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Travel Tech Insider

Travel Tech Insider

By: Gilad Berenstein and Cara Whitehill
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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.

If you would like to contribute to the conversation please reach out!

© 2026 Travel Tech Insider
Episodes
  • Private Equity Roundup & Rollups in Travel
    Feb 24 2026

    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
    Show More Show Less
    53 mins
  • Season Three Season Finale
    Dec 30 2025

    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
    Show More Show Less
    49 mins
  • Corporate Travel (Still) in Flux
    Dec 23 2025

    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

    Show More Show Less
    55 mins
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