All Episodes
Displaying 1 - 20 of 125 in total
The Future of PMS, AI & Vacation Rental Technology (With Rick van der Plas)
In this episode, we interview Rick, CTO of Hostaway, to talk all things vacation rental technology, the evolution of property management systems, AI co-hosts, automati...
Can AI Actually Deliver Better Hospitality? The Future of Vacation Rental Operations (With Cole Rubin)
In this episode, we interview Cole Rubin, co-founder and CEO of Conduit, to talk all things AI agents, guest communication, automation, hospitality tech, and what the ...
How Do You Scale Hospitality Without Losing What Makes It Special? (With Rachel Alday)
In this episode, we interview Rachel Alday of Abode Luxury Rentals to talk all things luxury vacation rentals, scaling with standards, hospitality and leadership, priv...
Are Experiences Changing the Way Guests Book Travel? (With Seth Borko)
In this episode, we interview Seth Borko of Skift Research to talk all things travel trends, the experience economy, vacation rentals, guest behavior, local experience...
From 6 Units to 430: The Unexpected Journey of Building Sojourn (With Dunniela Kaufman)
In this episode, we interview Dunniela Kaufman of Sojourn to talk all things building a hospitality brand, growing from 6 to 430 vacation rental units, short-term vs. ...
Why Niche Brands Are the Future of Vacation Rentals (With Bob Milne)
In this episode, Bob Milne discusses the lessons learned from scaling one of the industry's largest vacation rental companies, why niche hospitality brands are on the ...
The Biggest AI Shift Coming to Hospitality (With Christian Hyland)
In this episode, we interview Christian to discuss the future of AI in hospitality, the evolution of property management systems, why operators should rethink their AI...
An Industry Veteran Tells Us What's Going On In The Vacation Rental Space Today (With Annie Holcombe)
In this episode, we interview Annie Holcombe to talk all things OTAs, platforms, vacation rental management, podcasting as a growth platform, being independent and a l...
This Might Be The Best Way To Build A Vacation Rental Business? (With James Cornwell)
In this episode, we interview James Cornwell and his excellent accent to talk all things growth, profit, luxury, choosing the right properties to manage and a LOT more...
We've Got A Lot To Learn From The Top Euro Operators (With Cristiana Carpini)
In this episode, we interview Cristiana Carpini from her Italian home to talk all things Europe, regulations, where we're headed, a long-term view, AI disruption and a...
The Root Problems With Scaling Vacation Rental Brands (With Ashley Ching)
In this episode, we interview Ashley Ching (again!) with Inhaven to talk all things scale, AI, human vs AI, brand standards, why Vacation Rental brands keep failing to...
The Best Vacation Rental Marketing Data Might Be Here (With Jamey King)
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, ROAS improvements, ...
He's On The Bleeding Edge Of AI Adoption In The Vacation Rental Industry... (With Ivan Nikolov)
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 vacation rental industry...
Where Do PMS Platforms Go From Here In The New AI Era? (With Frank Bosi)
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 with software and o...
Are Vacation Rental SaaS Vendors Going Away? (With Richard Vaughton and Luca De Giglio)
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 platforms growth, h...
The Story Of AI Agents Running A 150 Unit Company With 1 Full Time Employee (With Jan Sahagun)
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 teams, 150 proper...
If We Were Going To Build A Vacation Rental Business, How Would We Do It? (With Adam Norko & Conrad O'Connell)
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? Grow it? What types...
Operator Series: These Vacation Rental Managers Are THE AI Pioneers (With JJ King, Jack Zoppa, Jacob Mueller)
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, Jack Zoppa and J...
The Vacation Rental Data God Is Back With An Update (With Jamie Lane)
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 impacting the AirDNA...
Operator Series: Winning In The Midwest With The Right Team (With Michael Friedman)
We're pumped to welcome Michael Friedman, Chief Executive Officer of Simple Life Rentals onto the show to talk all things AI, growth, team, profitability, smart homeow...