Travel Tech Insider

Gilad Berenstein and Cara Whitehill

Travel Tech Insider is a podcast for those building the future of travel.  Hosted by operators and investors, it’s where the smartest minds in the space go to hear bold takes, nuanced ideas, and practical insights from the people doing the work. If you’re tired of press release PR and trade-show buzzwords, this is your seat at the table.Co-hosted by industry veterans and investors Gilad Berenstein and Cara Whitehill, they are joined by guest experts from all corners of the travel & hospitality tech industry.If you would like to contribute to the conversation please reach out! 

  1. Sep 1

    Mobility: Where the &%$# Are We?

    Few sectors show the gap between technological promise and market reality like mobility. A decade ago, full self-driving felt imminent, rideshare was going to end car ownership, and EVs were about to go mainstream. Billions later, although we're still waiting, progress has been real. Autonomous vehicles are moving from proof of concept to limited commercial deployment. Peer-to-peer rental, subscriptions, and fleet operators evolving into full-spectrum platforms are reshaping how people access vehicles. EV adoption is underway but uneven, with electrification, charging infrastructure, and consumer uptake all moving at different speeds. Micromobility, e-bikes, and rail are reshaping traveler behavior in corridors. Nowhere is the contrast sharper than rail. In Europe, high-speed rail is now the dominant mode for regional travel — faster city-center to city-center than flying, cleaner, and increasingly seamless. The US remains fragmented: outside a handful of corridors, rail isn't competitive. What would it take to change that? The last mile cuts across all of this: getting travelers from airport to final stop remains travel's most friction-filled moment, and the missing link in frictionless, agentic travel planning.  This episode looks at where the mobility revolution stands and what it will take for ground transportation in all its forms to catch up. Follows Gilad Berenstein – host Cara Whitehill - host Mariano Menkes — guest Cameron Jones — guest Go Deeper Here at Last: The Evolution of the Robotaxi - BCGFleet management in 2026: AI, autonomous driving and new EV rules - TransInfoTop 10 Growth Opportunities in Urban Last-mile Mobility Solutions in 2026 - Frost & SullivanGetting America’s passenger rail back on track requires a radically different approach - Transportation for AmericaHow consumers are reshaping the future of mobility - McKinsey

  2. Aug 25

    Hotels in Flux: Owners' Perspective

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

  3. Aug 18

    Wellness Beyond the Spa

    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 NetTravelers Are Booking Vacations Just to Sleep Better — Inside the Sleep Tourism Boom — Hotel OnlineWellness Tourism Trends: What's Shaping Travel and Wellness in 2026 — Hospitality NetBeacons of Light: Chief Wellness Officers for Cities, Spa Business

  4. Aug 11

    Loyalty Revolution: Credit Cards, Memberships and More

    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 NetWhen Loyalty Points Stop Acting Like Money — The Wise MarketerHilton Honors Points Devaluation Hits Luxury Hotels Hard in 2025 — Aviation A2ZWhat’s Next for Hotel Loyalty in 2025 — Skift ResearchMorgan Stanley Sees Travel Credit Cards Testing Banks’ Edge — TheStreet

  5. Aug 5

    Future of the Funnel

    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 - SkiftThe future of travel distribution - AmadeusMastering generative engine optimization in 2026: Full guide - Search Engine LandWhat Is Generative Engine Optimization (GEO): A Complete 2026 Guide - SimilarWebAgentic commerce in travel: Who wins, who loses and what to do about it - PhocusWire

  6. Aug 5

    VC Roundup: Corporate Venture Edition

    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? - TNMTTravel funding deal volume hits new low in Q1 2026 - PhocusWireHow CEOs are turning corporate venture building into outsize growth - McKinseyCorporate Venture Building 2025 - Global Corporate Venturing InstituteThe way to win in corporate venturing: Serial building and AI - McKinsey

  7. Jul 21

    Is Sustainability Sustainable?

    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 - ESGAUGEAmadeus Travel Dreams 2026 - Amadeus InsightsBooking.com 2025 Sustainability Report - Booking.comAviation’s Decarbonization Bet Is Looking Shakier Than Ever - Skift [$]GBTA Sustainability Acceleration Challenge - Global Business Travel Association

  8. Jul 14

    Future Destinations: The Evolving Role of the DMO

    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 WeeklySmall businesses say they’re having a good summer as Americans travel closer to home - AP NewsWinning the Algorithm: Why Destination Marketing Must Evolve in the AI Era - SojernThe Five Foundations of a DMO: New Measures for a New Paradigm - ZarticoBuilding a Personal OS in Claude - Janette Roush

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Ratings & Reviews

5
out of 5
8 Ratings

About

Travel Tech Insider is a podcast for those building the future of travel.  Hosted by operators and investors, it’s where the smartest minds in the space go to hear bold takes, nuanced ideas, and practical insights from the people doing the work. If you’re tired of press release PR and trade-show buzzwords, this is your seat at the table.Co-hosted by industry veterans and investors Gilad Berenstein and Cara Whitehill, they are joined by guest experts from all corners of the travel & hospitality tech industry.If you would like to contribute to the conversation please reach out! 

Information

  • Creator
    Gilad Berenstein and Cara Whitehill
  • Years Active
    2023 - 2026
  • Episodes
    42
  • Rating
    Explicit
  • Copyright
    © 2026 Travel Tech Insider
  • Show Website
    Travel Tech Insider

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