Escaping the Odds Podcast: Former Illinois Inmates Turned Entrepreneurs

Escaping the Odds Podcast looks at Illinois Formerly Incarcerated Turned Entrepreneurs

When you’re making $8k-$15k a day, you’re probably good at what you’re doing or you’re doing something illegal or both.

For Black History Month, I had the opportunity to speak with Aaron Smith, Founder of Escaping the Odds Media. Aaron shares his story of how he was attending Columbia College and also running a heroin operation. For him, this later led to nine years in federal prison. During his time in prison, he noticed that there were business-savvy people. Today, he is changing the narrative of the formerly incarcerated be sharing their stories through his podcast, Escaping the Odds.

Those stories include Illinois inmates who now own a yoga studio or own Chicago restaurants or are real estate brokers and property investors revitalizing a Chicago neighborhood that they once helped to destroy.

“Escaping the Odds is not only a media company but a mindset of overcoming any disadvantage or obstacle. Its a constant state of every day breaking away from the odds of failure. This can be overcoming poverty, mental health issues, prison, etc.,” Aaron shared.

Below is Aaron’s story and how he’s trying to change the narrative of what the formerly incarcerated look like and how they are thriving in Chicago as Entrepreneurs.

Aaron Smith interviewing during Escaping the Odds Podcast
Aaron Smith recording an episode of Escaping the Odds Podcast

Windy City Cosmo: What inspired you to create Escaping the Odds podcast?   

Aaron: I was about seven years into my prison sentence and by this time I had the opportunity to meet brilliant men of all races who were once successful business men and aspiring entrepreneurs. I realized that society had no idea that prison housed such people. In most cases prisoners are depicted as craze criminals that can never change. Some people would go so far as to say they deserve to be there. It was my desire to highlight these men and women who returned to society and Escaped the Odds through entrepreneurship.

In addition my goal was to  humanize us  beyond our prison number. Further more, it would be a great way to build a professional network and combine my passion of prison reform and Entrepreneurship.

Windy City Cosmo: Can you share a little bit about your story – how you went to federal prison and have since rebuilt your life? 

Aaron: I grew up on the south side of Chicago and was the youngest of five children. Both of my parents work but we were still consider the working poor. Education was valued in our household, so I always knew that I would go to college to study business. However, I also wanted the finer thing in life and although I worked a job, I also begin to sell marijuana in high school which eventually led to selling crack cocaine on a small level.

The money became addictive as we averaged about $8k-$15k per day in sales. So by the day, I was a student at Columbia  College and also running a heroin operation.

Aaron Smith, Escaping the Odds

When I was about 19, I was introduced to selling heroin by my oldest brother. Selling heroin was a different level and I began to hustle with him in a  housing project on the South Side of Chicago. The money became addictive as we averaged about $8k-$15k per day in sales. So by the day, I was a student at Columbia College and also running a heroin operation.

At the age of 25, I was investigated by the DEA for heroin distribution and eventually charge and was facing 10 – life in federal prison as a first time offender. I subsequently plead guilty and was sentenced to 12 years in federal prison. I was released to a half way house in Aug. 2018 and was finally free in Feb. 2019.

Since May, I have been a part of Criminal justice reform Initiatives such as Cook County’s Safety and Justice challenge. I currently work a full time and part time position. The dream I had of  creating  a podcast became a reality  Nov. 26, 2018 when I released my 1st episode.

Aaron Smith, Founder of Escaping the Odds
Aaron Smith, Founder of Escaping the Odds Media

Windy City Cosmo: I love your statement: “This is my platform to advocate prison reform and assist in changing societies minds as it relates to the formerly incarcerated.” What are some areas that society gets wrong as it relates to the formerly incarcerated? 

Aaron: Some of the areas society gets wrong about the formerly incarcerated is that we hold no value and once a criminal  always a criminal. In addition,  we are all dangerous and lack the desire to be productive members of  society. 

I think a great place to start is to not believe everything we see/ hear in the media as it relates to prisoners. To take in consideration the person’s back story and to understand that  jail/prison can happen to anyone. Too many drinks at a bar and driving can lead to drastic circumstances which can place the best of society’s citizen in a prison cell. I would tell society to demonstrate empathy and be objective. Lastly I read “The New Jim Crow.”

…Individuals who were selling drugs or as I like to say “economic” crimes already understand the fundamental of business. They were just selling the wrong product.

Aaron Smith, Escaping the Odds

Windy City Cosmo: You interview the formerly incarcerated who become entrepreneurs? What are some of the obstacles these people have had to deal with as they start their business? 

Aaron: One particular obstacle that many formerly incarcerated individuals face to starting a business is the formal know how -setting up a company structure, accounting, payroll.

Based on my experience, individuals who were selling drugs or as I like to say “economic” crimes already understand the fundamental of business. They were just selling the wrong product.

Lastly, access to capital due to most of the formerly incarcerated have never had a strong credit file  or banking relationships.

Windy City Cosmo: Did you find mentors to help you? If so, how did you meet them? 

Aaron: Thankfully, coupled with studying while I was incarcerated and contacting organizations that were open to assisting formerly incarcerated like North lawn dale Employment Network and Sunshine Enterprises PERC program was pivotal to my success. The PERC program was a 12 week business course that assisted people with criminal records that wanted to start a business in Chicago.

Through this program, I begin to meet professionals who witnessed my drive and begin to connect me with others who can help with my goals. Finally, I attended events, where I began to build my professional network and step out of my comfort zone.

Windy City Cosmo: Beyond the podcast, is there anything else you’re doing to help prison reform? 

Aaron: I currently work with Cook County’ Safety and Justice Challenge which has an initiative to reduce the Jail population and Bond reform which  will release non violent,pretrial detainees who can’t afford bail. We facilitate dialogue sessions in  communities that are most affected  by mass incarcerations and receive input on how to best to create a fair justice system.

Support Escaping The Odds Podcast:

To support Aaron and Escaping the Odds Podcast, you can subscribe on Apple, Spotify, iHeart Radio,, Pandora, Google Podcast and anywhere Podcast are distributed. In addition, booking me for speaking engagements and donating to the podcast through

He can be reached at, @escapingtheoddspodcast on Instagram, or 312 871-8833.

Amanda Whitfield
Amanda Whitfield

Amanda Whitfield is a writer and speaker and a relationship builder. She believes that meeting people in person is important. After attending numerous fashion, startup, and creative events, she founded Windy City Cosmo is 2015 to help people make connections in the city as they build their businesses, start and end relationships and see and be seen. Over the past three years, the entrepreneurs she’s interviewed have become the most successful in Chicago and Windy City Cosmo won an award in 2017 for her work for female entrepreneurs.

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