OCTOBER 21, 2025  #155 Short-Term Rental Success: How Ashley Freeman Built a 115-Property EmpireHow do you rebuild your life—and create extraordinary success—after everything falls apart? In this episode, I sit down with Ashley Freeman, a former tennis pro who turned...
SEPTEMBER 30, 2025  #152 Vacation Rental Success: How Allison Bayley Built a 66-Property PowerhouseWhat does real vacation rental success look like? For Allison Bayley, it meant transforming her family’s real estate legacy into a thriving business—one that now manages...
Short-Term Rentals vs. Legacy Vacation Rentals: What Each Side Can Learn From the Other What separates a solo Airbnb host dealing with everything from cleaning companies, to bookings, to which covers to put on the throw pillows on the bed…from a large, professional...
SEPTEMBER 16, 2025 Â #150 Scaling Short-Term Rentals: How Chelsea Cutrer Grew to 25 Properties in Just One YearWhat would it take for you to leave behind a secure, six-figure tech career and bet on yourself instead? For Chelsea Cutrer, the decision came after a...
JULY 31, 2025 You’re a host in the STR world. That means you’re navigating a lot of moving parts. What if I told you that one super important, yet often overlooked, aspect is Airbnb's cancellation policies? To elevate yourself as a host, you need to understand these...
JULY 17, 2025 How much control do you actually have over your STR business? Are you waiting for things to happen, and then responding? Or are you tracking data so that you can stay ahead of the game? If you’re like most of the amazing students inside my STR Success...
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