Travel Tech Insider
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!
Travel Tech Insider
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 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