How to Sell Your Short-Term Rental for More Money with Tyler Coon

In this episode, Zeke sits down with Tyler Coon, founder and CEO of Savvy Realty, a network of over 50 short-term rental specialists across 25+ markets in the United States. Tyler shares how he went from renting out a spare bedroom to afford his first home in 2020 to building a nearly $20 million short-term rental portfolio in just six years. They dig into what makes a great STR agent, how Tyler's team uses local case studies instead of relying purely on data algorithms, and why experiential amenities like indoor laser tag arenas and outdoor pools are reshaping what investors need to compete. Tyler also breaks down market saturation, how appraisals are starting to catch up to luxury short-term rental values, tips for maximizing your sale price, and his read on where Airbnb and Booking.com are headed next. In This Episode, You'll Learn: How Tyler turned a single homestay rental into a $20 million short-term rental portfolio What separates a great short-term rental agent from a typical real estate agent Why Tyler relies on local case studies instead of trusting data algorithms alone How to tell if a short-term rental market is getting saturated What outdoor amenities and design features are driving bookings in 2026 The right way to price and prepare a short-term rental for a maximum sale Why appraisals are starting to catch up with luxury short-term rental value What's changing with Airbnb and Booking.com and what it means for hosts Chapters 00:00 Introduction to Short-Term Rentals and Tyler Coon 01:48 Tyler's Journey into Short-Term Rentals 05:24 Transitioning from Personal Success to Helping Others 07:29 What Makes a Great STR Agent? 09:32 Tools and Strategies for STR Success 13:18 Evaluating Property Potential and Market Trends 17:20 Pushing the Envelope in STR Investments 20:30 Base Camp vs. Destination Properties 22:53 Navigating Market Trends and Barriers to Entry 23:57 The Evolving Landscape of Short-Term Rentals 25:58 Investment Strategies and Budgeting for Success 29:03 Maximizing Value: Selling Short-Term Rentals 33:24 OTA Dynamics and the Future of Booking Platforms 38:54 Building a Brand and Portfolio in Short-Term Rentals Connect with Tyler Coon LinkedIn:   / tyler-coon   Website: https://www.savvy.realty/ Grab the free Radical Hospitality Starter Kit → root-ad.com/starter Connect with Zeke Freeman: Instagram: @zekefreeman_rootarchitecture and @rootarchitecture YouTube: @rootarchitecture Facebook: @RootArchitectureandDevelopment LinkedIn: Zeke Freeman X/Twitter: @zfreemanroot Ready to get started with your hospitality project? https://root-ad.com/ Get in Touch: Stay connected with the Radical Hospitality podcast for more episodes exploring the intersection of architecture, design, and unforgettable guest experiences. Follow, Rate & Review: If you enjoyed this episode, please subscribe, leave a review, and share it with your network! Your support helps us continue delivering conversations with industry leaders redefining hospitality.