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.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Annie Sloan — guest

Josh Kristoff — guest

Go Deeper

• Airbnb 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 - AirDNA
• Short-Term Rental Headwinds: U.S. Supply Growth Is Slowing - Skift
• Perplexity 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.

Follows

Gilad Berenstein – host

Cara Whitehill - host

Gaurav Tuli - guest

Chris Hemmeter - guest

Mia Morisset - guest

Go Deeper

• When Not to Take VC Advice - Sifted
• The great SaaS obituary: why reports of its death are greatly exaggerated - Medium
• The 3-Person Unicorn Startup - NfX
• How AI is disrupting the VC and startup ecosystem - Fast Company
• How AI is fundamentally changing the operational needs of startups - World Economic Forum

Book Recommendation: Quit: The Power of Knowing When to Walk Away, Annie Duke

In our first two seasons we took a deep dive into the venture investing scenes in both the US and European markets, comparing and contrasting the startup trends, approaches to risk, and styles of investing that are taking hold.

Now we shift our focus east, and take a look at the state of the APAC VC ecosystem. Given the multitude of different countries, cultures, and currencies the region encompasses, it has a far more diverse customer base to tap into than the US or EU.

How does that impact the type of startups that grow up and find success in that region? How easily (or not) can those startups scale beyond APAC? For investors, what do they look for in the startups they back across the region, and are there nuances within each corner of APAC itself? And given the current tumultuous geopolitical environment, is it more of a challenge or an opportunity for starups and investors across the region?

So for this mid-season break episode, we are tapping into some of the investors on the front lines across Asia salon-style, to see what we can learn from our friends there.

Follows:

Gilad Berenstein - host

Cara Whitehill - host

Nick Cocks - Founder & Director, Velocity Ventures

Murli Ravi - Co-founder, Tin Men Capital

Mizuho Hiraguri - Corporate Development for Recruit Co

Go Deeper:

• Trump, tariffs and travel: How will the turbulence play out in Asia? - Web In Travel
• Southeast Asia’s Travel Tech Sector at Pivotal Moment for Value Creation - PhocusWire
• Asia's Travel Surge Drives Moderate Global Growth - Skift
• 24-fold increase in Japanese corporate venture capital in the past decade - Global Corporate Venturing
• Unpacking Asia’s corporate investment trends in travel - TNMT

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 joined by four of the leading thinkers, writers and question-askers in the industry to learn what they see on the horizon for 2025 and beyond. 

Follows
Gilad Berenstein — host
Cara Whitehill — host
Jay Boehmer — guest
Michael Coletta — guest
Sarah Kopit — guest
Siew Hoon Yeoh — guest

 Go Deeper

• Skift Megatrends 2025 - Skift
• Travel Forward: Data, Insights and Trends for 2025 - PhocusWright
• 2025 What to Watch - Business Travel News
• Your Guide to 2025 – Problems to be fixed and trends no one is talking about yet - WIT / Web in Travel
• 12 technology and CX trends that can enhance airline and airport operations in 2025 - Future Travel Experience

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 to the founders for their perspective on the exit. Since most founders will only experience an M&A event once or twice in a career, there is considerable information asymetry in the process. Exits can also take many different forms, depending on who’s buying, whether the startup is bootstrapped or venture-backed, and what’s actually being sold.

We talked to three travel startup founders who have gone through this process (a couple of whom have done it multiple times), to hear what their experiences were like, lessons learned, what they might have done differently, and what their exits enabled them to go on to do next. Because after all, an exit is just an entrance to somewhere else.

Follows
Gilad Berenstein — host
Cara Whitehill — host
Sarah Dusek — guest
Sam Shank — guest
Jeroen Van Velzen — guest

Go Deeper

• Thinking Bigger - Sarah Dusek
• The Art Of The Founder Exit - Forbes
• Why Founders Are Afraid to Talk About Exit Strategies - Harvard Business Review
• What Founders Need to Know Before Selling Their Startup - Harvard Business Review
• European founders are thinking more creatively about exits. Here are some of the options - Sifted
• Exit strategies: When to sell and not to sell - Silicon Valley Bank

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, most trips revolved around food, drink, and relaxation. But even though we all know this, for some reason the arena of F&B Tech and Restaurant Innovation are often absent from major conversations, conferences, and events within our industry.

To begin to address this hole in our conversation, and to learn from the incredible innovation sweeping through this industry, we are excited to dig into all things Tech and Innovation in the restaurant space.

To kick off this conversation, we decided to slightly change our format and split this episode into two conversations. First, we will be joined by David Peller. David lives and works in Singapore, a region much more focused on restaurant tech than the American startup market. In his various roles, David invests in, sits on boards of, and helps lead both restaurants and restaurant concepts themselves and many technology companies innovating in this space. So he is the perfect person to give us a high-level overview of the scope and breadth of the innovation landscape in F&B on both the restaurant side and Technology company front.

And after that we will dive into the deep end with a conversation with 3 innovators working directly within these themes to learn what's actually going on, how meaningful it really is, and what lessons the rest of us can take.

Follows
Gilad Berenstein — host
Cara Whitehill — host
David Peller — guest
Wiggs Civitillo — guest
Ursula Siker — guest
Marc Zornes — guest

Go Deeper

• 2025 Food Industry Tech Trends: AI and Supply Chain Solutions Lead Investment Priorities - Food Industry Executive
• Embracing Advanced Tech In The Food And Beverage Industry, Part 2: AI And Automation - Forbes
• 6 Technologies That Boost F&B Revenue - HospitalityNet
• AI M&A Wave Coming in the Food and Beverage Sector - Mergers & Acquisitions
• What are the barriers to innovation in food and beverage? - Food Navigator

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 from concept to commercialization since the pandemic, this combination of dry powder, lower interest rates, and a new administration taking over that is anticipated to be more deal-friendly all seem to point to conditions ripening nicely for more M&A activity.

So, what does the state of M&A look like in the travel tech sector heading into 2025? Is the market open for business again, and if so, who is buying what?

Follows
Gilad Berenstein — host
Cara Whitehill — host
Morgann Lesne — guest
Roopak Pati — guest
Jonathan Weibrecht — guest

Go Deeper

• Venture Buyouts: Look Where Other Investors Aren’t Looking - Substack: The Capitalist
• Europe could lead the world for travel tech but needs more ambition says leading investment banker - Breaking Travel News
• Play or be played: M&A consolidation in corporate travel - BTN Europe
• Leisure M&A: Travel deals are back! - BDO UK
• What's driving the resurgent M&A interest in the travel sector? - TravelTrade Gazette

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 travel purchases and insurance-type products that help travelers protect their trip investments are all popular examples of this trend.

Now we’re seeing the convergence of fintech and travel in the reverse direction — call it the “Travelization of Finance” — where deep integration of travel offerings into financial services platforms is unlocking opportunities to explore the world that previously wouldn’t have been possible for many. Unlocking the spending power of things like rent and healthcare expenses, or creating new credit alternatives for pre-credit customers are activating new demand channels for travel sellers that they couldn’t reach before.

Tune in to our latest episode to hear from guests Ankur Jain, Founder & CEO of Bilt Rewards, and Hussein Fazal, Founder & CEO of Super.com, are pushing the cutting edge forward in this unique moment of digital transformation between travel and fintech.

Follows
Gilad Berenstein — host
Cara Whitehill — host
Ankur Jain — guest
Hussein Fazal — guest


Go Deeper

• How Fintech Companies Are Progressing in the Travel Space - PhocusWire
• Super apps’ secret sauce - PhocusWright
• Meet The Fintech Billionaire Making A Fortune Rewarding Home Renters - Forbes
• The rise of the theme-based super app - Finextra
• Travel Disruptors: Bringing fintech to travel booking - McKinsey & Company
• Why is FinTech in Travel accelerating while slowing down elsewhere? - LinkedIN

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’s been over 30 years since the last flight of the Concorde, new aviation technology is opening up alternative modes of transport that will make getting from here to there faster, cheaper, more accessible and more climate-friendly.

Follows
Gilad Berenstein — host
Cara Whitehill — host
Pasha Saleh — guest
Brian Cobb — guest

Go Deeper

• Alaska Airlines’ venture lab spins out its first startup: Odysee - Techcrunch
• The Future of Aviation Report - ICAO
• The race to become the world’s first document-free airport - CNN
• Supersonic passenger planes 1 step closer to return after successful Boom XB-1 test flight nears sound barrier - MSN
• Exploring the Future of Urban Air Mobility (UAM): Key Concepts and Innovative Technologies - Sustainable Review
• The future of air mobility: Electric aircraft and flying taxis - McKinsey & Company

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, and what relationships do you have with the various suppliers and service providers that are part of the experience.

This is one of the last few areas of the travel industry that hasn’t gone through a full digital transformation yet, but with the advances in AI, Gen AI and the evolution of cloud- and services-based architecture, it sure feels like all the ingredients are there. So where are we now with the concept of digital identity and a universal travel profile that can finally unlock a smoother, slicker journey?

Follows
Gilad Berenstein – host
Cara Whitehill - host
Vikas Bhola – guest

 
Go Deeper

• Digital identity models: What’s next for secure and seamless travel? - World Economic Forum
• Digital travel and decentralized identity reveal the value of simplicity - Indicio
• How Verifiable Credentials and Digital ID Will Transform Travel - PhocusWire
• Travel And Mobile Are Driving Decentralized Digital Identity (DDID) Growth - Forrester [$]
• Decentralized Identity Foundation Hackathon Kicks Off With Travel Solutions Track - PhocusWire