STR Investing, The Podcast
Unlock financial freedom through short-term rental investing with hosts Taylor Jones and Mark Lumpkin. Each week, they sit down with the biggest names in the STR industry to uncover what’s working right now — from acquisitions and design to operations, marketing, and scaling portfolios.
Taylor has helped acquire and manage over 500+ STRs, while Mark brings years of hands-on experience transforming properties into high-performing investments.
Together, they break down real strategies, real numbers, and real stories that help investors grow smarter and faster.
Whether you’re buying your first Airbnb or expanding a multi-market portfolio, this show is your roadmap to building wealth and freedom through short-term rentals.
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STR Investing, The Podcast
How To Underwrite A Short Term Rental
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Taylor Jones & Mark Lumpkin
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Episode 61
Fail forward, buy smarter.
In this solo deep-dive, Taylor breaks down real-world STR underwriting—no hype, just numbers. If you’ve ever “made a spreadsheet sing” to justify a deal, this one’s for you. Learn the exact framework he’s used to evaluate hundreds of thousands of properties over the past four years and how to stay disciplined when emotion wants the win.
What you’ll learn
- The anatomy of a winning pro forma: purchase price, debt structure, closing costs, and true Total OOP (down payment, reno, amenities, furniture, vendors).
- Building an optimization list that actually moves RevPAR (from paint to pickleball).
- Revenue the right way: comping like-for-like, using data tools (AirDNA/Rabbu), and modeling Low / Mid / High scenarios.
- Expense reality check: utilities, supplies, PM software, cleaning fees in vs. invoices out, HOA, taxes, insurance, CapEx & reserves.
- NOI vs. Free Cash Flow: what lives “above the fold,” why debt service ≠ mortgage, and how to compare deals apples-to-apples.
- Return stack 101: cash-on-cash, principal paydown, long-view appreciation (why you should zoom out 20–25 years), and a primer on the STR tax play.
- The baseball mindset: why looking at hundreds of deals to land a few great ones is normal—and healthy.
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Episode Sponsored By:
STR Search
STR Search is the industry leading property finder service. They've helped investors acquire over 265+ profitable STRs across the US. If you'd like the data professionals to help you find your next STR, reach out to STRsearch.com
