[SCHEDULE 13D/A] Inspirato Incorporated SEC Filing

Rhea-AI Filing Summary

Stoney Lonesome HF LP, Coghill Capital Management LLC, Drake Helix Holdings, LLC, CDC Financial, Inc., and Clint D. Coghill report beneficial ownership positions in Inspirato Inc. The filing covers Class A common stock and discloses that Stoney Lonesome directly owns 633,271 shares (~5.1% of outstanding shares) and Drake Helix directly owns 36,000 shares (~0.3%), with CDC Financial and Mr. Coghill potentially attributable to a combined 669,271 shares (~5.4%). The aggregate purchase prices disclosed are approximately $3,349,904 for Stoney Lonesome's shares and $121,947 for Drake Helix's shares, acquired with working capital.

The reporting persons state they issued a presentation on September 2, 2025 opposing the proposed merger between Inspirato and Buyerlink, asserting that the merger would harm minority stockholders, that the board’s approval process was flawed, that CEO Payam Zamani would receive a substantial windfall, and that the combined company would create a conglomerate without apparent synergies. Exhibits referenced include a transactions schedule and the presentation.

Positive

• Disclosure of exact holdings and percentages (633,271 shares = ~5.1%; combined attribution = ~5.4%), providing clear investor transparency
• Purchase prices disclosed for principal positions: ~$3,349,904 for Stoney Lonesome and ~$121,947 for Drake Helix, indicating material economic commitment
• Formal public presentation filed as Exhibit 99.1 to explain opposition to the proposed merger, increasing transparency of activist views

Negative

• Reporting persons publicly assert the proposed merger will cause "immense value destruction" for minority stockholders, a material adverse claim
• Allegation of a flawed board/special committee process in approving the merger, implying governance concerns
• Claim that CEO Payam Zamani would receive a substantial windfall, indicating potential conflict of interest highlighted in the filing

Insights

Securities Analyst

TL;DR: A shareholder group controlling about 5.4% of ISPO publicly opposes the proposed merger and disclosed open-market purchases totaling ~669k shares.

The filing documents that Stoney Lonesome holds 633,271 shares (~5.1%) and Drake Helix holds 36,000 shares (~0.3%), with combined attribution to CDC Financial and Mr. Coghill of ~5.4%. Purchase consideration figures are provided, indicating open-market acquisition financed with working capital. The reporting persons formally issued a presentation opposing the Inspirato–Buyerlink merger, detailing governance and valuation concerns and attaching that presentation as Exhibit 99.1. For investors, this represents an organized activist stance by holders large enough to merit attention but not a controlling block.

Corporate Governance Expert

TL;DR: Activist-oriented disclosure highlights alleged board process flaws and executive enrichment tied to the proposed merger.

The Schedule 13D/A supplements Item 3 and Item 4 to state specific objections to the merger process and outcomes, naming alleged minority-stockholder harm and a purported CEO windfall. The filing attaches a public presentation as the vehicle for those claims. Such disclosures typically precede shareholder engagement or solicitation efforts and could prompt further proxy-stage debate or supplemental disclosures from the company or special committee. The filing does not, however, state specific alternative proposals or planned transactions beyond voting opposition.

SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 13D

Under the Securities Exchange Act of 1934

(Amendment No. 1)

Inspirato Inc

(Name of Issuer)

Class A Common Stock, $0.0001 par value per share

(Title of Class of Securities)

45791E206

(CUSIP Number)

RYAN NEBEL
OLSHAN FROME WOLOSKY LLP, 1325 Avenue of the Americas
New York, NY, 10019
212-451-2300

(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)

09/02/2025

(Date of Event Which Requires Filing of This Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.

The information required on the remainder of this cover page shall not be deemed to be "filed" for the purpose of Section 18 of the Securities Exchange Act of 1934 ("Act") or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

SCHEDULE 13D

CUSIP No. 45791E206

1

Name of reporting person

Stoney Lonesome HF LP

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

WC

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

DELAWARE

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 633,271.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 633,271.00

11

Aggregate amount beneficially owned by each reporting person

633,271.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

5.1 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. 45791E206

1

Name of reporting person

COGHILL CAPITAL MANAGEMENT LLC

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

AF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

DELAWARE

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 633,271.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 633,271.00

11

Aggregate amount beneficially owned by each reporting person

633,271.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

5.1 %

14

Type of Reporting Person (See Instructions)

OO

SCHEDULE 13D

CUSIP No. 45791E206

1

Name of reporting person

Drake Helix Holdings, LLC

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

WC

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

WYOMING

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 36,000.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 36,000.00

11

Aggregate amount beneficially owned by each reporting person

36,000.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0.3 %

14

Type of Reporting Person (See Instructions)

OO

SCHEDULE 13D

CUSIP No. 45791E206

1

Name of reporting person

CDC Financial, Inc.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

AF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

ILLINOIS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 669,271.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 669,271.00

11

Aggregate amount beneficially owned by each reporting person

669,271.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

5.4 %

14

Type of Reporting Person (See Instructions)

CO

SCHEDULE 13D

CUSIP No. 45791E206

1

Name of reporting person

COGHILL CLINT D

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

AF

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

UNITED STATES

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 669,271.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 669,271.00

11

Aggregate amount beneficially owned by each reporting person

669,271.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

5.4 %

14

Type of Reporting Person (See Instructions)

IN

SCHEDULE 13D

Item 1.	Security and Issuer
(a)	Title of Class of Securities: Class A Common Stock, $0.0001 par value per share
(b)	Name of Issuer: Inspirato Inc
(c)	Address of Issuer's Principal Executive Offices: 1544 WAZEE STREET, DENVER, COLORADO , 80202.
Item 3.	Source and Amount of Funds or Other Consideration
	Item 3 is hereby amended and restated to read as follows: The Shares purchased by Stoney Lonesome and Drake Helix were purchased with working capital (which may, at any given time, include margin loans made by brokerage firms in the ordinary course of business). The aggregate purchase price of the 633,271 Shares directly owned by Stoney Lonesome is approximately $3,349,904, including brokerage commissions. The aggregate purchase price of the 36,000 Shares directly owned by Drake Helix is approximately $121,947, including brokerage commissions.
Item 4.	Purpose of Transaction
	Item 4 is hereby amended to add the following: On September 2, 2025, the Reporting Persons issued a presentation (the "Presentation") in connection with the Proposed Merger between the Issuer and Buyerlink. In the Presentation, the Reporting Persons announced their intention to vote against the Proposed Merger and the reasons therefor, including, among others, the Reporting Persons' belief that (i) minority stockholders will suffer immense value destruction, (ii) the Special Committee and the Board's process in approving the Proposed Merger was flawed, (iii) the Issuer's Chairman and CEO Payam Zamani is set to receive a substantial windfall at the expense of minority stockholders and (iv) the combined company will result in a non-sensical conglomerate structure without apparent synergies. The foregoing description of the Presentation is qualified in its entirety by reference to the full text of the Presentation, which is attached hereto as Exhibit 99.1 and incorporated by reference herein.
Item 5.	Interest in Securities of the Issuer
(a)	Item 5(a) is hereby amended and restated to read as follows: The aggregate percentage of Shares reported owned by each person named herein is based on 12,469,941 Shares outstanding as of August 18, 2025, which is the total number of Shares outstanding as disclosed in the Issuer's definitive proxy statement on Schedule 14A filed with the Securities and Exchange Commission on August 29, 2025. As of the date hereof, Stoney Lonesome directly beneficially owned 633,271 Shares, constituting approximately 5.1% of the Shares outstanding. CCM, as the general partner of Stoney Lonesome, may be deemed the beneficial owner of the 633,271 Shares directly owned by Stoney Lonesome, constituting approximately 5.1% of the Shares outstanding. As of the date hereof, Drake Helix directly beneficially owned 36,000 Shares, constituting approximately 0.3% of the Shares outstanding. CDC Financial, as the managing member of each of CCM and Drake Helix, may be deemed the beneficial owner of the (i) 633,271 Shares directly owned by Stoney Lonesome and (ii) 36,000 Shares directly owned by Drake Helix, constituting approximately 5.4% of the Shares outstanding. Mr. Coghill, as the President and sole shareholder of CDC Financial, may be deemed the beneficial owner of the (i) 633,271 Shares directly owned by Stoney Lonesome and (ii) 36,000 Shares directly owned by Drake Helix, constituting approximately 5.4% of the Shares outstanding. The filing of this Schedule 13D shall not be deemed an admission that the Reporting Persons are, for purposes of Section 13(d) of the Securities Exchange Act of 1934, as amended, the beneficial owners of any securities of the Issuer that he or it does not directly own. Each Reporting Person disclaims beneficial ownership of the Shares that he or it does not directly own.
(c)	Item 5(c) is hereby amended and restated to read as follows: The transactions in securities of the Issuer by the Reporting Persons since the filing of the Schedule 13D are set forth in Exhibit 2 and are incorporated herein by reference. All of such transactions were effected in the open market unless otherwise noted therein.
Item 7.	Material to be Filed as Exhibits.
	2 - Transactions in Securities. 99.1 - Presentation, dated September 2, 2025.

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

Stoney Lonesome HF LP

Signature:	/s/ Clint D. Coghill
Name/Title:	Clint D. Coghill, President and sole shareholder of the managing member of its general partner
Date:	09/02/2025

COGHILL CAPITAL MANAGEMENT LLC

Signature:	/s/ Clint D. Coghill
Name/Title:	Clint D. Coghill, President and sole shareholder of its managing member
Date:	09/02/2025

Drake Helix Holdings, LLC

Signature:	/s/ Clint D. Coghill
Name/Title:	Clint D. Coghill, President and sole shareholder of its managing member
Date:	09/02/2025

CDC Financial, Inc.

Signature:	/s/ Clint D. Coghill
Name/Title:	Clint D. Coghill, President and sole shareholder
Date:	09/02/2025

COGHILL CLINT D

Signature:	/s/ Clint D. Coghill
Name/Title:	Clint D. Coghill
Date:	09/02/2025

FAQ

What stake do the reporting persons hold in Inspirato (ISPO)?

Stoney Lonesome directly owns 633,271 shares (~5.1%); Drake Helix directly owns 36,000 shares (~0.3%); combined attribution to CDC Financial and Mr. Coghill is 669,271 shares (~5.4%).

How much did Stoney Lonesome and Drake Helix pay for their shares?

The filing discloses aggregate purchase prices of approximately $3,349,904 for Stoney Lonesome's 633,271 shares and $121,947 for Drake Helix's 36,000 shares, including commissions.

What action did the reporting persons take regarding the proposed Inspirato–Buyerlink merger?

They issued a public presentation on September 2, 2025 stating their intention to vote against the proposed merger and outlining reasons for opposition.

What reasons did the reporting persons give for opposing the merger?

They cited anticipated value destruction for minority stockholders, a flawed approval process by the Special Committee and board, a substantial windfall to CEO Payam Zamani, and concerns the transaction creates a conglomerate without synergies.

Are the share purchases open-market or private transactions?

The filing states that the transactions were effected in the open market unless otherwise noted and references Exhibit 2 for transaction details.