#276 - How to Turn Failure into Freedom with Real Estate Investing - Matt Aitchison

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 Kirby dive into his transition from single-family rentals to commercial properties, the power of mentorship, and the creative financing strategies he's using to close deals in today’s challenging market.

Key Takeaways:

[01:00] Introducing Matt Aitchison and his background
[02:00] The two types of people when facing adversities and setbacks
[08:06] Getting a mentor as a real estate investor
[13:59] If you want extraordinary results, be willing to do extraordinary things
[17:49] Transition from single-family rentals to commercial real estate investing
[23:23] There's a bull market in any bear market
[24:17] Season of seller finance
[31:22] The beauty of commercial real estate
[36:45] The journey of real estate investing is every deal is going to have challenges
[43:12] Real estate slowly becomes less about their money, and more about solving problems
[48:10] Connect with Matt Aitchison
[49:18] Outro

Guest Links:

Website: https://www.mattaitchison.com/
Imagos Group: https://www.imagosgroup.com/
Millionaire Mindcast Podcast: https://www.millionairemindcast.com/ 
Wise Investor Collective Mastermind Group: https://wiseinvestorcollective.com/

Show Links: 

Living Off Rentals YouTube Channel -https://www.youtube.com/c/LivingOffRentals
Living Off Rentals Facebook Group -www.facebook.com/groups/livingoffrentals
Living Off Rentals Website -www.livingoffrentals.com
Living Off Rentals Instagram -www.instagram.com/livingoffrentals
Living Off Rentals TikTok - www.tiktok.com/@livingoffrentals