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Aaron Smith Created a Podcast for the Formerly Incarcerated Who Have Started Their Own Businesses

If you compared Aaron Smith’s situation 13 years ago and compared it to his life today, it would be like night and day. In 2009, the Chicago native was serving time in prison for participating in a large drug operation. But in 2022, he owns and operates Escaping the Odds, a media company that produces positive content including a podcast by the same name where he sits down with other former inmates who’ve started businesses of their own. Aaron uses his online show to encourage and inspire people like him to seek financial freedom after incarceration.

We had the pleasure of speaking with him to discuss his opinions, business, and past.

What made you choose entrepreneurship instead of learning a trade or studying for a degree in prison?

Well, I’ve always been a hustler. Growing up in Chicago, me and all of my peers hustled. Whether it was helping an old lady down the street with her bags, pumping gas, raking leaves, things of that nature. So I’ve always had that entrepreneurial spirit. I also went to college too. I graduated with a business degree back in 2004, a bachelor’s degree. So it was a no-brainer for me. I knew that I didn’t want to work for someone for the rest of my life. I knew that I wanted to have my own independence and financial freedom. And the best way for me to obtain that was to provide some kind of service or product as an entrepreneur.

Why media? What drew you to that?

I graduated with a business major degree, but it was from an art school… I was really into the music business during that time, and I was always just drawn to different forms of media. I don’t know where it came from. I just always enjoyed it whether it was reading magazines, enjoying music, [watching] films. That attracted me.

The podcast, I thought of that when I was incarcerated. There were men that I had really learned a lot from that were former businessmen. And I was like, “You know what? Society has no idea they exist. Let me try this podcast thing out.” Even though I never utilized the podcast [format] before. They weren’t popular when I first went away in 2009, but I knew it was a low barrier to enter and start a podcast, so I wanted to start there.

Were you surprised at how many formerly incarcerated people go on to start their own businesses?

No man, I wasn’t. I knew there were thousands of guys like me. They were just selling the wrong product so we had to switch our hustles up. I knew that when I was on the streets but I really saw it while I was away. Just the ingenuity and the creativity behind those walls. They just don’t have the proper access, whether it’s the funding or different kind of resources to start their own business. So I knew that [the podcast] would take off because it was a voice that people weren’t hearing.

What’s a common misconception that many prisoners have about starting a business once they get out?

The misconception that you’re going to start a business today and be a billionaire next week. Because we come from a lifestyle… where there’s a quick fix. Where you’re broke today and then you have a hundred thousand dollars the next day. And I think that sometimes we take that same mentality when we try to start something legitimate. I’m not saying that you can’t have a wildly successful business in a short amount of time but the probability of it is low.

Why do you see encouraging entrepreneurship among the previously incarcerated important?

Because it’s not only freedom, it’s financial freedom. I’m not saying that if you start a business, you’re going to become a millionaire. Though that definitely can happen. But I think that we’re not given the best opportunities in the job market. And I believe strongly that when you can’t find a job or you can’t find a job that you want, you should create your own job. No doubt there’s going to be some barriers but nevertheless, it can be done. I do think that we hold a certain mentality. That hustler’s mentality. That perseverance. That resilience that successful entrepreneurs have.

As we on the outside accept friends and family back into our lives, what are some things we can do to help them once they return and decide to start their own business?

Connections. Connections, for sure. I’m a strong believer that social capital is peak. I had zero professional networks when I came home.

I like to say that we need butlers in our life. And what I mean by that is, a butler is someone who opens up doors for you, and you need that. You need that person who can leverage their relationship with someone else that can kind of make your situation a little better. And then you do the same thing for the next person. Oftentimes, it’s not going to the people that we know who’s going to support what we’re doing, it’s often the support of some kind of stranger. I think [support] should start with the people closest to you.

You can hear more about Aaron Smith’s story, learn more about his company, and listen to his podcast by visiting the website

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