Inspirato A : Q1 ’24 Earnings Presentation

COMPANY UPDATE

May 2024

N A U P A K A

K O H A L A C O A S T , H A W A I I

Disclaimer

Forward-Looking Statements

This presentation contains forward-looking statements within the meaning of Section 27A of the Securities Act of 1933, as amended (the "Securities Act") and Section 21E of the Securities Exchange Act of 1934, as amended (the "Exchange Act"), which statements involve substantial risks and uncertainties. Our forward-looking statements include, but are not limited to, statements regarding our and our management team's hopes, beliefs, intentions or strategies regarding the future or our future events or our future financial or operating performance. The words "anticipate," "believe," "continue," "could," "estimate," "expect," "intends," "may," "might," "plan," "possible," "potential," "predict," "project," "should," "will," "would" and similar expressions may identify forward-looking statements, but the absence of these words does not mean that a statement is not forward-looking.Forward-looking statements may include, for example, statements about: our partnership with Capital One Services, LLC ("Capital One"); our ability to service our outstanding indebtedness and satisfy related covenants; the impact of changes to our executive management team; our ability to comply with the continued listing standards of Nasdaq or the continued listing of our securities on Nasdaq; changes in our strategy, future operations, financial position, estimated revenue and losses, projected costs, prospects and plans; the implementation, market acceptance and success of our business model, growth strategy and new products; our expectations and forecasts with respect to the size and growth of the travel and hospitality industry; the ability of our services to meet members' needs; our ability to compete with others in the luxury travel and hospitality industry; our ability to attract and retain qualified employees and management; our ability to adapt to changes in consumer preferences, perception and spending habits and develop and expand our destination or other product offerings and gain market acceptance of our services, including in new geographic areas; our ability to develop and maintain our brand and reputation; developments and projections relating to our competitors and industry; the impact of natural disasters, acts of war, terrorism, widespread global pandemics or illness, including the COVID-19 pandemic, on our business and the actions we may take in response thereto; expectations regarding the time during which we will be an emerging growth company under the Jumpstart Our Business Startups Act of 2012 (the "JOBS Act"); our future capital requirements and sources and uses of cash; the impact of our reduction in workforce on our expenses; the impact of market conditions on our financial condition and operations, including fluctuations in interest rates and inflation; our ability to obtain funding for our operations and future growth; our ability to generate positive cash flow from operations, achieve profitability, and obtain additional financing or access the capital markets to manage our liquidity; the impact on our liquidity as a result of the obligations in our contractual agreements, including the covenants therein; our business, expansion plans and opportunities and other strategic alternatives that we may consider, including, but not limited to, mergers, acquisitions, investments, divestitures, and joint ventures; and other factors detailed under the section Risk Factors in Part I, Item 1A of our most recent Annual Report on Form 10-K that was filed with the Securities and Exchange Commission ("SEC,"), those discussed in Management's Discussion and Analysis of Financial Condition and Results of Operations in Part I, Item 2 of our Form 10-Q filed with the SEC on or about May 8, 2024, and those discussed in other documents we file with the SEC.

We caution you that the foregoing list does not contain all of the forward-looking statements made in this Presentation. Although we believe that the expectations reflected in any forward-looking statements are reasonable, we cannot guarantee future results, events, levels of activity, performance or achievements. Should one or more of the risks or uncertainties described herein or in any other documents we file with the SEC occur, or should underlying assumptions prove incorrect, our actual results and plans could differ materially from those expressed in any forward-looking statements.

Investors should consider the risks and uncertainties described herein and should not place undue reliance on any forward-looking statements. We do not undertake, and specifically disclaim, any obligation to publicly release the results of any revisions that may be made to any forward-looking statements, whether as a result of new information, future events or otherwise, except as required by law.

In addition, statements that "we believe" and similar statements reflect our beliefs and opinions on the relevant subject. These statements are based upon information available to us as of the date of this presentation and while we believe such information forms a reasonable basis for such statements, such information may be limited or incomplete, and such statements should not be read to indicate that we have conducted an exhaustive inquiry into, or review of, all potentially available relevant information. These statements are inherently uncertain, and investors are cautioned not to unduly rely upon these statements.

Use of Data

This presentation contains statistical data, estimates and forecasts that are based on independent industry publications or other publicly available information, as well as other information based on our internal sources. This information involves a number of assumptions and limitations, you are cautioned not to give undue weight to these estimates. We have not independently verified the accuracy or completeness of the data contained in these industry publications and other publicly available information. Accordingly, no representation is made as to the reasonableness of the assumptions made within or the accuracy or completeness of any projections or modeling or any other information contained herein. Any data on past performance or modeling contained herein is not an indication as to future performance. We assume no obligation to update the information in this presentation. Further, the Inspirato financial data, 2012 through 2017, included in this presentation were audited in accordance with private company AICPA standards.

May 2024

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Disclaimer

Trademarks

Inspirato owns or has rights to various trademarks, service marks and trade names that it uses in connection with the operation of its business. This presentation may also contain trademarks, service marks, trade names and copyrights of third parties, which are the property of their respective owners. The use or display of third parties' trademarks, service marks, trade names or products in this presentation is not intended to, and does not imply, a relationship with Inspirato, or an endorsement or sponsorship by or of Inspirato. Solely for convenience, the trademarks, service marks, trade names and copyrights referred to in this presentation may appear without the TM, SM, ® or © symbols, but such references are not intended to indicate, in any way, that Inspirato will not assert, to the fullest extent under applicable law, their rights or the right of the applicable licensor to these trademarks, service marks, trade names and copyrights.

Key Performance Metrics and Use of Non-GAAP Financial Measures

This presentation includes certain non-GAAP financial measures (including on a forward-looking basis) such as Adjusted Net Loss, Adjusted EBITDA and Adjusted EBITDA Margin. These non-GAAP measures are presented for supplemental informational purposes only, and not a substitute for measures of financial performance prepared in accordance with GAAP. These non-GAAP measures have limitations as analytical tools, and they should not be considered in isolation or as a substitute for analysis of other GAAP financial measures. Reconciliations of non-GAAP measures to their most directly comparable GAAP counterparts are included in this presentation. In addition, other companies may calculate non-GAAP measures differently, or may use other measures to calculate their financial performance, and therefore, Inspirato's non-GAAP measures may not be directly comparable to similarly titled measures of other companies. Additionally, to the extent that forward-lookingnon-GAAP financial measures are provided, they are presented on a non-GAAP basis without reconciliations of such forward-lookingnon-GAAP measures due to the inherent difficulty in forecasting and quantifying certain amounts that are necessary for such reconciliations.

This presentation includes certain key performance metrics, such as Active Subscriptions, Average Daily Rates (ADRs) and Total Nights Delivered. Inspirato's management uses these key performance metrics to evaluate our business, measure our performance, identify trends affecting our business, formulate business plans and make strategic decisions. Our key performance metrics may differ from estimates published by third parties or from similarly titled metrics of other companies due to differences in methodology.

May 2024

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Company Overview

F L O R A

G R A N D C A Y M A N , C A Y M A N I S L A N D S

May 2024

We inspire lasting memories and relationships by enriching the way our members experience the world

Key Statistics

$275 - $305mm	($15) - $5mm	~13,000
2024e Total Revenue	2024e Adj. EBITDA Loss	Active Subscriptions
		(as of 3/31/24)

~510	~41,300	$1,965
Controlled Accommodations	Total Nights Delivered	Paid Residence ADR
(as of 3/31/24)	(Q1 '24)	(Q1 '24)

J U N I P E R

V A I L , C O L O R A D O

Track Record of Innovation

Launches Inspirato For Good ("IFG") &	New Products With Signs of Momentum
Inspirato For Business ("IFB")
Since Launch in Sept. 2022

Launches Inspirato Pass

• Reaches $100mm of revenue
• Surpasses 10K subscribers

• Announces business combination with Thayer Ventures Acquisition Corp. which will result in Inspirato becoming a publicly listed company

• Formed strategic partnership with Capital One Ventures, including $25 million investment into Inspirato

2014

2015

2017

2019

2020

2021

2022

20232024

• Reaches $50mm of revenue

Launches partnership

with Wheels Up

• Reaches $200mmof revenue
• Achieves break-even Adj. EBITDA

• Resilient business model and	•	Began trading on the Nasdaq
flexible lease portfolio allow		(NASDAQ: ISPO)
for positive EBITDA	•	5 consecutive years of 70+NPS1

• Launched Inspirato Pass improvements aimed at increasing flexibility and functionality for members

May 2024	1. Represents NPS for Residences

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The Inspirato Platform

M U L T I P L E O F F E R I N G S :

F O R E X C L U S I V E A C C E S S T O :

W I T H E N D - T O - E N D S E R V I C E :

Inspiration

~430	240+
Residences1	Hotel & Resort
	Partners1

Personal

Advisor

Experiences

Partners & Events

Experience

Booking

S U P E R I O R T O T R A D I T I O N A L H O S P I TA L I T Y

Stable Base of Subscription Revenue

Luxury Portfolio Suitable for Strategic Partnerships

Beneficial to Travelers and Hospitality Partners

May 2024	(1) As of 3/31/24. Hotels include leased room within our managed and controlled portfolio and net rate options with our hotel partners.

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Core Offerings

Inspirato Club members have access to the full Inspirato Collection of exclusive homes,

hotels, resorts, and experiences by paying members-only nightly rates when they travel. They also receive first-class, personalized service from a team of hospitality experts-frompre-trip planning to an on-site concierge.

• Pay members-only nightly rates as they travel
• Have the ability choose specific destinations, accommodations, and dates from the full Inspirato Collection of homes, hotels, and experiences
• Access to incredible value with Jaunt, featuring weekly discounts

Inspirato Pass members can choose from a list of ~1 million trips in 400+ properties with check-in dates from two to 365 dates away. Includes all the benefits of the Inspirato Club, plus the flexibility to choose how many Pass Trips to take each year through annual dues that includes nightly rates, taxes, and fees.

• Inspirato Pass members enjoy all the benefits of the Inspirato Club, plus the flexibility to choose how many Pass Trips to enjoy each year
• Access to incredible value with Jaunt, featuring weekly discounts
• Ability to book with Flex Days, a premier tool to book last minute high -value trips to tens of thousands of locations

Annual dues: $7,800 per year		Annual dues: $30,600 per year
~10,400 members1		~1,900 members1
~10,900 Club Subscriptions		~2,100 Pass Subscriptions

May 2024

(1) As of 3/31/24. Inspirato members can have more than one Active Subscription, resulting in ~13,000 Active Subscriptions as of 3/31/24.

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Redefining Customer Acquisition Cost

Revenue Generating

Reduced Sales + Marketing Expense

Highly-Qualified,Pre-Screened Prospects

• Philanthropic partnerships aimed at accelerating charitable fundraising and increasing brand awareness among qualified prospects
• Membership package bundled with vacations to Inspirato's luxury residences and hotel suites
  - ~3,500 packages sold since inception in late 2022
• ~$2.8 million of total revenue in Q1 '24

• B2B platform geared toward incentive programs, retention initiatives and corporate benefit packages
• Custom-made,flat-rate travel packages inclusive of pre-determined number of trips and Inspirato Club access
• ~$2.5 million of total revenue in Q1 '24

May 2024	Note: Inspirato for Good and Inspirato for Business sales will be recognized as subscription revenue over the life of the contract and travel revenue at the time of travel.

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Exclusive Portfolio of Unique Luxury Residences

May 2024

*Figures represent residences available to book within the Company's Controlled Accommodations as of 3/31/24 and does not include signed, but not yet released Controlled Accommodations.

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