#261 - Sportscaster to failing entrepreneur to successful short-term rental investor - Kyle Stanley
Release Date: 02/12/2025
#286 - How to maximize a property insurance claim with a public adjuster - Andy Gurczak
Living Off Rentals
Joining us on this episode of Living Off Rentals is someone who helps property owners navigate one of the most stressful (and misunderstood) parts of real estate investing: insurance claims. Andy Gurczak is the founder of AllCity Adjusting, a public adjusting firm that advocates on behalf of property owners to ensure they get the full payout they’re owed—not just the first offer the insurance company throws at them. In this conversation, Andy breaks down the difference between public adjusters and insurance company adjusters, when to bring a public adjuster on board, and why most owners...
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#285 - How to Use Data to Find and Buy Profitable Short-Term Rentals - Taylor Jones
Living Off Rentals
Joining us on this episode of Living Off Rentals is someone who helps short-term rental investors find the best deals and scale faster using real data. Taylor Jones is a short-term rental investing specialist at STR Search who helps investors build and grow profitable Airbnb portfolios. Listen as he explains how to spot strong STR opportunities using real market and property data—and what red flags to watch for before you buy. You’ll also learn how amenities like pools, pickleball courts, fire pits, and even string lights can seriously boost your booking rates, and why great photography...
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#284 - Building Wealth Across Real Estate Asset Classes for Long-Term Freedom - Brandon Rickman
Living Off Rentals
Joining us on this episode of Living Off Rentals is someone who turned grit, experience, and strategy into over 500 successful home flips and now uses that same knowledge to build long-term wealth through long and short-term rentals, and self-storage. Brandon Rickman is a seasoned real estate investor based in Atlanta who scaled his flipping business to over 100 deals a year. He now owns 865 self-storage units, short and long-term rentals, and a private lending company. In this conversation, Brandon walks us through his journey from learning construction with his dad to building...
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#283 - Build Wealth While Protecting Your Time: The Zen Investor’s Mindset - Jonathan Greene
Living Off Rentals
In this episode of Living Off Rentals, we're joined by a thought leader in the real estate investing space who has built a diverse and intentional portfolio, all while designing a lifestyle rooted in peace, purpose, and efficiency. Jonathan Greene is the host of Zen and the Art of Real Estate Investing and has been investing in real estate since his early twenties. Raised by a real estate-savvy father, Jonathan learned firsthand the power of buying smart and holding long-term. But for Jonathan, it’s never been just about building wealth: it’s about doing it without sacrificing time or...
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#282 - How to Choose the Right Financing for Your First (or Next) Real Estate Deal - Christian Bachelder
Living Off Rentals
Joining us in this episode of Living Off Rentals is someone who brings clarity to one of the most confusing parts of real estate investing: financing. Christian Bachelder is the co-founder of The One Brokerage and one of the most trusted lending advisors in the real estate investing space. He is a UC Berkeley graduate, and a former chemical engineer turned seasoned investor. He now helps others invest in real estate by connecting them with the right financing strategies. Listen as he breaks down the different types of loans available to investors—from traditional mortgages to DSCR and hard...
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#281 - How to Scale a Rental Portfolio with $0 by Finding Overlooked Sellers - Daniel Kwak
Living Off Rentals
Joining us in this episode of Living Off Rentals is someone who proves that starting from scratch doesn’t mean staying stuck. Daniel Kwak is a real estate investor, coach, author, and one half of the renowned Kwak Brothers. By age 23, he and his brother had already syndicated over $10 million in real estate deals—but what makes Daniel’s journey remarkable is how it started: no money, no credit, and no connections. Yet in just one year, he scaled to 87 rental units. In this episode, Daniel shares exactly how he achieved financial freedom by focusing on overlooked sellers and creative...
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#280 - The Co-Host Model That Built a 130-Property STR Empire - Julie George
Living Off Rentals
Joining us in this episode of Living Off Rentals is someone who went from burnout in corporate sales to building and selling one of the most impressive short-term rental empires in the world. Julie George is the author of Million Dollar Host and the founder of a short-term rental business that scaled to 130 properties and generated $8 million in just three years. She did this through a unique co-hosting model where she scaled by empowering her team to take ownership within her business. In this episode, she breaks down how she turned a single Airbnb listing into an empire, the systems she put...
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#279 - Inside the Assisted Living Model That Nets $40K/Month - Brett Chotkevys
Living Off Rentals
Joining us in this episode of Living Off Rentals is someone who is redefining the way investors think about real estate—and doing it in one of the country's most needed and profitable niches. Brett Chotkevys is the co-founder of Platinum Assisted Living Luxury and the creator of a revolutionary assisted living mansion model that blends top-tier residential luxury with world-class elder care. After flipping 200+ homes, Brett transitioned to developing 16-bed luxury assisted living homes that generate $40,000 in monthly net income per facility. In this episode, Brett explains how assisted...
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#278 - How to Use Accelerated Depreciation to Save Thousands on Taxes - Dawn Polin
Living Off Rentals
Joining us on this episode of Living Off Rentals is someone who helps rental property investors unlock huge tax savings through accelerated depreciation. Dawn Polin is a Certified Public Accountant (CPA) with over 20 years of experience, including managing the cost segregation practice at a large CPA firm. Today, she’s the Managing Director of Rental Property Refund, a platform that simplifies and automates accelerated depreciation studies so everyday investors can take full advantage of this powerful tax strategy. Listen as she explains what cost segregation is, how this strategy can...
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#277 - The EASIEST Financing Option for Short Term Rental Investors: DSCR Loans - Jay Anderson
Living Off Rentals
Joining us on this episode of Living Off Rentals is someone who’s helped Kirby secure five different DSCR loans over the past year and a half. Jay Anderson is a lender with Visio Lending, a company that specializes in DSCR loans for investment properties. A DSCR (Debt Service Coverage Ratio) loan allows investors to qualify based on a property’s income—not their personal income. It’s a great option for self-employed investors, those without W2 income, or anyone looking to scale without hitting debt-to-income limits. As an active investor himself, Jay knows what it...
info_outlineIn this episode of Living Off Rentals, we’re joined by someone who went from sportscaster to struggling entrepreneur, before finally finding the success and fulfillment he was looking for through short term rental investing.
Kyle Stanley spent a decade as a serial entrepreneur before discovering real estate. At 31, he took a chance on investing and quickly realized the power of short-term rentals to generate significant cash flow and transform his financial future.
What started as listing a spare room on Airbnb turned into a thriving short-term rental business. Kyle scaled his portfolio, built a management company that grew to 70+ units, sold that company, and now lives off his own rentals while teaching others how to make money through real estate investing via his podcast and platform, The Fearless Investors.
This episode is full of valuable insights on scaling with intention, deciding on a real estate exit strategy, creative financing, and more. Enjoy the show!
Key Takeaways:
[00:00] Introducing Kyle Stanley and his background
[03:48] His decision to get started investing in short-term rentals
[06:59] Skills + Best Exit Strategy
[17:09] Kyle on building true financial freedom
[20:50] What is Creative Financing?
[27:26] Identifying properties to invest
[33:08] Difference between people who struggle and people who are successful in short-term rental investments
[37:31] Quantity versus Quality in short-term rentals
[46:21] Connect with Kyle Stanley
Guest Links:
Website: Visit https://thefearlessinvestors.co/ for a free 15-minute training
Email: [email protected]
Show Links:
Living Off Rentals YouTube Channel – youtube.com/c/LivingOffRentals
Living Off Rentals YouTube Podcast Channel - youtube.com/c/LivingOffRentalsPodcast
Living Off Rentals Facebook Group – facebook.com/groups/livingoffrentals
Living Off Rentals Website – https://www.livingoffrentals.com/
Living Off Rentals Instagram – instagram.com/livingoffrentals
Living Off Rentals TikTok – tiktok.com/@livingoffrentals