said payment or for any other expenses shall be provided unless there has been a determination that
such settlement or compromise is in the best interests of the BDC and that such Indemnitee appears to have acted in good faith in the reasonable belief that such Indemnitee’s action was in the best interest of the BDC and did not involve
disabling conduct by such Indemnitee and (3) with respect to any action, suit or other proceeding voluntarily prosecuted by any Indemnitee as plaintiff, indemnification shall be mandatory only if the prosecution of such action, suit or other
proceeding by such Indemnitee was authorized by a majority of the full Board of Directors of the BDC. 
 (b) The BDC may make advance
payments in connection with the expenses of defending any action with respect to which indemnification might be sought hereunder if the BDC receives a written affirmation of the Indemnitee’s good faith belief that the standard of conduct
necessary for indemnification has been met and a written undertaking to reimburse the BDC unless it is subsequently determined that such 

 
Indemnitee is entitled to such indemnification and if the Directors of the BDC determine that the facts then known to them would not preclude indemnification. In addition, at least one of the
following conditions must be met: (A) the Indemnitee shall provide security for such Indemnitee-undertaking, (B) the BDC shall be insured against losses arising by reason of any unlawful advance, or (C) a majority of a quorum
consisting of Directors of the BDC who are neither “interested persons” of the BDC (as defined in Section 2(a)(19) of the 1940 Act) nor parties to the proceeding (“Disinterested Non-Party
Directors”) or an independent legal counsel in a written opinion, shall determine, based on a review of readily available facts (as opposed to a full trial-type inquiry), that there is reason to believe that the Indemnitee ultimately will be
found entitled to indemnification. 
 (c) All determinations with respect to the standards for indemnification hereunder shall be made
(1) by a final decision on the merits by a court or other body before whom the proceeding was brought that such Indemnitee is not liable or is not liable by reason of disabling conduct, or (2) in the absence of such a decision, by
(i) a majority vote of a quorum of the Disinterested Non-Party Directors of the BDC, or (ii) if such a quorum is not obtainable or, even if obtainable, if a majority vote of such quorum so directs,
independent legal counsel in a written opinion. All determinations that advance payments in connection with the expense of defending any proceeding shall be authorized and shall be made in accordance with the immediately preceding clause
(2) above. 
 The rights accruing to any Indemnitee under these provisions shall not exclude any other right to which such Indemnitee
may be lawfully entitled. 
 10. Limitation on Liability. (a) The Advisor will not be liable for any error of judgment or
mistake of law or for any loss suffered by Advisor or by the BDC in connection with the performance of this Agreement, except a loss resulting from a breach of fiduciary duty with respect to the receipt of compensation for services or a loss
resulting from willful misfeasance, bad faith or gross negligence on its part in the performance of its duties or from reckless disregard by it of its duties under this Agreement. 

(b) Notwithstanding anything to the contrary contained in this Agreement, the parties hereto acknowledge and agree that, as provided in the
Certificate of Incorporation, this Agreement is executed by the Directors and/or officers of the BDC, not individually but as such Directors and/or officers of the BDC, and the obligations hereunder are not binding upon any of the Directors or
Shareholders individually but bind only the estate of the BDC. 
 11. Duration and Termination. This Agreement shall become effective
as of the date hereof and, unless sooner terminated with respect to the BDC as provided herein, shall continue in effect for a period of two years. Thereafter, if not terminated, this Agreement shall continue in effect with respect to the BDC for
successive periods of 12 months, provided such continuance is specifically approved at least annually by both (a) the vote of a majority of the BDC’s Board of Directors or the vote of a majority of the outstanding voting securities of the
BDC at the time outstanding and entitled to vote, and 

 (b) by the vote of a majority of the Directors who are not parties to this Agreement or interested persons of any
party to this Agreement, cast in person at a meeting called for the purpose of voting on such approval. Notwithstanding the foregoing, this Agreement may be terminated by the BDC at any time, without the payment of any penalty, upon giving the
Advisor 60 days’ notice (which notice may be waived by the Advisor), provided that such termination by the BDC shall be directed or approved by the vote of a majority of the Directors of the BDC in office at the time or by the vote of the
holders of a majority of the voting securities of the BDC at the time outstanding and entitled to vote, or by the Advisor on 60 days’ written notice (which notice may be waived by the BDC). This Agreement will also immediately terminate in the
event of its assignment. (As used in this Agreement, the terms “majority of the outstanding voting securities,” “interested person” and “assignment” shall have the same meanings of such terms in the 1940 Act.) If this
Agreement is terminated pursuant to this Section, the BDC shall pay the Advisor a pro rated portion of the Management Fee and the Incentive Fee. The Management Fee and the Incentive Fee due to the Adviser in the event of termination pursuant to this
Section will be determined according to the method set forth in the following paragraph. 
 The BDC will engage at its own expense a firm
acceptable to the BDC and the Advisor to determine the maximum reasonable fair value as of the termination date of the BDC’s consolidated assets (assuming each asset is readily marketable among institutional investors without minority discount
and with an appropriate control premium for any control positions and ascribing an appropriate net present value to unamortized organizational and offering costs and going concern value). After review of such firm’s work papers by the Advisor
and the BDC and resolution of any comments therefrom, such firm will render its report as to valuation, and the BDC will pay to the Advisor or its affiliates any Management Fees or Incentive Fee, as the case may be, payable pursuant to the
paragraphs above as if all of the consolidated assets of the BDC had been sold at the values indicated in such report and any net income and gain distributed. Such report will be completed within 90 days after notice of termination is delivered
hereto. 
 12. Notices. Any notice under this Agreement shall be in writing to the other party at such address as the other party may
designate from time to time for the receipt of such notice and shall be deemed to be received on the earlier of the date actually received or on the fourth day after the postmark if such notice is mailed first class postage prepaid. 

13. Amendment of this Agreement. No provision of this Agreement may be changed, waived, discharged or terminated orally, but only by an
instrument in writing signed by the party against which enforcement of the change, waiver, discharge or termination is sought. Any amendment of this Agreement shall be subject to the 1940 Act. 

14. Governing Law. This Agreement shall be governed by and construed in accordance with the laws of the State of New York for contracts
to be performed entirely therein without reference to choice of law principles thereof and in accordance with the applicable provisions of the 1940 Act. 

 15. Use of the Name BlackRock. The Advisor has consented to the use by the BDC of the name
or identifying word “BlackRock” in the name of the BDC. Such consent is conditioned upon the employment of the Advisor as the investment advisor to the BDC. The name or identifying word “BlackRock” may be used from time to time
in other connections and for other purposes by the Advisor and any of its affiliates. The Advisor may require the BDC to cease using “BlackRock” in the name of the BDC if the BDC ceases to employ, for any reason, the Advisor, any successor
thereto or any affiliate thereof as investment advisor of the BDC. 
 16. Miscellaneous. The captions in this Agreement are included
for convenience of reference only and in no way define or delimit any of the provisions hereof or otherwise affect their construction or effect. If any provision of this Agreement shall be held or made invalid by a court decision, statute, rule or
otherwise, the remainder of this Agreement shall not be affected thereby. This Agreement shall be binding on, and shall inure to the benefit of the parties hereto and their respective successors. 

17. Counterparts. This Agreement may be executed in counterparts by the parties hereto, each of which shall constitute an original
counterpart, and all of which, together, shall constitute one Agreement. 

 IN WITNESS WHEREOF, the parties hereto have caused the foregoing instrument to be executed by
their duly authorized officers, all as of the day and the year first above written. 
  

			
	BLACKROCK CAPITAL INVESTMENT CORPORATION
		
	By:	 	/s/ Michael Zugay
		 	Name: Michael Zugay
		 	Title: Chief Executive Officer
	
	BLACKROCK CAPITAL INVESTMENT ADVISORS, LLC
		
	By:	 	/s/ Laurence D. Paredes
		 	Name: Laurence D. Paredes
		 	Title: Secretary

 Annex A 

Examples of Fee Calculation Under Section 8 of the Agreement 

Example 1—Incentive Fee Based on Income(1) 

Formula 
 The formula for the portion of
the Incentive Fee based on income for any quarter can be expressed as follows: 
 Incentive Fee with respect to
Pre-Incentive Fee Net Investment Income — 
  

	 	•	 	When the Pre-Incentive Fee Net Investment Income for such quarter exceeds 1.75%(2) but does not exceed 2.1875% = 100% x (Pre-Incentive Fee
Net Investment Income – 1.75%) 

  

	 	•	 	When the Pre-Incentive Fee Net Investment Income for such quarter exceeds 2.1875% = 100% x (2.1875% – 1.75%) + 20% x (Pre-Incentive
Fee Net Investment Income – 2.1875%) 

 Notwithstanding the foregoing, if the Annualized Rate of Return for the most
recent four full calendar quarter period ending on or prior to the date such payment is to be made payment is less than 7.0% of the BDC’s net assets attributable to common stock at the beginning of such four quarter period, adjusted for the net
proceeds from any common stock issuances and the cost of any common stock repurchases during the period, the payment of such Incentive Fee will be deferred until the earliest quarter such four full calendar quarter Annualized Rate of Return
requirement is satisfied. “Annualized Rate of Return” in this context is computed by reference to the sum of (i) the aggregate distributions the BDC’s common stockholders during the period and (ii) the change in the
BDC’s net asset value attributable to common stock prior to calculation of any income or capital gain Incentive Fees during the period and does not take into account changes in the market price of the BDC’s common stock. 

Assumptions 
  

	 	•	 	Management fee(3) = 0.4375% 

  

	 	•	 	Other expenses (legal, accounting, custodian, transfer agent, etc.)(4) = 0.0625% 

  

	 	•	 	After accounting for the distribution of income during each period, there is no change in the Company’s net assets 

 

	(1)	The hypothetical amount of Pre-Incentive Fee Net Investment Income shown is based on a percentage of net assets attributable to common stock (defined as total assets less
indebtedness and preferred stock). The example assumes that during the most recent four full calendar quarter period ending on or prior to the date the payment set forth in the example is to be made, the sum of (a) the BDC’s aggregate
distributions to stockholders and (b) the BDC’s change in net assets attributable to common stock (defined as total assets less indebtedness and preferred stock) before taking into account any Incentive Fees accrued during the period, is
at least 7.0% of the BDC’s net assets attributable to common stock (defined as total assets less indebtedness and preferred stock) at the beginning of such four quarter period (as adjusted for the net proceeds from any common stock issuances
and the cost of any common stock repurchases during such four full calendar period). See Alternative 4 for an example of a failure to satisfy this assumption and Alternative 5 for an example of subsequent satisfaction of this assumption.

	(2)	Represents quarterly percentage of the value of net assets attributable to common stock at the beginning of the quarter, adjusted for the net proceeds from any common stock issuances and the cost of any common stock
repurchases during the quarter. 

	(3)	Represents quarterly portion of an annual base management fee of 1.75% of the value of total assets. 

	(4)	Expressed as a percentage of the value of net assets attributable to common stock at the beginning of the quarter, adjusted for the net proceeds from any common stock issuances and the cost of any common stock
repurchases during the period. 

 Alternative 1 

Additional Assumptions 
  

	 	•	 	Investment Income (including interest, dividends, fees, etc.) = 1.25% 

  

	 	•	 	Pre-Incentive Fee Net Investment Income 

 = (investment income – (management fee + other expenses)) 

= (1.25% - (0.4375% + 0.0625%)) 

= 0.75% 
 Conclusion 

Pre-Incentive Fee Net Investment Income does not exceed the Hurdle rate, therefore there is no Incentive Fee based on
income. 
 Alternative 2 
 Additional Assumptions

  

	 	•	 	Investment Income (including interest, dividends, fees, etc.) = 2.40% 

  

	 	•	 	Pre-Incentive Fee Net Investment Income 

 = (investment
income – (management fee + other expenses)) 
 = (2.40% - (0.4375% + 0.0625%)) 

= 1.90% 
 Determination of Incentive Fee

 Pre-Incentive Fee Net Investment Income for the quarter exceeds the Hurdle rate, therefore there is an
Incentive Fee payable with respect to net income for the quarter. 
  

	 	•	 	Incentive Fee Based on Income 

 = 100% x the lesser of (2.1875% – 1.75%) AND (Pre-Incentive Fee Net Investment Income – 1.75%) + the greater of 0% and 20% x (Pre-Incentive Fee Net Investment Income – 2.1875%) 

= 100% x (1.90% – 1.75%) + 0% 

= 100% x 0.15% 

= 0.15% 
 Alternative 3

 Additional Assumptions 
  

	 	•	 	Investment Income (including interest, dividends, fees, etc.) = 3.50% 

  

	 	•	 	Pre-Incentive Fee Net Investment Income 

 = (investment
income – (management fee + other expenses)) 
 = (3.50% - (0.4375% + 0.075%)) 

= 3.00% 
 Determination of Incentive Fee

 Pre-Incentive Fee Net Investment Income for the quarter exceeds the Hurdle rate, therefore there is an
Incentive Fee payable with respect to net income for the quarter. 
  

	 	•	 	Income Based Incentive Fee 

 = 100% x the lesser of (2.1875% – 1.75%) AND (Pre-Incentive Fee Net Investment Income – 1.75%) + the greater of 0% AND 20% x (Pre-Incentive Fee Net Investment Income – 2.1875%) 

= 100% x (2.1875% – 1.75%) + 20% x (3.0% - 2.1875%) 

= 0.4375% + (20% × 0.1825%) 

= 0.4375% + 0.1625% 
 = 0.60% 

 Alternative 4 

Additional Assumptions 
 During most recently completed
quarter (Q4): 
  

	 	•	 	Investment Income = 3.50% 

  

	 	•	 	Pre-Incentive Fee Net Investment Income 

 = (investment
income – (management fee + other expenses)) 
 = (3.50% - (0.4375% + 0.0625%)) 

= 3.00% 
 During four quarter period ending
with most recently completed quarter: 
  

	 	•	 	Q1 Pre-Incentive Fee Net Investment Income = 1.00% 

  

	 	•	 	Q2 Pre-Incentive Fee Net Investment Income = 1.00% 

  

	 	•	 	Q3 Pre-Incentive Fee Net Investment Income = 1.50% 

  

	 	•	 	All Pre-Incentive Fee Net Investment Income is distributed during the period. 

  

	 	•	 	After accounting for the distribution of the net investment income during the period, there is no change in the BDC’s net assets during the period. 

Determination of Incentive Fee 
 During most recently
completed quarter: 
 Pre-Incentive Fee Net Investment Income for the quarter exceeds the Hurdle rate, therefore
there is an Incentive Fee based on income payable for the quarter. 
  

	 	•	 	Incentive Fee Based on Income 

 = 100% x the lesser of (2.1875% – 1.75%) AND (Pre-Incentive Fee Net Investment Income – 1.75%) + the greater of 0% AND 20% x (Pre-Incentive Fee Net Investment Income – 2.1875%) 

= 100% x (2.1875% – 1.75%) + 20% x (3.00% – 2.1875%) 

= 0.4375% + 0.1625% 
 = 0.60% 

During four quarter period ending with most recently completed quarter: 
  

	 	•	 	Annualized Rate of Return (5) 

 = (Q1 Pre-Incentive Fee
Net Investment Income + Q2 Pre-Incentive Fee Net Investment Income + Q3 Pre-Incentive Fee Net Investment Income + Q4
Pre-Incentive Fee Net Investment Income) + (BDC’s change in net assets attributable to common stock) 

= (1.00% + 1.00% + 1.50% + 3.00%) + (0) 

= 6.50% 
  

	(5)	Annualized Rate of Return is measured before any calculation of Incentive Fees for income or capital gains. 

Conclusion 
 Although an Incentive Fee is payable for such
quarter, because the Annualized Rate of Return over the four quarter period is less than 7.00%, the payment is deferred until the first quarter for which the Annualized Rate of Return over the four quarter period including such subsequent quarter
equals or exceeds 7.00%. 
 Alternative 5 

Additional Assumptions 
 During most recently completed
quarter (Q4): 
  

	 	•	 	Investment Income = 4.00% 

  

	 	•	 	Pre-Incentive Fee Net Investment Income 

 = (investment income – (management fee + other expenses) 

= (4.00% - (0.4375% + 0.0625%)) 

= 3.50% 
 During four quarter period ending
with most recently completed quarter: 
  

	 	•	 	Q1 Pre-Incentive Fee Net Investment Income = 1.00% 

  

	 	•	 	Q2 Pre-Incentive Fee Net Investment Income = 1.50% 

  

	 	•	 	Q3 Pre-Incentive Fee Net Investment Income = 3.00% 

  

	 	•	 	All Pre-Incentive Fee Net Investment Income is distributed during the period. 

  

	 	•	 	After accounting for the distribution of the Pre-Incentive Fee Net Investment Income during the period, there is no change in the BDC’s net assets attributable to common
stock during the period. 

  

	 	•	 	Deferred income based Incentive Fee during the period = 0.60% 

 Determination of Incentive Fee 

During most recently completed quarter: 
 Pre-Incentive Fee Net Investment Income for the quarter exceeds the Hurdle rate, therefore there is an Incentive Fee based on income payable for the quarter. 

 

	 	•	 	Incentive Fee Based on Income 

 = 100% x the lesser of (2.1875% – 1.75%) AND (Pre-Incentive Fee Net Investment Income – 1.75%) + the greater of 0% AND 20% x (Pre-Incentive Fee Net Investment Income – 2.1875%) 

= 100% x (2.1875% – 1.75%) + 20% x (3.50% – 2.1875%) 

= 0.4375% + 0.2625% 
 = 0.70% 

During four quarter period ending with most recently completed quarter: 
  

	 	•	 	Annualized Rate of Return (5) 

 = (Q1 Pre-Incentive Fee
Net Investment Income + Q2 Pre-Incentive Fee Net Investment Income + Q3 Pre-Incentive Fee Net Investment Income + Q4
Pre-Incentive Fee Net Investment Income) + (BDC’s change in net assets attributable to common stock) 

= (1.00% + 1.50% + 3.00% + 3.50%) + (0) 

= 9.00% 
  

 

	 	(5)	Annualized rate of return is measured before any calculation of Incentive Fees for income or capital gains. 

Conclusion 
 Both the current quarter income based
Incentive Fee of 0.70% and the earlier deferred income based Incentive Fee of 0.60% are paid. 
 Example 1—Incentive Fee Based on Capital Gains

 Formula 
 The formula for the
capital gains portion of the Incentive Fee for each July 1 through June 30 “Annual Period” can be expressed as follows: 

Incentive Fee with respect to capital gains = 20% x (net realized capital gains to the extent in excess of gross unrealized capital
depreciation) 

 Alternative 1 

Assumptions 
  

	 	•	 	Year 1: $20.0 million investment made in Company A (“Investment A”), and $30.0 million investment made in Company B (“Investment B”) 

 

	 	•	 	Year 2: Investment A is sold for $50.0 million and fair value of Investment B determined to be $32.0 million 

  

	 	•	 	Year 3: fair value of Investment B determined to be $25.0 million 

  

	 	•	 	Year 4: Investment B sold for $31.0 million 

 Determination of Incentive Fee 

The capital gains portion of the Incentive Fee, if any, would be: 
  

	 	•	 	Year 1: None (No sales transactions) 

  

	 	•	 	Year 2: $6.0 million (20% multiplied by $30.0 million realized capital gains on sale of Investment A) 

  

	 	•	 	Year 3: None 

  

	 	•	 	Year 4: $1.2 million (20% multiplied by $6.0 million realized capital gains on sale of Investment B) 

Alternative 2 
 Assumptions 

 

	 	•	 	Year 1: $20.0 million investment made in Company A (“Investment A”), $30.0 million investment made in Company B (“Investment B”) and $25.0 million investment made in Company C
(“Investment C”) 

  

	 	•	 	Year 2: Investment A sold for $50.0 million, fair value of Investment B determined to be $25.0 million and fair value of Investment C determined to be $25.0 million 

 

	 	•	 	Year 3: fair value of Investment B determined to be $27.0 million and Investment C sold for $30.0 million 

  

	 	•	 	Year 4: fair value of Investment B determined to be $35.0 million 

  

	 	•	 	Year 5: Investment B sold for $20.0 million 

 Determination of Incentive Fee 

The capital gains portion of the Incentive Fee, if any, would be: 
  

	 	•	 	Year 1: None (No sales transactions) 

  

	 	•	 	Year 2: $5.0 million (20% multiplied by $25.0 million ($30.0 million realized capital gains on Investment A less $5.0 million unrealized capital depreciation on Investment B)) 

 

	 	•	 	Year 3: $1.0 million (20% multiplied by $5.0 million realized capital gains on Investment C) 

  

	 	•	 	Year 4: None (No sales transactions) 

  

	 	•	 	Year 5: NoneBlueprint

 

Exhibit 4.1

 

EXHIBIT A

 

FORM OF CONVERTIBLE NOTE

 

THE ISSUANCE OF THIS CONVERTIBLE PROMISSORY NOTE HAS NOT BEEN
REGISTERED UNDER THE SECURITIES ACT OF 1933 OR REGISTERED OR
QUALIFIED UNDER ANY APPLICABLE STATE SECURITIES LAWS IN RELIANCE ON
EXEMPTIONS FROM SUCH REGISTRATION AND QUALIFICATION REQUIREMENTS.
THIS CONVERTIBLE PROMISSORY NOTE MAY NOT BE SOLD OR OTHERWISE
TRANSFERRED EXCEPT IN COMPLIANCE WITH ALL APPLICABLE FEDERAL AND
STATE SECURITIES LAWS.

 

THE OBLIGATIONS OF THE COMPANY UNDER THIS CONVERTIBLE PROMISSORY
NOTE ARE SUBJECT TO THE TERMS OF THAT CERTAIN SUBORDINATION
AGREEMENT DATED AS OF MARCH 28, 2018 BETWEEN INVESTOR AND WESTERN
ALLIANCE BANK.

 

SHARPSPRING, INC.

 

CONVERTIBLE PROMISSORY NOTE

 

	
$8,000,000 

	
 March 28,
2018

FOR
VALUE RECEIVED, SharpSpring, Inc. a Delaware corporation (the
“Company”), hereby promises to pay to SHSP Holdings,
LLC (“Investor”), a Delaware limited liability company,
Eight Million Dollars ($8,000,000) in principal amount together
with interest accrued and unpaid thereon as provided herein.
Interest shall accrue at a rate of 5.0% per annum, beginning on the
date hereof until such principal amount and all accrued but unpaid
interest thereon have been paid or converted into shares of the
Company’s capital stock as provided herein. This Convertible
Promissory Note (this “Note”) is not
secured.

 

1.          Maturity
Date.

 

1.1.           Maturity
Date. The principal amount of this Note shall be due and
payable in full on the fifth anniversary of the date of this Note,
or if such day is not a business day, then on the first business
day thereafter (the “Maturity Date”). Interest under
this Note shall be due and payable on each anniversary of the date
of this Note (each, an “Interest Payment Date”) by the
issuance of an additional convertible promissory note of like tenor
to this Note (each, a “PIK Note” and this Note and any
outstanding PIK Notes, the “Notes”), dated as of the
applicable Interest Payment Date and with a principal amount equal
to the accrued interest being paid by delivery of such PIK Note.
The Company may not prepay any amounts under any of the Notes
without the prior written consent of Investor.

 

 

 

 

1.2.           Company’s
Right to Extend the Maturity Date. The provisions of
Section 1.1
notwithstanding, the Company shall have the right to extend the
Maturity Date for up to six (6) months on up to three separate
occasions (each such six- (6-) month period, an “Extension
Period”). To exercise this extension right for the initial
Extension Period, the Company shall give written notice of such
extension to Investor no later than sixty (60) days prior to the
original Maturity Date. To exercise this extension right during the
first or second Extension Periods, the Company shall give written
notice of such extension to Investor no later than sixty (60) days
prior to the end of such Extension Period. In the event of any such
extension of the Maturity Date, (i) except as otherwise noted, the
term “Maturity Date” as used in this Note shall refer
to the Maturity Date as so extended and (ii) the rate at which
interest shall accrue on the outstanding principal amount of this
Note shall increase during the Extension Periods from five percent
(5%) per annum to ten percent (10%) per annum, subject to any
limitation on such rate under Section 4.6 (which limits the
maximum rate of interest payable hereunder to the maximum rate of
interest payable under applicable law). Investor agrees that it
will not buy or sell any shares of Common Stock, or otherwise take
any other affirmative actions that could impact the price of the
Common Stock, during the six- (6-) month period prior to the
Maturity Date or during any of the Extension Periods.

 

2.            

Conversion of the
Note.

 

2.1.           Voluntary
Conversion by Investor. The principal amount of this Note
and any accrued interest thereon may be converted by Investor, in
whole or in part, into shares of the Company’s common stock,
par value $0.001 per share (“Common Stock”), at any
time prior to the Maturity Date as provided in this Section 2. (The shares of
Common Stock issued or issuable upon conversion of this Note are
referred to herein as the “Conversion
Shares”.)

 

2.2.           Conversion
Shares Issuable Upon Conversion. The number of Conversion
Shares to be issued upon conversion of all or any portion of this
Note shall be equal to (i) the principal amount and accrued but
unpaid interest that is being converted divided by (ii) $7.50 (the
“Conversion Price”) (except as otherwise provided in
Section 2.8(b)).
The Conversion Price is subject to adjustment as provided in
Section
2.5.

 

2.3.           Method
of Conversion. To convert all or any portion of this Note
into Conversion Shares, Investor shall deliver to the Company (i) a
conversion notice in the form attached hereto as Annex I (a
“Conversion Notice”) and (ii) this Note. An election to
convert all or any part of this Note shall be deemed effective, and
Investor shall be deemed to be the holder of record of the
Conversion Shares, at the time the Conversion Notice and this Note
are delivered to the Company (the “Conversion Date”),
regardless of when the Conversion Shares are actually issued. The
amount of interest that will be converted in connection with any
partial conversion of this Note will be equal to the accrued
interest with respect to the principal amount being converted
computed through the Conversion Date. Upon any conversion of this
Note in whole or in part, the Company shall promptly (and in any
event within ten (10) business days) issue and promptly deliver to
Investor, at no cost to Investor, one or more stock certificates
registered in Investor’s name evidencing the Conversion
Shares issued upon such conversion. In lieu of delivering physical
certificates representing the Conversion Shares, provided the
Company’s transfer agent is participating in the Depository
Trust Company (“DTC”) Fast Automated Securities
Transfer (“FAST”) program, upon request of Investor, to
the extent permitted by Law, the Company shall use commercially
reasonable efforts to cause its transfer agent to electronically
transmit such shares issuable upon conversion to Investor by
crediting the account of Investor’s prime broker with DTC
through its Deposit Withdrawal at Custodian system. If only a
portion of this Note is being converted, then the Company shall
deliver to Investor without charge a new Note of like tenor to this
Note registered in the name of Investor with a principal amount
equal to the principal amount that was not converted, and the
accrued interest with respect to such principal amount from the
last Interest Payment Date will remain accrued with respect thereto
and interest will continue to accrue with respect to such principal
amount until the next Interest Payment Date.

 

 

2

 

 

2.4.           No
Obligation to Issue Fractional Shares. Any fractional shares
that would otherwise be issuable upon conversion of this Note shall
be paid in cash based on the closing price of a share of Common
Stock on the applicable Conversion Date.

 

2.5.           Adjustment
of the Conversion Price. The Conversion Price shall be
subject to adjustment from time to time as follows:

 

(i)           Stock
Splits and Dividends. If at any time while this Note is
outstanding, the number of outstanding shares of Common Stock is
increased by means of a stock split or a stock dividend payable in
shares of Common Stock, or other similar event, then, on the
effective date of such event, the Conversion Price shall be
decreased in proportion to such increase in the number of
outstanding shares of Common Stock. (By way of example, if there
were to be a 2:1 stock split with respect to the Common Stock, the
Conversion Price would be reduced from $7.50 to
$3.75.)

 

(ii)           Reverse
Stock Splits and Share Combinations. If at any time while
this Note is outstanding, the number of outstanding shares of
Common Stock is decreased by means of a reverse stock split or a
stock combination, or other similar event, then, on the effective
date of such event, the Conversion Price shall be increased in
proportion to such decrease in the number of outstanding shares of
Common Stock. (By way of example, if there were to be a 1:2 reverse
stock split with respect to the Common Stock, the Conversion Price
would be increased from $7.50 to $15.00.)

 

2.6.           Other
Adjustments. If the outstanding shares of Common Stock are
converted at any time into another class of securities as a result
of any reclassification, reorganization, merger, consolidation or
similar transaction, then from and after such event, upon the
conversion of the Notes, provision shall be made such that Investor
shall receive such number and kind of securities as Investor would
have received if the conversion had occurred immediately prior to
such reclassification, reorganization, merger, consolidation or
similar transaction and Investor had held the Conversion Shares
issuable upon such conversion at the time of such reclassification,
reorganization, merger, consolidation or similar
transaction.

 

 

3

 

 

2.7.           Notice
of Adjustments. Whenever the Conversion Price is adjusted
pursuant to Section
2.5 or any adjustment occurs pursuant to Section 2.6, the Company shall
promptly deliver to Investor a notice describing such adjustment in
reasonable detail.

 

2.8.           Conversion
by the Company.

 

(a)           If
the closing price of the Common Stock on the Nasdaq Capital Market
(or, if the Common Stock is not listed for trading on the Nasdaq
Capital Market, on such market as it may be listed for trading) is
greater than 175% of the then applicable Conversion Price for a
period of 120 consecutive trading days, the Company shall have the
right, on at least thirty (30) days’ prior written notice to
Investor, which notice must be given no later than thirty (30) days
after the last day of such period of 120 consecutive trading days,
to convert all outstanding Notes into such number of Conversion
Shares as would be issuable as of the date of delivery of such
notice to Investor (a “Mandatory Conversion”);
provided, however, that in the event of any Mandatory Conversion
prior to the Maturity Date, the Company shall, immediately prior to
such Mandatory Conversion, issue to Investor such additional PIK
Notes as would have been issued hereunder if this Note had remained
outstanding through the Maturity Date (excluding any Extension
Period), and all such PIK Notes shall be converted in connection
with such Mandatory Conversion.

 

(b)           At
the Maturity Date, the Company may, in lieu of paying the
outstanding principal amount of, and any accrued interest on, the
Notes, elect, on at least thirty (30) days’ prior written
notice to Investor, to convert all outstanding Notes into shares of
Common Stock at a Conversion Price equal to 80% of the volume
weighted average closing price of the Common Stock on the Nasdaq
Capital Market (or, if the Common Stock is not listed for trading
on the Nasdaq Capital Market, on such market as it may be listed
for trading) over the thirty (30) trading days prior to and
including the Maturity Date (the “VWA Price”). The
foregoing notwithstanding, Investor shall irrevocably elect in a
writing delivered to the Company no later than 120 days prior to
the Maturity Date, to either (i) convert all of the outstanding
Notes on the Maturity Date, in which case Investor shall deliver
the Notes to the Company prior to the Maturity Date and the Notes
shall be so converted on and as of the Maturity Date in accordance
with Section 2, or
(ii) not convert any of the outstanding Notes on or prior to the
Maturity Date, in which case the Company shall either pay the
outstanding principal amount of, and any accrued interest on, the
Notes in cash on the Maturity Date or convert the outstanding Notes
into shares of Common Stock on and as of the Maturity Date at a
conversion price equal to 80% of the VWA Price as provided
above.

 

(c)           In
the event of any conversion of the Notes by the Company as provided
in this Section
2.8, the Company shall take all such actions under this
Section 2 as it
would have taken if the Notes had been voluntarily converted by
Investor.

 

 

4

 

 

2.9.           Change
in Control Transactions.

 

(a)           In
the event of any Change in Control Transaction (as defined below)
prior to the Maturity Date, the Company shall, subject to
Section 4.6,
issue to Investor such additional PIK Notes as would have been
issued hereunder if this Note had remained outstanding through the
Maturity Date (excluding any Extension Period).

 

(b)           In
connection with any Change in Control Transaction, Investor shall
have the right, at its option, to either (i) convert the Notes, in
whole or in part in accordance with the terms hereof, into the
shares of stock and other securities, cash or property receivable
upon or deemed to be held by holders of Common Stock in connection
with such Change in Control Transaction, in which case Investor
shall receive such securities, cash or property as Investor would
have been entitled to receive if such conversion had occurred
immediately prior to such Change in Control Transaction and
Investor had held the Conversion Shares issuable upon such
conversion at the time of such Change of Control Transaction or
(ii) require the Company or its successor to pay the outstanding
principal amount of, and all accrued interest on, the Notes
concurrently with the consummation of such Change in Control
Transaction.

 

(c)           As
used in this Note, the term “Change of Control
Transaction” means any transaction in which any
“person” or “group” (within the meaning of
section 13(d) and 14(d)(2) of the 1934 Act) becomes the
“beneficial owner” (as defined in Rule 13d-3 of the
1934 Act), directly or indirectly, of a sufficient number of shares
of all classes of the Company’s stock then outstanding
ordinarily entitled to vote in the election of directors,
empowering such “person” or “group” to
elect a majority of the members of the Company’s Board
Directors, who did not have such power before such
transaction.

 

2.10.                      Notice
of Certain Other Events. If any time while this Note is
outstanding, the Company shall propose to (i) declare a dividend or
other distribution payable in cash with respect to its Common
Stock, or (ii) grant all holders of Common Stock any rights or
warrants to subscribe for or purchase shares of its capital stock,
then, in any such case, the Company shall give Investor at least
ten (10) days prior written notice of the record date for
determining stockholders of record for such event.

 

2.11.                      Reservation
and Issuance of Conversion Shares. The Company shall at all
times keep authorized and reserved and available for issuance, free
of preemptive rights, such number of shares of Common Stock as are
issuable upon conversion of the Notes at any time. If the Company
determines at any time that it does not have a sufficient number of
authorized shares of Common Stock to reserve and keep available for
issuance as described in this Section 2.11, the Company shall
use all commercially reasonable efforts to increase the number of
authorized shares of Common Stock by seeking stockholder approval
for the authorization of such additional shares. The Company shall
take any and all actions to ensure that the Conversion Shares, when
issued in accordance with the terms hereof, will be validly issued,
fully paid for and non-assessable and free from all taxes, liens
and charges with respect to the issue thereof.

 

 

5

 

 

2.12.                      Limitation
on Conversion. Notwithstanding anything herein to the
contrary, Investor shall not attempt to convert any portion of this
Note, and the Company shall not issue to Investor any Conversion
Shares upon any attempted conversion of this Note, if the number of
shares of Common Stock issuable upon such conversion, plus (i) the
number of Conversion Shares issued prior thereto and (ii) the
number of shares of Common Stock beneficially owned by any
Affiliate of Investor would (x) equal 20% or more of the number of
the outstanding shares of Common Stock (computed in accordance with
the Nasdaq Stock Market Rules) (the “Maximum Number of
Shares”) or (y) represent 20% or more of the total voting
power of the Company’s securities outstanding immediately
after giving effect to such issuance that are entitled to vote on a
matter being voted on by holders of the Common Stock (computed in
accordance with the Nasdaq Stock Market Rules) (the “Maximum
Aggregate Voting Amount”), unless and until the Company
obtains stockholder approval permitting such issuance in accordance
with Nasdaq Stock Market Rule 5635(d) (or any corresponding rule
under any other applicable national securities exchange)
(“Stockholder Approval”). If, in connection with any
attempted conversion of this Note by Investor, the resulting
issuance of Conversion Shares would exceed the Maximum Number of
Shares or the Maximum Aggregate Voting Amount and the Company shall
not have previously obtained Stockholder Approval at the time of
conversion, then the Company shall only issue to Investor such
number of Shares as may be issued below the Maximum Number of
Shares and the Maximum Aggregate Voting Amount. The Company hereby
covenants and agrees to seek Stockholder Approval at the 2018
annual meeting of the Company’s stockholders (the “2018
Annual Stockholders Meeting”) and to cause the
Company’s Board of Directors to make an affirmative
recommendation to the Company’s stockholders in the proxy
statement relating to the 2018 Annual Stockholders Meeting to vote
their shares in favor of Stockholder Approval and to use the
Company’s best efforts to solicit such votes. If Stockholder
Approval is not obtained at the 2018 Stockholders Meeting, the
Company shall call a special meeting of its stockholders to be held
no later than 90 days after the 2018 Annual Stockholders Meeting at
which it shall again seek Stockholder Approval and shall again
cause the Company’s Board of Directors make an affirmative
recommendation to the Company’s stockholders in the proxy
statement relating to such special stockholders meeting to vote
their shares in favor of Stockholder Approval and to use the
Company’s best efforts to solicit such votes. If Stockholder
Approval is not obtained at such special meeting of the
Company’s stockholders, the Company shall continue to call
special meetings of its stockholders at least quarterly until
Stockholder Approval is obtained. If Stockholder Approval is not
obtained in accordance with this Section 2.12 within two years
of the date of this Note and Affiliates of Investor elect to sell
shares of Common Stock held by them in order to permit the
conversion of the Notes without exceeding the Maximum Number of
Shares and the Maximum Voting Amount, the Company will reimburse
such Affiliates for any underwriting commissions and other
reasonable and documented out-of-pocket transaction costs of any
such sales. Any failure to obtain Stockholder Approval at a
stockholders meeting conducted in accordance with this Section 2.12 shall not
constitute an Event of Default under Section 3.1. As used in this
Note, the term “Affiliate” means a person that
directly, or indirectly through one or more intermediaries,
controls or is controlled by, or is under common control with, the
person specified.

 

3.           Events
of Default; Remedies.

 

3.1.           Definition
of Event of Default. Except as set forth in Section 2.12,
each of the following shall constitute an “Event of Default”
hereunder:

 

(a)           The
Company shall fail to issue any PIK Note when due and such failure
is not remedied within ten (10) business days after demand from
Investor;

 

(b)           The
Company shall fail to issue the Conversion Shares (or other
securities) upon and in accordance with terms hereof and such
failure continues for ten (10) business days after demand from
Investor;

 

(c)           The
Company’s Common Stock shall at any time cease to be listed
for trading on the Nasdaq Capital Market or another national
securities exchange;

 

 

6

 

 

(d)           The
Company shall (i) voluntarily terminate operations or apply for or
consent to the appointment of, or the taking of possession by, a
receiver, custodian, trustee or liquidator of the Company or of all
or a substantial part of the assets of the Company, (ii) admit in
writing its inability to pay debts as the debts become due, (iii)
make a general assignment for the benefit of its creditors, (iv)
commence a voluntary case under the Federal Bankruptcy Code (as now
or hereafter in effect), (v) file a petition seeking to take
advantage of any other law relating to bankruptcy, insolvency,
reorganization, winding-up, or composition or adjustment of debts,
(vi) fail to controvert in a timely and appropriate manner, or
acquiesce in writing to, any petition filed against it in an
involuntary case under the Federal Bankruptcy Code or applicable
state bankruptcy laws, or (vii take any corporate action for the
purpose of effecting any of the foregoing;

 

(e)           Without
the Company’s application, approval or consent, a proceeding
shall be commenced, in any court of competent jurisdiction, seeking
in respect of the Company for the liquidation, reorganization,
dissolution, winding-up, or composition or readjustment of debt,
the appointment of a trustee, receiver, liquidator, or like relief
in respect of the Company or all or any substantial part of the
assets of the Company, or other like relief in respect of the
Company under any law relating to bankruptcy, insolvency,
reorganization, winding-up, or composition or adjustment of debts
and, if the proceeding is being contested in good faith by the
Company, the same shall continue undismissed, or unstayed and in
effect for any period of 90 consecutive days, or an order for
relief against the Company shall be entered in any case under the
Federal Bankruptcy Code or applicable bankruptcy laws;
and

 

(f)           The
Company breaches any material obligation to Investor under that
certain Investors’ Rights Agreement of even date herewith by
and among the Company, Investor, an Affiliate of Investor and
certain management stockholders of the Company (the
“Investors’
Rights Agreement”) and such breach is not remedied within ten
(10) business days after demand from Investor.

 

3.2.           Consequences
of an Event of Default. If any Event of Default (as defined
above) shall occur, then, at any time thereafter while such Event
of Default is continuing, Investor by written notice to the Company
may declare the entire outstanding principal amount of this Note
and all accrued but unpaid interest to be immediately due and
payable. During the continuance of an Event of Default, Investor
shall have recourse to any and all remedies available to it under
applicable law.

 

4.           Miscellaneous.

 

4.1.           Restrictions
on Transfer.

 

(a)           The
issuance of this Note was not registered under the Securities Act
of 1933 or registered or qualified under any applicable state
securities laws in reliance upon exemptions from such registration
and qualification requirements, and the issuance of the Conversion
Shares will also not be so registered or qualified in reliance on
available exemptions. Accordingly, this Note, each PIK Note and any
Conversion Shares shall bear substantially the following
legend:

 

THE
ISSUANCE OF THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE
SECURITIES ACT OF 1933 OR REGISTERED OR QUALIFIED UNDER ANY
APPLICABLE STATE SECURITIES LAWS IN RELIANCE ON EXEMPTIONS FROM
SUCH REGISTRATION AND QUALIFICATION REQUIREMENTS. THIS SECURITY MAY
NOT BE SOLD OR OTHERWISE TRANSFERRED EXCEPT IN COMPLIANCE WITH ALL
APPLICABLE FEDERAL AND STATE SECURITIES LAWS.

 

 

7

 

 

(b)           
Investor covenants that it will not sell, pledge, assign or
transfer this Note or any Conversion Shares except in compliance
with all applicable federal and state securities laws.
Notwithstanding the foregoing, the Company shall issue a
certificate evidencing any Conversion Shares without such legend in
connection with any sale of such Conversion Shares that is
registered under the Securities Act or at any other time that such
legend can be removed under applicable securities
laws.

 

(c)         
Investor agrees that (i) it will not transfer this Note, and (ii)
it will not permit transfers of equity interests in Investor to any
person other than the owners of such equity interests as of the
date of this Agreement (the “Investor Owners”), in each
case without the Company’s prior written consent, which
consent may be granted or withheld in the Company’s sole
discretion; provided, however, that no such consent
shall be required (x) for any transfer by Investor to any of its
members or any Affiliate of Investor so long as such transferee(s)
agree to similar restrictions on further transfers, or (y) for any
transfer of equity interests in Investor to any Affiliate of the
Investor Owners; and provided further that, if at any time
Investor reasonably determines upon the advice of Investor’s
outside legal counsel that it is required to transfer this Note to
a third party in order to ensure that Investor and its Affilitates
will be in compliance with any applicable regulatory requirements,
the Company shall not unreasonably withhold, condition or delay its
consent to such transfer, it being agreed that the Company may
reasonaby withhold its consent to any such transfer, without
limitation, if the proposed transferee is the beneficial owner of
three percent (3%) or more of the outstanding shares of Common
Stock immediately prior to such proposed transfer.

 

4.2.           Exchange
of Note. Upon receipt of evidence reasonably satisfactory to
the Company of the loss, theft, destruction, or mutilation of this
Note, the Company will issue a new Note, of like tenor and
principal amount and dated the date to which interest has been
paid, in lieu of such lost, stolen, destroyed or mutilated Note,
and in such event Investor agrees to indemnify and hold harmless
the Company in respect of any such lost, stolen, destroyed, or
mutilated Note.

 

4.3.           No
Rights as Stockholder. This Note, by itself, does not
entitle Investor to any voting rights or other rights as a
stockholder of the Company and nothing herein shall be construed as
conferring upon Investor the right to vote as a stockholder on any
matter. The foregoing notwithstanding, the Company acknowledges
that Investor has certain additional rights and obligations
pursuant to the terms of the Investors’ Rights
Agreement.

 

4.4.           Notices.
Any notice required or permitted hereunder shall be given in
writing and shall be conclusively deemed effectively given (i) upon
personal delivery, (ii) on the next business day if sent by a
nationally recognized overnight delivery service, (iii) upon
confirmed transmission if sent by facsimile or electronic mail, or
(iv) three business days after deposit if sent by United States
mail, by registered or certified mail, postage prepaid. Any such
notice to either party shall be sent to the address, facsimile
number or electronic mail address set forth below such
party’s name on the signature page of this Note or at such
other address as either party may designate by advance written
notice to the other party.

 

 

8

 

 

4.5.           Governing
Law. This Note shall be governed by and construed in
accordance with the laws of the State of Delaware, without
reference to principles of conflict of laws or choice of
laws.

 

4.6.           Severability.
If any provision of this Note is held by a court of competent
jurisdiction to be excessive in scope or otherwise invalid or
unenforceable, such provision shall be adjusted rather than voided,
if possible, so that it is enforceable to the maximum extent
possible, and the validity and enforceability of the remaining
provisions of this Note will not in any way be affected or impaired
thereby. In no event shall the amount of interest paid hereunder
exceed the maximum rate of interest on the unpaid principal balance
hereof allowable by applicable law. If any sum is collected in
excess of the applicable maximum rate, the excess collected shall
be applied to reduce the principal debt. If the interest actually
collected hereunder is still in excess of the applicable maximum
rate, the interest rate shall be reduced so as not to exceed the
maximum allowable under law.

 

4.7.           Jurisdiction
and Venue. Any action, proceeding or claim arising out of,
or relating in any way to this Note shall be brought and enforced
in the New York Supreme Court, County of New York, or in the United
States District Court for the Southern District of New York. The
Company and Investor irrevocably submit to such jurisdiction, which
jurisdiction shall be exclusive and hereby waive any objection to
such exclusive jurisdiction or that such courts represent an
inconvenient forum. The prevailing party in any such action shall
be entitled to recover its reasonable and documented
attorneys’ fees and out-of-pocket expenses relating to such
action or proceeding.

 

4.8.           WAIVER
OF RIGHT TO JURY TRIAL. THE COMPANY AND INVESTOR HEREBY
IRREVOCABLY WAIVE, TO THE FULLEST EXTENT PERMITTED BY APPLICABLE
LAW, ANY AND ALL RIGHT TO TRIAL BY JURY IN ANY LEGAL PROCEEDING
ARISING OUT OF OR RELATING TO THIS NOTE.

 

4.9.           Waiver
of Presentment, etc. The Company hereby waives presentment,
protest, notice of protest, demand for payment, notice of dishonor
or nonpayment and any and all other notices or demands in
connection with the delivery, acceptance, performance, default, or
enforcement of this Note. The invalidity or unenforceability of any
provision hereof shall in no way affect the validity or
enforceability of any other provision.

 

4.10.        
Costs of
Collection. The Company shall, subject only to any
limitation imposed by applicable law, pay all expenses, including
reasonable attorneys’ fees, incurred by Investor in
endeavoring to collect any amounts payable hereunder which are not
paid when due.

 

4.11.        
Amendments and
Waivers. No provision of this Note may be amended other than
by an instrument in writing signed by the party against which such
amendment is to be enforced. No provision of this Note may be
waived other than by an instrument n writing signed by the party
against which enforcement of such provision is sought.

 

4.12.        
Successors and
Assigns. This Note shall be binding upon, and inure to the
benefit of and be enforceable by, the Company and Investor and
their respective successors and assigns.

 

 

 [Remainder of
page intentionally left blank. Signature page
follows.]

 

 

 

 

 

9

 

 

 

IN
WITNESS WHEREOF, each of the undersigned has caused this instrument
to be executed by its duly authorized officers as of the date first
above written.

 

 

THE
COMPANY:

 

SHARPSPRING,
INC.

 

By:
/s/ 
         
                 
            
 

 

Name: 
         
                 
            
 

 

Title:   

         
                 
            
 

 

Notice Address:

 

550 SW
2nd Avenue

Gainesville, FL
32601

Facsimile:
(___)                                  

Attention:
Richard A.
Carlson

 

 

ACCEPTED AND
AGREED:

 

INVESTOR:

 

SHSP
HOLDINGS, LLC

 

By:
/s/ 
         
                 
            
 

 

Name: 
         
                 
            
 

 

Title:   

         
                 
            
 

 

Notice Address:

 

228 Park Avenue South

Suite 90959

New York, New York 10003

Facsimile:
(___)                                 

Attention:           
                 
           
 

 

 

10

 

 

Annex I

 

Form of Conversion Notice

 

Reference is made
to that certain Convertible Promissory Note (the
“Note”) issued by SharpSpring, Inc., a Delaware
corporation (the “Company”), pursuant to that certain
Convertible Note Purchase Agreement dated as of March 28, 2018
between the undersigned and the Company. Defined terms used below
have the meaning given to them in the Note.

 

The
undersigned hereby elects to convert $_________ in principal amount
of the Note being tendered herewith, together with all accrued but
unpaid interest thereon through the Conversion Date, to acquire
such number of Conversion Shares as are issuable upon such
conversion as provided under the terms of the Note.

 

Please
issue the Conversion Shares in the name of the undersigned and, if
applicable, please issue a new Note (also registered in the name of
the undersigned) representing any principal amount of the Notes
tendered herewith that is not being converted into
Shares.

 

                                                           
       
   

[Print
or Type Name of Investor Above]*

 

By:                                                                 

 

Name                                                                          

 

Title:                                                                         

 

Address
to which shares should be delivered or account and DTC
participation information for DWAC:

 

 

                                                           
        

 

                                                           
        

 

                                                           
        

 

                                                           
        

 

 

 

* The
signature to this form must correspond with the name as written
upon the face of the Note(s) being converted without alteration or
enlargement or any change whatsoever.

 

 

11

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