DiscoverLiving Off Rentals#303 - From 9th Grade Dropout to Early Retirement with 150 Real Estate Units - Matt Hawkins
#303 - From 9th Grade Dropout to Early Retirement with 150 Real Estate Units - Matt Hawkins

#303 - From 9th Grade Dropout to Early Retirement with 150 Real Estate Units - Matt Hawkins

Update: 2025-12-03
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What does it take to go from dropping out of school in ninth grade to owning more than 150 rental units and retiring in your 40s?

Matt Hawkins, also known as the Lumberjack Landlord, is a self-taught investor who now manages over 50 buildings and 400 tenants with just one employee — all from his phone. He joins us on this episode of Living Off Rentals to unpack his incredible journey from humble beginnings to financial freedom.

Listen as he shares how early mistakes, creative deal-making (like buying a city-owned police station), and consistent systems helped him build a real estate empire that now provides freedom, flexibility, and purpose. Enjoy the show!

Chapters:

[00:00 ] Introducing Matt Hawkins and his background

[01:45 ] From dropping out of high school to becoming a real estate investor

[05:40 ] Investing in the stock market and losing everything

[07:41 ] How his first real estate deals evolved over time

[08:44 ] Use house hacking as the ultimate foundation for financial freedom

[13:49 ] Retire early by designing a business that funds your ideal life

[18:21 ] Scale a rental portfolio efficiently using systems and one key employee

[20:52 ] Think like an asset manager, not just a landlord

[24:34 ] Win competitive deals using the "reverse offer strategy"

[28:00 ] Why great deals matter more than more deals

[29:03 ] Connect with Matt Hawkins

[30:51 ] Outro

Guest Links:

Website: https://www.lumberjacklandlord.com/ 

Instagram: https://www.instagram.com/lumberjack_landlord/?hl=en 

YouTube: https://www.youtube.com/c/LumberjackLandlord 

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 

 

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#303 - From 9th Grade Dropout to Early Retirement with 150 Real Estate Units - Matt Hawkins

#303 - From 9th Grade Dropout to Early Retirement with 150 Real Estate Units - Matt Hawkins

Kirby Atwell