The Best Short-Term Rental Podcast

With: Jasper Ribbers & Kaye Putnam

Jasper Ribbers and Kaye Putnam from Freewyld discuss why pricing remains a priority yet often lacks strategic execution, outlining the value of expert revenue management routines, flat ADR amid inflation, mid-sized tech-forward operators’ growth potential, OTA versus direct booking dynamics, and upcoming World Cup-driven opportunities.

With: Eric Moeller & Kaye Putnam

Kaye Putnam and Eric Moeller from Freewyld examine Sonder’s collapse, explaining how the rental-arbitrage model, persistent unprofitability and the Marriott integration costs led to bankruptcy, while highlighting lessons on fixed-cost risks, dependence on single channels and emerging opportunities for operators in the newly vacated markets.

With: Jasper Ribbers

Jasper Ribbers outlines how booking windows and seasonality shape effective cancellation policies, reviews Airbnb’s upcoming dynamic option, contrasts VRBO’s fixed rules with Booking.com’s flexible rate plans, and explains how strategic flexibility, simplified choices, and channel diversification help protect revenue and build early momentum.

With: Kaye Putnam & Eli Pritykin

Kaye Putnam and Eli Pritykin break down what truly drives revenue on direct booking websites. They explore branding, trust, frictionless booking, and how AI-driven search (AEO/GEO) will reshape discovery. Pritykin explains why WordPress plus HomeRunner unlocks real conversion power for STR operators.

With: Jasper Ribbers

Jasper Ribbers explains how Airbnb’s updated cancellation policies influence visibility and bookings, and why overly strict settings reduce demand. He outlines when to use flexible or moderate options depending on booking windows and market dynamics. He also shows how temporary flexibility can help revive underperforming listings.

With: Eric Moeller & Kaye Putnam

Kaye Putnam and Eric Moeller share how Freewyld Foundry reached its first profitable quarter and created a team bonus plan. They explain how sharing profit strengthens alignment, culture, and ownership across the company. They also reveal their long-term vision of helping team members invest in Freewyld’s future real estate projects.

With: Jasper Ribbers

Jasper Ribbers breaks down why the 2026 World Cup will create massive demand across host cities.
He explains why hosts should raise prices early as six million visitors look for places to stay.
With the right strategy, Ribbers says two months could match a full year of revenue.

With: Eric Moeller, Kaye Putnam

Kaye Putnam and Eric Moeller explore how leadership shifts during Freewyld’s rapid growth. They discuss building intentional culture, leading with humility and hunger, and keeping a remote team aligned as the company scales.