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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.
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32 Episodes
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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 a...
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 us...
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...
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...
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 Alp...
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 agai...
Wrapping up season two of the Travel Tech Insider podcast, we turn the tables on our favorite trade media voices to hear what they’re keeping an eye on for 2025. What are they most excited to cover? What under-the-radar trends do they think will have an outsized impact on the ways we plan, shop, book and experience travel? And how do they go about their day-to-day jobs in the media world, identifying stories and cultivating their sources to find their unique angles and insights? We’re j...
In part 1 of our exploration of M&A trends in the travel sector, we talked to the bankers and advisors who have a front row seat to the circus that is the M&A process. Given this is their job day-in and day-out, they have a deep understanding of the steps involved in buying or selling a business, can anticipate the gotcha’s and stumbling blocks, and are primed to help their customers avoid pitfalls that can unexpectedly snag a deal. Now we turn to the other side of the table and talk...
Dining out, room service, fine dining, continental breakfasts, a fancy cocktail, and food and drink in general have always been a part of the travel experience and hospitality offering. Today more than ever before Michelin Stars, hidden gems, street eats, food tours, cooking classes, Agriturismo, and gastropubs are the central aspirations of an enormous percentage of the traveling public. As we learned from 100’s of millions of travelers at Utrip, for most Americans, and everyone else too, m...
We’ve spent a lot of time on the pod talking about startups, and now we’re going to shift gears to talk about the finish line, and what the climate is looking like for exits. The IPO market has been virtually non-existent the past couple years, and M&A activity (particularly for Big Tech) has been stagnant. That said, there is a ton of capital sitting on the sidelines, seemingly ready to jump in when conditions improve. Coupled with the volume of early-stage companies that have matured f...
The fintech sector has expanded massively beyond its origins as a way to modernize and connect the plumbing across the various segments of the financial services world. The intersection of fintech and travel — the “Financialization” of the travel sector — is leading to some incredibly interesting applications that help consumers find value and help merchants more efficiently serve those consumers. Alternative forms of payment, loyalty program extensions, creative new approaches to funding tra...
It might be hard to tell at times, but we’re in the midst of a renaissance when it comes to the air travel experience. Everything from the aircraft we fly to the routes they take to the in-flight experience is getting a major redesign. The pandemic and subsequent Infrastructure Act provided the downtime and funds for our airports to get badly needed investment, enabling them to modernize their operations and overhaul the passenger experience into something that is actually pleasant. While it’...
We’ve talked a lot on the pod about the mythical Connected Trip concept, and the vision for a unified travel experience across all the different touchpoint throughout the journey. One that is personalized and understands the context of the trip — is it for work or for fun, with family or solo, international or local — and what type of support we might need throughout the journey. One key foundational element of this vision is the concept of identity: who you are, what are your preferences, a...
Last season we took a deep dive into the venture investing scene here in the US, including the different approaches taken by corporate ventures teams and institutional funds, and the growth of new platforms like studios and accelerators. Now it’s Europe’s turn. We’ll take a look at the European venture scene and what investors are seeing on that side of the pond. Valuations, M&A activity, implications of governmental regulation, and fundraising trends for both VCs and startups. The ecos...
Ancillaries! It’s such a nebulous term for the travel industry that it’s incredibly hard to figure out exactly how big the market is — but we know it’s massive and getting bigger by the day. In some cases, what we refer to as ancillary products are actually the primary reason for the trip to begin with! Think Disney park tickets or the surfing lessons you booked for that major milestone birthday trip. In other cases, they’re things we used to get for free before folks like RyanAir realized ...
Corporate travel has been ripe for disruption for quite some time, so why is it taking so long? Road warriors hate the tools they are compelled to use (and frequently bypass), travel managers hate the cat-and-mouse games they have to play to enforce policy on their employees and to police rates and configuration rules with their TMC partners. Suppliers hate the complexity involved in getting the right offers to the right customers. TMCs hate the goat rodeo of program leakage and shoe-horning...
The season finale is here! Episode 10 wraps up with some special guests to help us check in on the latest goings-on among all the hot topics we covered in Season 1. Cliffhangers abound... What's next with NDC, loyalty program changes, regulatory trends, and all things AI? Luxury and Zillennials, venture capital funding (or lack thereof?) and the future of destination marketing are all looking a little different from when we covered them just months ago. Thanks to Friends of the Pod Janette ...
This week we continue our deep dive into what we know so far about AI, and how it’s being used, being disruptive, being overestimated and perhaps underestimated across the travel ecosystem. In our last episode we spoke to two startup founders who have incorporated AI into their applications to get the perspective of the early-stage company and how AI is changing the landscape for these new players. Today we talk to two leaders from the other end of the spectrum, Marilyn Markham of AMEX Globa...
It’s been a little over a year now since ChatGPT burst on the scene like a cannonball into a pool, soaking us all. The initial waves have settled down, giving us a chance to see what kind of ideas and applications are making the best use of this fascinating technology. And while AI isn’t exactly new, the democratized access to it that ChatGPT introduced means virtually anyone can make use of large language models and generative AI tools without needing a PhD. This expanded access in turn is ...
The way we travel has evolved pretty dramatically since the pandemic. The traditional “Dream/Plan/Book/Go/Share/Repeat” lifecycle has essentially been replatformed as a result of macro trends like the shift to remote work, multiple rounds of stimmie checks, a growing loneliness epidemic, and an acute appreciation for authenticity and sustainability in the travel brands we engage with. We have more time, more money, and more desire to see the world, and we want to do it on our terms. We’re als...
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