269: How To Start Living Off Rentals with Kirby Atwell

In this episode of Zen and the Art of Real Estate Investing, Jonathan welcomes Kirby Atwell, an Army veteran, real estate investor, and host of the Living Off Rentals podcast. Kirby’s journey from military service to financial freedom offers a practical roadmap for investors seeking a sustainable, high-cash-flow strategy. Kirby’s interest in real estate began in 2006 while stationed in El Paso, Texas, after reading “Rich Dad Poor Dad.” His first purchase, a turnkey property across the street, sparked a career that would include multiple rental acquisitions before leaving the Army in 2011. Initially, Kirby built a high-volume house-flipping business, completing around 75 projects in five years. While the operation looked successful from the outside, the overhead, contractor management, and constant pressure to “feed the machine” made it an unsustainable treadmill. Recognizing that his initial goal was freedom, not endless hustle, Kirby pivoted. After a short return to corporate work, he began acquiring long-term rentals in Northwest Indiana. A chance experiment, turning a basement apartment into an Airbnb, netted $22,000 in one summer, far exceeding the annual income from some of his long-term units. This discovery led him to transition entirely to short-term rentals, focusing on modestly priced multi-unit properties that could also work as long-term rentals if needed. Kirby now manages 39 short-term rental listings, primarily clustered near Michigan City and Valparaiso, Indiana, with additional properties in southwest Florida. By concentrating on one region before expanding, he built economies of scale in operations, supply management, and cleaning services. His strategy centers on risk-averse investing—buying affordable properties in areas with steady demand drivers, from national parks to local universities—while maintaining the flexibility to pivot between rental strategies. Jonathan and Kirby discuss the power of “reps” in real estate, why clustering investments boosts efficiency, and how to vet short-term rental opportunities by analyzing local competition. Kirby also shares his process for furnishing units cost-effectively, his rule of thumb for net returns (1% of purchase price monthly), and the importance of avoiding over-leverage. Today, through his Living Off Rentals platform, Kirby coaches other investors to build similar portfolios. His philosophy combines conservative acquisition criteria with creative income strategies, allowing investors to create both cash flow and long-term equity without the burnout of high-volume flipping. In this episode, you will hear: The importance of taking action before having everything figured out Why scaling a flipping business often leads to burnout and thin margins How an experimental basement Airbnb reshaped Kirby’s investing approach The advantages of clustering short-term rentals in one market Identifying risk-averse properties with strong cash flow potential Follow and Review: We’d love for you to follow us if you haven’t yet. Click that purple '+' in the top right corner of your Apple Podcasts app. We’d love it even more if you could drop a review or 5-star rating over on Apple Podcasts. Simply select “Ratings and Reviews” and “Write a Review” then a quick line with your favorite part of the episode. It only takes a second and it helps spread the word about the podcast. Supporting Resources: Living Off Rentals website - www.livingoffrentals.com Living Off Rentals on YouTube - www.youtube.com/@LivingOffRentals Find Living Off Rentals on Facebook - www.facebook.com/LivingOffRentals Living Off Rentals on Instagram - www.instagram.com/livingoffrentals Connect with Kirby Atwell on LinkedIn - www.linkedin.com/in/kirbyatwell Living Off Rentals on TikTok - www.tiktok.com/@livingoffrentals 4 Steps to Living Off Rentals - www.livingoffrentals.com/start Website - www.streamlined.properties YouTube - www.youtube.com/c/JonathanGreeneRE/videos Instagram - www.instagram.com/trustgreene Instagram - www.instagram.com/streamlinedproperties TikTok - www.tiktok.com/@trustgreene Zillow - www.zillow.com/profile/StreamlinedReal Bigger Pockets - www.biggerpockets.com/users/TrustGreene Facebook - www.facebook.com/streamlinedproperties Email - [e-mail] Episode Credits If you like this podcast and are thinking of creating your own, consider talking to my producer, Emerald City Productions. They helped me grow and produce the podcast you are listening to right now. Find out more at https://emeraldcitypro.com Let them know we sent you.