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Switching the hustle: interview with Aaron Smith

Since his release from federal prison, Aaron Smith has devoted his energies to helping others emerging from incarceration make a fresh start—by finding jobs in the trucking industry.

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We all make mistakes. What matters is what we learn from them and what we do moving forward with our lives.

For those who have served time in prison, the stigma can last a long time, and that can make it hard for them to reacclimate upon release. It helps to have guidance from someone who’s been there and can help them start off on the right foot. Part of that is having a job that allows them to build a new life and not turn back to whatever landed them in prison in the first place.


Aaron Smith has been there. After serving his time in prison, he founded a media company and program known as Escaping the Odds to provide others with practical assistance in life skills, job training, and an entrepreneurial path toward becoming truck owner-operators.

Smith was recently a guest on DC Velocity’s “Logistics Matters” podcast, where he spoke with Senior Editor Victoria Kickham about his work. 

Q: What is Escaping the Odds, and why did you start it?

A: Escaping the Odds Media is a multimedia company based in Chicago. It initially started off with a podcast, as that was the quickest and most cost-efficient way to get [the word] out about what we wanted to do.

I was formerly incarcerated, and I wanted to change the narrative and actually get stories out there from an unlikely source—men and women who had been incarcerated. I wanted to provide a platform where they could talk not just about their experience being incarcerated, but also about what led to their [fulfilling their] entrepreneurial dreams and being able to start businesses.

That is where it started, and it eventually spiraled off into [the world of] trucking and transportation.

Q: Your organization has a heavy focus on trucking, transportation, and logistics. How did you become interested in this field, and why do you continue to focus on supply chains?

A: Back when I was going through adjudication of my criminal case, I had to get a job. I was on bond, and I started working for one of the largest 3PLs [third-party logistics service providers] in the country. So, I learned the trucking industry from a broker’s perspective. 

Once I was released, I had to get a job, and since I had experience working in the dispatch brokerage arena, I figured that I would get a job doing that. But my end goal was to actually start my own transportation company and also offer opportunities for men and women—not just those who had been incarcerated, but really all men and women with an interest in the field—to help them get their start in the trucking or logistics industry. So that is what I have been doing.

Q: On your website, you talk a lot about “switching the hustle,” going from what you were doing before you were incarcerated to a different career. Why is switching the hustle to logistics and transportation an attractive option for people looking to make a fresh start?

A: Believe it or not, truck driving is one of the most popular positions for people—especially men—who have been incarcerated. There are two reasons for that: First and foremost, the money is somewhat comparable to the money they were making with illicit activities. The other big thing is freedom. You don’t have to go work for a trucking company—although you can, and you can make a nice living that way. You also have the option of being an owner/operator. Those are the reasons it is very appealing to this population.

That is what I’ve been seeing with a lot of my colleagues and people that I was incarcerated with. They get released and get their commercial driver’s license [CDL] and they begin their journey, so to speak.

Q: One of your primary offerings through Escaping the Odds is a class on starting a box truck business. Can you tell us a little bit about that?

A: I partnered with a company called Stretch Finance, [which provides] banking services for formerly incarcerated people. They wanted to pivot a little bit and start offering courses [geared toward] this particular population of people who were formerly incarcerated or individuals who just wanted to do something different with their lives.

I also partnered up with another gentleman, Ed Hennings, who had a trucking company [Go Time Trucking] that used box trucks, which you don’t have to have a commercial driver’s license to operate. We knew that there was a lot of freight out there that could move in box trucks, mainly last-mile delivery stuff. So, we created an “A to Z” course where we could teach people how to become a truck owner/operator without having to obtain a commercial driver’s license. Escaping the Odds Media is the producer of that concept.

[Editor’s Note:Escaping the Odds now offers the box truck class via partnerships with correctional institutions.]

Q: It can be costly to get a commercial driver’s license, right? So, since driving a box truck doesn’t require a CDL, this becomes a more affordable route into the trucking industry.

A: Absolutely. It is also a program in which [the classes are offered] on-demand, so it is very flexible for the working person.

Q: We write often about the need for truck drivers and for workers in general throughout logistics. Could you talk about why the broader industry should be paying attention to efforts like yours and about your ultimate goals for the program?

A: The ultimate goal for Escaping the Odds within trucking is to be the conduit for men and women who have a desire to step into this new arena. It is more than just getting a job, right? There are a lot of things that a person who is reintegrating back into society may have to get adjusted to. We want to be that handoff to some of these companies and to continue training and partnering with more and more logistics companies. It is about bringing that credibility to what we’re doing.

Q: Where can people who are interested in your work find you?

A: The Escaping the Odds podcast can be found on Escapingtheodds.com or YouTube. We have another podcast that I am producing called “The Urban Trucker” that tells stories of people of all backgrounds, mainly women and men of color in the logistics industry. It is a great concept for something different.


Listen to the interview.


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