Benito Castro of Freedom Rides: “Take a moment to reflect on what you accomplish daily”

Take a moment to reflect on what you accomplish daily. I do that every day. I look at my job, my bank account, what I’ve achieved, and what I own. You have to give importance to the things you created for yourself in life. As a part of my series about people who made the journey […]

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Take a moment to reflect on what you accomplish daily. I do that every day. I look at my job, my bank account, what I’ve achieved, and what I own. You have to give importance to the things you created for yourself in life.

As a part of my series about people who made the journey from an addict to an entrepreneur, I had the pleasure to interview Benito Castro, founder of Freedom Rides.

Benito was born and raised in New Orleans, Louisiana. He began his career as a disc jockey at a local radio station and later hosted the popular talk show Hollywood South. With this new job came a larger salary, which in turn fed a gambling habit and eventually led to 150,000 dollars of check fraud. After his release from Elayne Hunt Correctional Center, he founded a non-profit called Freedom Rides, which helps inmates obtain a legal car, liability insurance, and a license upon release.

Thank you so much for doing this with us! Can you describe your childhood for us?

I grew up in New Orleans in the 60s and 70s, which was a very interesting time to grow up in a city like that. My family was typical middle class, though my father was a steamship captain so he was gone months at a time. I was raised by my mother and I didn’t have a lot of friends my own age. With a lot of adults around me, I feel like I grew up very quickly.

Can you share with us how were you initially introduced to your addiction? What drew you to the addiction you had?

There were a lot of neighborhood clubs with illegal gambling rooms in the back during the 1960s and 1970s. My mother used to go to these clubs and would bring me along, even to the racetrack. I was very young when I developed a knowledge of gambling, and I knew how to gamble before most kids even knew what it was.

What do you think you were really masking or running from in the first place?

There’s a lot of self-introspection you have to do to answer this question. Maybe I was hiding that I didn’t have the success I dreamed of when I was young. I was in a sort of narcissistic job in media and radio — I was just a late night radio DJ making 8 dollars or 9 dollars an hour and I wanted the world to think I was doing better than I actually was.

Can you share what the lowest point in your addiction and life was?

I was sitting in a game house parking lot having just lost everything to my name. I don’t want to say I thought about suicide, but you definitely think to yourself, “What’s the next step?” Suicide didn’t cross my mind but I knew everything was coming to a head. I had mounting debts and even sold my dad’s Rolex to a stranger at a game house. I took 300 dollars for something worth thousands — I’ll never forget that.

Can you tell us the story about how you were able to overcome your addiction?

After a while I just knew that there had to be something better. The turning point for me occurred even after I completed my incarceration sentence. I had an extremely rough day at work and after I got home I actually thought about going to the game house. I went outside, hit the start button on the keys for my brand new car, and began to walk towards it. But something stopped me in my tracks — I looked at my phone and checked my bank accounts. I looked at my car, my house. I thought to myself, “If I get into that car, I’d be taking the first step towards losing everything once again.” I turned the car off and went back inside.

How did you reconcile within yourself and to others the pain that addiction caused to you and them?

Taking personal inventory of what I’ve wasted and what I have left has given me an incredible drive to accomplish as much as I can before it’s too late. I know I hurt people around me, so I try to pay back any debts I owe and make myself available to them for anything they need.

When you stopped your addiction, what did you do to fill in all the newfound time you had?

I focused on work. From my job managing marketing at supermarkets, to the time I put into launching Freedom Rides. Work became my life and that kept me from falling back into my old habits. I wanted to make sure my time served meant something, so from bettering myself to giving back to my facility and the system that changed my life, work has become incredibly important to me.

What positive habits have you incorporated into your life post addiction to keep you on the right path?

Staying busy. Ever since the COVID-19 crisis began, we’ve been feeding so many people and communities and I really don’t have much free time. When I’m not at my day job, all of my spare time is spent donating back to the community with Freedom Rides.

Can you tell us a story about how your entrepreneurial journey started?

Access to education played a major role in my success. It gave me an opportunity and a second chance. A lot of people when they come in think they’ll never get another bridge. When I was incarcerated, I used a Securus tablet to access free courses that gave me the credits to earn a degree from Ashland University. I can’t express how invaluable free education and reentry resources were while in prison. It changed the trajectory of my life. I was in a pre-release process at the facility and I was just getting ready to graduate from Ashland. A gentleman from the Department of Corrections (DOC) showed up to tell people how they could go about getting a license once released. There were about 100 people in the room, and when they asked how many had a license before, only three people raised their hands, myself included. Even though they had no license, most of these people indicated they did have cars and had driven, which is when I discovered the concept of “riding dirty.” Many of these people had been violating the law their entire life and had no idea. They would get a car from a friend and just drive without a license of insurance. These men would be violating the law — and their parole — the moment they started a car on the outside. This kind of thing could easily land them back in jail.

My term paper was due for my entrepreneurship class right around that time — the topic was to create a program that would help my community. My community at that time was the incarcerated, and I thought these guys needed access to transportation. We partnered with a local vo-tech to help get legal vehicles. Guys enrolled in job-release programs could save money in a separate Freedom Rides account through JPay and have enough funds so they can have a legal vehicle, insurance and a driver’s license the moment they walk out of prison.

There are so many vehicles just sitting around. Think about used car lots — there are so many junkers that cannot be resold — but they can be refurbished by/for incarcerated individuals. I think that’s why Freedom Rides was born, to put legal drivers on the road. So many folks don’t think they’re violating the law because driving dirty can be a part of culture. They get a car and think they don’t need insurance, but to have a license and insurance is the first step towards a positive, legal release. One of the best feelings is that when a cop gets behind me on the road, I have no fears that I’m doing anything in violation of my probation.

What character traits have you transferred from your addiction to your entrepreneurship. Please share both the positive and negative.

The drive. As a gambling addict, I was always desperate for a win which requires drive, even though it’s negative. I still have that drive, but have learned to channel it towards the positive. I want to see Freedom Rides succeed and be incorporated in other states — that’s what I’m driven towards right now. Once we do a three year study and show we can reduce recidivism we will be able to license the program to other states. That’s what I look for. I’m 60 years old now, I have 10 or 15 good years left, and during that time I want to see Freedom Rides become something throughout this country that changes lives. I have a limited amount of time to make it happen — I wasted too many years.

Why do you think this topic is not discussed enough?

Gambling addiction isn’t discussed more because so many people have it and it doesn’t have the stigma of drug or liquor addiction. People view it as just having a good time in the game houseeven though your “vacation” really consisted of your losing 10,000 dollars. Gambling is marketed differently too — you don’t see ads for remedy, but with gambling it’s everywhere. And look at the commercials. Everyone is having a good time. Not once do you see the guy standing at the ATM with that forlorn look on his face. They don’t show the dark side to gambling.

Can you share three pieces of advice that you would give to the entrepreneur who is struggling with some sort of addiction but ashamed to speak about it or get help?

As long as you are a slave to addiction you will never get that business going. If you have a business idea that needs to be your priority. There are three priorities in life: family, God and business. Addiction should never be a part of that package. These factors are much more important than your addiction, and when you focus on them, you’ll see your addiction take a back seat.

Take a moment to reflect on what you accomplish daily. I do that every day. I look at my job, my bank account, what I’ve achieved, and what I own. You have to give importance to the things you created for yourself in life.

Have a positive attitude. Most people who gamble have a negative attitude, and they’re always blaming some other problems for their addiction. Don’t fall into that trap.

How can our readers follow you on social media?

You can follow us at our website,, as well as on our Facebook page. You can go through my personal page — Ben Castro — and connect to Freedom Rides. This is all in its infancy, but hopefully within next 30–60 days we can get initial funding for Louisiana Correctional System, and then we grow from there.

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