The hospitality industry has no shortage of voices — brands, operators, technology vendors, consultants — all with strong opinions about where hotels are headed. But one voice has historically been underrepresented in this conversation: the owner.

Hotel owners — from institutional investors to independent ownership groups — are the ones writing the checks. They absorb the capital risk, negotiate the management agreements, and ultimately decide which bets to make on technology, renovation, brand affiliation, and long-term strategy. And right now, those decisions have never been more consequential.

The macro environment is genuinely complicated: interest rates have remained elevated, labor costs have structurally repriced, and RevPAR growth has moderated after years of post-pandemic tailwinds. At the same time, demand fundamentals remain strong in leisure and group travel, and there’s growing conviction that AI-driven operational efficiency could finally deliver on years of promises about margin improvement.

But owners aren’t just passive observers of the technology revolution; they’re increasingly active participants. Decisions about when and how to invest in AI-powered operations, dynamic pricing tools, and guest experience tech are now part of the core ownership calculus. And that’s changing the relationship between owner, brand, and operator.

The rise of asset-light brand strategies has put brands in the business of selling affiliation rather than managing assets,  which creates an inherent tension with owners who need returns, not just flags. Are the interests of brands and owners still aligned? Or is the franchise model under strain?

This episode puts the ownership perspective front and center, examining what today’s most sophisticated hotel investors are seeing in the market, how they’re thinking about technology as both risk and opportunity, and what they need from brands, operators, and tech providers to succeed.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Deanne Brand  — guest

Alex Cabañas — guest

Go Deeper

• The Squeeze: Inside the Crisis Crushing Americas Hotel Owners - Skift
• Economic Impact of the US Hotel Industry - US Report - AHLA
• My Take on Skift's The Squeeze: Inside the Crisis Crushing America's Hotel Owners - HospitalityNet
• Hotel Owners Demand a Bigger Piece of the Marriott Bonvoy Pie – Wall Street Journal [$]
• Hilton targets owner profitability with lower costs – Hotel Management

Wellness has been one of the fastest-growing categories in travel for the better part of a decade. What started as a forgotten gym, a yoga mat, and a "heart-friendly" room service menu has evolved into a $6.8 trillion global industry — and for a growing share of travelers, wellness isn't an amenity anymore. It's the entire reason for the trip.

This episode traces that arc from spa to ecosystem, unpacking how wellness went from a niche, prescriptive fix-what's-broken offering to a mainstream movement built around optimization, longevity, and the "quantified self", and why so-called secondary wellness travelers (those bolting wellness onto a business trip or vacation) now outspend primary wellness travelers 2x over. 

The conversation also digs into the blurry lines between wellness, well-being, and longevity, the backlash brewing against wearables, and why getting the basics right — sleep, above all — still trips up hotels at every price point.

Lastly, we zoom in on wellness infrastructure: the modern bathhouse boom bringing ancient bathing cultures — Roman thermae, Korean jjimjilbangs, Moroccan hammams — to American cities at a scale of football fields, not individual treatment rooms.

Together, the conversations raise the questions every operator and investor is asking: Is wellness a durable, differentiated business, or an amenities arms race that fades with the next trend? Can it be democratized beyond ultra-luxury resorts, or does authentic programming require capital that only the top of the market can afford? And as biohacking, longevity clinics, and NASA-grade recovery tech go mainstream, how do brands separate real outcomes from expensive wellness theater?

Follows

Gilad Berenstein – host

Cara Whitehill - host

Mia Kyricos — guest

Susie Arnett — guest

Robbie Hammond – guest

Go Deeper

• Bathhouse Is Changing The Face Of Wellness Across America — Forbes [$]
• Ten Big Longevity Trends and Their Hotel Applications for 2026 — Hospitality Net
• Travelers Are Booking Vacations Just to Sleep Better — Inside the Sleep Tourism Boom — Hotel Online
• Wellness Tourism Trends: What's Shaping Travel and Wellness in 2026 — Hospitality Net
• Beacons of Light: Chief Wellness Officers for Cities, Spa Business

Loyalty programs have always been travel’s most powerful retention tool — but the game is changing faster than most brands can keep up with. The credit card co-brand has long been the engine that funds loyalty ecosystems, but a new generation of challengers is rewriting the rules of what loyalty actually means and who gets to play.

Bilt Rewards turned the humble rent payment into a travel currency. Suppliers have continually devalued their own loyalty currencies to the point of irrelevance. Cardless is building co-branded credit products for brands that previously couldn’t afford the table stakes. And the established giants — Chase, Capital One, and AMEX — are in a constant arms race for wallet share, each investing billions to stay relevant to the modern traveler.

But is all this competition actually good for the consumer? Or are we reaching a point of loyalty fatigue, where the proliferation of programs, points currencies, and co-brand offers creates more confusion than value? The redemption landscape has never been more complex, and the value of a point has never been harder to pin down.

Meanwhile, the rise of agentic AI and the personalization it promises could upend loyalty all over again. If an AI agent is managing your travel search and booking, whose loyalty program does it optimize for — yours or the algorithm’s? And if the booking is invisible to the consumer, what happens to the emotional bond that loyalty programs have traditionally built?

At the same time, hotels, airlines, and OTAs are asking harder questions about who actually owns the customer relationship — and whether loyalty points are even the right currency to build it around. Subscription models, membership programs, and lifestyle-first brands are emerging as serious alternatives to the points-and-miles playbook.

With a remarkable range of players — from legacy banks to fintech disruptors to next-gen co-brand platforms — converging on the same consumer, this episode digs into what loyalty really means right now. Are we on the cusp of a loyalty renaissance, or watching a system built for a different era crack under the weight of its own complexity?

Follows

Gilad Berenstein – host

Cara Whitehill - host

Brian Kelly — guest

Aaron Glick — guest

Go Deeper

• Loyalty Programs May Be the One Asset Agents Can’t Take — Hospitality Net
• When Loyalty Points Stop Acting Like Money — The Wise Marketer
• Hilton Honors Points Devaluation Hits Luxury Hotels Hard in 2025 — Aviation A2Z
• What’s Next for Hotel Loyalty in 2025 — Skift Research
• Morgan Stanley Sees Travel Credit Cards Testing Banks’ Edge — TheStreet

For more than two decades, travel’s marketing funnel has been anchored by a familiar set of certainties: Google at the top, OTAs in the middle, and brand.com at the bottom. The entire industry was built around this architecture — SEO strategies, meta-search plays, display retargeting, and paid search campaigns all tuned to move consumers from inspiration to booking.

That architecture is now being dismantled in real time, or is it?

Generative AI search engines, from Perplexity to ChatGPT to Google’s own AI Overviews, are fundamentally changing how travelers discover, research, and evaluate options. When an AI gives you a direct answer, you don’t click. You don’t visit. You don’t convert the way you used to. For brands that have spent years building SEO moats and content strategies optimized for traditional search, this is an existential challenge.

But the story doesn’t end with search. Agentic AI introduces an even more radical disruption: the possibility that travelers won’t be doing the searching at all. If an AI agent is planning and booking on your behalf, what does “top of funnel” even mean? Does marketing need to reach the human — or the model?

Distribution and marketing as we’ve known them are being renegotiated from scratch. That means new questions about where brands spend, how they measure attribution, and whether reach, frequency, and click-through rates are even the right metrics anymore.

The travel brands best positioned for this shift may be the ones willing to throw out the old playbook and start fresh — partnering directly with AI platforms, investing in content that AI can parse and cite, and rethinking the relationship between brand equity and algorithmic visibility. This episode brings together the architects of the new distribution infrastructure and the marketers navigating the transition in real time. 

Follows

Gilad Berenstein – host

Cara Whitehill - host

Brennen Bliss  — guest

Rob Torres — guest

Go Deeper

• The High Cost of Infinite Search: How AI Agents Break Travel Economics - Skift
• The future of travel distribution - Amadeus
• Mastering generative engine optimization in 2026: Full guide - Search Engine Land
• What Is Generative Engine Optimization (GEO): A Complete 2026 Guide - SimilarWeb
• Agentic commerce in travel: Who wins, who loses and what to do about it - PhocusWire

If you want to understand where travel tech is going, follow the money. And right now, the money is doing some very interesting things.

Venture capital investment in travel has been in a complicated place since the post-COVID boom ran out of steam. Rising interest rates reshaped return expectations, a string of high-profile late-stage corrections reset valuations, and many LPs grew cautious about the capital intensity of marketplace and infrastructure businesses. But underneath that macro turbulence, the investment thesis for travel tech is quietly getting more compelling — not less.

AI has changed the calculus dramatically. The marginal cost of building software is collapsing. Founders are doing more with less. And the potential to layer intelligence on top of what has historically been a fragmented, data-rich but technology-poor industry is generating genuine excitement among investors who understand the space.

At the same time, the exit landscape remains constrained. IPO markets have shown selective green shoots, M&A activity is picking up, but vintage 2020–2022 funds are sitting on portfolios that still need resolution. That creates pressure — and in some cases, creative dealmaking.

Corporate venture is also playing a bigger role. These firms are investing not just for financial return but to understand and shape the technology ecosystem around their core business. That creates a different kind of capital, with different motivations and a different relationship to founders.

This episode takes the temperature of travel tech investment with three investors who see the landscape from very different vantage points — and asks what the next vintage of travel tech winners might actually look like.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Laly Vandenberghe — guest

Kevin Tsang – guest 

Shiro Matsuzaki — guest

Go Deeper

• How Much is Travel Actually Changing? - TNMT
• Travel funding deal volume hits new low in Q1 2026 - PhocusWire
• How CEOs are turning corporate venture building into outsize growth - McKinsey
• Corporate Venture Building 2025 - Global Corporate Venturing Institute
• The way to win in corporate venturing: Serial building and AI - McKinsey

Sustainability in travel hasn’t disappeared,  it’s just gone quiet.

After a decade of bold net-zero commitments, ESG branding, and high-profile climate pledges, the conversation in the U.S. has cooled. Political pressure and cultural backlash have pushed sustainability out of the spotlight, leaving many to assume momentum has stalled.

But beneath the surface, the opposite may be true.

Major airlines are still investing in SAF. Hotels continue to fund energy efficiency and retrofit programs. Corporate travel buyers are increasingly factoring emissions into procurement decisions. And even in unlikely places, like Texas, the energy mix is shifting faster than headlines suggest.

In other words: the labeling may have gone underground, but the capital hasn’t.

 At the same time, hard questions remain. Travelers say they care about sustainability, but rarely act on it. Decarbonization costs are real, timelines are long, and the ROI is anything but clear.

So where does that leave the industry?

In this episode, we unpack whether sustainability in travel is truly durable — not just politically, but economically — and what it will take to move from quiet progress to meaningful impact.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Matt Ridley  — guest

Anna Feinberg — guest

Javier Arredondo – guest

Go Deeper

• ESG INTELLIGENCE & ANALYTICS - ESGAUGE
• Amadeus Travel Dreams 2026 - Amadeus Insights
• Booking.com 2025 Sustainability Report - Booking.com
• Aviation’s Decarbonization Bet Is Looking Shakier Than Ever - Skift [$]
• GBTA Sustainability Acceleration Challenge - Global Business Travel Association

Destination management organizations occupy a strange place in the travel ecosystem. They exist to promote places — countries, cities, regions — to travelers around the world. But they rarely control the product, they almost never touch the transaction, and their ROI has always been notoriously difficult to measure. Which raises a question that’s hard to avoid right now: do DMOs still matter?

The short answer is yes, but not in the way they used to.

The traditional DMO playbook — trade show presence, destination campaigns, visitor guides, and PR pushes — is being upended by a combination of forces: AI-generated travel content, the rise of social media as a discovery channel, and a traveler who is increasingly self-sufficient and algorithmically guided. The role of the DMO as information gatekeeper is effectively over. The new role is something harder to define, and far more interesting.

At the same time, destinations are under new pressures. Over-tourism, climate-related disruptions, and the political volatility of international travel — particularly for inbound US travel in today’s geopolitical moment — are forcing DMOs to think not just about driving more visitors, but about attracting the right visitors. That’s a fundamentally different mission, requiring a fundamentally different skill set.

This episode examines how DMOs are reinventing themselves for an AI-native, socially connected, and politically complex travel landscape, and what destination marketing done right can look like when it creates durable economic value for the places and communities it serves.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Janette Roush  — guest

Meaghan Ferrigno — guest

Go Deeper

• Destinations’ high-stakes game with AI - Travel Weekly
• Small businesses say they’re having a good summer as Americans travel closer to home - AP News
• Winning the Algorithm: Why Destination Marketing Must Evolve in the AI Era - Sojern
• The Five Foundations of a DMO: New Measures for a New Paradigm - Zartico
• Building a Personal OS in Claude - Janette Roush

Travel is one of the largest industries in the world, yet its economic significance is chronically underappreciated — by consumers, by policymakers, and even by the markets that price it.

In the United States alone, domestic travel accounts for the vast majority of the industry’s GDP contribution — yet public discourse and government measurement almost exclusively focus on inbound international tourism.

Meanwhile, the World Travel & Tourism Council estimates that travel and tourism represents over 10% of global GDP and supports more than 330 million jobs worldwide, a figure that rivals the economic footprint of manufacturing or financial services in many countries.

But the industry is under siege from multiple directions simultaneously. Geopolitical instability, pandemic-era demand shocks (COVID-19, SARS, Zika), and escalating immigration enforcement are creating headwinds for both inbound and outbound travel. Labor shortages remain a structural challenge across hospitality, aviation, and ground transportation — with wage inflation, workforce attrition, and immigration policy all converging to constrain capacity. At the same time, climate change is rewriting the risk calculus for the entire sector: hurricanes, wildfires, and floods are disrupting operations, stranding real estate assets, and inflating insurance costs from Miami to Maui.

This episode brings together three of the most credible voices in travel economics to examine what the data actually shows about travel’s role in the broader economy, the compounding threats reshaping the industry, and what a more durable framework for measuring and defending travel’s economic contribution might look like.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Alex Dichter — guest

Ryan Propis — guest

Adam Sacks – guest

Go Deeper

• Beyond Hormuz: How a World on Edge Is Reshaping Every Corner of Tech - North Ridge Partners
• Iran conflict – The impact on tourism and GCC macroeconomic outlook - Oxford Economics
• The Case for Smarter Global Advocacy For Travel — Not More Cheerleading - Skift [$]
• Reimagining the $9 Trillion Tourism Economy — What Will It Take? - McKinsey & Company
• The Future of Work in Travel & Tourism: The key trends shaping workforce strategies - World Travel and Tourism Council
• How climate risks are impacting real estate insurance costs - JLL

Private equity is playing an increasingly visible — and influential — role across travel and hospitality. From platform rollups and carve-outs to growth equity investments in scaled travel tech, PE capital is reshaping who owns what, how companies grow, and what “success” looks like beyond venture-backed exits.

This episode unpacks how private equity really works, how it differs from late-stage venture capital, and why travel and hospitality have become such compelling hunting grounds for PE firms right now. We start with the fundamentals: what private equity is, how funds are structured, who the LPs are, and how different types of PE strategies — from growth equity to buyout funds — show up in travel. From there, we dig into what makes a strong PE investment target, including the metrics, moats, and operational characteristics that matter most at this stage of a company’s life.

The conversation then turns to M&A strategy, including how PE firms evaluate acquisition opportunities, when rollups make sense versus single-asset plays, and what founders should (and shouldn’t) do to prepare for future M&A conversations. We also demystify the PE process itself — how firms engage with founders, what diligence looks like, and what realistic timelines founders should expect.

Whether you’re a founder, operator, or investor, this episode offers a clear, candid look at how private equity is shaping the future of travel.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Evelyn Duan — guest

Vinay Shah — guest

Go Deeper

• Travel industry trends and the opportunity for private equity - McKinsey & Company
• M&A trends in travel, leisure and hospitality - KPMG
• Economic uncertainty ‘reshaping deal-making’ as travel and tourism M&A slows — HotelDive
• The coming wave: Consolidation in tours and experiences — PhocusWire
• M&A Activity Continues to Escalate in the Global Hotel Operator Sector - Goodwin

As we close out Season 3 of Travel Tech Insider, we’re stepping back to reflect on the conversations, debates, and signals that defined the past year—and to look ahead at what 2026 may have in store for travel, hospitality, and the technology shaping it all.

We kick things off at the macro level, asking our guests to share one or two defining lessons from 2025. Those insights span far beyond any single theme—touching on investing, AI, business building, travel behavior, and even how leaders are adapting personally in a rapidly changing world. We’ll also hear from our investors on one standout investment from 2025 that they’re particularly excited about, alongside a look back at which major industry trends truly hit the mark this year.

From there, we revisit the core topics that shaped Season 3, offering fresh perspective, candid reflections, and a few hot takes along the way. We unpack what’s really happening in the vacation rental market, the growing influence of social commerce, and the continued evolution of AI from experimentation to infrastructure. We explore the expanding role of FinTech and stablecoins in enabling frictionless, agent-driven commerce, examine cruising as a microcosm of innovation in travel, and reflect on why corporate travel remains in flux amid shifting work patterns and economic pressures. We also touch on the state of private equity and rollups in travel, and what consolidation signals about the maturity of the sector.

We close the season by turning our gaze forward, asking each guest to share their predictions, priorities, and areas of focus for 2026. From emerging business models to changing power dynamics and new opportunities on the horizon, this season finale ties together the threads of Season 3 while setting the stage for what comes next.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Max Niederhofer — guest

Besty Mulé — guest

Sarah Kopit — guest

Go Deeper

• How AI Bookings Will Rewrite the Travel Company Playbook - Bain & Company
• Skift Megatrends 2026 - Skift
• Hot Travel Startups 2026 - PhocusWire
• Clear Skies for Corporate Travel in 2026 - Morgan Stanley
• 2026: Going Public. Going Global. Going Big. - Arival Travel