In 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: info@fearlesskyle.com

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