Travel Tech Insider

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.FollowsGilad Berenstein – hostCara Whitehill - hostMax Niederhofer — guestBesty Mulé — guestSarah Kopit — guestGo DeeperHow AI Bookings Will Rewrite the Travel Company Playbook - Bain & CompanySkift Megatrends 2026 - SkiftHot Travel Startups 2026 - PhocusWireClear Skies for Corporate Travel in 2026 - Morgan Stanley2026: Going Public. Going Global. Going Big. - Arival Travel

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.FollowsGilad Berenstein – hostCara Whitehill - hostCory Garner — guestJay Boehmer — guestGo DeeperDeloitte: Corporate Travel Forecast a Mixed Bag Amid Complex Conditions - DeloitteHow Corporate Travel & Payments Could Change by 2030 - PhocusWireThe State of Corporate Travel and Expense 2025 - SkiftMeet Tomorrow’s Business Travelers - AMEX Global Business TravelHow artificial intelligence is reshaping the future of travel and expense management - ITBrief 

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! FollowsGilad Berenstein – hostCara Whitehill - hostShane Buksh — guestThatcher Brown — guestSam Chamberlain — guestCaptain Bill Wright — guest Go DeeperState 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 - SkiftVirtuoso’s New Vice President of Global Cruise Shares Current and Future Trends - Travel Age WestGen Z and millennials fuel cruise industry rebound - Hospitality Today

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.FollowsGilad Berenstein – hostCara Whitehill - hostRandall Davies — guestJames Lemon — guestGo DeeperWhat’s up with stablecoins after the GENIUS Act? - BrookingsAre Stablecoins the Game-Changer for Cross-Border Payments? - Edgar Dunn & CompanyThe 2025 McKinsey Global Payments Report - McKinsey & CompanyKYAPay: Toward an Open Payment and Identity Layer for Agentic AI - ***KYAPay.ai & Skyfire.xyzWhitepaper***The era of payment stablecoins has arrived - Deloitte

Show NotesAgentic 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. FollowsGilad Berenstein – hostCara Whitehill - hostKosta Krauth — guestCharles Packer — guest Go Deeper4 scenarios on the future of agentic AI in travel - PhocusWireReady for takeoff: Reimagining travel and hospitality with agentic AI - Google CloudPersonalized agentic AI experiences are coming - Fast CompanySeizing the agentic AI advantage - McKinsey QuantumBlackEnabling Personalized Long-term Interactions in LLM-based Agents through Persistent Memory and User Profiles - Rebecca Westhäußer, Wolfgang Minker, Sebatian Zepf

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?FollowsGilad Berenstein – hostCara Whitehill - hostJosh Dow — guestSJ Sawhney — guestGo DeeperFrom Prompts To Products: The Business Of No-Code AI Is Booming - Forbes [$]McKinsey Technology Trends Outlook 2025 - McKinsey & CompanyThis Week in Lessons from (Technical) Founders - Gilad BerensteinBuilding the Foundation for Agentic AI - Bain & CompanyAgentic AI in the enterprise: An evolution, not a revolution - Red Hat Blog

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. FollowsGilad Berenstein – hostCara Whitehill - hostLayton Han — guestChristian Watts — guest Go DeeperRemapping Travel with Agentic AI - McKinsey & CompanyAltimeter Capital Partner Says AI Will Transform Travel Search: ‘It’s Already Happening’ - Skift [$]How hotels should be thinking about their visibility on AI platforms - PhocusWireForget the funnel. Welcome to AI: The new distribution channel - CoStarThe Great Tech Reset: Agentic AI and the Coming Rebalance of Power in Hospitality - Hotel Online 

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?FollowsGilad Berenstein – hostCara Whitehill - hostHannah Bennett — guestAbby Dichter — guest Go DeeperState of the Consumer 2025: When disruption becomes permanent - McKinsey & CompanyHow Social Media Is Shaping Travel Planning and Booking - SkiftUnder the influence: Social media's role in trip planning - PhocusWrightU.S. Traveler Trends 2025: More Social Media and AI, a Rebound for Online Travel Agencies - SkiftIs your brand ready for the $3 trillion social commerce marketplace? - PWC

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.FollowsGilad Berenstein – hostCara Whitehill - hostAnnie Sloan — guestJosh Kristoff — guest Go DeeperAirbnb 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 - AirDNAShort-Term Rental Headwinds: U.S. Supply Growth Is Slowing - SkiftPerplexity Travel for Vacation Rentals: How AI Is Powering Trip Search - RentalScaleUp

In this emerging AI era, what’s different this time when it comes to tech investing? We’ve seen major disruptions before, both business model (eg, internet > mobile > social > AI) and cultural/structural/economic (eg, ZIRP, gig workers, Covid, remote working, cloud computing).Prior eras followed a similar playbook: irrational exuberance leading to the trough of despair, followed by the emergence of a handful of market leaders with escape velocity and long tail of minor players, all setting into a level of market maturity that keeps things in balance.Will the AI era follow same? Or does the velocity of tech evolution and democratization of access to these sophisticated technologies mean something different?What have investors learned from these past cycles that informs how they select investments and support their portfolio companies? What past mistakes have they made that they are correcting for now, and how?We unpack all these topics with another Salon episode featuring three leading travel tech investors to share their battle scars and assessment of this new climate of investing.FollowsGilad Berenstein – hostCara Whitehill - hostGaurav Tuli - guestChris Hemmeter - guestMia Morisset - guestGo DeeperWhen Not to Take VC Advice - SiftedThe great SaaS obituary: why reports of its death are greatly exaggerated - MediumThe 3-Person Unicorn Startup - NfXHow AI is disrupting the VC and startup ecosystem - Fast CompanyHow AI is fundamentally changing the operational needs of startups - World Economic ForumBook Recommendation: Quit: The Power of Knowing When to Walk Away, Annie Duke