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!

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S4 · E10
September 15 · 1 hr 2 min
Are We Entering the Post-VC Era in Travel Tech?
Travel venture capital has fundamentally changed. Funding that hit a decade low in 2023 has rebounded, but it's no longer the growth-at-all-costs era of the 2010s. Today's VC market is disciplined, bifurcated, and concentrated in fewer, larger bets on proven companies. At the same time, alternative funding structures (venture debt, corporate venture, strategic capital) are proliferating. Innovation in travel is increasingly coming from cross-industry partnerships (tech companies entering travel, airlines partnering with outside tech) rather than pure startups. B2B is outpacing consumer. So the real question: Is venture capital even the right funding path for most travel tech innovation in 2026? Or has the ecosystem shifted so dramatically that founders and investors need to fundamentally rethink capital structures? And most critically, where does that leave the startups who are actively building in this new capital paradigm today? Follows Gilad Berenstein – host Cara Whitehill - host Rafat Ali — guest Erik Blackford — guest Chelsea Salamone - guest Go Deeper Don’t Start a Travel Startup - Skift Go Big or Go Broke - Ethan Kurzweil, Co-Founder and Managing Partner at Chemistry What Makes a Travel-Tech Startup Investable in 2026? - Velocity Ventures Top Investors in Travel Tech 2026 - PhocusWire How VCs are winning in a bifurcated venture landscape - SVB
S4 · E9
September 1 · 59 min
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 - BCG Fleet management in 2026: AI, autonomous driving and new EV rules - TransInfo Top 10 Growth Opportunities in Urban Last-mile Mobility Solutions in 2026 - Frost & Sullivan Getting America’s passenger rail back on track requires a radically different approach - Transportation for America How consumers are reshaping the future of mobility - McKinsey
S4 · E8
August 25 · 1 hr 12 min
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 - 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
S4 · E7
August 18 · 1 hr
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 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
S4 · E6
August 11 · 1 hr 3 min
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 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
S4 · E4
August 5 · 1 hr 1 min
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? - 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
S4 · E5
August 5 · 50 min
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 - 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
S4 · E3
July 21 · 48 min
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 - 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
S4 · E2
July 14 · 57 min
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 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
S4 · E1
July 7 · 51 min
Travel and the Economy: Navigating Chaos
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
S3 · E9
February 24 · 53 min
Private Equity Roundup & Rollups in Travel
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
S3 · E9
Dec 30, 2025 · 49 min
Season Three Season Finale
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
S3 · E8
Dec 23, 2025 · 54 min
Corporate Travel (Still) in Flux
When we last visited the corporate travel side of the industry with OG Steve Singh about a year and a half ago, most of us were still kicking tires on ChatGPT and “agents” still referred to humans. Fast forward to today, and the implications of agentic AI are reaching into every nook and cranny of even the most slow-moving corners of the industry, like corporate travel. With travelers getting more comfortable relying on LLMs to help them plan leisure travel, will they naturally extend that usage for their business trips? And if so, what would that mean for the managed travel industrial complex that exists to optimize the budget and policy rules for corporate travel? Everything feels up for grabs, from how suppliers distribute their inventory and service the traveler, to how corporate travel managers ensure compliance and keep travelers safe, to how the TMCs (travel management companies) to whom much of this responsibility has been outsourced continue to earn the right to even exist. On the M&A front, we’re seeing the gravitational force of scale take hold, with AMEX GBT’s acquisition of CWT (and subsequent rumors of them being up for sale) and Navan’s recent IPO. And we haven’t even gotten to GDSes or NDC yet. What does business travel look like for all these stakeholders in this moment of extended transformation? We’ll dig in with two industry experts to unpack where corporate travel is headed. Follows Gilad Berenstein – host Cara Whitehill - host Cory Garner — guest Jay Boehmer — guest Go Deeper Deloitte: Corporate Travel Forecast a Mixed Bag Amid Complex Conditions - Deloitte How Corporate Travel & Payments Could Change by 2030 - PhocusWire The State of Corporate Travel and Expense 2025 - Skift Meet Tomorrow’s Business Travelers - AMEX Global Business Travel How artificial intelligence is reshaping the future of travel and expense management - ITBrief
Dec 9, 2025 · 1 hr 2 min
Cruising into the Future: How Technology Is Transforming the High Seas
The cruise industry has quietly become one of the most fascinating — and technologically advanced — corners of the travel sector. Once viewed as a niche for retirees and sun-seekers, it’s now riding a powerful wave of innovation, luxury, and digital transformation. From ultra-high-end yachts to fully connected smart ships, cruising has evolved into a microcosm of where travel is headed next. In this episode, we unpack the major trends shaping the modern cruise market — and explore what makes it such a compelling space for travelers, technologists, and investors alike. From the luxury side of the industry, global hospitality icons like Four Seasons, Ritz-Carlton, Belmond, and Aman are extending their brands into the water, bringing the same elevated design and service ethos that they’re known for on land. At the same time, around-the-world itineraries and the rise of residential cruise lines — floating communities where travelers actually live aboard — are blurring the lines between hospitality, real estate, and adventure. Then there’s the family dimension. Cruising has become a top choice for multi-generational travel — offering everything from kids’ discovery camps to Michelin-level dining for grandparents — all within a single, self-contained experience. And while sustainability is often a buzzword across the travel industry, cruising may actually be leading the way. From LNG-powered vessels and advanced waste treatment systems to experiments with alternative fuels and onboard recycling ecosystems, major cruise operators are investing billions to minimize their environmental footprint. But perhaps the most underappreciated story — at least for the digital crowd — is the astonishing level of connectivity that exists onboard. In many ways, cruise lines have already built what other sectors of travel are still chasing — a truly connected trip experience, where data flows across every stage of the customer journey. In today’s conversation, we’ll bring together several leaders from across the sector to explore the forces driving this boom. Welcome aboard! Follows Gilad Berenstein – host Cara Whitehill - host Shane Buksh — guest Thatcher Brown — guest Sam Chamberlain — guest Captain Bill Wright — guest Go Deeper State of the Cruise Industry Report 2025 - Cruise Lines International Association (CLIA) Inside the Strange and Lonely Test Run of a New Cruise Ship - Wall Street Journal [$] Next Growth Phase for Cruises and a New Sustainability Test - Skift Virtuoso’s New Vice President of Global Cruise Shares Current and Future Trends - Travel Age West Gen Z and millennials fuel cruise industry rebound - Hospitality Today
S3 · E6
Dec 2, 2025 · 57 min
Adventures in FinTech: Stablecoins, Blockchain and Crypto
Fintech has quietly become one of the most transformative forces in the travel industry — shaping how we pay, how we earn and redeem loyalty, and increasingly, how companies manage global transactions behind the scenes. From B2B payment flows between hotels, OTAs, and suppliers to B2C innovation in digital wallets, loyalty currencies, and embedded finance, fintech is no longer just an enabler — it’s a strategic differentiator. Fintech also plays a role in the expanding agentic AI space. After all, agents can’t really “agent” without the ability to execute a transaction. How will autonomous digital agents transact on behalf of travelers? What role could blockchain and digital identity play in enabling trusted, frictionless payments between humans and machines? We’ll also examine the regulatory shifts reshaping the playing field — including the GENIUS Act and other global efforts to modernize payment infrastructure and consumer protection. Follows Gilad Berenstein – host Cara Whitehill - host Randall Davies — guest James Lemon — guest Go Deeper What’s up with stablecoins after the GENIUS Act? - Brookings Are Stablecoins the Game-Changer for Cross-Border Payments? - Edgar Dunn & Company The 2025 McKinsey Global Payments Report - McKinsey & Company KYAPay: Toward an Open Payment and Identity Layer for Agentic AI - ***KYAPay.ai & Skyfire.xyzWhitepaper*** The era of payment stablecoins has arrived - Deloitte
S3 · E5
Nov 25, 2025 · 1 hr 4 min
The AI Effect (Part 3): Agentic AI & Future of Personalization
Show Notes Agentic AI is the latest buzzword in travel tech — but beyond the hype, it raises big questions about how travelers will discover, plan, and book their journeys. Will the power of agentic AI reinforce the dominance of OTAs like Expedia and Booking, or will it open the door for smaller travel brands to compete on equal footing? In this episode, we explore what agentic AI means for personalization in travel retailing and service delivery: how it could reshape loyalty, rewire customer expectations, and redefine the role of intermediaries versus suppliers. We’ll look at emerging best practices, potential pitfalls, and the debates shaping how our industry adapts to this next era of AI-driven travel. This week we are joined by two leaders building for this new agentic world, Kosta Krauth, CTO of Bilt, the next-gen loyalty and payments platform, and Charles Packer, Co-Founder & CEO of Letta, the operating platform for building stateful agents. Follows Gilad Berenstein – host Cara Whitehill - host Kosta Krauth — guest Charles Packer — guest Go Deeper 4 scenarios on the future of agentic AI in travel - PhocusWire Ready for takeoff: Reimagining travel and hospitality with agentic AI - Google Cloud Personalized agentic AI experiences are coming - Fast Company Seizing the agentic AI advantage - McKinsey QuantumBlack Enabling Personalized Long-term Interactions in LLM-based Agents through Persistent Memory and User Profiles - Rebecca Westhäußer, Wolfgang Minker, Sebatian Zepf
Nov 11, 2025 · 57 min
Agentic AI (Part 2): The Emerging AI Tech Stack
Generative AI is not only impacting how travel is bought and sold as we heard in Part 1 of our AI Effect series, it’s also impacting how companies are building and delivering the travel services that are bought and sold. Companies used to stockpile servers, engineers and access to bandwidth, all of which required considerable capital. In this new AI era, anyone can use Replit or Lovable to spin up their own travel app in a matter of hours. Companies no longer need teams of expensive engineers to code up a new application — the just need a Cursor subscription and a few developers with some free time to vibe code. Legacy infrastructure is getting deprecated in favor of AI-based solutions that didn’t exist a few months ago. So what does the enterprise tech stack look in this era of AI? Is it proving to be more cost-effective than the legacy platforms our industry was built on? Is it unlocking opportunity for startups with fresh ideas to take share from incumbents? Or is it enabling the incumbents to finally catch up to startups in terms of speed of innovation? Or is it a combination (or collaboration) of both? Follows Gilad Berenstein – host Cara Whitehill - host Josh Dow — guest SJ Sawhney — guest Go Deeper From Prompts To Products: The Business Of No-Code AI Is Booming - Forbes [$] McKinsey Technology Trends Outlook 2025 - McKinsey & Company This Week in Lessons from (Technical) Founders - Gilad Berenstein Building the Foundation for Agentic AI - Bain & Company Agentic AI in the enterprise: An evolution, not a revolution - Red Hat Blog
Nov 4, 2025 · 48 min
The AI Effect (Part 1): The Future of Travel Distribution
Generative AI has upended just about every part of the travel lifecycle for both buyers and sellers of travel services. From the consumer perspective, the resources available to inspire, research, plan, book and share your favorite trips have simultaneously expanded the possibilities for consideration and curated that consideration set to a handful of suggestions — all in a matter of seconds. From the perspective of those selling travel services, that path to reach your buyers has become exponentially more complicated. The old reliable model of online search (primarily through Google) has a half life that is accelerating faster than anyone could have predicted. The promise of agentic AI in the hands of consumers may feel more like a curse to travel suppliers who haven’t yet figured out how to be relevant to the constantly evolving LLMs. At the same time, traditional SEO- and SEM-based acquisition channels, which have been economically dominated by the OTAs for a generation, are now being replaced by this new algorithmic approach of the proliferating LLMs, providing an opening for direct booking channels that could level the playing field. Likewise, the fine-tuning that AI tools provide to brands for optimizing pricing, offers and channels could be an opportunity…or a race to the bottom. We’re still in Act I of this AI era, and we’ll talk to a couple experts for their take on where we are and where we are headed. Follows Gilad Berenstein – host Cara Whitehill - host Layton Han — guest Christian Watts — guest Go Deeper Remapping Travel with Agentic AI - McKinsey & Company Altimeter Capital Partner Says AI Will Transform Travel Search: ‘It’s Already Happening’ - Skift [$] How hotels should be thinking about their visibility on AI platforms - PhocusWire Forget the funnel. Welcome to AI: The new distribution channel - CoStar The Great Tech Reset: Agentic AI and the Coming Rebalance of Power in Hospitality - Hotel Online
S3 · E2
Oct 28, 2025 · 51 min
Social Commerce: Dead or Alive?
With all the debate over agentic AI and its impact on the traditional search ecosystem, we seem to have forgotten all about that other massive acquisition channel — social commerce. TikTok, Instagram, YouTube, Reddit, Twitter, and other popular commuity sites around the globe all continue to garner a significant share of top-of-funnel attention and mid-funnel intent. This is acutely true for the Gen Z and younger millennial cohorts when it comes to travel planning and even more so for Gen Alphas who may not be buying travel yet but who are heavily relying on social for their retail commerce purchases. What we haven’t yet seen is a clear winner, a household name emerge when it comes to translating that attention to revenue. Does that mean there is no real winner here, or do we just lack a good attribution model that connects the dots from social to booking? Social also seems to be leveling the playing feel between brands and individuals. The creator economy is massive in categories like fashion and beauty — but how does it play out for big ticket, highly considered purchases like travel? And as agentic AI takes over from traditional search, will that help or hurt social commerce as a channel for discovery, planning and potentially booking? Are social and agentic AI parallel channels that will coexist to serve complementary use cases, or are they on a commercial collision course? Follows Gilad Berenstein – host Cara Whitehill - host Hannah Bennett — guest Abby Dichter — guest Go Deeper State of the Consumer 2025: When disruption becomes permanent - McKinsey & Company How Social Media Is Shaping Travel Planning and Booking - Skift Under the influence: Social media's role in trip planning - PhocusWright U.S. Traveler Trends 2025: More Social Media and AI, a Rebound for Online Travel Agencies - Skift Is your brand ready for the $3 trillion social commerce marketplace? - PWC
S3 · E1
Oct 21, 2025 · 1 hr 1 min
Vacation Rentals in Flux
The vacation rental industry has transformed from a scrappy alternative to hotels into a global powerhouse—but is the model starting to strain under its own weight? In this episode, we explore how the ecosystem is evolving, and where fault lines are beginning to show. Can tech keep pace with rising guest expectations? Will hosts, managers, and platforms ever find equilibrium in their tug-of-war over economics, control, and trust? And what happens when regulators and communities push back against the very growth that made vacation rentals mainstream? We look at the opportunities and tensions shaping the next phase of this category—where innovation collides with customer demands, and where the future may depend less on scale and more on who can truly deliver a consistent, high-quality experience. Follows Gilad Berenstein – host Cara Whitehill - host Annie Sloan — guest Josh Kristoff — guest Go Deeper Airbnb Lets You Add a Private Chef to Your Rental. Your Host Might Not Like It. - Wall Street Journal [$] **How much opportunity is there for STR ancillaries? Experts weigh in - PhocusWire** U.S. 2025 Mid-Year Short-Term Rental Outlook Report - AirDNA Short-Term Rental Headwinds: U.S. Supply Growth Is Slowing - Skift Perplexity Travel for Vacation Rentals: How AI Is Powering Trip Search - RentalScaleUp

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