Episode 26: “Modern Day Robin Hood”

Jason Wheeler, 47

San Bernardino, CA • Green River, UT • Denver, CO • Pikes Peak, CO

What started as casual conversation on a cross-country trip quickly revealed something bigger: two strangers headed to Los Angeles to visit their sisters and see Kendrick Lamar & SZA. That chance meeting turned into an unlikely friendship—and a story worth telling.

Jason’s early life began in Indianapolis’ Hallville neighborhood, shadowed by family tragedy before he was even born. Despite earning multiple basketball scholarships, his energy gravitated toward hustling more than academics. After a run as a successful mortgage broker, he plunged into the “scam game”—a decision that would catch up with him later.

At 40, Jason faced his first prison sentence. Six months in solitary confinement during COVID forced him into a brutal kind of introspection. As he puts it: “Prison is a young man’s sport.” That wake-up call shifted his focus to building something real.

Today, Jason manages 42 Airbnb properties nationwide, with a goal of 100 by 2026. His philosophy—everything happens for a reason—drives both his business and his outlook on life.

Part three of our conversation unfolded at 6am in Colorado, recording while searching for a runaway horse named Conway (after Conway the Machine).

From the streets of Cali to the quiet of Colorado, Jason’s journey is a testament to transformation, resilience, and the strange ways paths cross when you stay open.

Thank you Jason, for sparing time from your extremely busy life, to come slow down for a bit. & making the first flight out to my new spot. Thus becoming the first recurring guest on the podcast. Part 4/5 are still ahead.

To follow Jason’s adventures LIVE: https://www.instagram.com/jason.wheeler.297?igsh=a3A4bjAzMmlmdHdj

& Shoutout to Quality Control Music 🎼

#LongLiveYoungSlo-Be

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