What if your short-term rental could save you hundreds of thousands in taxes and generate serious cash flow? That’s exactly what happened to Derek Gisreal. In this episode of STR Investing, Derek shares how a single investment—originally just a tax strategy—became a full-fledged short-term rental business.

We cover:

• The tax loophole that saved him nearly $200K
• How he tripled the revenue of an existing STR
• Using a cash-out refi to scale faster
• The power of personalized guest experiences—handwritten notes, welcome screens, and more
• Partnering with developers to create STR-ready homes

Derek and his wife turned their passion for travel and design into a profitable STR business. Tune in to hear their journey and get practical tips to optimize your own rental!

Are you tired of high OTA fees eating into your short-term rental profits? In this episode, Mark Lumpkin sits down with direct booking expert Mark Simpson, founder of Boostly, to uncover the secrets to maximizing direct bookings while keeping a balanced approach to Airbnb, Booking.com, and other platforms.

Mark shares valuable insights on:

• The real percentage breakdown of direct vs. OTA bookings and why 65% direct is the sweet spot.
• Why going 100% direct booking can be just as risky as relying entirely on OTAs.
• Simple but powerful strategies to drive direct bookings—including a game-changing messaging tactic that can land you instant reservations.
• The biggest mistakes hosts make with pricing and why some direct booking sites charge more than Airbnb (and how to fix it!).
• The top tools and tactics for increasing direct bookings, including Get Directo and other must-have resources.
• How to structure your OTA listings to drive traffic to your direct booking site without breaking platform rules.

Mark Simpson has helped set up over 1,000 direct booking websites, and he’s here to share his playbook on how to make your short-term rental business thrive.

Connect with Mark Simpson and get the exact template he uses to generate bookings: DM him “template” on Instagram @boostlyuk.

Don’t forget to like, subscribe, and share this episode with your fellow hosts.

Let’s take control of our bookings!

Host Taylor sits down with tax strategist Nathan Sosa to break down the biggest tax advantages available to short-term rental investors. They dive deep into key strategies, including material participation, real estate professional status, cost segregation, bonus depreciation, and the game-changing 1031 exchange.

Whether you’re a first-time investor or managing a growing portfolio, this episode is packed with expert insights to help you maximize deductions, optimize cash flow, and legally minimize your tax burden.

Don’t leave money on the table—tune in and learn how to make tax laws work in your favor!