#261 - Sportscaster to failing entrepreneur to successful short-term rental investor - Kyle Stanley
Release Date: 02/12/2025
#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...
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#276 - How to Turn Failure into Freedom with Real Estate Investing - Matt Aitchison
Living Off Rentals
Joining us on this episode of Living Off Rentals is Matt Aitchison — a hotelier, investor, and host of the Millionaire Mindcast podcast — whose journey through adversity is nothing short of remarkable. After hitting rock bottom in college and spending time in jail, Matt made a pivotal decision to transform his life. He went on to flip hundreds of homes, build a massive single-family portfolio, and is now scaling a commercial and hospitality real estate empire as CEO of Imagos Hospitality Group. Matt shares how he learned to fail forward, using early setbacks as fuel for success. He and...
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#275 - Creating a Lifestyle by Design With Turnkey Real Estate Investing - Ali Boone
Living Off Rentals
Joining us on this episode of Living Off Rentals is someone who escaped the corporate grind and built a lifestyle by design through turnkey real estate. Ali Boone is an engineer, rugby player, pilot, adventurer, and the founder of Hipster Investments. She’s also the author of three different real estate books, including Not Your How-To Guide to Real Estate Investing. In this conversation, Ali shares how she transitioned from aerospace engineering to buying hands-off rental properties—and how that led to her helping others do the same. She breaks down the fundamentals of what turnkey...
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#274 - How Going All In on One Real Estate Market Built Big Wealth (And Community) - Jonna Weber
Living Off Rentals
Joining us in this episode of Living Off Rentals is Jonna Weber, a seasoned buy-and-hold investor with two decades of experience investing in single-family and small multifamily properties in Idaho. Jonna runs the Boise Real Estate Investor Network, where she helps connect and support investors across the state. She is also the host of the Idaho Real Estate Investors Podcast. Listen as she shares her journey from buying her first property in 2003 to building a thriving investor community. You’ll hear how she gradually grew her portfolio, why she chose to focus on one market, and how building...
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#273 - Converting Garages to ADU's to create massive value
Living Off Rentals
In this episode of Living Off Rentals, we’re joined by Henry Russell—a Navy veteran, entrepreneur, and multifamily real estate investor with over 15 years of experience. Henry Russell attended the U.S. Naval Academy and went on to complete multiple combat tours in Iraq as a Naval officer. After leaving the Navy, he returned to Baltimore, where he founded a construction company, a property management company, and, in 2020, launched RFC Capital, a veteran-owned investment firm based in San Diego. RFC Capital specializes in a unique and impactful strategy: converting underutilized carports...
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#272 - Key Legal Considerations When Scaling a Rental Business - Diana Khan
Living Off Rentals
Joining us on this episode of Living Off Rentals is an award-winning attorney, entrepreneur, and mom of three who owns seven businesses—including her own law firm. Diana Khan, named one of the Top 40 Young Lawyers in the country, simplifies the legal side of real estate investing and shares how to structure your business to protect your assets and scale with confidence. From LLCs to holding companies to personal trusts, she walks through what each one is and what every rental property owner needs to know to grow the right way. Whether you’re buying your first rental or rapidly...
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#271 - How He Replaced His Tech Salary with Short Term Rentals - Stylianos Kalamaras
Living Off Rentals
Joining me on this episode of Living Off Rentals is someone who’s been an athlete, Navy veteran, cyber engineer, and now, a short-term rental investor. Stylianos “Steve” Kalamaras is a fighter in every sense of the word. A former boxer turned real estate investor, he’s built an impressive short-term rental portfolio that brings in solid cash flow to rival his tech salary. He is also a member of my First Vacation Rental Investment Blueprint Program, and since joining, he’s closed on a handful of standout deals, including one where he converted a two-unit into a three-unit...
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#270 - The Social Media Strategy That Generated $50K in Direct Bookings - Kamille Longstreet
Living Off Rentals
Joining us in this episode of Living Off Rentals is someone with a 20-year background in the digital media space. Kamille Longstreet is a real estate investor, influencer, and co-founder of Stay Booked, a company that helps vacation rental owners master independent marketing to grow their bookings. With over 20 years of experience in the media and digital marketing industry, Kamille was able to generate over $50K in direct bookings (on top of her Airbnb revenue) and grow her Instagram following to 10K+ in less than 9 months. Listen as she shares the social media strategies to get...
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#269 - How to Boost Rental Revenue with Direct Bookings - Ollie Laing
Living Off Rentals
In this episode of Living Off Rentals, we’re joined by UK-based short-term rental investor Ollie Laing, who’s cracked the code on direct bookings. While most hosts rely heavily on platforms like Airbnb and Booking.com, Ollie generates over 50% of his revenue from direct bookings through his own website. In this episode, he shares exactly how he does it. He also talks about some of the key lessons he’s learned while building a successful vacation rental business, including how he manages properties remotely, his go-to tactics for driving direct bookings, and the strategies he uses to...
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#268 - Figuring out your true net worth and gaps in your wealth - Donald Pearson
Living Off Rentals
Joining us in this episode of Living Off Rentals is Donald Pearson, a Wealth Management Advisor at Westpac Wealth Partners who holds an impressive list of certifications. Donald is a CERTIFIED FINANCIAL PLANNER™ (CFP®) and a Retirement Income Certified Professional® (RICP®), and he helps individuals and business owners reach their financial goals as efficiently as possible. A graduate of the United States Naval Academy, Donald was commissioned as a Marine Corps officer and later served as a Financial Manager in the Marine Corps. Listen as he shares his full financial journey, the key...
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