Exhibit 10.1


 


January 13, 2021


 


Monument Circle Acquisition Corp.


One EMMIS Plaza


40 Monument Circle, Suite 700


Indianapolis, IN 46204


317-266-0100


 


Re:      Initial Public Offering


 


Ladies and Gentlemen:


 


This letter (this “Letter
Agreement”) is being delivered to you in accordance with the Underwriting Agreement (the “Underwriting
Agreement”) to be entered into by and between Monument Circle Acquisition Corp., a Delaware corporation (the
 “Company”) and Cantor Fitzgerald & Co. and Moelis & Company LLC, as representatives (the “Representative”)
of the several underwriters (each, an “Underwriter” and collectively, the
 “Underwriters”), relating to an underwritten initial public offering (the “Public
Offering”), of 25,070,000 of the Company’s units (including up to 3,270,000 units that may be purchased to
cover over-allotments, if any) (the “Units”), each comprised of one share of the Company’s Class A
common stock, par value $0.0001 per share (the “Common Stock”), and one-half of one redeemable Warrant.
Each whole Warrant (each, a “Warrant”) entitles the holder thereof to purchase one share of Common Stock
at a price of $11.50 per share, subject to adjustment, as described in the Prospectus (as defined below). The Units will be
sold in the Public Offering pursuant to a registration statement on Form S-1 and prospectus (the
 “Prospectus”) filed by the Company with the U.S. Securities and Exchange Commission (the
 “Commission”) and the Company has applied to have the Units listed on The Nasdaq Stock Market LLC. Certain
capitalized terms used herein are defined in paragraph 11 hereof.


 


In order to induce the Company and the Representative,
on behalf of the Underwriters, to enter into the Underwriting Agreement and to proceed with the Public Offering and for other good
and valuable consideration, the receipt and sufficiency of which are hereby acknowledged, Monument Circle Sponsor LLC (the “Sponsor”),
and each of the undersigned individuals, each of whom is a member of the Company’s board of directors and/or management team
(each, an “Insider” and, collectively, the “Insiders”), hereby severally (and not jointly
and severally) agrees with the Company as follows:


 


1.                 
The Sponsor and each Insider agrees that if the Company seeks stockholder approval of a proposed Business Combination (as
defined below), then in connection with such proposed Business Combination, it, he or she shall (i) vote any shares of Capital
Stock (as defined below) owned by it, him or her in favor of such proposed Business Combination and (ii) not redeem any shares
of Common Stock owned by it, him or her in connection with such stockholder approval. If the Company seeks to consummate a proposed
Business Combination by engaging in a tender offer, the Sponsor and each Insider agrees that it, he or she will not sell or tender
any shares of Capital Stock owned by it, him or her to the Company in connection therewith.


 






     


     


    

 


2.                 
The Sponsor and each Insider hereby agrees that in the event that the Company fails to consummate a Business Combination
within 24 months from the closing of the Public Offering (the “Completion Window”), or such later period approved
by the Company’s stockholders in accordance with the Company’s amended and restated certificate of incorporation (the
 “Charter”), the Sponsor and each Insider shall take all reasonable steps to cause the Company to (i) cease all
operations except for the purpose of winding up, (ii) as promptly as reasonably possible but not more than 10 business days thereafter,
subject to lawfully available funds therefor, redeem 100% of the Common Stock sold as part of the Units in the Public Offering
(the “Offering Shares”), at a per-share price, payable in cash, equal to the aggregate amount then on deposit
in the Trust Account (as defined below) including interest earned on the funds held in the Trust Account, less amounts withdrawn
to pay the Company’s taxes (“Permitted Withdrawals”) and less up to $100,000 of interest to pay dissolution
expenses, divided by the number of then outstanding Offering Shares, which redemption will completely extinguish all Public Stockholders’
(as defined below) rights as stockholders (including the right to receive further liquidating distributions, if any), subject to
applicable law, and (iii) as promptly as reasonably possible following such redemption, subject to the approval of the Company’s
remaining stockholders and the Company’s board of directors, dissolve and liquidate, subject in each case to the Company’s
obligations under Delaware law to provide for claims of creditors and the requirements of other applicable law. The Sponsor and
each Insider agrees to not propose any amendment to the Charter that would modify the substance or timing of the Company’s
obligation to redeem 100% of the Offering Shares if the Company does not complete a Business Combination within the Completion
Window or with respect to any other material provisions relating to stockholders’ rights or pre-initial Business Combination
activity, unless the Company provides its Public Stockholders with the opportunity to redeem their Offering Shares upon approval
of any such amendment at a per-share price, payable in cash, equal to the aggregate amount then on deposit in the Trust Account,
including interest (net of Permitted Withdrawals), divided by the number of then outstanding Offering Shares.


 


The Sponsor and each Insider acknowledges
that it, he or she has no right, title, interest or claim of any kind in or to any monies held in the Trust Account as a result
of any liquidation of the Company with respect to the Founder Shares (as defined blow) held by it, him or her. The Sponsor and
each Insider hereby further waives, with respect to any shares of Common Stock held by it, him or her, if any, any redemption rights
it, he or she may have in connection with the consummation of a Business Combination, including, without limitation, any such rights
available in the context of a stockholder vote to approve such Business Combination or in the context of a tender offer made by
the Company to purchase shares of Common Stock (although the Sponsor, the Insiders and their respective affiliates shall be entitled
to redemption and liquidation rights with respect to any Offering Shares it or they hold if the Company fails to consummate a Business
Combination within the time period set forth in the Charter or in connection with a stockholder vote to approve an amendment to
the Charter to modify the substance or timing of the Company’s obligation to redeem 100% of the Offering Shares if the Company
does not complete a Business Combination within the time period set forth in the Charter or with respect to any other material
provisions relating to stockholders' rights or pre-initial Business Combination activity).


 






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3.                 
During the period commencing on the effective date of the Underwriting Agreement and ending 180 days after such date, the
Sponsor and each Insider shall not, without the prior written consent of the Representative, (i) sell, offer to sell, contract
or agree to sell, hypothecate, pledge, grant any option to purchase or otherwise dispose of or agree to dispose of, directly or
indirectly, or establish or increase a put equivalent position or liquidate or decrease a call equivalent position within the meaning
of Section 16 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), and the rules and regulations
of the Commission promulgated thereunder, with respect to any Units, shares of Capital Stock, Warrants or any securities convertible
into, or exercisable, or exchangeable for, shares of Common Stock owned by it, him or her, (ii) enter into any swap or other arrangement
that transfers to another, in whole or in part, any of the economic consequences of ownership of any Units, shares of Capital Stock,
Warrants or any securities convertible into, or exercisable, or exchangeable for, shares of Common Stock owned by it, him or her,
whether any such transaction is to be settled by delivery of such securities, in cash or otherwise, or (iii) publicly announce
any intention to effect any transaction specified in clause (i) or (ii). Each of the Insiders and the Sponsor acknowledges and
agrees that, prior to the effective date of any release or waiver of the restrictions set forth in this paragraph 3 or paragraph
7 below, the Company shall announce the impending release or waiver by press release through a major news service at least two
business days before the effective date of the release or waiver. Any such release or waiver granted shall only be effective two
business days after the publication date of such press release. The provisions of this paragraph will not apply if (i) the release
or waiver is effected solely to permit a transfer of securities without consideration and (ii) the transferee has agreed in writing
to be bound by the same terms described in this Letter Agreement to the extent and for the duration that such terms remain in effect
at the time of the transfer.


 


4.                 
In the event of the liquidation of the Trust Account, the Sponsor (which for purposes of clarification shall not extend
to any other shareholders, members or managers of the Sponsor or any other Insider) agrees to indemnify and hold harmless the Company
against any and all loss, liability, claim, damage and expense whatsoever (including, but not limited to, any and all legal or
other expenses reasonably incurred in investigating, preparing or defending against any litigation, whether pending or threatened,
or any claim whatsoever) to which the Company may become subject as a result of any claim by (i) any third party (other than
the Company’s independent accountants) for services rendered or products sold to the Company or (ii) a prospective target
business with which the Company has entered into a letter of intent, confidentiality or other similar agreement for a Business
Combination (a “Target”); provided, however, that such indemnification of the Company by the Sponsor
(x) shall apply only to the extent necessary to ensure that such claims by a third party (other than the Company’s independent
accountants) for services rendered or products sold to the Company or a Target do not reduce the amount of funds in the Trust Account
to below the lesser of (i) $10.00 per Offering Share or (ii) the actual amount per Offering Share held in the Trust Account as
of the date of the liquidation of the Trust Account, if less than $10.00 per Offering Share is then held in the Trust Account due
to reductions in the value of the trust assets less Permitted Withdrawals, (y) shall not apply to any claims by a third party (including
a Target) that executed a waiver of any and all rights to the monies held in the Trust Account (whether or not such waiver is enforceable)
and (z) shall not apply to any claims under the Company’s indemnity of the Underwriters against certain liabilities, including
liabilities under the Securities Act of 1933, as amended. The Sponsor shall have the right to defend against any such claim with
counsel of its choice reasonably satisfactory to the Company if, within 15 days following written receipt of notice of the claim
to the Sponsor, the Sponsor notifies the Company in writing that it shall undertake such defense. For the avoidance of doubt, none
of the Company’s officers or directors will indemnify the Company for claims by third parties, including, without limitation,
claims by vendors and prospective target businesses.


 






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5.                 
To the extent that the Underwriters do not exercise their over-allotment option to purchase up to an additional 3,270,000
Units within 45 days from the date of the Prospectus (and as further described in the Prospectus), the Sponsor agrees that it shall
forfeit, at no cost, an aggregate number of Founder Shares equal to the product of 817,500 multiplied by a fraction, (i) the numerator
of which is 3,270,000 minus the number of Units purchased by the Underwriters upon the exercise of their over-allotment option,
and (ii) the denominator of which is 3,270,000. The forfeiture will be adjusted to the extent that the over-allotment option is
not exercised in full by the Underwriters so that the Initial Stockholders (as defined below) will own an aggregate of 20.0% of
the Company’s issued and outstanding shares of Capital Stock after the Public Offering. To the extent that the size of the
Public Offering is increased or decreased, the Company will effect a capitalization or share repurchase, redemption or stock split
or other appropriate mechanism, as applicable, immediately prior to the consummation of the Public Offering in such amount as to
maintain the ownership of the Capital Stock of the Initial Stockholders prior to the Public Offering at 20.0% of the Company’s
issued and outstanding Capital Stock upon the consummation of the Public Offering. In connection with such increase or decrease
in the size of the Public Offering, (A) references to 3,270,000 in the numerator and denominator of the formula in the first sentence
of this paragraph shall be changed to a number equal to 15% of the number of shares included in the Units issued in the Public
Offering and (B) the reference to 817,500 in the formula set forth in the immediately preceding sentence shall be adjusted to such
number of Founder Shares that the Sponsor would have to return to the Company in order to hold (with all of the Initial Stockholders)
an aggregate of 20.0% of the Company’s issued and outstanding Capital Stock after the Public Offering.


 


6.                 
The Sponsor and each Insider hereby agrees and acknowledges that: (i) the Underwriters and the Company would be irreparably
injured in the event of a breach by the Sponsor or an Insider of its, his or her obligations under paragraphs 1, 2, 3, 4, 5, 7(a),
7(b), and 9, as applicable, of this Letter Agreement (ii) monetary damages may not be an adequate remedy for such breach and (iii)
the non-breaching party shall be entitled to injunctive relief, in addition to any other remedy that such party may have in law
or in equity, in the event of such breach.


 






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7.            
(a)          Subject to the exceptions set forth herein, the Sponsor and each Insider agrees that it, he or she shall not Transfer
(as defined below) any Founder Shares (or shares of Common Stock issuable upon conversion thereof) until the earlier of (A) one
year after the completion of the Company’s initial Business Combination or (B) subsequent to the Business Combination, (x)
if the closing price of the Common Stock equals or exceeds $12.00 per share (as adjusted for stock splits, stock dividends, reorganizations,
recapitalizations and the like) for any 20 trading days within any 30-trading day period commencing at least 150 days after the
Company’s initial Business Combination or (y) the date on which the Company completes a liquidation, merger, capital stock
exchange, reorganization or other similar transaction that results in all of the Company’s stockholders having the right
to exchange their shares of Common Stock for cash, securities or other property (the “Founder Shares Lock-up Period”).


 


(b)         
Subject to the exceptions set forth herein, the Sponsor and each Insider agrees that it, he or she shall not Transfer any
Private Placement Warrants (as defined below) or shares of Common Stock issued or issuable upon the exercise of the Private Placement
Warrants, until 30 days after the completion of a Business Combination (the “Private Placement Warrants Lock-up Period”,
together with the Founder Shares Lock-up Period, the “Lock-up Periods”).


 


(c)         
Notwithstanding the provisions set forth in paragraphs 3 and 7(a) and (b), Transfers of the Founder Shares, Private Placement
Warrants and shares of Common Stock issued or issuable upon the exercise or conversion of the Private Placement Warrants or the
Founder Shares and that are held by the Sponsor, any Insider or any of their permitted transferees (that have complied with this
paragraph 7(c)), are permitted (a) to the Company’s officers or directors, any affiliates or family members of any of the
Company’s officers or directors, any members of the Sponsor, or any affiliates of the Sponsor; (b) in the case of such person,
transfers by gift to a member of the individual’s immediate family, to a trust, the beneficiary of which is a member of the
individual’s immediate family or an affiliate of such person, or to a charitable organization; (c) in the case of an individual,
transfers by virtue of laws of descent and distribution upon death of the individual; (d) in the case of an individual, transfers
pursuant to a qualified domestic relations order; (e) transfers by private sales or transfers made in connection with the consummation
of the Company’s Business Combination at prices no greater than the price at which the securities were originally purchased;
(f) transfers in the event of the Company’s liquidation prior to the completion of the Company’s initial Business Combination;
(g) transfers by virtue of the laws of the State of Delaware or the Sponsor’s limited liability company agreement upon dissolution
of the Sponsor; (h) in the event of the Company’s completion of a liquidation, merger, stock exchange, reorganization or
other similar transaction which results in all of the Company’s Public Stockholders having the right to exchange their shares
of Class A common stock for cash, securities or other property subsequent to the completion of the initial Business Combination;
and (i) to a nominee or custodian of a person or entity to whom a disposition or transfer would be permissible under clauses (a)
through (h) above; provided, however, that in the case of clauses (a) through (e) and (i), these permitted transferees
must enter into a written agreement with the Company agreeing to be bound by the transfer restrictions herein and the other restrictions
contained in this Agreement (including provisions relating to voting, the Trust Account and liquidating distributions).


 






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8.                 
The Sponsor and each Insider represents and warrants that it, he or she has never been suspended or expelled from membership
in any securities or commodities exchange or association or had a securities or commodities license or registration denied, suspended
or revoked. Each such Insider’s biographical information furnished to the Company (including any such information included
in the Prospectus) is true and accurate in all respects and does not omit any material information with respect to such Insider’s
background. Each Insider’s questionnaire furnished to the Company is true and accurate in all respects. The Sponsor and each
Insider represents and warrants that: it, he or she is not subject to or a respondent in any legal action for, any injunction,
cease-and-desist order or order or stipulation to desist or refrain from any act or practice relating to the offering of securities
in any jurisdiction; it, he or she has never been convicted of, or pleaded guilty to, any crime (i) involving fraud, (ii) relating
to any financial transaction or handling of funds of another person, or (iii) pertaining to any dealings in any securities and
it, he or she is not currently a defendant in any such criminal proceeding.


 


9.                 
Except as disclosed in the Prospectus, neither the Sponsor nor any Insider nor any affiliate of the Sponsor or any Insider,
nor any director or officer of the Company, shall receive from the Company any finder’s fee, reimbursement, consulting fee,
monies in respect of any repayment of a loan or other compensation prior to, or in connection with any services rendered in order
to effectuate the consummation of the Company’s initial Business Combination (regardless of the type of transaction that
it is), other than the following, none of which will be made from the proceeds held in the Trust Account prior to the completion
of the initial Business Combination: repayment of a loan and advances of up to $300,000 made to the Company by the Sponsors to
cover expenses related to the organization of the Company and the Public Offering; reimbursement for any reasonable out-of-pocket expenses
related to identifying, investigating and consummating an initial Business Combination, and repayment of loans, if any, and on
such terms as to be determined by the Company from time to time, made by the Sponsor or certain of the Company’s officers
and directors to finance transaction costs in connection with an intended initial Business Combination, provided, that, if the
Company does not consummate an initial Business Combination, a portion of the working capital held outside the Trust Account may
be used by the Company to repay such loaned amounts so long as no proceeds from the Trust Account are used for such repayment.
Up to $1,500,000 of such loans may be convertible into warrants of the post Business Combination entity at a price of $1.00 per
warrant at the option of the lender. Such warrants would be identical to the Private Placement Warrants, including as to exercise
price, exercisability and exercise period.


 


10.             
The Sponsor and each Insider has full right and power, without violating any agreement to which it is bound (including,
without limitation, any non-competition or non-solicitation agreement with any employer or former employer), to enter into this
Letter Agreement and, as applicable, to serve as an officer and/or a director on the board of directors of the Company and hereby
consents to being named in the Prospectus as an officer and/or a director of the Company.


 






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11.             
As used herein, (i) “Business Combination” shall mean a merger, capital stock exchange, asset acquisition,
stock purchase, reorganization or similar business combination, involving the Company and one or more businesses; (ii) “Capital
Stock” shall mean, collectively, the Common Stock and the Founder Shares; (iii) “Founder Shares” shall
mean the 6,267,500 shares of the Company’s Class B common stock, par value $0.0001 per share (up to 817,500 of which are
subject to complete or partial forfeiture if the over-allotment option is not exercised by the Representative) initially held by
the Sponsor; (iv) “Initial Stockholders” shall mean the Sponsor and any other holder of Founder Shares immediately
prior to the Public Offering; (v) “Private Placement Warrants” shall mean the warrants to purchase 6,360,000
shares of Common Stock of the Company (or up to 7,014,000 shares of Common Stock if the Underwriters’ over-allotment option
is exercised in full) that the Sponsor has agreed to purchase for an aggregate purchase price of $6,360,000 in the aggregate (or
$7,014,000 if the over-allotment option is exercised in full), or $1.00 per warrant, in a private placement that shall occur simultaneously
with the consummation of the Public Offering; (vi) “Public Stockholders” shall mean the holders of securities
issued in the Public Offering; (vii) “Trust Account” shall mean the trust fund into which a portion of the net
proceeds of the Public Offering and the sale of the Private Placement Warrants shall be deposited; and (viii) “Transfer”
shall mean the (a) sale or assignment of, offer to sell, contract or agreement to sell, hypothecate, pledge, grant of any option
to purchase or otherwise dispose of or agreement to dispose of, directly or indirectly, or establishment or increase of a put equivalent
position or liquidation with respect to or decrease of a call equivalent position within the meaning of Section 16 of the Exchange
Act and the rules and regulations of the Commission promulgated thereunder with respect to, any security, (b) entry into any swap
or other arrangement that transfers to another, in whole or in part, any of the economic consequences of ownership of any security,
whether any such transaction is to be settled by delivery of such securities, in cash or otherwise, or (c) public announcement
of any intention to effect any transaction specified in clause (a) or (b).


 


12.             
This Letter Agreement constitutes the entire agreement and understanding of the parties hereto in respect of the subject
matter hereof and supersedes all prior understandings, agreements, or representations by or among the parties hereto, written or
oral, to the extent they relate in any way to the subject matter hereof or the transactions contemplated hereby. This Letter Agreement
may not be changed, amended, modified or waived (other than to correct a typographical error) as to any particular provision, except
by a written instrument executed by all parties hereto.


 


13.             
Except as otherwise provided herein, no party hereto may assign either this Letter Agreement or any of its rights, interests,
or obligations hereunder without the prior written consent of the other parties. Any purported assignment in violation of this
paragraph shall be void and ineffectual and shall not operate to transfer or assign any interest or title to the purported assignee.
This Letter Agreement shall be binding on the Sponsor and each Insider and their respective successors, heirs and assigns and permitted
transferees.


 






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14.             
Nothing in this Letter Agreement shall be construed to confer upon, or give to, any person or entity other than the parties
hereto any right, remedy or claim under or by reason of this Letter Agreement or of any covenant, condition, stipulation, promise
or agreement hereof. All covenants, conditions, stipulations, promises and agreements contained in this Letter Agreement shall
be for the sole and exclusive benefit of the parties hereto and their successors, heirs, personal representatives and assigns and
permitted transferees.


 


15.             
This Letter Agreement may be executed in any number of original or facsimile counterparts and each of such counterparts
shall for all purposes be deemed to be an original, and all such counterparts shall together constitute but one and the same instrument.


 


16.             
This Letter Agreement shall be deemed severable, and the invalidity or unenforceability of any term or provision hereof
shall not affect the validity or enforceability of this Letter Agreement or of any other term or provision hereof. Furthermore,
in lieu of any such invalid or unenforceable term or provision, the parties hereto intend that there shall be added as a part of
this Letter Agreement a provision as similar in terms to such invalid or unenforceable provision as may be possible and be valid
and enforceable.


 


17.             
This Letter Agreement shall be governed by and construed and enforced in accordance with the laws of the State of New York,
without giving effect to conflicts of law principles that would result in the application of the substantive laws of another jurisdiction.
The parties hereto (i) all agree that any action, proceeding, claim or dispute arising out of, or relating in any way to, this
Letter Agreement shall be brought and enforced in the courts of New York City, in the State of New York, and irrevocably submit
to such jurisdiction and venue, which jurisdiction and venue shall be exclusive and (ii) waive any objection to such exclusive
jurisdiction and venue or that such courts represent an inconvenient forum.


 


18.             
Any notice, consent or request to be given in connection with any of the terms or provisions of this Letter Agreement shall
be in writing and shall be sent by express mail or similar private courier service, by certified mail (return receipt requested),
by hand delivery or facsimile transmission.


 


19.             
This Letter Agreement shall terminate on the earlier of (i) the expiration of the Lock-up Periods or (ii) the liquidation
of the Company; provided, however, that this Letter Agreement shall earlier terminate in the event that the Public
Offering is not consummated and closed by March 31, 2021; provided further that paragraph 4 of this Letter Agreement shall survive
such liquidation for a period of six (6) years.


 


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	 	Sincerely,
	 	 
	 	Monument Circle Sponsor LLC
	 	 
	 	By:	Emmis Operating Company,
	 	 	its managing member
	 	 	 
	 	By:	/s/ J. Scott Enright
	 	 	Name: J. Scott Enright
	 	 	Title: Executive Vice President, General Counsel and Secretary



 


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	 	/s/ Jeffrey H. Smulyan
	 	Jeffrey H. Smulyan




 


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	 	/s/ Patrick M. Walsh
	 	Patrick M. Walsh



 


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	 	/s/ Ryan A. Hornaday
	 	Ryan A. Hornaday



 


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	 	/s/ J. Scott Enright
	 	J. Scott Enright



 


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	 	/s/ Thomas J. "Chase" Rupe
	 	Thomas J. "Chase" Rupe



 


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	 	/s/ Stanley P. Gold
	 	Stanley P. Gold



 


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	 	/s/ Stephen Goldsmith
	 	Stephen Goldsmith



 


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	 	/s/ Traug Keller
	 	Traug Keller



 


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Acknowledged and Agreed:


 


Monument Circle Acquisition Corp. 


 


	By:	/s/ J. Scott Enright	 
	 	Name: J. Scott Enright

                                     Title:   Executive Vice President, General Counsel and Secretary
	 



 


[Signature Page
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