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November 2025 INSPIRATO Nasdaq: ISPO
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2 INSPIRATO Nasdaq: ISPO 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. This presentation does not contain material non-public information and is intended to comply with Regulation FD. 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,” “repositioned”, “strategy”, “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 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 membership 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, 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-Qs filed with the SEC on or about November 5, 2025, and those discussed in other documents we file with the SEC. This list does not include all forward-looking statements in this presentation. While we believe the expectations in these statements are reasonable, we cannot guarantee future outcomes. If any risks or uncertainties described herein or in any other documents we file with the SEC occur, or if assumptions prove incorrect, our actual results could differ materially from those the forward-looking statements. Investors should consider the risks described here and not rely too heavily on forward-looking statements. We disclaim any obligation to publicly update these statements due to new information, future events, or otherwise, unless required by law. Forward looking statements should be interpreted in conjunction with our most recent public filings with the SEC, including detailed risk disclosures. Statements like "we believe" reflect our opinions based on available information as of this presentation. While we believe the information is reasonable, it may be limited or incomplete. These statements are uncertain, and investors should not place undue reliance on them. Use of Data This presentation includes data, estimates, and forecasts from independent industry sources and our internal information. These figures involve assumptions and limitations, so please don't place undue weight on them. We have not independently verified the data's accuracy or completeness, and make no guarantees about the reasonableness of assumptions, projections, or modeling. Past performance is not indicative of future results, and we assume no obligation to update this presentation. Inspirato's financial data from 2012-2017 was audited under private company AICPA standards. Trademarks Inspirato owns various trademarks, service marks and trade names related to its business operations. This presentation may also contain third-party trademarks and copyrights, which belong to their respective owners. The use of third-party marks does not imply any relationship or endorsement by Inspirato. For convenience, some trademarks may appear without the TM, SM, ® or © symbols, but such references shall not indicate, in any way, that Inspirato will not assert all their rights to these trademarks and copyrights. Key Performance Metrics and Use of Non-GAAP Financial Measures This presentation includes certain non-GAAP financial measures such as free cash flow, Net Promoter Score, Average Daily Rate, Adjusted Gross Margin, Profitability, Annualized Cost Savings, Adjusted EBITDA and Adjusted EBITDA Margin. These 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 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. Forward-looking non-GAAP measures are presented without reconciliations due to the difficulty in forecasting certain amounts necessary for these 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.
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3 INSPIRATO Nasdaq: ISPO Company Overview Inspirato (Nasdaq: ISPO) is a luxury vacation club and property technology company offering curated access to exclusive vacation homes, five-star hotel partners, and custom travel experiences through a model designed to deliver exceptional service, certainty, and value. Beaver Creek, Colorado Los Cabos, Mexico Florence, Italy Maldives St. Croix, U.S. Virgin Islands
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4 INSPIRATO Nasdaq: ISPO Inspirato by the Numbers MEMBERS 1 10,700+ VACATION HOMES 1,2 320 HOTEL & RESORT PARTNERS 1 220 NET PROMOTER SCORE 3 70+ AVERAGE DAILY RATE 4 $1,800+ DESTINATIONS 1 160 1. As of 9/30/2025. Subject to change. 2. Includes all Controlled Accommodations as of 09/30/25 3. As of 12/31/2024. Subject to change. 4. Inspirato defines ADR as the total paid travel revenue, divided by total paid nights, which includes Inspirato for Good (“IFG”) and Inspirato for Business (“IFB”), in both leased residences or hotel rooms and suites. ADR does not include Pass nights utilized. Occupancy is defined as all paid, Pass, IFG, IFB, employee and complimentary nights in all at-risk properties divided by the total number of at-risk nights available. Net-rate hotel partners are excluded from Hotel Occupancy as these are dependent on the hotel having capacity for Inspirato requests. 5. Adjusted Net Loss, Adjusted EBITDA, and Free Cash Flow are non-GAAP financial measures. See slide 19 for reconciliations. 2025E Revenue Guidance $235M-$240M 2025E EBITDA 5 Guidance $2M-$4M Nantucket, Massachusetts
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5 INSPIRATO Nasdaq: ISPO PRICING 1 ENROLLMENT FEE: $195,000 ANNUAL DUES : N/A Variable Nightly Rates, Taxes, & Fees <5% of Membership Base PRICING 1 ENROLLMENT FEE: $15,000 ANNUAL DUES : ~$6,000 Variable Nightly Rates, Taxes, & Fees 80%-85% of Membership Base The Inspirato Membership Suite Access to Inspirato’s full suite of luxury offerings Luxury travel club with fixed pricing Valuable member benefits and members only events and experiences Access to Inspirato’s full suite of luxury offerings Exceptional travel with date and destination certainty at variable rates Five-star service, at exclusive, member’s only rates Flexible travel at significant value through predefined trips Access to Club Discounted luxury hotels PRICING 1 ENROLLMENT FEE: None ANNUAL DUES : ~$40,000 No Nightly Rates, Taxes, & Fees 10%-15% of Membership Base 1: Current list price as of September 2025, subject to change
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6 INSPIRATO Nasdaq: ISPO WHY BUY ONE VACATION HOME… WHEN YOU CAN HAVE 320+ HOMES AT INSPIRATO APPROXIMATE SPEND OVER 5 YEARS ~$2.5M – $3.5M ~$240k – $265k Note: $2M - $3.5M vacation home ownership spend after 5 years assumes a $5M home value (approximate Inspirato home value in a portfolio), 30% down payment, and $300k total annual dues inclusive of principal and interest, maintenance, insurance, HOA, property taxes, gas, utilities, and other household costs. $240k -$265k Inspirato spend after 5 years assumes annual dues of $6,000; a $9,000 initiation fee, and annual travel spend of $40k - $45k. Vacation Home Ownership Excluding any additional costs for traveling outside of vacation home
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7 INSPIRATO Nasdaq: ISPO The Inspirato Difference CERTAINTY FOR EVERY VACATION Experience what it's like to have all the details handled for you, no matter where or how you travel with us, you can be certain to have the same level of quality and care WORLD - CLASS SERVICE Inspirato members receive the highest level of personalized attention from a dedicated team that gets to know you and your family's travel preferences METICULOUSLY CURATED LUXURY HOMES Our homes are carefully curated and expertly managed for the most discerning of travelers, ensuring a consistently exceptional experience across the portfolio Punta de Mita, Mexico
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8 INSPIRATO Nasdaq: ISPO Bespoke Travel Performance Turn almost any trip you imagine, anywhere in the world, into an Inspirato custom vacation Personalization at Scale YTD REVENUE $12.5M REVENUE / TRIP ~$60k YTD TRIPS DELIVERED 210 YTD REVENUE $13.3M REVENUE / PROGRAM ~$532k YTD EXPERIENCES 25 Inspirato Only Experiences Performance One-of-a-kind boutique experiences—from safaris to sporting events—with exclusive itineraries and behind-the-scenes access Note: YTD through 09/30/25
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9 INSPIRATO Nasdaq: ISPO Inspirato will power the future of the luxury travel market Category Whitespace Established Brand Poised for Growth Strong Foundation
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10 INSPIRATO Nasdaq: ISPO Path to Growth Deepening member engagement to drive loyalty, retention, and increase paid nights Building a scalable, tech-enabled platform to drive efficient, digital- driven growth From a Neighborhood Country Club to a Global Luxury Platform Shaping the next generation of luxury travel with a distinctive, technology-first brand Inspirato Pass, a high-end travel subscription redefined for the increasingly flexible lifestyles of modern travelers
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11 INSPIRATO Nasdaq: ISPO • Integrating prop-tech and digital marketing to enhance demand generation • Modernizing how luxury travel is discovered, booked, and optimized • Building a flexible, data-powered model to meet the needs of today’s traveler The Modern Luxury Travel Platform Evolving into a technology-enabled, scalable platform • Streamlining cost structures and reducing fixed commitments • Expanding margins through disciplined, data-driven execution • Sustained focus on profitability and positive free cash flow 1 Operational Excellence Intense focus on efficiency, profitability, and scalability Driving Transformation of the Core Business 1. Adjusted Net Loss, Adjusted EBITDA, and Free Cash Flow are non-GAAP financial measures. See slide 19 for reconciliations. St. Kitts, West Indies Sun Valley, Idaho
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12 INSPIRATO Nasdaq: ISPO SCALING PREDICTABLE, RECURRING REVENUE Provides effortless all-inclusive access to luxury homes, resorts, and villas worldwide The new Inspirato Pass launches January 1, 2026, with refreshed inventory, no nightly rates or fees, and one simple annual membership Just 2.5 months into early rollout, demand has already surpassed the previous 12 months of sales
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13 INSPIRATO Nasdaq: ISPO Inspirato Financial Summary
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14 INSPIRATO Nasdaq: ISPO Inspirato 2025 Updated GuidanceA Transformative Year Stabilized Revenue Operational Discipline Profitable $235M - $240M TOTAL REVENUE $2M - $4M ADJUSTED EBITDA 1 1. Adjusted Net Loss, Adjusted EBITDA, and Free Cash Flow are non-GAAP financial measures. See slide 19 for reconciliations.
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15 INSPIRATO Nasdaq: ISPO YTD Financial Improvement Cash Operating Expenses as % of Revenue 38% 33% YTD'24 YTD'25 Free Cash Flow2 ($28M) ($10M) YTD'24 YTD'25 Gross Margin %1 31% 33% YTD'24 YTD'25 EBITDA2 ($8) $5 YTD'24 YTD'25 1. Gross Margin is Revenue Less Cost of Revenue; Gross Margin percentage is Gross Margin divided by Revenue; 2024 Excludes Gain o Lease Termination 2. Adjusted Net Loss, Adjusted EBITDA, and Free Cash Flow are non-GAAP financial measures. See slide 19 for reconciliations. Gross margin reflects a $2.0M FX translation headwind in 2025, compared with a $0.4M tailwind in 2024, with FX effects masking a solid underlying year-over-year expansion $13M of EBITDA improvement YoY driven by continued discipline in reducing fixed costs without compromising the guest experience Excluding lease termination payments in Q1’25 of $2.6M and $1.6M of transaction related costs, free cash flow is ($6.1M), significant YoY improvement of +78%
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16 INSPIRATO Nasdaq: ISPO Consolidated Statement of Operations 1. Gross Margin is defined as Total Revenue Less Cost of Revenue; and gross margin is defined as gross margin as a percent of Total Revenue 2. Adjusted Net Loss, and Adjusted EBITDA are non-GAAP financial measures. See slide 19 for reconciliations. 3. Adjusted EBITDA Margin defined as Adjusted EBITDA as a percent of Total Revenue ($ in thousands) Q3 ’25 Q3 ’24 YTD'25 YTD'24 Total Revenue $55,541 $69,114 $184,538 $216,741 Cost of Revenue 38,120 49,620 124,200 149,345 Gain on lease termination 0 (29,895) 0 (29,895) Gross Margin1 $17,421 $49,389 $60,338 $97,291 Gross Margin (%) 1 31.4% 71.5% 32.7% 44.9% General & Administrative 9,658 19,795 31,396 48,438 % of Revenue 17% 29% 17% 22% Sales & Marketing 5,706 7,209 16,038 24,707 % of Revenue 10% 10% 9% 11% Operations 3,820 5,269 13,232 17,058 % of Revenue 7% 8% 7% 8% Technology & Development 929 1,728 3,133 6,044 % of Revenue 2% 3% 2% 3% Total Operating Expense 20,113 34,001 63,799 96,247 % of Revenue 36.2% 49.2% 34.6% 44.4% Depreciation and amortization 948 1,010 2,967 3,024 Interest expense, net 513 454 1,467 1,150 Loss (gain) on fair value instruments 281 158 55 (3,675) Restructuring charges 0 6,985 0 6,985 Other expense (income), net 2 8 53 (269) Net income (loss) and comprehensive income (loss) ($4,436) $6,773 ($8,003) ($6,171) Adjusted EBITDA2 ($88) ($3,354) $4,800 ($8,347) Adjusted EBITDA Marg in 3 (0.2%) (4.9%) 2.6% (3.9%)
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17 INSPIRATO Nasdaq: ISPO Appendix
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18 INSPIRATO Nasdaq: ISPO Non-GAAP Reconciliation 1. Depreciation and amortization is included within cost of revenue, general and administrative and depreciation and amortization within the Condensed Consolidated Statements of Operations and Comprehensive (Loss) Income 2. Included in general and administrative on the Condensed Consolidated Statements of Operations and Comprehensive (Loss) Income 3. Adjusted Net Loss, Adjusted EBITDA, and Free Cash Flow are non-GAAP financial measures. See slide 19 for reconciliations. Free Cash Flow ($ in thousands) Q3 ’25 Q3 ’24 YTD ’25 YTD ’24 Net cash used in operating activities ($2,205) ($13,744) ($7,750) ($22,713) Development of internal-use software (777) (1,135) (2,272) (4,305) Purchase of property and equipment 0 (172) (254) (528) Free Cash Flow3 ($2,982) ($15,051) ($10,276) ($27,546) Adjusted EBITDA ($ in thousands) Q3 ’25 Q3 ’24 YTD ’25 YTD ’24 Net income (loss) and comprehensive income (loss) ($4,521) $6,622 ($8,212) ($6,522) Interest, net 513 454 1,467 1,150 Income tax expense 85 151 209 351 Depreciation & amortization¹ 2,498 3,064 7,665 8,512 Equity-based compensation 240 7,279 2,029 12,829 Loss (gain) loss on fair value instruments 281 158 55 (3,675) Gain on lease termination 0 (29,895) 0 (29,895) Restructuring charges² 0 6,985 0 6,985 Other non-recurring professional fees 0 1,828 0 1,828 Transaction costs 816 0 1,587 0 Adjusted EBITDA³ ($88) ($3,354) $4,800 ($8,437)
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19 INSPIRATO Nasdaq: ISPO Key Definitions Adjusted EBITDA. Adjusted EBITDA is a non-GAAP financial measure that Inspirato defines as net income (loss) and comprehensive income (loss) less interest, income taxes, depreciation and amortization, equity-based compensation expense, and fair value gains and losses on financial instruments, asset impairments and (gain) on lease termination, restructuring charges and other non- recurring professional fees. Adjusted EBITDA Margin is defined as Adjusted EBITDA as a percentage of total revenue for the same period.The above items are excluded from Inspirato’s Adjusted EBITDA measure because management believes that these costs and expenses are not indicative of core operating performance and do not reflect the underlying economics of Inspirato’s business. Free Cash Flow. Inspirato defines Free Cash Flow as net cash provided by (used in) operating activities less purchases of property and equipment and development of internal-use software. Inspirato believes that Free Cash Flow is a meaningful indicator of liquidity that provides information to management and investors about the amount of cash generated from operations, after purchases of property and equipment and development of internal-use software, that can be used for strategic initiatives, if any. Free Cash Flow. Inspirato defines free cash flow as net cash provided by (used in) operating activities excluding a nonrecurring lease termination fee, less purchases of property and equipment and development of internal-use software. Inspirato believes that Free Cash Flow is a meaningful indicator of liquidity that provides information to management and investors about the amount of cash generated from operations, after purchases of property and equipment and development of internal-use software, that can be used for strategic initiatives, if any. Key Business and Other Operating Metrics We use a number of operating and financial metrics, including the following key business metrics, to evaluate our business, measure our performance, identify trends affecting our business, formulate financial projections and business plans, and make strategic decisions. We regularly review and may adjust our processes for calculating our internal metrics to improve their accuracy. Average Daily Rates (“ADR”) and Total Occupancy. Inspirato defines ADR as the total paid travel revenue, divided by total paid nights in leased residences or hotel rooms and suites. ADR does not include Pass nights utilized. Occupancy is defined as all paid, Pass, Inspirato for Good (“IFG”), Inspirato for Business (“IFB”), employee and complimentary nights in all at-risk properties divided by the total number of at-risk nights available. Net-rate hotel partners are excluded from Hotel Occupancy as these are dependent on the hotel having capacity for Inspirato requests. Controlled Accommodations.Controlled Accommodations includes leased residences, hotel penthouses, suites and rooms, and residences under net rate agreements, including those that have executed agreements but have not yet been released for booking by our members.