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

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

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

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

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

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

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

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