#112: Incarcerated Life and Second Chances with Aaron Smith

Many of us want to make more money. We’ll find side hustles, or work hard in our main gig so we can negotiate for more. Would you take up to $15,000 a day?

Aaron Smith, founder of Escaping The Odds, was doing just that on the south side of Chicago. The problem: His business with a heroin drug operation. He was later indicted and sentenced to 12 years in federal prison, serving nearly a decade of that time.

While in jail, Aaron’s mindset changed. He decided it was time to switch hustles, or as he puts it, to go from selling dope to chasing dreams. But that entrepreneurial spirit never left him, and today Aaron is a business owner, podcast producer, and mentor. He’s out to change the narrative that people who have been incarcerated are beyond hope. They deserve a second chance.

And through Escaping the Odds, Aaron is helping them get those opportunities.

Highlights of our conversation

  • Something most people wouldn’t expect about being incarcerated, and the mindset shift Aaron had to go from selling dope to chasing dreams. (3:12)

  • The first thing Aaron did when he got out of prison. (4:53)

  • Why Aaron started Escaping the Odds and how he learned about podcasting while incarcerated. (7:32)

  • The ways Aaron has built up his podcasting network and why Instagram has been such a powerful tool for finding guests. Plus, some of the other opportunities that have come from podcasting. (10:18)

  • One of the most unusual guests Aaron has had on his podcast — you can listen to that episode here. (13:28)

  • The most surprising part about running his business U-Turn Transport and some of the resources and opportunities he’s seen throughout the pandemic. (16:32)

  • Some additional Instagram tips to help you grow your brand or business. (22:14)

  • What to do when you’ve got an idea but aren’t sure where to start. (25:43)

  • Stereotypes we should stop thinking about incarcerated people. (26:45)

Where to find Aaron Smith

Learn more about Aaron and his podcast at escapingtheodds.com.

Connect with the show on Instagram.

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Buy a copy of Kind, But Kind of Weird: Short Stories on Life's Relationships.

Pick up some merch at the shop.

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