Freeway Rick Ross on Making Millions, Prison, and the 3 Books That Changed Everything

Summary

Podcast Summary: For Good with Joseph "JoJo" Simmons

Episode Title: Freeway Rick Ross on Making Millions, Prison, and the 3 Books That Changed Everything
Release Date: August 5, 2025

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Introduction

In this compelling episode of For Good, host Joseph "JoJo" Simmons sits down with the legendary Freeway Rick Ross. Known for his tumultuous journey from the heights of the drug trade to redemption and advocacy, Rick Ross shares his personal transformation, the lessons learned during his time in prison, and his mission to inspire the next generation.

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Life Before and Entry into the Drug Trade

[00:29] Freeway Rick Ross: "I played tennis, was an athlete, and I went to selling drugs. I was looking for a way to get out the ghetto."

Rick Ross opens up about his transition from a disciplined athlete to a prominent figure in the drug trade. He describes himself as a "square" before entering the illicit business, highlighting his athletic background and lack of prior involvement with drugs or alcohol.

[04:59] Freeway Rick Ross: "He was like a big brother to me, and he's the one that introduced me to drugs for the first time."

His entry into the drug business was influenced by someone he trusted deeply, challenging the stereotypical notion that strangers are the primary introducers of drugs. This personal connection underscores the complex social dynamics that often lead individuals into such paths.

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Rise in the Drug Business and the Impact of Money

[00:42] Freeway Rick Ross: "At least a million dollars every day."

During their conversation, JoJo and Rick discuss the staggering amounts of money Rick managed to generate. While Rick clarifies that making $3 million daily wasn't consistent, he maintained that his average was still around a million dollars per day. This immense wealth transformed him from "a nobody to a superstar."

[05:51] JoJo Simmons: "When Thriller was out."

Rick reminisces about how, during the height of his success, he was compared to icons like Michael Jackson, illustrating the level of fame and admiration he attained before his downfall.

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Imprisonment and Self-Reflection

[06:12] JoJo Simmons: "In 96, you were sentenced to life in prison under the three strikes law. What was going through your mind during that time?"

Rick Ross delves into the pivotal moment when his life took a drastic turn. Facing a life sentence, he grapples with the possibility of never seeing his children grow up and acknowledges the pain of becoming absent for his family, mirroring the absence he experienced from his own father.

[07:49] Freeway Rick Ross: "You do that for three years. You've done a lot of thinking, a lot of contemplating..."

Spending 23 hours a day in solitary confinement, Rick reflects deeply on his past actions, analyzing every facet of his life and relationships. This period becomes a catalyst for his eventual transformation.

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Education in Prison and Transformational Books

[08:03] JoJo Simmons: "You learned to read at 28 while in prison. What pushed you to take that first step?"

Rick attributes his self-education to a pivotal conversation that emphasized personal responsibility. Realizing that no one else would prioritize his case or well-being, he took it upon himself to learn and grow.

[16:11] Freeway Rick Ross: "Think and Grow Rich by Napoleon Hill. One Richest Man in Babylon by George Classy. As a Man Thinks by James Allen."

He recommends three transformative books that provided him with the principles to redefine his life. These books not only shaped his mindset but also served as foundational texts in his later advocacy work.

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Reentry into Society and Current Ventures

[20:30] JoJo Simmons: "So you would say that just shelter, food and an opportunity. That's what real reentry support looks like to you."

Upon release, Rick faced homelessness and a family in disarray. He emphasizes the critical need for comprehensive reentry programs that provide stable housing, clothing, transportation, and time to acclimate. Without these supports, individuals risk reverting to old habits.

[21:07] Freeway Rick Ross: "I was pissed off... I didn't really want no T-shirt idea, right? But I stayed open minded..."

Rick narrates the inception of his T-shirt business, initially met with skepticism. However, an opportunity with a talented designer transformed his struggles into a lucrative venture, marking the beginning of his successful entrepreneurial journey post-incarceration.

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Legacy and Advocacy for the Next Generation

[23:13] Freeway Rick Ross: "I try to go around just to give them a touch... I can compete with anybody."

Rick dedicates his time to mentoring youth, emphasizing self-education, discipline, and self-belief. He aims to instill the same principles that transformed his life in the hopes of steering others away from the paths he once treaded.

[29:43] Freeway Rick Ross: "I want to be somebody that they say the world was better because he lived."

His vision for legacy is profound yet simple—being remembered as someone who positively impacted the world and left it better than he found it.

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Key Insights and Takeaways

1. Personal Responsibility: Rick Ross underscores the importance of taking charge of one's own destiny, especially during times of adversity. His transformation began with the realization that he alone was responsible for his future.

2. Power of Education: Self-education, particularly through the three books he recommends, played a pivotal role in reshaping his mindset and life trajectory.

3. Comprehensive Reentry Support: Effective reentry programs must address not just the immediate needs of shelter and food but also provide avenues for personal and professional growth to prevent recidivism.

4. Mentorship and Advocacy: Rick's current endeavors focus on giving back to the community, especially the youth, by sharing his experiences and lessons to guide them towards positive choices.

5. Legacy Over Wealth: Despite his past wealth from illicit activities, Rick's current emphasis is on building a meaningful legacy centered around positive impact rather than mere financial success.

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Notable Quotes

• [00:29] Freeway Rick Ross: "I was looking for a way to get out the ghetto."
• [05:18] Freeway Rick Ross: "At least a million dollars every day."
• [14:11] Freeway Rick Ross: "Somebody was me, that the only person in the world that would put my case in front of everything was me."
• [16:24] Freeway Rick Ross: "Think and Grow Rich by Napoleon Hill. One Richest Man in Babylon by George Classy. As a Man Thinks by James Allen."
• [29:43] Freeway Rick Ross: "I want to be somebody that they say the world was better because he lived."

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Conclusion

This episode of For Good presents a powerful narrative of redemption, responsibility, and the relentless pursuit of positive change. Freeway Rick Ross embodies the essence of transformation, turning his life around from the depths of the drug trade and imprisonment to becoming a beacon of hope and mentorship for many. His story serves as a testament to the human capacity for change and the profound impact of self-education and personal accountability.

Listeners are left inspired to reflect on their own lives, recognize the power of choice, and embrace the continuous journey of growth and healing.

Transcript

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[Freeway Ricky Ross]

I played tennis, was an athlete, and I went to selling drugs. I was looking for a way to get out the ghetto.

[JoJo Simmons]

At one point, you were reportedly making $3 million a day.

[Freeway Ricky Ross]

Not every day.

[JoJo Simmons]

Hey, what would you say your average was if you had the average?

[Freeway Ricky Ross]

At least a million dollars every day.

[JoJo Simmons]

Wow.

[Freeway Ricky Ross]

I'm not the same person that went in prison. I didn't come out the same way. I read over 300 books while I was gone.

[JoJo Simmons]

If you had to recommend just three that everyone should read.

[Freeway Ricky Ross]

Once you read those three books, you got all the principles to do whatever you want to do in the world.

[JoJo Simmons]

You were essentially homeless. And then you came into this T shirt idea. What were you thinking when Joe Rogan first suggested it?

[Freeway Ricky Ross]

He said the real Rick Ross is not a rapper. And I thought it was the corniest in the whole world. But I kept an open mind.

[JoJo Simmons]

What's good, everybody? It's your guy, JoJo Simmons. And this is the For Good podcast where we focus on the good, never the bad, where we're measured on what we do and not what we have. Today, I'm sitting down with the legendary Freeway Ricky Ross, a man who turned into the drug trade in the 80s because there weren't many options making over $3 million a day before it all came crashing down. After serving more than 20 years in prison, he came out with a new mindset and a new mission. Today we talk about what happens when you know better and you decide to do better. Not just for yourself, but for your community. From surviving the crack era to showing up for the next generation, Ricky's story is one of taking responsibility, redemption, and relentless vision. Like, let's get into it, everybody. Freeway Ricky Ross. Thank you for coming on here, brother.

[Freeway Ricky Ross]

I appreciate you for having me on, man. Thank you. I love that introduction, too.

[JoJo Simmons]

No problem. We us over here, universe. In three is four. We give every guest a proper introduction because we're very Intentional on who we have on this podcast and who we talk to and people that are really inspiring. And you are somebody that's super inspiring. Very excited to have this conversation. We're super excited when your name came across the desk that I. I'll be sitting down with Freeway Ricky Ross. It's an honor to have you here. So we'll get into the questions. I won't keep you all day because I know how we're all pretty busy, but we're gonna get it going, so let's.

[Freeway Ricky Ross]

All right, let's do it.

[JoJo Simmons]

Life before and after prison. So you've talked about how growing up in South Central Los Angeles, there weren't many options and how to financial freedom. What was the moment you realized that you were all in on selling drugs?

[Freeway Ricky Ross]

Well, you know, when I first started, I. I never. I never saw any drugs before. You know, I was. I would be what they call a square.

[JoJo Simmons]

Okay.

[Freeway Ricky Ross]

You know, I played tennis, was. Was an athlete, had never smoked a cigarette and never smoked weed, never drunk a beer. You know what I'm saying? I was like a square, really. And I went from that to selling drugs. You know, one of my friends called me one day. You know, I felt like I was down on my luck, you know, because I couldn't read it right, so I couldn't get my scholarship to college. And I was looking for. For a way to. To get out the ghetto. And he called me and he showed me drugs. And when I first got it, I didn't believe what he said. You know, he had. Something was so small that you. You would never believe that it was worth 50 bucks. And he was like, this is worth 50 bucks. And. And I said to myself, man, if this worth 50 bucks, I'm going to get rich. So my first sale didn't go well. I got beat out of my first sale, but I was determined to figure out if that was what I was going to be doing. So it probably took me about two months before I finally got it going to where I said, you know what? I know what I'm doing now a little bit.

[JoJo Simmons]

Wow, that's. That's crazy. So you were not even dealing with drugs, Never did a drug. You were a tennis player. You were, what you say, square. And you happen to see a way out basically in a way to make money, in a way to see, support yourselves and others around you and say, you know what? I'm seeing the money in this. I'm not really looking at the other side of it.

[Freeway Ricky Ross]

Absolutely. And you know what, too? And I Say this. When I go to schools and stuff, when I talk to the kids, I talk about, you know, the commercials always have this strange guy that come up on you and try to give you drugs. And I'm saying, no, it don't happen like that. It's usually a friend, a uncle, a dad, a brother, a sister, a mom or a dad that. That introduces people to drugs for the first time. It's not some stranger that they don't know, because, you know, if a stranger come up on most people, they. They ducking them. You know, they trying to get out the way. So it's somebody that you trust, and it was somebody that I trust, that I love. And, you know, he was like a big brother to me, and he's the one that introduced me to drugs for the first time.

[JoJo Simmons]

Wow. So at one point, you were reportedly making $3 million a day. What does that kind of money?

[Freeway Ricky Ross]

Not every day. Not. Not every day. It was, you know, maybe. Maybe four or five times a month. Wow. So what would you say your average.

[JoJo Simmons]

Was if you had to average it?

[Freeway Ricky Ross]

At least a million dollars every day.

[JoJo Simmons]

So making that much money a day. And in those times, what did that kind of money do to someone that never had anything like yourself? Like, what did that do to you? How did that make you feel?

[Freeway Ricky Ross]

Well, well, it gave me a sense of being. You know, I became from being a nobody to a superstar. You know, one time I had. I had a. A young girl come up to me and she was like, man, you like Michael Jackson in the hood?

[JoJo Simmons]

Wow.

[Freeway Ricky Ross]

And this is when. When Thriller was out.

[JoJo Simmons]

What? Wow.

[Freeway Ricky Ross]

Yes. She was like, they talk about Michael Jackson and then you. You know, so it was. It was like, unbelievable. And this is before you. You know, crack had a bad name. You know, at that time, nobody. There was no crackheads. You know, people wasn't strung out. You know, it was. They were smoking, but nobody knew what was to come.

[JoJo Simmons]

Right, Right. So then everything kind of changed. In 96, you were sentenced to life in prison under the three strikes law. What was going through your mind during that time?

[Freeway Ricky Ross]

Oh, man. You know, I was wondering, was this the way my mom's son was gonna wind up, you know, in prison for the rest of his life without the possibility of parole? That my kids would wind up growing up without a dad. And one of the things that I always said is that I wanted to be there for my kids because my dad wasn't there for me. And then when I looked back at it, I was like, you did the same thing to your Kids that your dad did to you. You know, even though mine was a little different, he could have came and seen me, I couldn't go and see my kids, but I voluntarily committed a crime that put me in the same position.

[JoJo Simmons]

Yeah. So that's very interesting. You know what I mean? And I think that, you know, obviously, what, at your highest of highs, you didn't think of that, but once, once that kind of came down on you, you had that time to really sit with your thoughts and really understand, you know, what you were going through.

[Freeway Ricky Ross]

Well, you know, you in a sale, you in a cell by yourself 23 hours a day, you know, nobody to talk to, you know, really nothing to do but sit back and contemplate, you know, look at your life, analyze your life, analyze yourself, analyze the people around you. You know, these are the kind of things that you do. If you stand a cell for 23 hours a day for three years.

[JoJo Simmons]

Right.

[Freeway Ricky Ross]

You know, you do that for three years. You've done a lot of thinking, a lot of contemplating and. And so many things have run through your life because there no more future.

[JoJo Simmons]

Right.

[Freeway Ricky Ross]

So the only thing that you can think about is the past and you just analyze your past.

[JoJo Simmons]

Yeah. You know, I think you said something super interesting earlier in the conversation when you said that having money and access to money gave you access to education because you were somebody that didn't know how to read, really didn't know how to write. You weren't very educated. But once you were able to obtain money, you said that you were able to educate yourself. You think that having money really helped you educate yourself better, educate yourself more, give you a little bit more business acumen?

[Freeway Ricky Ross]

Oh, absolutely. Well, it puts you. It puts you in the room with people that you wouldn't normally be able to be in the room with.

[JoJo Simmons]

Right. Wow.

[Freeway Ricky Ross]

Even. Even tennis. You know, when I look back at my life, tennis put me in a rooms that my brothers who didn't play tennis didn't get in those same rooms. So they didn't have the same mentality that I had about life. So exposure definitely changes the mindset and influences a person.

[JoJo Simmons]

I love that. Exposure changes the mindset and influences the person. That's powerful now.

[Freeway Ricky Ross]

Absolutely.

[JoJo Simmons]

You've once said, nobody told me I could have used that same discipline to build something else. I just didn't know what would that something else have been for you if someone had helped you see your own potential? Would it be tennis? Because I hear you speak about tennis a lot.

[Freeway Ricky Ross]

Well, well, now I know I can do anything you Know, movies, records. You know, I've helped, I've helped numerous artists get into the record business. I helped guys get into the NFL, really the NBA. You know, I had a couple guys that I assisted got into the NBA. So there's no limit to what these skills can be used for. You know, right now I'm doing boxing. I'm in a situation with boxing that I really believe that I'll wind up being the key to boxing in the near future. To where if you're doing boxing, you're gonna come see Rick Ross, the marijuana industry. You know, I got a dispensary. I went around the country and helped states open up their dispensary licenses. Detroit, Chicago, Pennsylvania. I was there at the cutting edge. When they were talking about going legal, the senators who wrote the bills called me down to speak about social equity and why blacks and minorities should be allowed to be in the business and the business should be affordable so that they could get into the industry. So. So, you know, I'm working on, I'm working on my own movie right now about my life story and I'm one of the producers, so I'm hands on, I mean, and I, and I realized that I always had all of this stuff inside of me that I could have been doing all of this had I only knew that it was possible.

[JoJo Simmons]

So a two part question. First of all, how does it feel to be legally selling drugs, which they, they call cannabis a drug, right. From, you know, going through so many legal issues with selling drugs in the past? Well, how's that feeling for you in like seeing the, the transition of how we or cannabis is being treated now? I know back in the day when you were selling, when you were selling weed wasn't as powerful, but it was still something that was frowned upon and you can get a lot of time for. How does that feel to be in cannabis business?

[Freeway Ricky Ross]

It feels wonderful. You know, it's a great business to be in, you know, when you can, can be actually assisting people in, in their mental, you know, because some people use a recreation, some people use it mentally. But just to be able to assist people and put people in a space that makes them comfortable is, is wonderful. You know, anytime that you can help somebody else, it, it makes you feel good.

[JoJo Simmons]

Yeah, I love hearing all the things you have going on now and all the things that you've worked on, but when you didn't have that access to the money and like I said, knowing that you could have used this same discipline to be anything else in the world back in the day, what would you think you would have been if you had somebody behind you telling you to go the other way? Would it have been tennis?

[Freeway Ricky Ross]

Definitely. Tennis would have been one. You know, if I knew what I knew now with tennis about tennis, I probably would have been a tennis pro. Now I know to add a little more, you know, to my push. Yeah, you know, I was pushing good, but you know, I could have added a little more to the push. Right, but, but I probably, you know, I probably would have been, you know, a Walmart or I mean, if I wouldn't went to prison. No telling where I would have been, you know, probably invested in Walmart, Nike or Microsoft or some of those companies that I know about now. You know, because I'm always right now looking for the next opportunity.

[JoJo Simmons]

Were those companies that you knew about back in the day went before you went in jail, or these just companies that you're seeing are big now and you're like, I could have probably researched.

[Freeway Ricky Ross]

Yeah, they're big now. But you know, at one time I had them kind of money that if I were to put a hundred thousand in Nike, you know, it would be worth a hundred, maybe $100 million right now, you know, so when you, when you look at and, and you know, I used to blow a hundred thousand dollars, you know.

[JoJo Simmons]

Right, right, right. I know it. Oh, don't I know it.

[Freeway Ricky Ross]

So you know, when you look back, you'd be like, wow, had you not if I would have been who I am right now. I mean, and, but you know, I don't really look at the past so much no more, you know, because I already analyzed my past. And, and, and while I was in prison, I studied. You know, I'm not the same person that went in prison. I didn't come out the same way. I read over 300 books while I was gone. And right now I'm looking for the next big opportunity, you know, the next startup, the next young genius is coming around and I want to be there to assist them in their, in their journey.

[JoJo Simmons]

So speaking of young geniuses that's coming around and assisting them in their journey, what advice would you have for someone right now who is sitting on skills that they don't even recognize are valuable yet?

[Freeway Ricky Ross]

I would tell anybody, you know, follow your dream. Don't allow other people to kill your dream because it's your dream and nobody's going to see your dream the way you see it. And you have to be the one that makes sure that your dream come to fruition.

[JoJo Simmons]

Right, right. Agreed. So you learned to read at 28 while in prison. What pushed you to take that first step while you were in prison to learn to teach yourself how to read?

[Freeway Ricky Ross]

Well, guys were telling me that I shouldn't depend on my lawyer to get me out. And this is a lesson that I teach when I go speak at schools. I tell the young people that. The guy told me something like this. I'm gonna try to paraphrase it. I know I ain't gonna get it right. He said, do your lawyer have other clients? And I said, yes. Does he put your case in front of all his other clients? And my answer to him was no. He said, does he have kids? I said, yes. He said, does he put your case in front of his kids? And I said, no. He said, does he have a wife? I said, yes. He said, do we put your case in front of his wife? I said, no. He said, your case should be so important to somebody that it's more important than all those things that I just announced to you. And when we left that conversation and I contemplate what he said and what he was telling me is that somebody was me, that the only person in the world that would put my case in front of everything was me. And that's what I did. And I started studying and studying, and boom, it just came to me.

[JoJo Simmons]

That's dope. That's inspiring. That's. That's amazing that you took that turn when you realized the only person that can save you is yourself. And you took that and saved yourself. So.

[Freeway Ricky Ross]

And I use that with everything. Everything that I do now, I take that same mentality, because I understood when. When I sold drugs, I put it all on the line.

[JoJo Simmons]

Right.

[Freeway Ricky Ross]

You know, I used to carry a gun. And when I was in prison, I was asking myself, why was you carrying a gun? Oh. Cause somebody might try to rob you and kill you. So what that told me is that I was putting my life on the line every single morning that I got up and went outside my door and sold drugs.

[JoJo Simmons]

Wow.

[Freeway Ricky Ross]

My life was literally on the line. And not just my life, but my freedom as well.

[JoJo Simmons]

You told me you read over 300 books while incarcerated. If you had to recommend just three that everyone should read, what would they be?

[Freeway Ricky Ross]

And why everybody know those books? I don't tell everybody in the world about those three books, but I want to hear them.

[JoJo Simmons]

I want to hear them on the 4Best podcast. I want to hear. I want that. I want that content, too, OG all.

[Freeway Ricky Ross]

Right, I'm gonna give it to you. Think and Grow Rich by Napoleon Hill. Get the original version. One Richest man in Babylon by George Classy. Get that original version. As a man think or as a woman think by James Allen. Once you read those three books, you got all the principles to do whatever you want to do in the world. What I found out is all those books that I read, everybody use those principles that those three books talked about.

[JoJo Simmons]

Dope. Appreciate that. I know you said it before, but I just wanted to get that. I may have to read those books as well. I haven't read any of those.

[Freeway Ricky Ross]

Well, if you read them, then. If you go. If you go read them, it'll be good. Because ain't none of your listeners gonna listen to them now.

[JoJo Simmons]

They will. My listeners are different, man. My listeners always want to learn. My listeners always want to be educated. My listeners always want to be uplifted as they uplift others. So they definitely are going to be jotting it down.

[Freeway Ricky Ross]

Well, that's good, because, you know, when I go to these black schools and I tell these kids about these books and. And I. I look for. I look for a reaction. You know, I spoke at Brown University one time in the auditorium. It was full of kids. You know, they didn't. They didn't look like us, though. And when I told him about those three books, I saw almost the whole audience reach behind their back into their backpack and pull out pens and papers and wrote the names down. And when I go to black schools and I say the same thing, I don't get that reaction. And it'd be kind of sad that, you know, they would have the opportunity. If somebody would have told me about those books, how valuable those books were when I was coming up, my life would have been totally different.

[JoJo Simmons]

I hear that. And it is sad that young black men. Black. Young black kids. Not all the time do they feel like they're listening. But with growth and age comes education and trust and believe they're gonna remember that conversation you had with them. And they may not implement that now, but they may implement that in the future. So never give up on talking to these young black kids. They may seem like they're not listening, but they listening. And some of them, they are knuckleheads, but they get it right and they get it straight. So, like, I see that too, in some places that it seems like black kids are just uninterested in education or they uninterested in hearing something that can truly help them. But it's just that they got so many things going on, I think, is that they just are straight narrow on how to survive right that day. But trust me when I say they hear you. I think every young black kid hears when we lecture. Like, I remember being young and my dad lectured me every day, and I didn't like it at those times. But now I implement and I say all those quotes that my dad told me as a kid. That used to piss me off. That used to make me mad. That used to make me feel like, man, what does this even mean? And now I just use it in every day of my life. So trust and believe. When you're talking to these kids, they may not seem like they're listening, but they listening, Ricky. They listening.

[Freeway Ricky Ross]

So. All right.

[JoJo Simmons]

We speaking about books. So you said your book, Freeway Rick Ross, the Untold Autobiography, is almost like a how to manual, not to glamorize the lifestyle, but to show what comes with it. What was the writing process like? What writing it teach you about yourself?

[Freeway Ricky Ross]

Well, like I said, I was in prison. I had a life sentence without the possibility of parole in. I had read an article about Tookie's book, and I thought that if Tookie did a book on gang banging, then I should do a book on selling drugs. And as I was writing a book, I was also reading those three books that I was telling you about. So those books started to influence my writing a lot. This book was going to be a letter to black, young black people who may be thinking about going into the drug business or just be thinking about doing business, period. And I tried to put my mentality down of how I was able to take literally $125 and my partner had one 25 and run it up to where we was making $3 million a day sometimes. So it's kind of like my letter, you know, to the streets. You know, oh, I ain't gonna never get to see you, but this is my letter to you.

[JoJo Simmons]

I love it. You give back to the streets. You give back of saying, you don't have to go this route, but if you do go this route, this is what comes with it. I love that. And. And it is needed, you know, so people can understand what comes with that life. I want to talk about you coming home because obviously I don't want to talk about you being incarcerated the whole time because you're not incarcerated anymore and you are home and you have been doing great things. So when you came home, you were essentially homeless and had $200 in your name. And then you came into this T shirt idea. Can you take us back to that moment? What were you thinking when Joe Rogan first suggested it and how did it all happen?

[Freeway Ricky Ross]

I was pissed off. I was like, if you respect me so much, you should have gave me, you know, a bag. Give me some working capital, you know, you need some working capital out here, man. So when I told him I was doing bad, I was telling him because, you know, I'm looking like, man, you on tv, you got all this stuff going on. Throw a brother a bone, you know.

[JoJo Simmons]

Right, right, right.

[Freeway Ricky Ross]

You know what I'll do with a bone?

[JoJo Simmons]

Right, right.

[Freeway Ricky Ross]

So I didn't really want no T shirt idea, right? But I stayed open minded and didn't know how I was going to start a T shirt, you know, like, how the fuck I'm going to start a T shirt? So I'm walking down the street and this young kid came up to me, young white kid. And I didn't know who he was, you know, I didn't know he was like one of the top T shirt designers in the world. And he was like, man, I heard you on Joe Rogan and I got a great T shirt idea for you. And he said, the real Rick Ross is not a rapper. And I thought it was the corniest in the whole world. But I kept an open mind. I said, okay, I'm listening. And he told me that he would print the T shirt up and do everything. And all I had to do was just come there and take a picture in it. And I jumped on the opportunity.

[JoJo Simmons]

Dope. So that one shirt turned into $188,000. What did that feel like and what did that teach you about your own value?

[Freeway Ricky Ross]

Well, you know, I hustled that T shirt though. You know, I was standing in front of gas stations and supermarkets and I mean, I did just like I did because I already had my crack experience, so I already knew how to go straight to the people, right? And I took it straight to the people. And, you know, it just started to sell. And then I thought about, what if I go back to Joe and tell him I did what he told me to do and I did that. And he put the T shirt on on camera and it just went crazy.

[JoJo Simmons]

Super dope. So now you speak across the country to mentor the youth and support reentry programs. Can you walk us through the work that you're doing today and what drives that work?

[Freeway Ricky Ross]

Well, I think that young people like myself, I wish I would have had me, you know, when I was coming up, being in the mindset that I'm in now, I know my life would have been different. So I try to go around just to give them a touch of. Because, you know, usually I'm only with the kids like 45 minutes. So I go around them and try to touch them just in 45 minutes. And hopefully I can, you know, wake something up within them to let them know that. That they're great, that they're special, and that they can compete with anybody. All they have to do is. Because, you know, I used to believe that to be smart, you know, one day you just. You pray hard and one day you wake up and you're smart. Well, I found out that's not the case. You know, you have to get in those books, you have to study, you have to analyze. And those are the things that make people smart. So I try to transfer those lessons to other young people who might be going down the same path that I went down.

[JoJo Simmons]

What are some of the biggest misconceptions about people coming home from prison?

[Freeway Ricky Ross]

Well, you know, that they believe that most people coming home from prison are lazy. They lie, they steal. But, you know, drug dealers are a little different. You know, drug dealers are not the normal prisoner. You know, drug dealers, when they go to prison, they went to prison because they was trying to make some money.

[JoJo Simmons]

Right.

[Freeway Ricky Ross]

You know, and selling drugs is a business, Even though it's not a legal business, but it's still a business in itself. And if you can run a successful drug business, you know, you can be a great worker.

[JoJo Simmons]

So everybody talks about reentry and all that, but you've been somebody that actually came home from prison. And you know what this looks like. So what does real re entry support look like to you? What does somebody need to come home and fully get reentered into the world?

[Freeway Ricky Ross]

We should have a system set up where people come out of prison. They have a place to stay, a stable place to stay. They got clothes, they have transportation. Just enough time to get re. Acclimated back into society because, you know, you come home. You know, I came home to a mess. You know, my family was in, in, in, in shambles. You know, brothers were sleeping in garages and staying with women they couldn't stand. You know, just, just so they have a roof over their head. My mom was behind on her, her house note. She had took out one of those. Yeah. When I. That's what I came home to. Wow.

[JoJo Simmons]

After making all that money and then serving all that time, you came home to nothing.

[Freeway Ricky Ross]

Yeah, to nothing.

[JoJo Simmons]

Wow. Wow. That just shows you, like, what that life really does. So, so, so you would say that just shelter, food and an opportunity. That's what real re entry support looks like to you.

[Freeway Ricky Ross]

Absolutely, absolutely. And if you ain't got that, it ain't real re entry.

[JoJo Simmons]

Yeah.

[Freeway Ricky Ross]

You know, you really setting them up for, for to go back to what they know because, you know, when a person runs into a bump in the road, the first thing they do is go back to today. Old habits.

[JoJo Simmons]

But if they have an opportunity, then they won't, you know, they'll be able to see different and do different.

[Freeway Ricky Ross]

Correct.

[JoJo Simmons]

Right. I think we spoke a lot about your past in this interview and I kind of want to talk about the next generation. Towards the end of this interview for you, you credit your success then and now to discipline. How did your experience as a tennis player shape the way you approach life and business?

[Freeway Ricky Ross]

Oh, it helped me out tremendously because when I started selling drugs, I noticed that the other drug dealers weren't disciplined. You know, they didn't put in the time. They would go out and make enough money to go to the movies, you know, to put gas in the car, to buy. The jury. When I started selling drugs, my goal was to accumulate as many points as I could. Like in tennis. In tennis, you know, you want to win every single point. You don't want your opponent to win a point.

[JoJo Simmons]

Right.

[Freeway Ricky Ross]

And that's the way that I approached the drug business. I didn't want nobody else to win a point.

[JoJo Simmons]

I like that. So you, so it's safe to say you, you used your sport to, to, to, to relate to whatever you do in life. That's dope.

[Freeway Ricky Ross]

Absolutely. Still, still today.

[JoJo Simmons]

That's what's up. That's what's up.

[Freeway Ricky Ross]

You know, I'm vegan.

[JoJo Simmons]

I'm vegan.

[Freeway Ricky Ross]

I don't smoke, I don't drink, I don't gamble. You know, I live a simple life, you know, no big cars. Everything that I do is, is the win.

[JoJo Simmons]

Yeah, yeah. Just like in tennis. No losing, no love for nobody. No love.

[Freeway Ricky Ross]

Right, exactly. Exactly.

[JoJo Simmons]

All over the tennis stuff. I played some tennis, my daughter plays tennis. So I got, I know a little bit of the technology. Yeah, she's working on it. She's working on it. She's working on it.

[Freeway Ricky Ross]

Yeah. My 12 year old daughter, she plays, she plays as well.

[JoJo Simmons]

Dope, dope. You know, maybe we'll get our daughters together and your daughter could teach mine a thing or two about it. She's still learning.

[Freeway Ricky Ross]

All right. Yeah, yeah, yeah, we can do that.

[JoJo Simmons]

So you've seen firsthand how systemic barriers keep people trapped. What do you Think needs to change on a policy or community level to make that. To make a difference.

[Freeway Ricky Ross]

Well, I think we got to start educating ourselves. I think everybody should pick up those three books and learn those principles and apply those principles to their lives. I mean, those principles alone would start to change our community immediately, you know, because, you know, I host a lot of parties and clubs and I watch our people throw away tens of thousands of dollars, you know, on champagne and bottles and, you know, just stuff that has no real value, you know, something that you're gonna piss out the next day.

[JoJo Simmons]

Yeah, yeah, you're right. The mindset needs to change for the whole community to change, really. And that may not never happen or may take a really long time to happen, But I believe that the mindset that needs to change of a whole race for us to really, you know, see things differently and do things differently, you know, but we're very capable of. Absolutely. We're very powerful, very strong, very authentic and very leading of a race. For sure.

[Freeway Ricky Ross]

Absolutely.

[JoJo Simmons]

So you've once said that you just want to see your kids grow up. What kind of legacy do you want to leave for them and for the people who see themselves in your story?

[Freeway Ricky Ross]

Well, I want to be somebody that they said the world was better because he lived. As long as they say that, I'm good.

[JoJo Simmons]

I love that. A simple and right to the point answer. I love that.

[Freeway Ricky Ross]

Yes.

[JoJo Simmons]

What gives you hope when it comes to the future, especially for the next generation growing up in a similar circumstance?

[Freeway Ricky Ross]

Well, like you said, some of these kids are listening. You know, I do hear them. They do come up to me and say they listening. Not to the point that I think they should, but I know if 10 listen and get becomes like a disease and it just keeps spreading and keeps spreading and keeps spreading, and the mindset that we have right now will be totally obliterated, you know, with this violence with. I don't want to see you with nothing. If you got something, I'm going to take it from you. I think that all of that is going to disappear soon. Wow. And I want to be a part of getting rid of it.

[JoJo Simmons]

There you go. I mean, you were once a part of what was not right, and now you're on the part of the side what is right and trying to be different. And I think that's a very commendable thing, is that you're like, hey, I've lived this life. I've done all of this. I know what this is is. And there's no way I'll go back to that. But there is a way that I'll lead everybody else the other way. So I think that's very commemorative, for sure. So, as we wrap it up on the last question, I want to know one thing. So for someone listening who feels stuck, who feels like they've already made too many mistakes, what would you say to them?

[Freeway Ricky Ross]

Would only take one second to change who you are. You know, like, you could. You could right now say that I'm gonna be a different person. You know, you could say I'm gonna be a vegan. And in one second, if you stick to that, you become a vegan. Right? Then, yeah, you can say, I'm no longer gonna be. I'm no longer gonna be a dummy. I'm gonna get smart. As soon as you say that, you become smart, because you're supposed to start going after that, that. That you.

[JoJo Simmons]

So it's safe to say you just got to make that choice. You got to wake up, make that choice. Stop. Stop bullshitting around and wake up and make that choice to be different and do different.

[Freeway Ricky Ross]

Yeah, but I. I've had people tell me that they don't want to be different.

[JoJo Simmons]

Wow. And what does that feel like for you when somebody says that?

[Freeway Ricky Ross]

Sad. It's sad that you don't want better. Better for yourself.

[JoJo Simmons]

Now, why do you think that is? That they don't want better for themselves? They think there's no better. Like you once said, you didn't know any better. You didn't know any other options. You didn't have any money to have access to these other things that inspired you to essentially want to do other things.

[Freeway Ricky Ross]

Well, like you said, if you don't know better, then you can't do better. So what we got to do, we got to do a better job of letting them know that there is better and that they can accomplish it.

[JoJo Simmons]

Thank you, man. I really appreciate you coming on here. Ricky Ross. This was a wonderful talk. Very inspiring talk. I never believe I'd be able to sit down with somebody like you that got so much game and knowledge and gems for the people. So I really appreciate it. I appreciate all you do.

[Freeway Ricky Ross]

I appreciate you, too.

[JoJo Simmons]

Thank you.

[Freeway Ricky Ross]

Keep doing your thing, man. We need more young people like you to get out and put the word out.

[JoJo Simmons]

Thank you, man. That means a lot to me. I hear that a lot. And that's my mission in life, is to be younger dude that leads the people to the water and hopefully that they drink. This is the four good podcasts that you got, Jojo Simmons. Lou, we focus on the good, never the bad. Where we're measured on what we do and not what we have. We out. Peace. Till next time.

[Freeway Ricky Ross]

Thank you.

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