EX-10.2





 Exhibit 10.2 

SPONSOR SIDE LETTER AGREEMENT 

This SPONSOR SIDE LETTER AGREEMENT (this “Agreement”), dated as of June 30, 2021, is made by and among Thayer Ventures
Acquisition Corporation, a Delaware corporation (“Buyer”), Inspirato LLC, a Delaware limited liability company (the “Company”), Thayer Ventures Acquisition Holdings LLC, a Delaware limited liability company (the
“Sponsor”), the other holders of Buyer Class B Common Stock set forth on Schedule 1 hereto (the “Other Class B Holders”, and together with the Sponsor, collectively, the “Supporting
Holders”). Buyer, the Company and the Supporting Holders shall be referred to herein from time to time collectively as the “Parties”. Capitalized terms used but not otherwise defined herein shall have the meanings ascribed
to such terms in the BCA (as defined below). Each of Buyer, the Company and the Support Holders are sometimes referred to herein individually as a “Party” and collectively as the “Parties”. 

WHEREAS, Buyer, Passport Merger Sub I Inc., Passport Merger Sub II Inc., Passport Merger Sub III Inc., KPCB Investment I, Inc., Inspirato
Group, Inc., W Capital Partners III IBC, Inc., Passport Company Merger Sub, LLC and the Company have simultaneously entered into that certain Business Combination Agreement, dated as of the date hereof (as it may be amended, restated or otherwise
modified from time to time in accordance with its terms, the “BCA”); 
 WHEREAS, as of the date hereof, each Supporting
Holder is the record owner of the number of shares of Buyer Class A Common Stock and Class B Common Stock set forth across from such Supporting Holder’s name on Schedule 1 (together with any shares of Buyer Capital Stock that
the Supporting Holder may hereafter acquire prior to the termination of this Agreement in accordance with Section 5, the “Supporting Holder Equity Securities”); 

WHEREAS, the BCA contemplates that the Parties will enter into this Agreement concurrently with the entry into the BCA by the parties thereto,
pursuant to which, among other things, each Supporting Holder will agree to vote, at the Buyer Shareholder Meeting, all of the Supporting Holder Equity Securities in favor of the Buyer Shareholder Voting Matters; and 

WHEREAS, in consideration for the benefits to be received by the Supporting Holder under the terms of the BCA and as an inducement to Buyer
and the Company to enter into the BCA and to consummate the transactions contemplated therein, the Parties desire to agree to certain matters as set forth herein. 

NOW, THEREFORE, in consideration of the premises and the mutual promises contained herein and for other good and valuable consideration, the
receipt and sufficiency of which are hereby acknowledged, the Parties, each intending to be legally bound, hereby agree as follows: 
 1.
Binding Effect of the BCA. Each Supporting Holder hereby acknowledges that it has read the BCA and this Agreement and has had the opportunity to consult with its tax and legal advisors. During the period commencing on the date hereof and
ending on the earlier to occur of (a) the Effective Time, and (b) such date and time as the BCA shall be terminated in accordance with Section 12.1 thereof (the “Expiration Time”), each Supporting Holder shall be
bound by and 












 
comply with Section 8.5 (Confidential Information), Section 8.10(a) (Communications; Press Release), Section 8.21(f) (Exclusivity), Section 13.14 (No Recourse) of the BCA (and
any relevant definitions contained in any such Sections) as if (x) such Supporting Holder was an original signatory to the BCA with respect to such provisions, and (y) each reference to the “Buyer” or a “Buyer Party”
contained in such provisions also referred to each such Supporting Holder. 
 2. Agreement to Vote. The undersigned Supporting
Holder hereby unconditionally and irrevocably agrees from the date hereof until the Expiration Time, at any meeting of the holders of Buyer Capital Stock, duly called and convened in accordance with the Buyer Governing Documents, whether or not
adjourned and however called, including at the Buyer Shareholder Meeting, and in any action by written consent of the holders of Buyer Capital Stock, the Supporting Holder shall, cause such Supporting Holder’s Supporting Holder Equity
Securities to be voted (including via proxy): (w) in favor of the Buyer Shareholder Voting Matters, (x) against any proposal in opposition to approval of the Buyer Shareholder Voting Matters, (y) against any proposal, action or agreement
that would (i) impede, frustrate, prevent or nullify any provision of this Agreement, the BCA, or any of the Buyer Shareholder Voting Matters, (ii) result in a breach in any respect of any covenant, representation, warranty or any other
obligation or agreement of the Buyer Parties under the BCA, and (iii) result in any of the conditions set forth in Article XI of the BCA not being fulfilled, and (z) against and withhold consent with respect to any Buyer Competing
Transaction. The undersigned Supporting Holder agrees not to commence, join in, facilitate, assist or encourage, and agrees to take all actions necessary to opt out of any class in any class action with respect to, any claim, derivative or
otherwise, against Buyer, the Company or any of their respective successors or directors or managers (i) challenging the validity of, or seeking to enjoin the operation of, any provision of this Agreement or (ii) alleging a breach of any
fiduciary duty of any person in connection with the evaluation, negotiation or entry into the BCA. 
 3. Waiver of Anti-dilution
Protection. Each Supporting Holder hereby (a) waives, subject to, and conditioned upon, the occurrence of the Closing (for himself, herself or itself and for his, her or its, successors, heirs and assigns), and (b) agrees not to assert
or perfect, any rights to adjustment or other anti-dilution protections with respect to the rate that the shares of Buyer Class B Common Stock held by him, her or it convert into shares of Buyer Class A Common Stock, including those set
out in Section 4.3(b)(ii) of the Buyer Governing Documents, in connection with the transactions contemplated by the BCA or otherwise. Buyer hereby acknowledges and agrees to such waiver. Each Supporting Holder hereby
acknowledges and agrees that upon the Closing, each share of Buyer Class B Common Stock will be converted into one (1) share of Buyer Class A Common Stock. 

4. Waiver of Redemption. Each Supporting Holder hereby agrees that it shall not exercise or submit a request to exercise the Buyer Share
Redemption with respect to any shares of Buyer Capital Stock held by him, her or it. 
 5. Forfeiture of Shares. Effective as of
immediately prior to the Closing, Sponsor hereby forfeits, at no cost, 1,500,000 shares of Buyer Class B Common Stock held by Sponsor (the “Forfeited Shares”), and such Forfeited Shares shall be cancelled, cease to exist and
shall no longer be outstanding, and following the Closing, Sponsor shall have no right, title or interest to such Forfeited Shares. 

  
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 6. Transfer of Units. The undersigned Supporting Holder hereby agrees that, prior to
the Effective Time, without the prior written consent of each of Buyer (such consent not to be unreasonably withheld, conditioned or delayed) and the Company, such Supporting Holder shall not, directly or indirectly, (a) sell, assign, transfer
(including by operation of law), hypothecate, place a lien on, pledge, dispose of, grant any option to purchase, distribute or otherwise encumber any of such Supporting Holder’s Supporting Holder Equity Securities or otherwise agree to do any
of the foregoing (each, a “Transfer”), (b) deposit any of such Supporting Holder’s Supporting Holder Equity Securities into a voting trust or enter into a voting agreement or arrangement or grant any proxy or power of attorney
with respect to any of such Supporting Holder’s Supporting Holder Equity Securities that conflicts with any of the covenants or agreements set forth in this Agreement, (c) enter into any Contract, option or other arrangement or undertaking
with respect to the direct or indirect acquisition or sale, assignment, transfer (including by operation of law) or other disposition of any of such Supporting Holder’s Supporting Holder Equity Securities, (d) engage in any hedging or
other transaction which is designed to, or which would (either alone or in connection with one or more events, developments or events (including the satisfaction or waiver of any conditions precedent)), lead to or result in a sale or disposition of
such Supporting Holder’s Supporting Holder Equity Securities or (e) take any action that would reasonably be expected to have the effect of preventing or materially delaying the performance of such Supporting Holder’s obligations
hereunder ; provided, however, that the foregoing shall not apply to any Transfer (i) to such Supporting Holder’s Affiliates, employees, officers or directors, any affiliates or family members of any of such Supporting
Holder’s officers or directors, any employees, officers, directors; (ii) in the case of an individual, by gift to a member of one of the individual’s immediate family, an estate planning vehicle, or to a trust, the beneficiary of
which is a member of the individual’s immediate family, an affiliate of such Person or to a charitable organization; (iii) in the case of an individual, by virtue of laws of descent and distribution upon death of the individual;
(iv) in the case of an individual, pursuant to a qualified domestic relations order; (v) by private sales or transfers made in connection with the transactions contemplated by the BCA; (vi) by pro rata distributions from such
Supporting Holder to its members, partners, or shareholders pursuant to such Supporting Holder’s organizational documents; (vii) by virtue of applicable law or such Supporting Holder’s organizational documents upon liquidation or
dissolution of such Supporting Holder; provided, that any transferee of any Transfer of the type set forth in clauses (i) through (vii) must enter into a written agreement in form and substance reasonably satisfactory to the Company
agreeing to be bound by this Agreement prior to the occurrence of such Transfer. 
 7. Consent to Disclosure. Each Supporting Holder
hereby consents to the publication and disclosure in the Form S-4 (and, as and to the extent otherwise required by applicable securities Laws or the SEC or any other securities authorities, any other documents
or communications provided by the Company or Buyer to any Governmental Entity or to securityholders of Buyer) of such Supporting Holder’s identity and beneficial ownership of Supporting Holder Equity Securities and the nature of such Supporting
Holder’s commitments, arrangements and understandings under and relating to this Agreement and, if deemed appropriate by the Company or Buyer, a copy of this Agreement. Each Supporting Holder will promptly provide any information reasonably
requested by the Company or Buyer for any regulatory application or filing made or approval sought in connection with the Transactions (including filings with the SEC). 

  
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 8. Representations and Warranties. The undersigned Supporting Holder represents and
warrants to Buyer and the Company as follows: (a) if such Supporting Holder is not an individual, it is duly organized, validly existing and in good standing under the laws of the jurisdiction in which it is incorporated, formed, organized or
constituted, and the execution, delivery and performance of this Agreement and the consummation of the transactions contemplated hereby are within such Supporting Holder’s corporate, limited liability company or organizational powers and have
been duly authorized by all necessary corporate, limited liability company or organizational actions on the part of such Supporting Holder; (b) if such Supporting Holder is an individual, such Supporting Holder has full legal capacity, right
and authority to execute and deliver this Agreement and to perform his or her obligations hereunder; (c) this Agreement has been duly executed and delivered by such Supporting Holder and, assuming due authorization, execution and delivery by
the other Parties, this Agreement constitutes a legally valid and binding obligation of such Supporting Holder, enforceable against such Supporting Holder in accordance with the terms hereof (except as enforceability may be limited by bankruptcy,
insolvency, reorganization or other Laws affecting creditors’ rights generally and by general equitable principles); (d) the execution and delivery of this Agreement by such Supporting Holder does not, and the performance by such Supporting
Holder of such Supporting Holder’s obligations hereunder will not, (i) if such Supporting Holder is not an individual, conflict with or result in a violation of the organizational documents of such Supporting Holder, or (ii) require
any consent or approval that has not been given or other action that has not been taken by any third party (including under any Contract binding upon such Supporting Holder or such Supporting Holder’s Supporting Holder Equity Securities), in
each case, to the extent such consent, approval or other action would prevent, enjoin or materially delay the performance by such Supporting Holder of such Supporting Holder’s obligations under this Agreement; (e) there are no actions
pending against such Supporting Holder or, to the knowledge of such Supporting Holder, threatened against such Supporting Holder, before (or, in the case of threatened actions, that would be before) any arbitrator or any Governmental Entity, which
in any manner challenges or seeks to prevent, enjoin or materially delay the performance by such Supporting Holder of such Supporting Holder’s obligations under this Agreement; (f) such Supporting Holder has had the opportunity to read the
BCA and this Agreement and has had the opportunity to consult with its tax and legal advisors in connection therewith; (g) such Supporting Holder has not entered into, and shall not enter into, any agreement that would reasonably be expected to
restrict, limit or interfere with the performance of such Supporting Holder’s obligations hereunder and (h) such Supporting Holder is the record and beneficial owner of all of such Supporting Holder’s Supporting Holder Equity
Securities, and there exist no Liens or any other limitation or restriction (including, without limitation, any restriction on the right to vote, sell or otherwise dispose of such securities), other than pursuant to (i) this Agreement,
(ii) the BCA, (iii) the Buyer Governing Documents and (iii) any applicable securities laws. 
 9.
Termination. This Agreement shall automatically terminate, without any notice or other action by any Party, and be void ab initio upon the earlier of (a) the Closing; and (b) the valid termination of the BCA in
accordance with its terms. Upon termination of this Agreement as provided in the immediately preceding sentence, none of the Parties shall have any further obligations or liabilities under, or with respect to, this
Agreement. Notwithstanding the foregoing or anything to the contrary in this Agreement, (i) the termination of this Agreement shall not affect any liability on the part of any Party for a Willful Breach of any covenant or agreement set
forth in this Agreement prior to such termination or Fraud, and (ii) Sections 9, 10, 11, 13, 16 (solely to the extent related to Section 10, 11 or 13) shall survive any
termination of this Agreement pursuant to Section 8(a).

  
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 10. No Recourse. Except for claims pursuant to the BCA or any other Ancillary
Agreement by any party(ies) thereto against any other party(ies) thereto, as applicable, each Party agrees that, notwithstanding anything that may be expressed or implied herein (except in the case of the immediately succeeding sentence), or any
document, agreement, or instrument delivered contemporaneously herewith, and notwithstanding the fact that any Party may be a partnership or limited liability company, each Party hereto, by its acceptance of the benefits of this Agreement,
covenants, agrees and acknowledges this Agreement may only be enforced against, and any claim or cause of action based upon, arising out of, or related to this Agreement or the transactions contemplated hereby may only be brought against, the
entities that are expressly named as parties hereto, and then only with respect to the specific obligations set forth herein with respect to such party. Except to the extent a named party to this Agreement (and then only to the extent of the
specific obligations undertaken by such named party in this Agreement), (a) no past, present or future director, officer, employee, incorporator, member, partner, stockholder, Affiliate, agent, attorney, advisor or representative or Affiliate of any
named party to this Agreement and (b) no past, present or future director, officer, employee, incorporator, member, partner, stockholder, Affiliate, agent, attorney, advisor or representative or Affiliate of any of the foregoing shall have any
liability (whether in contract, tort, equity or otherwise) for any one or more of the representations, warranties, covenants, agreements or other obligations or liabilities of any of the Parties under this Agreement of or for any claim based on,
arising out of or related to this Agreement or the transactions contemplated hereby). 
 11. Further Assurances. The undersigned
Supporting Holder shall use reasonable best efforts to execute and deliver, or cause to be delivered, such additional documents and take, or cause to be taken, all such further actions and do, or cause to be done, all things reasonably necessary
(including under applicable Laws), or reasonably requested by Buyer or the Company, to effect the actions and consummate the Mergers and the other transactions contemplated by this Agreement and the BCA (including the transactions contemplated
thereby), in each case, on the terms and subject to the conditions set forth therein and herein, as applicable. 
 12. Fiduciary
Duties. Notwithstanding anything in this Agreement to the contrary, (a) the undersigned Supporting Holder makes no agreement or understanding herein in any capacity other than in such Supporting Holder’s capacity as a record
holder and beneficial owner of such Supporting Holder’s Supporting Holder Equity Securities and not in such Supporting Holder’s capacity as a director, officer or employee of Buyer, if applicable, and (b) nothing herein will be
construed to limit or affect any action or inaction expressly permitted under the BCA by such Supporting Holder or by any representative of such Supporting Holder in such Person’s capacity as a member of the board of managers of Buyer or as an
officer, employee or fiduciary of the Company or an Affiliate of Buyer, in each case, acting in such Person’s capacity as a director, officer, employee or fiduciary of Buyer. 

13. No Third Party Beneficiaries. This Agreement shall be for the sole benefit of the Parties and their respective successors and
permitted assigns and is not intended, nor shall be construed, to give any Person, other than the Parties and their respective successors and assigns, any legal or equitable right, benefit or remedy of any nature whatsoever by reason this
Agreement. Nothing in this Agreement, expressed or implied, is intended to or shall constitute the Parties, partners or participants in a joint venture. 

  
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 14. No Ownership Interest. Nothing contained in this Agreement will be deemed to vest
in the Company any direct or indirect ownership or incidents of ownership of or with respect to the Supporting Holder Equity Securities. All rights, ownership and economic benefits of and relating to the Supporting Holder Equity Securities shall
remain vested in and belong to Supporting Holder, and the Company shall have no authority to manage, direct, superintend, restrict, regulate, govern or administer any of the policies or operations of Buyer or exercise any power or authority to
direct the Supporting Holder in the voting of any of the Supporting Holder Equity Securities, except as otherwise expressly provided herein with respect to the Supporting Holder Equity Securities. Except as expressly set forth in Section 2, the
Supporting Holder shall not be restricted from voting in favor of, against or abstaining with respect to any other matters presented to the stockholders of Buyer. Without limiting the foregoing, nothing in this Agreement shall limit the right of the
Supporting Holder, or obligate or require the Supporting Holder to, exercise an option to purchase any Supporting Holder Equity Securities. 

15. Acknowledgements. Each party to this Agreement acknowledges that (a) Cooley LLP, counsel for Buyer, is representing Buyer in
connection with this Agreement, the BCA and the other transactions contemplated thereby, (b) Wilson Sonsini Goodrich & Rosati, Professional Corporation, counsel for the Company, is representing the Company in connection with the BCA
and the other transactions contemplated thereby, (c) neither of the foregoing firms is representing the Supporting Holder in connection with this Agreement, the Mergers, the BCA or the other transactions contemplated hereby, thereby or
otherwise and (d) the Supporting Holder acknowledges that he, she or it has had the opportunity to consult with its, his or her own counsel. 

16. Incorporation by Reference. Sections 13.1 (Amendment and Waiver), 13.2 (Notices), 13.3 (Assignment), 13.4 (Severability), Sections
13.5 (Interpretation), 13.6 (Entire Agreement), 13.7 (Governing Law; Waiver of Jury Trial; Jurisdiction), 13.8 (Non-Survival), 13.10 (Counterparts; Electronic Delivery) and 13.11 (Specific Performance) of the
BCA are incorporated herein and shall apply to this Agreement mutatis mutandis. 
 [signature pages follow] 

  
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 IN WITNESS WHEREOF, each of the Parties has caused this Agreement to be duly executed
on its behalf as of the day and year first above written. 
  

					
	THAYER VENTURES ACQUISITION CORPORATION
		
	By:	 	 /s/ Mark E. Farrell

		 	Name:	 	Mark E. Farrell
		 	Title:	 	Co-Chief Executive Officer, Co-President and Chief Financial Officer


  

  
 [Signature Page to
Sponsor Side Letter] 













 IN WITNESS WHEREOF, each of the Parties has caused this Agreement to be duly executed
on its behalf as of the day and year first above written. 
  

			
	THAYER VENTURES ACQUISITION HOLDINGS, LLC
		
	By:	 	 /s/ Mark E. Farrell

		 	Name: Mark E. Farrell
		 	Title: Manager
	
	OTHER CLASS B HOLDERS
	
	/s/ H. Charles Floyd
	  
 H. Charles
Floyd

	
	/s/ Ren Riley
	  
 Ren Riley

	
	/s/ Lawrence M. Kutscher
	  
 Lawrence M.
Kutscher

	
	/s/ Caroline Shin
	  
 Caroline
Shin

	
	/s/ R. David Edelman
	  
 R. David
Edelman



  

  
 [Signature Page to
Sponsor Side Letter] 













 IN WITNESS WHEREOF, each of the Parties has caused this Agreement to be duly executed
on its behalf as of the day and year first above written. 
  

					
	INSPIRATO LLC
		
	By:	 	 /s/ Brent Handler

		 	Name:	 	Brent Handler
		 	Title:	 	Founder and Chief Executive Officer


  

  
 [Signature Page to
Sponsor Side Letter] 













 Schedule 1 

Supporting Holder Equity Securities 

(as of June 30, 2021) 
  

					
	 Name of Supporting

Holder
	  	 Buyer Class A

Common Stock
	  	 Buyer Class B

Common Stock

	 H. Charles Floyd
	  	0	  	25,000
	 Ren Riley
	  	0	  	25,000
	 Lawrence M. Kutscher
	  	0	  	25,000
	 Caroline Shin
	  	0	  	25,000
	 R. David Edelman
	  	0	  	25,000