Podcast Episodes
Back to SearchThe Root Problems With Scaling Vacation Rental Brands (With Ashley Ching)
Episode 183
In this episode, we interview Ashley Ching (again!) with Inhaven to talk all things scale, AI, human vs AI, brand standards, why Vacation Rental bran…
2 months, 1 week ago
The Best Vacation Rental Marketing Data Might Be Here (With Jamey King)
Episode 182
We're joined this week by Jamey King, industry veteran to talk all things data, finding new sources of data and research to improve your marketing, R…
2 months, 2 weeks ago
He's On The Bleeding Edge Of AI Adoption In The Vacation Rental Industry... (With Ivan Nikolov)
Episode 181
We're joined this week by Ivan Nikolov of Repull & FantasticStay to talk all things AI, building with agents, workflows, "levels" to AI in the vacati…
2 months, 3 weeks ago
Where Do PMS Platforms Go From Here In The New AI Era? (With Frank Bosi)
Episode 180
We're joined this week by Frank Bosi from Hostfully to talk all things AI, PMS platforms, building tech today vs several years ago, growth, winning w…
3 months ago
Are Vacation Rental SaaS Vendors Going Away? (With Richard Vaughton and Luca De Giglio)
Episode 179
We're joined this week by Luca De Giglio and Richard Vaughton to talk all things SaaS, the growth of agents, building your own PMS platform, coding p…
3 months, 1 week ago
The Story Of AI Agents Running A 150 Unit Company With 1 Full Time Employee (With Jan Sahagun)
Episode 178
We're joined this week by Jan Sahagun of Trellis (backed by YC) to talk all things agents, the future of STR/Vacation Rentals tech, running with lean…
3 months, 2 weeks ago
If We Were Going To Build A Vacation Rental Business, How Would We Do It? (With Adam Norko & Conrad O'Connell)
Episode 177
We're solo this week to explore a fun thought experiment: what if we had to open our own vacation rental company? How would we operate it? Fund it? G…
3 months, 3 weeks ago
Operator Series: These Vacation Rental Managers Are THE AI Pioneers (With JJ King, Jack Zoppa, Jacob Mueller)
Episode 176
We're joined by an all-star cast from all over the US to talk AI, practical use-cases and growth in tooling that is going to move the needle. JJ King…
3 months, 4 weeks ago
The Vacation Rental Data God Is Back With An Update (With Jamie Lane)
Episode 175
We're joined by a favorite guest, Jamie Lane of Airdna to talk all things q1 2026 wrap up, World Cup demand, reading data the right way, how AI is im…
4 months ago
Operator Series: Winning In The Midwest With The Right Team (With Michael Friedman)
Episode 174
We're pumped to welcome Michael Friedman, Chief Executive Officer of Simple Life Rentals onto the show to talk all things AI, growth, team, profitabi…
4 months, 1 week ago