Travel Tech Insider
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! 
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 ...
Feb 24
53 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 a...
Dec 30, 2025
49 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 us...
Dec 23, 2025
54 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 ...
Dec 9, 2025
1 hr 2 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...
Dec 2, 2025
57 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...
Nov 25, 2025
1 hr 4 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...
Nov 11, 2025
57 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 expo...
Nov 4, 2025
48 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 Alp...
Oct 28, 2025
51 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 agai...
Oct 21, 2025
1 hr 1 min
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