ISPOW / Inspirato Incorporated - Equity Warrant - Документы SEC, Годовой отчет, Доверенное заявление

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 4, 2025 Inspirato Incor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 4, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissio

Inspirato Confirms Receipt of an Unsolicited Non-Binding Proposal from Exclusive Investments, LLC

Inspirato Confirms Receipt of an Unsolicited Non-Binding Proposal from Exclusive Investments, LLC DENVER—(BUSINESS WIRE)—September 4, 2025—Inspirato Incorporated (NASDAQ: ISPO) (“Inspirato” or the “Company”) today confirmed it has received an unsolicited non-binding written proposal (the “Exclusive Proposal”) from Exclusive Investments, LLC (“Exclusive”) to acquire Inspirato for an all-cash purchase price of $3.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 15, 2025 Inspirato Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 15, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

TERMINATION AGREEMENT

Execution Version TERMINATION AGREEMENT This Termination Agreement, dated as of August 15, 2025 (the “Termination Agreement”), is by and among Inspirato Incorporated, a Delaware corporation (the “Company”), Inspirato LLC, a Delaware limited liability company (“Inspirato LLC”), the subsidiaries of the Company set forth on the signature pages hereto (the “Subsidiary Guarantors”), Oakstone Ventures, Inc.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2025 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

Inspirato Reports Q2 Financial and Operating Results Strong operational execution continues ahead of strategic combination with Buyerlink to form One Planet Platforms, a leading platform for building and operating online marketplaces, enhancing Inspi

Inspirato Reports Q2 Financial and Operating Results Strong operational execution continues ahead of strategic combination with Buyerlink to form One Planet Platforms, a leading platform for building and operating online marketplaces, enhancing Inspirato’s luxury travel offerings and global reach DENVER, August 12, 2025 – Inspirato Incorporated (“Inspirato” or the “Company”) (Nasdaq: ISPO), the premier luxury vacation club and property technology company, today reported results for the second quarter (“Q2 2025”) ended June 30, 2025.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2025 Inspirato Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. 1) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 1

CALCULATION OF FILING FEE TABLES

Exhibit 107 Calculation of Filing Fee Tables Schedule 14A (Form Type) INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation Proposed Maximum Aggregate Value of Transaction Fee Rate Amount of Filing Fee Fees to be Paid $326,300,000 $153.

CALCULATION OF FILING FEE TABLES

Exhibit 107 Calculation of Filing Fee Tables Schedule 14A (Form Type) INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Table 1: Transaction Valuation Proposed Maximum Aggregate Value of Transaction Fee Rate Amount of Filing Fee Fees to be Paid $326,300,000 $153.

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 25, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. )

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 (Amendment No. ) Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defin

Inspirato and Buyerlink Announce Definitive Agreement to Combine Companies, Forming One Planet Platforms Through a reverse merger valuing Buyerlink equity at approximately $326 million, Inspirato and Buyerlink will combine to establish a leading plat

NOT FOR IMMEDIATE RELEASE June 26, 2025 Inspirato and Buyerlink Announce Definitive Agreement to Combine Companies, Forming One Planet Platforms Through a reverse merger valuing Buyerlink equity at approximately $326 million, Inspirato and Buyerlink will combine to establish a leading platform for building and operating online marketplaces across multiple verticals -Combined companies expected to

Agreement and Plan of Merger by and among Inspirato Incorporated and Buyerlink, Inc. dated June 2

CONFIDENTIAL EXECUTION AGREEMENT AND PLAN OF MERGER by and among INSPIRATO INCORPORATED, RR MERGER SUB, INC.

A Multi-Vertical Marketplaces Company OPERATING AT S CA L E THROUGH STRATEGIC COMBINATION © 2025 One Planet Platforms. All Rights Reserved. JUNE 2025 Disclaimer © 2025 One Planet Platforms. All Rights Reserved. 2 Forward-Looking Statements This prese

A Multi-Vertical Marketplaces Company OPERATING AT S CA L E THROUGH STRATEGIC COMBINATION © 2025 One Planet Platforms.

Financial Statements and Exhibits, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): June 12, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fi

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) x QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2025 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 7, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission File

Inspirato Reports Record Q1 Profitability and Reiterates Full Year Guidance Improved Gross Margins and Operational Efficiencies Drive Most Profitable Quarter in Company History

Inspirato Reports Record Q1 Profitability and Reiterates Full Year Guidance Improved Gross Margins and Operational Efficiencies Drive Most Profitable Quarter in Company History DENVER, May 7, 2025 – Inspirato Incorporated (“Inspirato” or the “Company”) (Nasdaq: ISPO), the premier luxury vacation club and property technology company, today reported results for the first quarter (“Q1 2025”) ended March 31, 2025.

Amendments to Articles of Incorporation or Bylaws; Change in Fiscal Year, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): April 23, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

Amended and Restated Bylaws of the Company.

AMENDED AND RESTATED BYLAWS OF INSPIRATO INCORPORATED (adopted on April 23, 2025) TABLE OF CONTENTS Page The table of contents is empty.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): April 22, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant To Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

UNITED STATES

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant To Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

Description of Capital Stock

Exhibit 4.1 DESCRIPTION OF SECURITIES The following description of the capital stock of Inspirato Incorporated (“us,” “our,” “we,” “Inspirato” or the “Company”) is a summary of the rights of our securities and certain provisions of our Second Amended and Restated Certificate of Incorporation, dated February 11, 2022 (as amended on September 29, 2023 and October 16, 2023, the “Certificate of Incorp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) x ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2024 OR o TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Warrant to Purchase Shares of Class A Common Stock of Inspirato Incorporated, dated September 13, 2024, between Inspirato Incorporated and One Planet Group LLC.

Execution Version THIS WARRANT AND THE UNDERLYING SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR UNDER THE SECURITIES LAWS OF ANY STATE.

Master Services Agreement between Capital One Services, LLC and Inspirato LLC dated September 29, 2023.

DocuSign Envelope ID: BC0118C0-7D8D-4D57-9E7F-9B103E2F1016 MASTER SERVICES AGREEMENT between Capital One Services, LLC and Inspirato LLC dated September 29, 2023 AGREEMENT NO.

Amendment to Warrant, dated December 18, 2024, between Inspirato Incorporated and One Planet Group LLC.

Docusign Envelope ID: 9779CB67-CDD9-4BC2-8DFD-17CB6ED70666 AMENDMENT TO WARRANT December 18, 2024 WHEREAS, One Planet Group, a Delaware limited liability company (the “Holder”), is the beneficial holder of warrants to purchase up to 2,915,451 shares of Class A common stock, par value $0.

Forbearance and Amendment Agreement between Oakstone Ventures, Inc. and Inspirato Incorporated dated March 21, 2025

Exhibit 10.16 OAKSTONE VENTURES, INC. 1680 Capital One Drive McLean, Virginia 22102 March 21, 2025 Inspirato Incorporated Attn: LEGAL 1544 Wazee St. Denver, CO 80202 Re: Forbearance and Amendment Agreement (this “Forbearance and Amendment Agreement”) Ladies and Gentlemen: Reference is hereby made to (i) that certain Investment Agreement, dated as of August 7, 2023 (as amended, modified or suppleme

List of Subsidiaries.

Exhibit 21.1 1 Inspirato Incorporated Subsidiaries 2 Bayside Villas, LLC 3 Beach Front Villas Ltd 4 Best of 52 LLC 5 Cenotes Holdings LLC 6 Clouser Bight, Ltd 7 Coral Reef Properties, LLC 8 Faraway Land, LLC 9 HighRoad Holdings, LLC 10 Inspirato LLC 11 Inspirato Real Estate Services LLC 12 Inspriato Mexico S. de R.L. de C.V. 13 Island Holdings, LLC 14 Leward Breeze, Inc. 15 Ocean Cliff Holdings, L

Inspirato Reports Fourth Quarter Profitability and Positive Cash Flow from Operations 2025 plan targets full-year profitability through improved gross margins and operational efficiencies

Exhibit 99.1 Inspirato Reports Fourth Quarter Profitability and Positive Cash Flow from Operations 2025 plan targets full-year profitability through improved gross margins and operational efficiencies DENVER, February 24, 2025 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the premier luxury vacation club, today announced its 2024 fourth quarter and full year financial and

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 24, 2025 Inspirato Incor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 24, 2025 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissio

Annex I Information With Respect to Transactions of Common Stock

EX-99.1 2 tm255304d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 Annex I Information With Respect to Transactions of Common Stock Reporting Person Who Effected the Transaction Date of Transaction Nature of Transaction Amount of Securities Average Price Per Share Where and How the Transaction was Effected Brent L. Handler Revocable Trust 12/6/2024 Sale of Common Stock 5,000 $ 3.5818 Effected on the open ma

JOINT FILING AGREEMENT

EXHIBIT 99.1 JOINT FILING AGREEMENT The undersigned hereby agree that a single Schedule 13D (or any amendment thereto) relating to the Class A Common Stock of Inspirato Incorporated shall be filed on behalf of each of the undersigned and that this Joint Filing Agreement shall be filed as an exhibit to such Schedule 13D. Dated: December 19, 2024 Revolution Portico Holdings LLC By: Revolution Manage

Unregistered Sales of Equity Securities

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 9, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizat

INSPIRATO INCORPORATED Secondary Offering of 6,588,478 Shares of Class A Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(3)  Registration No. 333-282905 PROSPECTUS INSPIRATO INCORPORATED Secondary Offering of 6,588,478 Shares of Class A Common Stock This prospectus relates to the resale by the selling securityholders named in this prospectus (or their permitted transferees) (the “Selling Securityholders”) of up to 6,588,478 shares of Class A common stock, par value $0

December 2, 2024

December 2, 2024 Via EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549-6010 Re: Inspirato Incorporated Registration Statement on Form S-3, filed on October 30, 2024 File No. 333- 282905 Request for Acceleration of Effectiveness Ladies and Gentlemen: Pursuant to Rule 461 of the Securities Act of 1933, as amended, Inspirato Incorporat

November 19, 2024

November 19, 2024 Via EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.

Inspirato Announces Third Quarter Financial and Operating Results Implemented reorganization plan, including consolidating dual class share structure, refreshing Board of Directors and executing plans with more than $40 million in annualized cost sav

Exhibit 99.1 Inspirato Announces Third Quarter Financial and Operating Results Implemented reorganization plan, including consolidating dual class share structure, refreshing Board of Directors and executing plans with more than $40 million in annualized cost savings Relentless focus on operating efficiencies in third quarter contributed to significant year-over-year Adjusted EBITDA improvement DE

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2024 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables S-3 (Form Type) INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered (1)(2) Proposed Maximum Offering Price Per Share (3) Maximum Aggregate Offering Price (3) Fee Rate Amount of Registration Fee Newly Registered Shares Fees to be paid Equity Class A Common Stock, $0.

As filed with the Securities and Exchange Commission on October 30, 2024

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on October 30, 2024 Registration No.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 28, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 28, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizat

US45791E1073 / INSPIRATO INC / REVOLUTION MANAGEMENT CO LLC - SC 13D/A Activist Investment

SC 13D/A 1 tm2426967d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 3)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, $0.0001 par value per share (Title of Class of Securities) 45791E107 (CUSIP Number) Kerry L. Killeen Revolution LLC 1717 Rhode Island Avenue, N.W. 10t

Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 22, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizat

Investment Agreement, dated as of October 22, 2024, by and among Inspirato Incorporated, Tribridge Limited, and Julian MacQueen

Exhibit 10.1 INVESTMENT AGREEMENT This INVESTMENT AGREEMENT (this “Agreement”), dated as of October 22 2024 is by and between Inspirato Incorporated, a Delaware corporation (the “Company”), Tribridge Limited, a Cayman Island Company with principal offices located at 43A Block 1, 80 Robinson Road, Hong Kong (the “Lead Purchaser”), and Julian MacQueen (the “Secondary Purchaser,” and together with th

INSPIRATO INCORPORATED Secondary Offering of 3,922,203 Shares of Class A Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(3)  Registration Statement No. 333-282181 PROSPECTUS INSPIRATO INCORPORATED Secondary Offering of 3,922,203 Shares of Class A Common Stock This prospectus relates to the resale by the selling securityholders named in this prospectus (or their permitted transferees) (the “Selling Securityholders”) of up to 3,922,203 shares of Class A common stock, pa

October 21, 2024

October 21, 2024 Via EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549-6010 Re: Inspirato Incorporated Registration Statement on Form S-3/A, filed on October 8, 2024 File No. 333- 282181 Request for Acceleration of Effectiveness Ladies and Gentlemen: Pursuant to Rule 461 of the Securities Act of 1933, as amended, Inspirato Incorpora

As filed with the Securities and Exchange Commission on October 8, 2024

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on October 8, 2024 Registration No.

October 8, 2024

October 8, 2024 By EDGAR Securities and Exchange Commission Division of Corporation Finance 100 F Street, N.

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 1, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

Offer Letter between Company and Mr. Arthur dated October 1, 2024

Exhibit 10.1 Portions of this document have been redacted pursuant to Item 601(b)(10)(iv) of Regulation S-K because it is both not material and is the type that the registrant treats as private or confidential. Redacted portions are indicated with the notation “[***]”. TO: Michael Arthur FROM: Payam Zamani | CEO DATE: October 1st, 2024 RE: Promotion I am pleased to offer you the position of Chief

INSPIRATO INCORPORATED Up to $17,582,393 Class A Common Stock

Filed Pursuant to Rule 424(b)(5) Registration Statement No. 333-281880 PROSPECTUS SUPPLEMENT (to Prospectus dated September 19, 2024) INSPIRATO INCORPORATED Up to $17,582,393 Class A Common Stock This prospectus supplement updates and amends certain information contained in the prospectus supplement, dated September 24, 2024 (the “Original Prospectus Supplement”), to the prospectus, dated Septembe

US45791E1073 / INSPIRATO INC / One Planet Group LLC - FORM SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 2)* INSPIRATO INCORPORATED (Name of Issuer) Class A Common Stock, par value $ 0.0001 per share (Title of Class of Securities) 45791E 107 (CUSIP Number) Payam Zamani 1820 Bonanza Street Walnut Creek, California 94596 (925) 983-3401 (Name, Address and Teleph

Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 30, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organiz

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported):September 24, 2024 (September 19, 2024) Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of inco

INSPIRATO INCORPORATED $10,671,158 Class A Common Stock

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(5)  Registration Statement No. 333-281880 PROSPECTUS SUPPLEMENT (to Prospectus dated September 19, 2024) INSPIRATO INCORPORATED $10,671,158 Class A Common Stock We have entered into an equity distribution agreement (the “Sales Agreement”) with Northland Securities, Inc. (“Northland”) relating to the shares of our Class A Common Stock, par value $0.0

Equity Distribution Agreement, dated September 24, 2024, by and between Inspirato Incorporated and Northland Securities, Inc.

Exhibit 1.1 Execution Version INSPIRATO INCORPORATED Common Stock ($0.0001 par value per share) Equity Distribution Agreement September 24, 2024 Northland Securities, Inc. 150 South Fifth Street, Suite 3300 Minneapolis, MN 55402 Ladies and Gentlemen: Inspirato Incorporated, a Delaware corporation (the “Company”), confirms its agreement (this “Agreement”) with Northland Securities, Inc. (the “Agent

INSPIRATO INCORPORATED Common Stock Preferred Stock Warrants Units

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(2)  Registration No. 333-281880 PROSPECTUS INSPIRATO INCORPORATED $50,000,000 Common Stock Preferred Stock Warrants Units Inspirato Incorporated (“Inspirato,” the “Company,” “we,” “us,” or “our”) may offer and sell from time to time up to $50,000,000 of our Class A common stock, $0.0001 par value per share (“Class A Common Stock”), preferred stock,

ISPO / Inspirato Incorporated / W Capital Partners III, L.P. - SC 13D/A Activist Investment

SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 3)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 45791E 206 (CUSIP Num

As filed with the Securities and Exchange Commission on September 17, 2024

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on September 17, 2024 Registration No.

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables S-3 (Form Type) INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation or Carry Forward Rule Amount Registered (1)(2) Proposed Maximum Offering Price Per Share (3) Maximum Aggregate Offering Price (3) Fee Rate Amount of Registration Fee Newly Registered Shares Fees to be paid Equity Class A Common Stock, $0.

September 17, 2024

September 17, 2024 Via EDGAR U.S. Securities and Exchange Commission Division of Corporation Finance 100 F Street, NE Washington, DC 20549-6010 Re: Inspirato Incorporated Registration Statement on Form S-3, filed on August 30, 2024 File No. 333-281880 Request for Acceleration of Effectiveness Ladies and Gentlemen: Pursuant to Rule 461 of the Securities Act of 1933, as amended, Inspirato Incorporat

Unregistered Sales of Equity Securities, Submission of Matters to a Vote of Security Holders

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 13, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissi

US45791E1073 / INSPIRATO INC / One Planet Group LLC - FORM SC 13D/A Activist Investment

SC 13D/A 1 dp218051sc13da-1.htm FORM SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* INSPIRATO INCORPORATED (Name of Issuer) Class A Common Stock, par value $ 0.0001 per share (Title of Class of Securities) 45791E 107 (CUSIP Number) Payam Zamani 1820 Bonanza Street Walnut Creek, California

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 3, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissio

Letter agreement amending Investment Agreement dated August 12, 2024

Exhibit 10.2 Inspirato Incorporated 1544 Wazee Street Denver, Colorado 80202 August 30, 2024 One Planet Group LLC 1820 Bonanza Street Walnut Creek, CA 94596 Re: Investment Agreement, dated August 12, 2024 (the “Investment Agreement”), between Inspirato Incorporated, a Delaware corporation (the “Company”) and One Planet Group LLC, a Delaware limited liability company (“One Planet”) Ladies and Gentl

Financial Statements and Exhibits, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 30, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

As filed with the Securities and Exchange Commission on August 30, 2024

TABLE OF CONTENTS As filed with the Securities and Exchange Commission on August 30, 2024 Registration No.

Power of attorney

EX-99.7 4 d851181dex997.htm EX-99.7 EXHIBIT 7 Power of attorney The undersigned AXA Investment Managers S.A, a corporation duly organized under the laws of France (the “Company”), does hereby make, constitute and appoint each of Anthony Gilsoul, Mireille Kahindo, Rena Kam, Isaac Eade and Monique Diaz acting severally, as its true and lawful attorneys-in-fact, for the purpose of, from time to time,

AGREEMENT

EX-99.5 2 d851181dex995.htm EX-99.5 EXHIBIT 5 AGREEMENT In accordance with Rule 13d-1(k) promulgated under the Securities Exchange Act of 1934, as amended, the undersigned hereby agree to the joint filing with all other Reporting Persons (as such term is defined in the Schedule 13D referred to below) on behalf of each of them of a statement on Schedule 13D (including amendments thereto) with respe

ISPO / Inspirato Incorporated / W Capital Partners III, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 d851181dsc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 2)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Sec

Power of attorney

EX-99.6 3 d851181dex996.htm EX-99.6 EXHIBIT 6 Power of attorney The undersigned AXA S.A., a corporation duly organized under the laws of France (the “Company”), does hereby make, constitute and appoint each of Anthony Gilsoul, Victoria Warmé, Rena Kam, Isaac Eade and Monique Diaz acting severally, as its true and lawful attorneys-in-fact, for the purpose of, from time to time, executing in its nam

Filing Fee Table.

Exhibit 107 Calculation of Filing Fee Tables S-3 (Form Type) INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title (1) Fee Calculation or Carry Forward Rule Amount Registered (2) Proposed Maximum Offering Price Per Share (3) Maximum Aggregate Offering Price (2) Fee Rate Amount of Registration Fee (4) Newly Registered Shares Fees to be paid Equity Common Stock, $0.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

DEF 14A 1 tm2421301-3def14a.htm DEF 14A TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

Inspirato Announces Inducement Grants Under Nasdaq Listing Rule 5635(c)(4)

Exhibit 99.1 Inspirato Announces Inducement Grants Under Nasdaq Listing Rule 5635(c)(4) DENVER, August 16, 2024 (GLOBE NEWSWIRE) – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel club, today announced its Board of Directors approved the grant of equity awards on August 13, 2024 as a material inducement to the employment of newly-hired Chairman and

US45791E1073 / INSPIRATO INC / One Planet Group LLC - FORM SC 13D Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. N/A)* INSPIRATO INCORPORATED (Name of Issuer) Class A Common Stock, par value $ 0.0001 per share (Title of Class of Securities) 45791E 107 (CUSIP Number) Payam Zamani 1820 Bonanza Street Walnut Creek, California 94596 (925) 983-3401 (Name, Address and Teleph

Inspirato Incorporated 2024 Inducement Plan

Exhibit 10.1 INSPIRATO INCORPORATED 2024 INDUCEMENT AWARD PLAN 1.            Purposes of the Plan; Award Types. (a)            Purposes of the Plan. The purposes of this Plan are to attract and retain the best available personnel, to provide for an inducement material for such persons to enter into employment with the Company Group (within the meaning of Rules 5635(c)(4) of the NASDAQ Listing Rule

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizati

Separation and Release Agreement, dated as of August 13, 2024, between Inspirato LLC and Brad Handler

Exhibit 10.4 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Bradley Handler (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was terminated without cause by the Company as Executive Chairman of Inspirato Incorporated, a Delaware corporation

Investment Agreement, dated as of August 12, 2024, between Inspirato Incorporated and One Planet Group LLC

Exhibit 10.1 Execution Version INVESTMENT AGREEMENT This INVESTMENT AGREEMENT (this “Agreement”), dated as of August 12, 2024 is by and between Inspirato Incorporated, a Delaware corporation (the “Company”), and One Planet Group LLC, a Delaware limited liability company (the “Purchaser”). Capitalized terms not otherwise defined where used shall have the meanings ascribed thereto in Section 1.01. W

Executive Employment Agreement, dated as of August 13, 2024, between Inspirato LLC and Payam Zamani

Exhibit 10.3 EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (“Agreement”) is made by and between Inspirato LLC, a Delaware limited liability company (the “Company”), and Payam Zamani, a California resident (“Executive”), effective as of August 13, 2024 (the “Effective Date”). WHEREAS, the Company desires to employ Executive upon the terms and conditions set forth herein, and Ex

Separation and Release Agreement, dated as of August 13, 2024, between Inspirato LLC and Eric Grosse

Exhibit 10.5 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Eric Grosse (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was employed by the Company as Chief Executive Officer; WHEREAS, the Executive has separated from employment with the Co

Separation and Release Agreement, dated as of August 13, 2024, between Inspirato LLC and Eric Grosse

Exhibit 10.5 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Eric Grosse (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was employed by the Company as Chief Executive Officer; WHEREAS, the Executive has separated from employment with the Co

Separation and Release Agreement, dated as of August 13, 2024, between Inspirato LLC and Brad Handler

Exhibit 10.4 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Bradley Handler (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was terminated without cause by the Company as Executive Chairman of Inspirato Incorporated, a Delaware corporation

Form of Voting Agreement

Exhibit 10.2 VOTING AGREEMENT This VOTING AGREEMENT (this “Agreement”), dated as of August [], 2024, is entered into by and among (i) One Planet Group LLC, a Delaware limited liability company (“Purchaser”), (ii) Inspirato Incorporated, a Delaware corporation (the “Company”), and (iii) the stockholders of the Company listed on Schedule A and the signature pages hereto (each, a “Stockholder” and, c

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizati

Executive Employment Agreement, dated as of August 13, 2024, between Inspirato LLC and Payam Zamani

Exhibit 10.3 EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (“Agreement”) is made by and between Inspirato LLC, a Delaware limited liability company (the “Company”), and Payam Zamani, a California resident (“Executive”), effective as of August 13, 2024 (the “Effective Date”). WHEREAS, the Company desires to employ Executive upon the terms and conditions set forth herein, and Ex

Form of Voting Agreement

Exhibit 10.2 VOTING AGREEMENT This VOTING AGREEMENT (this “Agreement”), dated as of August [], 2024, is entered into by and among (i) One Planet Group LLC, a Delaware limited liability company (“Purchaser”), (ii) Inspirato Incorporated, a Delaware corporation (the “Company”), and (iii) the stockholders of the Company listed on Schedule A and the signature pages hereto (each, a “Stockholder” and, c

Investment Agreement, dated as of August 12, 2024, between Inspirato Incorporated and One Planet Group LLC

Exhibit 10.1 Execution Version INVESTMENT AGREEMENT This INVESTMENT AGREEMENT (this “Agreement”), dated as of August 12, 2024 is by and between Inspirato Incorporated, a Delaware corporation (the “Company”), and One Planet Group LLC, a Delaware limited liability company (the “Purchaser”). Capitalized terms not otherwise defined where used shall have the meanings ascribed thereto in Section 1.01. W

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizati

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2024 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Inspirato Announces Second Quarter Results and Closing of $10 Million Investment Agreement with One Planet Group LLC

Exhibit 99.1 Inspirato Announces Second Quarter Results and Closing of $10 Million Investment Agreement with One Planet Group LLC DENVER, August 13, 2024 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel club, today announced its 2024 second quarter financial and operating results, the closing of its previously announced $10 million Investment Agr

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 13, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

Dear Inspirato Team,

Exhibit 99.4 Dear Inspirato Team, Following our recent public announcements, I am excited and deeply honored to introduce myself as your new CEO & Chairman of the Board at Inspirato. We are entering a transformative period filled with both significant changes and promising opportunities. The investment from One Planet Group is a testament to the faith in our potential and provides a strong foundat

Email to Inspirato Employees from President David Kallery, dated as of August 12, 2024

Exhibit 99.3 Dear Inspirato Team, I am writing to let you know that we just issued a press release announcing two major developments at Inspirato: · A $10 million investment in the company. · The appointment of a new CEO and Chairman of the Board. Read the press release here. [link to unique URL with the release] We usually aim to give you advance notice of announcements like these. However, due t

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizati

Inspirato Announces $10 Million Capital Infusion by One Planet Group, Appoints Payam Zamani as CEO and Chairman New CEO Focused on Profitable Growth, Remains Committed to Delivering Exceptional Service and World Class Experiences for its Members Impl

Exhibit 99.1 Inspirato Announces $10 Million Capital Infusion by One Planet Group, Appoints Payam Zamani as CEO and Chairman New CEO Focused on Profitable Growth, Remains Committed to Delivering Exceptional Service and World Class Experiences for its Members Implementing Immediate Efficiencies to Reduce Annualized Costs by Approximately $25 Million DENVER, August 12, 2024 (GLOBE NEWSWIRE) – Inspir

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorpo

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 12, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation or organizati

Email to Inspirato Members, dated as of August 12, 2024

Exhibit 99.2 I am thrilled to introduce myself as the incoming CEO & Chairman of the Board at Inspirato. Read the full update | View online Dear Inspirato Members, Following the press release issued earlier today, I am thrilled to introduce myself as the incoming CEO & Chairman of the Board at Inspirato. The investment from One Planet Group marks a significant milestone that not only strengthens o

I am thrilled to introduce myself as the incoming CEO & Chairman of the Board at Inspirato. Read the full update | View online

Exhibit 99.2 I am thrilled to introduce myself as the incoming CEO & Chairman of the Board at Inspirato. Read the full update | View online Dear Inspirato Members, Following the press release issued earlier today, I am thrilled to introduce myself as the incoming CEO & Chairman of the Board at Inspirato. The investment from One Planet Group marks a significant milestone that not only strengthens o

Email to Inspirato Employees from CEO and Chairman Payam Zamani, dated as of August 12, 2024

Exhibit 99.4 Dear Inspirato Team, Following our recent public announcements, I am excited and deeply honored to introduce myself as your new CEO & Chairman of the Board at Inspirato. We are entering a transformative period filled with both significant changes and promising opportunities. The investment from One Planet Group is a testament to the faith in our potential and provides a strong foundat

Press Release, dated as of August 12, 2024

Exhibit 99.1 Inspirato Announces $10 Million Capital Infusion by One Planet Group, Appoints Payam Zamani as CEO and Chairman New CEO Focused on Profitable Growth, Remains Committed to Delivering Exceptional Service and World Class Experiences for its Members Implementing Immediate Efficiencies to Reduce Annualized Costs by Approximately $25 Million DENVER, August 12, 2024 (GLOBE NEWSWIRE) – Inspir

Dear Inspirato Team,

Exhibit 99.3 Dear Inspirato Team, I am writing to let you know that we just issued a press release announcing two major developments at Inspirato: · A $10 million investment in the company. · The appointment of a new CEO and Chairman of the Board. Read the press release here. [link to unique URL with the release] We usually aim to give you advance notice of announcements like these. However, due t

Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 9, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

ISPO / Inspirato Incorporated / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 tm2420621d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 8)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Se

ISPO / Inspirato Incorporated / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 tm2420250d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 7)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Se

ISPO / Inspirato Incorporated / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 6)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 45791E206 (CUSIP Number) Tracy H

ISPO / Inspirato Incorporated / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 tm2417712d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 5)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Se

ISPO / Inspirato Incorporated / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 tm2416886d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 4)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Se

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 30, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 16, 2024 Inspirato Incorporat

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 16, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fil

First Amendment to the Inspirato Incorporated 2021 Equity Incentive Plan.

  Exhibit 10.1   Annex A INSPIRATO INCORPORATED 2021 EQUITY INCENTIVE PLAN First Amendment   THIS FIRST AMENDMENT to the Inspirato Incorporated 2021 Equity Incentive Plan (the “Plan”) is adopted as of February 7, 2024.   WHEREAS, the Board of Directors (the “Board”) of Inspirato Incorporated (the “Company”) has the general authority to amend the Plan pursuant to Section 19 of the Plan;   WHEREAS,

2

Exhibit 99.2 C O R P O R A T E P A R T I C I P A N T S Kyle Sourk Inspirato Inc - IR Eric Grosse Inspirato Inc – CEO, Director Robert Kaiden Inspirato Inc - Chief Financial Officer C O N F E R E N C E C A L L P A R T I C I P A N T S Brett Knoblauch Cantor Fitzgerald & Co. - Analyst P R E S E N T A T I O N Operator Good day and welcome to the Inspire auto first quarter 2024 earnings call. (Operator

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2024 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 7, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission File

Inspirato Announces First Quarter 2024 Results; Improved Occupancy Rates Contribute to Margin Expansion and Quarterly Profits

Exhibit 99.1 Inspirato Announces First Quarter 2024 Results; Improved Occupancy Rates Contribute to Margin Expansion and Quarterly Profits DENVER, May 7, 2024 (GLOBE NEWSWIRE) – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel club, today announced its 2024 first quarter financial and operating results. Except as otherwise stated, all financial res

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 22, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

Robert Kaiden Executive Employment, signed as of March 22, 2024.

Exhibit 10.1 EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (“Agreement”) is made by and between Inspirato LLC, a Delaware limited liability company (the “Company”), and Robert Kaiden, a California resident (“Executive”), effective as of March 20, 2024 (the “Effective Date”). WHEREAS, the Company and the Executive are parties to an Offer Letter signed on March 21, 2023 (“Prior

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables S-8 (Form Type) INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Table 1: Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Share Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Class A Common Stock, $0.

As filed with the Securities and Exchange Commission on March 14, 2024

As filed with the Securities and Exchange Commission on March 14, 2024 Registration No.

Exhibit 4.4

Exhibit 4.4 DESCRIPTION OF SECURITIES The following description of the capital stock of Inspirato Incorporated (“us,” “our,” “we,” “Inspirato” or the “Company”) is a summary of the rights of our securities and certain provisions of our Second Amended and Restated Certificate of Incorporation (the “Certificate of Incorporation”) and Amended and Restated Bylaws (the “Bylaws”) as currently in effect.

List of Subsidiaries

Exhibit 21.1 1 Inspirato Incorporated Subsidiaries: 2 Bayside Villas, LLC 3 Beach Front Villas Ltd 4 Best of 52 LLC 5 Cenotes Holdings LLC 6 Clouser Bight, Ltd 7 Coral Reef Properties, LLC 8 Faraway Land, LLC 9 HighRoad Holdings, LLC 10 Inspirato LLC 11 Inspirato Real Estate, LLC 12 Inspriato Mexico S. de R.L. de C.V. 13 Island Holdings, LLC 14 Leward Breeze, Inc. 15 Ocean Cliff Holdings, LLC 16 O

Clawback Policy

INSPIRATO INCORPORATED COMPENSATION RECOVERY POLICY As adopted on November 28, 2023 Inspirato Incorporated (the “Company”) is committed to strong corporate governance.

Code of Ethics

‌Exhibit 14.1 Inspirato Code of Business Conduct and Ethics Introduction We are committed to the highest standards of ethical and legal business conduct. Inspirato’s Code of Business Conduct and Ethics (the “Code of Conduct”) is intended to be a summary of guiding principles and standards that promote a culture of honesty, accountability, ethical and compliant conduct, and prompt internal reportin

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) ☒ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2023 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Inspirato Announces 2023 Revenue and Adjusted EBITDA within Previously Guided Ranges, Provides 2024 Guidance

Exhibit 99.1 Inspirato Announces 2023 Revenue and Adjusted EBITDA within Previously Guided Ranges, Provides 2024 Guidance DENVER, March 5, 2024 (GLOBE NEWSWIRE) – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel club, today announced its 2023 fourth quarter and full-year results and provided 2024 guidance aimed at improving its path to profitabilit

1

‌Exhibit 99.2 C O R P O R A T E P A R T I C I P A N T S Kyle Sourk Inspirato Inc - VP, IR Eric Grosse Inspirato Inc - CEO Robert Kaiden Inspirato Inc - Chief Financial Officer C O N F E R E N C E C A L L P A R T I C I P A N T S Mike Grondahl Northland Securities, Inc. - Analyst P R E S E N T A T I O N Operator Good day, and thank you for standing by, and welcome to the Inspirato fourth quarter 202

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 5, 2024 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fi

ISPO / Inspirato Incorporated / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 tm248188d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 3)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Sec

US45791E2063 / Inspirato Inc / Kleiner Perkins Caufield & Byers XIV, LLC - SC 13G/A Passive Investment

SC 13G/A 1 tm246036d2sc13ga.htm SC 13G/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Schedule 13G INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULES 13d-1 (b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO 13d-2 (b) (Amendment No.1)* Inspirato Incorporated (Name of Issuer) Class A Common Stock (Title of Class of Securities) 45791E206 (CUSIP Number) December 31, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 31, 2023 Inspirato Incor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): December 31, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissio

Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 27, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissio

US45791E1073 / INSPIRATO INC / REVOLUTION MANAGEMENT CO LLC - SC 13D/A Activist Investment

SC 13D/A 1 tm2331169d1sc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 2)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, $0.0001 par value per share (Title of Class of Securities) 45791E107 (CUSIP Number) Kerry L. Killeen Revolution LLC 1717 Rhode Island Avenue, N.W. 10t

Second Amended and Restated Certificate of Incorporation of the Company.

Exhibit 3.1 SECOND AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF THAYER VENTURES ACQUISITION CORPORATION Thayer Ventures Acquisition Corporation, a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), DOES HEREBY CERTIFY AS FOLLOWS: 1.The name of the Corporation is “Thayer Ventures Acquisition Corporation”. The original certificate of incorporation

Inspirato Incorporated Consolidated Statements of Operations and Comprehensive Loss (in thousands, except per share data) (unaudited)

Exhibit 99.1 Inspirato Announces Third Quarter Results November 6, 2023 DENVER, Nov. 06, 2023 (GLOBE NEWSWIRE) - Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2023 third quarter financial and operating results. Except as otherwise stated, all financial results discussed below are presented in accordance wi

Regulation FD Disclosure, Financial Statements and Exhibits, Results of Operations and Financial Condition

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): November 6, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

C O R P O R A T E P A R T I C I P A N T S

Exhibit 99.2 C O R P O R A T E P A R T I C I P A N T S Kyle Sourk Inspirato Incorporated - Investor Relations Eric Grosse Inspirato Incorporated - CEO, Director Robert Kaiden Inspirato Incorporated - CFO C O N F E R E N C E C A L L P A R T I C I P A N T S Shweta Khajuria Evercore ISI - Analyst Mike Grundle Northland Insurance - Analyst Jed Kelly Oppenheimer & Co. Inc. - Analyst P R E S E N T A T I

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended September 30, 2023 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Certificate of Amendment to the Second Amended and Restated Certificate of Incorporation of the Company, dated October 16, 2023.

Exhibit 3.2 CERTIFICATE OF AMENDMENT TO THE SECOND AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF INSPIRATO INCORPORATED Inspirato Incorporated, a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), hereby certifies as follows: A. The Corporation was originally incorporated under the name of Thayer Ventures Acquisition Corporation, and the original

Inspirato Announces Reverse Stock Split

Exhibit 99.1 Inspirato Announces Reverse Stock Split Denver, October 16, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that it will effect a reverse stock split of its Class A common stock, Class B Non-Voting common stock and Class V common stock (collectively, “Common Stock”) at a ratio of 1-for-20, effective as of the

Eleventh Amended and Restated Limited Liability Company Agreement of Inspirato LLC, dated October 16, 2023.

Exhibit 3.1 ELEVENTH AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF INSPIRATO LLC DATED AS OF OCTOBER 16, 2023 THE LIMITED LIABILITY COMPANY INTERESTS IN INSPIRATO LLC HAVE NOT BEEN REGISTERED UNDER THE U.S. SECURITIES ACT OF 1933, THE SECURITIES LAWS OF ANY STATE, OR ANY OTHER APPLICABLE SECURITIES LAWS, AND HAVE BEEN OR ARE BEING ISSUED IN RELIANCE UPON EXEMPTIONS FROM THE REGISTRAT

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 16, 2023 Inspirato Incorp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): October 16, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 7 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 7 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 7 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 7 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Tenth Amended and Restated Limited Liability Company Agreement of Inspirato LLC, dated as of September 29, 2023

Exhibit 3.1 TENTH AMENDED AND RESTATED LIMITED LIABILITY COMPANY AGREEMENT OF INSPIRATO LLC DATED AS OF SEPTEMBER 29, 2023 THE LIMITED LIABILITY COMPANY INTERESTS IN INSPIRATO LLC HAVE NOT BEEN REGISTERED UNDER THE U.S. SECURITIES ACT OF 1933, THE SECURITIES LAWS OF ANY STATE, OR ANY OTHER APPLICABLE SECURITIES LAWS, AND HAVE BEEN OR ARE BEING ISSUED IN RELIANCE UPON EXEMPTIONS FROM THE REGISTRATI

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 29, 2023 Inspirato Inco

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 29, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissi

Certificate of Amendment to the Second Amended and Restated Certificate of Incorporation of the Company, dated September 29, 2023.

Exhibit 3.2 CERTIFICATE OF AMENDMENT TO THE SECOND AMENDED AND RESTATED CERTIFICATE OF INCORPORATION OF INSPIRATO INCORPORATED Inspirato Incorporated, a corporation organized and existing under the laws of the State of Delaware (the “Corporation”), hereby certifies as follows: A. The Corporation was originally incorporated under the name of Thayer Ventures Acquisition Corporation, and the original

Inspirato Completes $25 Million Investment from Capital One Ventures, Solidifying New Strategic Partnership

Exhibit 99.1 Inspirato Completes $25 Million Investment from Capital One Ventures, Solidifying New Strategic Partnership Denver, October 4, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that it has closed its $25 million senior secured convertible note issued by Inspirato to Capital One Ventures (the “investment”). On S

Regulation FD Disclosure, Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing, Other Events, Submission of Matters to a Vote of Security Holders, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): September 21, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commissi

Executive Employment Agreement between Inspirato LLC and Eric Grosse, dated September 22, 2023

Exhibit 10.1 EXECUTIVE EMPLOYMENT AGREEMENT This Executive Employment Agreement (“Agreement”) is made by and between Inspirato LLC, a Delaware limited liability company (the “Company”), and Eric Grosse, a California resident (“Executive”), effective as of September 25, 2023 (the “Effective Date”). WHEREAS, the Company desires to employ Executive upon the terms and conditions set forth herein, and

Inspirato Announces CEO Transition Co-Founder Brent Handler to Step Down; Independent Director Eric Grosse Appointed Chief Executive Officer Effective September 25, 2023

Exhibit 99.1 Inspirato Announces CEO Transition Co-Founder Brent Handler to Step Down; Independent Director Eric Grosse Appointed Chief Executive Officer Effective September 25, 2023 Denver, September 25, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that Co-Founder and Chief Executive Officer (CEO), Brent Handler, has

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 6 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Separation and Release Agreement between Inspirato LLC and Brent Handler, dated September 22, 2023

Exhibit 10.2 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Brent Handler (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was employed by the Company as Chief Executive Officer; WHEREAS, the Executive has resigned from employment with the C

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 6 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant x Filed by a party other than the Registrant ¨ Check the appropriate box: ¨ Preliminary Proxy Statement ¨ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ¨ Definitive Proxy State

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 5 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 5 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

Separation and Release Agreement, dated as of August 21, 2023, between Inspirato LLC and R. Webster Neighbor.

Exhibit 10.1 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Robert Webster Neighbor (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was employed by the Company; WHEREAS, the Executive has separated from employment with the Company effective

Separation and Release Agreement, dated as of August 21, 2023, between Inspirato LLC and R. Webster Neighbor.

Exhibit 10.1 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Robert Webster Neighbor (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was employed by the Company; WHEREAS, the Executive has separated from employment with the Company effective

Separation and Release Agreement, dated as of August 21, 2023, between Inspirato LLC and R. Webster Neighbor.

Exhibit 10.1 Separation and Release Agreement This Separation and Release Agreement (“Agreement”) is made between Inspirato LLC, a Delaware limited liability company (the “Company”) and Robert Webster Neighbor (“Executive”) (each a “party” and together the “parties”): WHEREAS, the Executive was employed by the Company; WHEREAS, the Executive has separated from employment with the Company effective

Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers; Compensatory Arrangements of Certain Officers, Financial Statements and Exhibits

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 21, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☒ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☐ Defi

US45791E1073 / INSPIRATO INC / SELLERS R SCOT - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* INSPIRATO INCORPORATED (Name of Issuer) Class A Common Stock, par value $ 0. 0001 per share (Title of Class of Securities) 45791E 107 (CUSIP Number) Scot Sellers 1544 Wazee Street Denver, Colorado (303) 586-7771 (Name, Address and Telephone Number of Person A

US45791E1073 / INSPIRATO INC / REVOLUTION MANAGEMENT CO LLC - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, $0.0001 par value per share (Title of Class of Securities) 45791E107 (CUSIP Number) Kerry L. Killeen Revolution LLC 1717 Rhode Island Avenue, N.W. 10th Floor Washington, D.C. 20036 (202) 776-1

US45791E1073 / INSPIRATO INC / Handler Brent L - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* INSPIRATO INCORPORATED (Name of Issuer) Class A Common Stock, par value $ 0. 0001 per share (Title of Class of Securities) 45791E 107 (CUSIP Number) Brent Handler 1544 Wazee Street Denver, Colorado (303) 586-7771 (Name, Address and Telephone Number of Person

Exhibit 5 Voting Agreement.

EX-99.5 Exhibit 5 VOTING AGREEMENT This VOTING AGREEMENT (this “Agreement”), dated as of August 7, 2023, is by and among (i) Oakstone Ventures, Inc., a Delaware corporation (“Purchaser”), (ii) Inspirato Incorporated, a Delaware corporation (the “Company”), and (iii) the stockholders of the Company listed on Schedule A and the signature pages hereto (each, a “Stockholder” and, collectively, the “St

US45791E1073 / INSPIRATO INC / Kallery David S - SC 13D/A Activist Investment

SC 13D/A SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D Under the Securities Exchange Act of 1934 (Amendment No. 1)* INSPIRATO INCORPORATED (Name of Issuer) Class A Common Stock, par value $ 0. 0001 per share (Title of Class of Securities) 45791E 107 (CUSIP Number) David Kallery 1544 Wazee Street Denver, Colorado (303) 586-7771 (Name, Address and Telephone Number of Person

Exhibit 5 Voting Agreement.

EX-99.5 Exhibit 5 VOTING AGREEMENT This VOTING AGREEMENT (this “Agreement”), dated as of August 7, 2023, is by and among (i) Oakstone Ventures, Inc., a Delaware corporation (“Purchaser”), (ii) Inspirato Incorporated, a Delaware corporation (the “Company”), and (iii) the stockholders of the Company listed on Schedule A and the signature pages hereto (each, a “Stockholder” and, collectively, the “St

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 4 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 4 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Investment Agreement, dated as of August 7, 2023, between Inspirato Incorporated and Oakstone Ventures, Inc.

Exhibit 10.1 INVESTMENT AGREEMENT by and among Inspirato Incorporated, Inspirato LLC, the Other Guarantor Subsidiaries, as defined herein and Oakstone Ventures, Inc. Dated as of August 7, 2023 TABLE OF CONTENTS Page INVESTMENT AGREEMENT 1 Article I. DEFINITIONS 2 Section 1.01 Definitions 2 Section 1.02 Certain Other Definitions 9 Section 1.03 General Interpretive Principles 10 Article II. SALE AND

TVACU / Thayer Ventures Acquisition Corp - Units (1 Ord Class A & 1/2 War) / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 2)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 88332T209 (CUSIP Number) Tracy H

Press Release dated August 8, 2023 announcing the Company’s financial results.

Exhibit 99.1 Inspirato Announces Second Quarter Results and Updates Full-Year 2023 Guidance DENVER, August 8, 2023 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2023 second quarter financial and operating results, entry into a definitive agreement for a new $25 million convertible note investment from Ca

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 3 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Investment Agreement, dated as of August 7, 2023, between Inspirato Incorporated and Oakstone Ventures, Inc.

Exhibit 10.1 INVESTMENT AGREEMENT by and among Inspirato Incorporated, Inspirato LLC, the Other Guarantor Subsidiaries, as defined herein and Oakstone Ventures, Inc. Dated as of August 7, 2023 TABLE OF CONTENTS Page INVESTMENT AGREEMENT 1 Article I. DEFINITIONS 2 Section 1.01 Definitions 2 Section 1.02 Certain Other Definitions 9 Section 1.03 General Interpretive Principles 10 Article II. SALE AND

Press Release dated August 8, 2023 announcing the Transaction.

Exhibit 99.2 Capital One Ventures Enters into Agreement to Invest in Inspirato, Forging a New Strategic Partnership Denver, August 8, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that it has entered into a definitive agreement for a new $25 million convertible note investment from Capital One Ventures. The capital is e

Press Release dated August 8, 2023 announcing the Transaction.

Exhibit 99.2 Capital One Ventures Enters into Agreement to Invest in Inspirato, Forging a New Strategic Partnership Denver, August 8, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that it has entered into a definitive agreement for a new $25 million convertible note investment from Capital One Ventures. The capital is e

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 3 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended June 30, 2023 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Press Release dated August 8, 2023 announcing the Company’s financial results.

Exhibit 99.1 Inspirato Announces Second Quarter Results and Updates Full-Year 2023 Guidance DENVER, August 8, 2023 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2023 second quarter financial and operating results, entry into a definitive agreement for a new $25 million convertible note investment from Ca

First Amendment to the Warrant Agreement, dated March 13, 2023, by and between Inspirato Incorporated and Saks.com LLC

Exhibit 10.1 FIRST AMENDMENT TO WARRANT TO PURCHASER SHARES OF CLASS A COMMON STOCK OF INSPIRATO INCORPORATED THIS FIRST AMENDMENT TO WARRANT TO PURCHASER SHARES OF CLASS A COMMON STOCK OF INSPIRATO INCORPORATED (this “First Amendment”) is made as of June 7, 2023 (the “First Amendment Date”) between Inspirato Incorporated, a Delaware corporation (“Company”), and Saks.com LLC, a Delaware limited li

Investment Agreement, dated as of August 7, 2023, between Inspirato Incorporated and Oakstone Ventures, Inc.

Exhibit 10.1 INVESTMENT AGREEMENT by and among Inspirato Incorporated, Inspirato LLC, the Other Guarantor Subsidiaries, as defined herein and Oakstone Ventures, Inc. Dated as of August 7, 2023 TABLE OF CONTENTS Page INVESTMENT AGREEMENT 1 Article I. DEFINITIONS 2 Section 1.01 Definitions 2 Section 1.02 Certain Other Definitions 9 Section 1.03 General Interpretive Principles 10 Article II. SALE AND

Press Release dated August 8, 2023 announcing the Transaction.

Exhibit 99.2 Capital One Ventures Enters into Agreement to Invest in Inspirato, Forging a New Strategic Partnership Denver, August 8, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that it has entered into a definitive agreement for a new $25 million convertible note investment from Capital One Ventures. The capital is e

Press Release dated August 8, 2023 announcing the Company’s financial results.

Exhibit 99.1 Inspirato Announces Second Quarter Results and Updates Full-Year 2023 Guidance DENVER, August 8, 2023 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2023 second quarter financial and operating results, entry into a definitive agreement for a new $25 million convertible note investment from Ca

Form of 8% Senior Secured Convertible Notes due 2028.

Exhibit 10.1 INVESTMENT AGREEMENT by and among Inspirato Incorporated, Inspirato LLC, the Other Guarantor Subsidiaries, as defined herein and Oakstone Ventures, Inc. Dated as of August 7, 2023 TABLE OF CONTENTS Page INVESTMENT AGREEMENT 1 Article I. DEFINITIONS 2 Section 1.01 Definitions 2 Section 1.02 Certain Other Definitions 9 Section 1.03 General Interpretive Principles 10 Article II. SALE AND

Regulation FD Disclosure, Entry into a Material Definitive Agreement, Unregistered Sales of Equity Securities, Financial Statements and Exhibits, Creation of a Direct Financial Obligation or an Obligation under an Off-Balance Sheet Arrangement of a Registrant, Results of Operations and Financial Condition, Other Events

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 7, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

Inspirato Announces Second Quarter Results and Updates Full-Year 2023 Guidance

Exhibit 99.1 Inspirato Announces Second Quarter Results and Updates Full-Year 2023 Guidance DENVER, August 8, 2023 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2023 second quarter financial and operating results, entry into a definitive agreement for a new $25 million convertible note investment from Ca

Capital One Ventures Enters into Agreement to Invest in Inspirato, Forging a New Strategic Partnership

Exhibit 99.2 Capital One Ventures Enters into Agreement to Invest in Inspirato, Forging a New Strategic Partnership Denver, August 8, 2023 – Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced that it has entered into a definitive agreement for a new $25 million convertible note investment from Capital One Ventures. The capital is e

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 7, 2023 Inspirato Incorpor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): August 7, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

TVACU / Thayer Ventures Acquisition Corp - Units (1 Ord Class A & 1/2 War) / Institutional Venture Partners XIII, L.P. - SC 13D/A Activist Investment

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 1)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 88332T209 (CUSIP Number) Tracy H

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 2 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 2 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 18, 2023 Inspirato Incorporat

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 18, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fil

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 16, 2023 Inspirato Incorporat

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 16, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission Fil

1 NAUPAKA KOHALA COAST, HAWAII 1 Member Update and Overview MAY 16, 2023

Exhibit 99.2 1 NAUPAKA KOHALA COAST, HAWAII 1 Member Update and Overview MAY 16, 2023 2 Disclaimer Forward - Looking Statements This presentation contains forward - looking statements within the meaning of federal securities laws. Forward - looking statements generally relate to future events or our future financial or operating performance. In some cases, you can identify forward - look ing state

PART 1 OF 4 ENDS [00:11:04]

Exhibit 99.1 Brent Handler (00:36): Hello everybody. Greetings from a very rainy Denver, Colorado. I'm super excited to get today's member update started. My name is Brent Handler. I'm the co-founder and CEO of Inspirato. I have Brett Knoblauch with us from Cantor Fitzgerald. He's going to be facilitating today's conversation. Just to get started, I wanted to give the quick disclaimer that we'll b

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 1 (To the Prospectus dated March 30, 2023) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated March 30, 2

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 1 (To the Prospectus dated March 30, 2023) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pros

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-Q (Mark One) ☒QUARTERLY REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the quarterly period ended March 31, 2023 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 16 (To the Prospectus dated March 10, 2022) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pro

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 12 (To the Prospectus dated May 9, 2022) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated May 9, 2022 (

Inspirato Announces First Quarter Financial and Operating Results

Exhibit 99.1 Inspirato Announces First Quarter Financial and Operating Results DENVER, May 8, 2023 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2023 first quarter financial and operating results. Except as otherwise stated, all financial results discussed below are presented in accordance with generally

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 3, 2023 Inspirato Incorporate

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): May 3, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission File

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934

TABLE OF CONTENTS UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 14A Proxy Statement Pursuant to Section 14(a) of the Securities Exchange Act of 1934 Filed by the Registrant ☒ Filed by a party other than the Registrant ☐ Check the appropriate box: ☐ Preliminary Proxy Statement ☐ Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2)) ☒ Defi

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock INSPIRATO INCORPORATED

TABLE OF CONTENTS   Filed Pursuant to Rule 424(b)(3)  Registration No. 333-264598 Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock INSPIRATO INCORPORATED This prospectus relates to the issuance by us of up to 69,780,665 shares of Inspirato Class A com

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 15,925,385 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock INSPIRATO INCORPORATED

TABLE OF CONTENTS  Filed Pursuant to Rule 424(b)(3)  Registration No. 333-262472 Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 15,925,385 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock INSPIRATO INCORPORATED This prospectus relates to the resale by the selling securityholders name

As filed with the Securities and Exchange Commission on March 22, 2023

Table of Contents As filed with the Securities and Exchange Commission on March 22, 2023 Registration No.

As filed with the Securities and Exchange Commission on March 22, 2023

Table of Contents As filed with the Securities and Exchange Commission on March 22, 2023 Registration No.

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 15 (To the Prospectus dated March 10, 2022) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pro

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 11 (To the Prospectus dated May 9, 2022) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated May 9, 2022 (

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 21, 2023 Inspirato Incorpor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 21, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

Offer Letter between the Company and Robert Kaiden, dated as of March 17, 2023.

Exhibit 10.1 March 21, 2023 Robert Kaiden [email protected] Dear Robert, I am pleased to offer you employment with Inspirato LLC (“Inspirato” or the “Company”) as Chief Financial Offer, effective as of March 21, 2023 (the “Start Date”), reporting to Brent Handler, CEO. This offer letter amends and supersedes the offer letter dated March 17, 2023. I have outlined the key elements of our employmen

Inspirato Announces Appointment of Former Twitter Executive as Chief Financial Officer

Exhibit 99.1 Inspirato Announces Appointment of Former Twitter Executive as Chief Financial Officer DENVER, March 21, 2023 (GLOBE NEWSWIRE) - Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced the appointment of Robert Kaiden as Chief Financial Officer, effective immediately. Mr. Kaiden was most recently with Twitt

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 14 (To the Prospectus dated March 10, 2022) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pro

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 10 (To the Prospectus dated May 9, 2022) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated May 9, 2022 (

As filed with the Securities and Exchange Commission on March 15, 2023

As filed with the Securities and Exchange Commission on March 15, 2023 Registration No.

Filing Fee Table

Exhibit 107 Calculation of Filing Fee Tables Form S-8 (Form Type) Inspirato Incorporated (Exact name of registrant as specified in its charter) Table 1 – Newly Registered Securities Security Type Security Class Title Fee Calculation Rule Amount Registered(1) Proposed Maximum Offering Price Per Unit Maximum Aggregate Offering Price Fee Rate Amount of Registration Fee Equity Class A common stock, $0.

Inspirato Announces 2022 Results, CFO Succession Plan and Provides 2023 Guidance

Exhibit 99.1 Inspirato Announces 2022 Results, CFO Succession Plan and Provides 2023 Guidance DENVER, March 15, 2023 – Inspirato Incorporated (“Inspirato” or the “Company”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, today announced its 2022 fourth quarter and full-year financial and operating results and provided updated 2023 guidance. 2022 Fourth Quarter and Full-Year Highli

List of Subsidiaries

Exhibit 21.1 1 Inspirato Incorporated Subsidiaries: 2 Bayside Villas, LLC 3 Beach Front Villas Ltd 4 Best of 52 LLC 5 Cenotes Holdings LLC 6 Clouser Bight, Ltd 7 Coral Reef Properties, LLC 8 Faraway Land, LLC 9 HighRoad Holdings, LLC 10 Inspirato LLC 11 Inspirato Real Estate, LLC 12 Inspriato Mexico S. de R.L. de C.V. 13 Island Holdings, LLC 14 Leward Breeze, Inc. 15 Ocean Cliff Holdings, LLC 16 O

Description of Capital Stock

Exhibit 4.4 DESCRIPTION OF SECURITIES The following description of the capital stock of Inspirato Incorporated (“us,” “our,” “we,” “Inspirato” or the “Company”) is a summary of the rights of our securities and certain provisions of our Second Amended and Restated Certificate of Incorporation (the “Certificate of Incorporation”) and Amended and Restated Bylaws (the “Bylaws”) as currently in effect.

UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K

Table of Contents UNITED STATES SECURITIES AND EXCHANGE COMMISSION WASHINGTON, DC 20549 FORM 10-K (Mark One) ☒ANNUAL REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the fiscal year ended December 31, 2022 OR ☐TRANSITION REPORT PURSUANT TO SECTION 13 OR 15(d) OF THE SECURITIES EXCHANGE ACT OF 1934 For the transition period from to Commission File Number: 001-39791 INSPIRATO INCORPORATED (Exact Name of Registrant as Specified in its Charter) Delaware 85-2426959 (State or other jurisdiction of incorporation or organization) (I.

R. Webster Neighbor Amended and Restated Employment Agreement, dated March 15, 2023.

Exhibit 10.1 EMPLOYMENT AGREEMENT This Amended and Restated Employment Agreement (“Agreement”) is made between Inspirato LLC (the “Company”), and Web Neighbor (the “Executive”) and is effective on the date signed by both the Executive and on behalf of the Company below (the “Effective Date”). WHEREAS, the Company and the Executive are parties to an employment agreement signed on September 15, 2021

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 15, 2023 Inspirato Incorpor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 15, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 13, 2023 Inspirato Incorpor

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): March 13, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission F

Saks Partners with Inspirato to Bring Luxury Travel Subscriptions to Saks Customers

EX-99.1 3 tm239466d1ex99-1.htm EXHIBIT 99.1 Exhibit 99.1 Saks Partners with Inspirato to Bring Luxury Travel Subscriptions to Saks Customers NEW YORK, MARCH 14, 2023 – Saks, the premier digital platform for luxury fashion, and Inspirato Incorporated (“Inspirato”) (NASDAQ: ISPO), the innovative luxury travel subscription brand, have entered into a strategic marketing partnership. Through the new pa

Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-264598 PROSPECTUS SUPPLEMENT NO. 9 (To the Prospectus dated May 9, 2022) Primary Offering of 69,780,665 Shares of Class A Common Stock Issuable Upon the Exchange of New Common Units and Class V Common Stock Secondary Offering of 94,278,420 Shares of Class A Common Stock This prospectus supplement supplements the prospectus, dated May 9, 2022 (t

Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock

Filed Pursuant to Rule 424(b)(3) Registration No. 333-262472 PROSPECTUS SUPPLEMENT NO. 13 (To the Prospectus dated March 10, 2022) Primary Offering of 15,800,000 Shares of Class A Common Stock Issuable Upon Exercise of Warrants Secondary Offering of 16,025,284 Shares of Class A Common Stock 7,175,000 Warrants to Purchase Shares of Class A Common Stock This prospectus supplement supplements the pro

Warrant Agreement, dated March 13, 2023 by and between Inspirato Incorporated and Saks.com LLC.

Exhibit 10.1 Execution Version THIS WARRANT AND THE UNDERLYING SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR UNDER THE SECURITIES LAWS OF ANY STATE. THESE SECURITIES MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED EXCEPT AS PERMITTED UNDER THE ACT AND APPLICABLE STATE SECURITIES LAWS IN ACCORDANCE WITH APPLICABLE REGISTR

US45791E1073 / INSPIRATO INC / TANG CAPITAL PARTNERS LP - AMENDMENT NO. 1 Passive Investment

Securities and Exchange Commission Washington, DC 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No.

US45791E1073 / INSPIRATO INC / CVI Investments, Inc. - SC 13G/A Passive Investment

SC 13G/A 1 tm235037d3sc13ga.htm SC 13G/A CUSIP No: 45791E107 SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO § 240.13d-1(b), (c) AND (d) AND AMENDMENTS THERETO FILED PURSUANT TO § 240.13d-2. (Amendment No. 1)* Inspirato Incorporated (formerly Thayer Ventures Acquisition Corporation) (Name of Issuer) Cl

US45791E1073 / INSPIRATO INC / Hudson Bay Capital Management LP - TVAC Passive Investment

SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G/A Under the Securities Exchange Act of 1934 (Amendment No. 1)* Inspirato Incorporated (f/k/a Thayer Ventures Acquisition Corporation) (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Securities) 45791E107 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statement

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 9, 2023 Inspirato Incorp

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 FORM 8-K CURRENT REPORT PURSUANT TO SECTION 13 OR 15(D) OF THE SECURITIES EXCHANGE ACT OF 1934 Date of Report (Date of earliest event reported): February 9, 2023 Inspirato Incorporated (Exact name of registrant as specified in its charter) Delaware 001-39791 85-2426959 (State or other jurisdiction of incorporation) (Commission

US45791E1073 / INSPIRATO INC / MILLENNIUM TECHNOLOGY VALUE PARTNERS II, L.P. - SC 13G/A Passive Investment

SC 13G/A 1 d458379dsc13ga.htm SC 13G/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13G UNDER THE SECURITIES EXCHANGE ACT OF 1934 (Amendment No. 1)* Inspirato Incorporated (Name of Issuer) CLASS A COMMON STOCK, PAR VALUE $0.0001 PER SHARE (Title of Class of Securities) 45791E107 (CUSIP Number) December 31, 2022 (Date of Event Which Requires Filing of this Statem

US45791E1073 / INSPIRATO INC / W Capital Partners III, L.P. - SC 13D/A Activist Investment

SC 13D/A 1 d445333dsc13da.htm SC 13D/A UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 SCHEDULE 13D/A (Rule 13d-102) INFORMATION TO BE INCLUDED IN STATEMENTS FILED PURSUANT TO RULE 13d-l(a) AND AMENDMENTS THERETO FILED PURSUANT TO RULE 13d-2(a) (Amendment No. 1)* Inspirato Incorporated (Name of Issuer) Class A Common Stock, par value $0.0001 per share (Title of Class of Sec