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

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.

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.

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.

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.

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.

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.

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.

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.

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."

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.