112: Incarcerated Life and Second Chances with Aaron Smith

112: Incarcerated Life and Second Chances with Aaron Smith

Author: Joey Held May 4, 2022 Duration: 32:01

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.


Each week, Joey Held sits down for a genuine chat with someone quietly building, creating, or exploring something fascinating. Good People, Cool Things moves beyond the usual headlines to find the entrepreneurs sketching ideas in coffee shops, the musicians crafting albums in home studios, and the writers piecing together stories that haven't yet found a mainstream audience. These conversations live in the rich space where society, business, and culture overlap, revealing the personal journeys behind interesting projects. You'll hear the unpolished stories of how things actually get made-the late-night doubts, the unexpected breakthroughs, and the simple joys of doing work that matters. It’s less about generic advice and more about the specific, often quirky, paths people take. This podcast has a simple premise: good people are out there doing cool things, and their experiences are worth sharing. Tuning in feels like pulling up a chair with friends who remind you that passion projects and side hustles can grow into meaningful lives. The tone is consistently warm and curious, making every episode an engaging dive into the human side of entrepreneurship and creativity. Discover a new story each week, and you might just find the spark for your own next endeavor.
Author: Language: English Episodes: 100

Good People, Cool Things
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