Habits and Hustle, Episode 491: Jay "Jeezy" Jenkins

The $4M Bet That Built an Empire + His 7-Question Mentor Method

Host: Jennifer Cohen (and Habit Nest)
Guest: Jay "Jeezy" Jenkins
Date: October 7, 2025

Overview

In this episode, Jennifer Cohen sits down with rap icon and entrepreneurial force Jay "Jeezy" Jenkins (formerly known as Young Jeezy). The discussion is a deep dive into Jeezy’s evolution from hustling in Georgia to building business empires, his multi-million dollar self-investment, formative mentors, and the deliberate habits and mindsets that propelled him from music stardom to boardrooms and beyond. Jeezy unpacks his signature "7-Question Mentor Method," shares never-before-heard stories behind his major business plays, and reflects on seeking peace, impact, and legacy after early chaos.

Key Discussion Points & Insights

Jeezy’s Origin & Early Hustle

Timestamp: 01:08 – 05:32

• Nickname Story: "People in my neighborhood used to call me Jeezy because of my voice ... my name is Jay ... it just kind of fit when I started to do music." (Jeezy, 01:08)
• Entrepreneurial Roots: From cutting grass for $5-$10 to selling watermelons with his uncle, hustling was ingrained in family and community.
• Business in the Streets: Jeezy describes his first ‘ecosystem’—family, card games, and “clients”—that honed his early business skills.

"That was like my first company ... it was a very lucrative company for me to be that age." (Jeezy, 05:04)

Music as Escape — and Blueprint

Timestamp: 06:15 – 09:48

• Music as Learning: "It was like a college course. Like, I just listened to music to learn ... same way I listen to podcasts today." (Jeezy, 06:16)
• Turning Point: After losing almost everything investing millions in others, Jeezy decided to become an artist himself.
• Self-Belief: "I just started on this mission ... it took, like, 10 years ... I had to hustle even harder because now I’m supporting my own career." (Jeezy, 09:48)

Transition to Business & Lessons from the Streets

Timestamp: 09:48 – 12:18

• Advantages in Business: His “street savvy” let him thrive in corporate boardrooms.
• "If I’m sitting in the boardroom and everybody panicking ... What’s the worst can happen? You lose your job. That's it ... For you, everybody calm down." (Jeezy, 10:54)
• Learning Costs: “Education costs, even if it doesn’t work, you learn.” (Jeezy, 11:06)

Mentors and the “Board of Directors”

Timestamp: 12:18 – 15:21

• A List of Advisors: Jeezy cultivates authentic relationships with Tony Robbins, Robert Greene, Robin Sharma, John Maxwell, Lewis Howes, Dave Gibson, and more.
• Reciprocity: "But these are real relationships... I can call Tony Robbins and be like, hey—he’s like, lay it on me, Jeezy." (Jeezy, 14:15)
• Giving Back: Through foundations and programs, Jeezy mentors others but doesn’t see himself as a traditional role model.

Jeezy’s “Set of Skills” For Living

Timestamp: 15:21 – 18:19

• Integrity as a Superpower: "Integrity is a skill set ... It's a slow grind, but it will get you farther than anything." (Jeezy, 15:29)
• Resilience: Overcame being banned from radio and other setbacks by sticking to values and adapting.
• Staying Curious and Out-of-the-Box: Solo trip to Italy to get centered; emphasizes taking risks and continuous self-discovery.

The 7-Question Mentor Method

Timestamp: 17:31 – 23:41

• Seeking Wisdom: Details reaching out personally to Robin Sharma in Tuscany with seven carefully crafted questions.
• Method Origins: Inspired by John Maxwell, who said, "Come with seven questions. And they better be good." (Jeezy / John Maxwell, 19:06)
• Key Mentor Advice: John Maxwell reframes change: “You don’t leave something. You go to something.”
• Intentionality: "It’s intentional, and you're not rambling ... Having the clarity ... and not rushing." (Jeezy, 22:38)

Defining Success: From “Stuff” to Quality of Life

Timestamp: 23:33 – 26:28

• Inspired by Mentors' Lifestyles: A visit to Sharma’s villa reframes what matters: "When I left, I clearly understood there’s a difference between living and the quality of life." (Jeezy, 23:53)
• Simplification: “Sell all the cars... I want to live a simple life.” (Jeezy, 24:24)
• Peace > Chaos: “The end goal is peace ... Coming from chaos, you won’t want peace if you didn’t come from chaos.” (Jeezy, 25:02)

Major Business Moves: The Avión Tequila Deal

Timestamp: 26:28 – 29:02

• Tequila’s Power Move: Brought culture to Avión Tequila, securing equity and catalyzing a successful exit.
• Cultural Leverage: “How do you mobilize people to like something at one time? That’s the skill set I had.” (Jeezy, 28:17)
• Leadership and Community: “Filling arenas ... President can’t get up and say any speech that people are going to recite for an hour and a half.” (Jeezy, 28:59)

The Power of Self-Belief and Betting Big

Timestamp: 34:19 – 35:55

• $4 Million Bet: Spent around $4 million of his own money on mixtapes, production, and marketing—especially on iconic Snowman T-shirts as gorilla advertising.
• On Taking Risks: “I tell anyone to bet on themselves ... I watch people budget things out and I’m just like ... Let’s go.” (Jeezy, 34:44)
• On Using Your Own Money: “If I get your money, then I might treat it like it’s free money. But if I’m spending my money, I’m going to work.” (Jeezy, 35:28)

Cultural Moments and Social Impact

Timestamp: 37:04 – 39:17

• My President Is Black: Song became a cultural milestone during Obama’s run.
• Voting Drives and Community: Rented buses, organized campaigns; got recognition from Obama himself with a letter and a shoutout at a White House Correspondents’ Dinner.
• “That was definitely a big moment.” (Jeezy, 38:19)

Philosophy on Purpose, Legacy, and Leadership

Timestamp: 40:09 – 41:43

• Purpose Before Profit: “This is my purpose ... I’m locked in because I know that I have to navigate this very well.” (Jeezy, 40:15)
• Legacy Moves: Orchestrates his own tours and business deals, always betting on himself and retaining independence.

Big Projects & What’s Next

Timestamp: 32:27 – 44:15

• Book: “Adversity for Sale” hit NYT bestseller list.
• Orchestra Tour: Black tie events selling out 23 cities, now evolving into a 101-piece orchestra residency at Planet Hollywood, Vegas, celebrating 20 years of his debut album.
  • “I’m bringing 101 piece Orchestra ... this is going down in history. Nobody’s done this.” (Jeezy, 55:03)
• Upcoming Album: “Still Snowing,” with DJ Drama, out 9/28.
• New Ventures: Energy drink (Edge), growing through Georgia; previous companies include Defiance Fuel.

Memorable Quotes & Moments

• "Integrity is a skill set ... it's a slow grind, but it'll get you farther than anything." — Jeezy (15:29)
• "Education costs, even if it doesn’t work, you learn." — Jeezy (11:06)
• "I tell anyone to bet on themselves ... Let's go." — Jeezy (34:44)
• "You don't leave something. You go to something. So you're not leaving music, you're going to this new life you want to go to. That’ll always be there, but you’re not leaving it." — John Maxwell via Jeezy (20:47)
• "Once I got to this position that I can do world class things ... I would hate to just be this person who just made great music." — Jeezy (31:56)
• "There's a difference between living and the quality of life." — Jeezy (23:53)

Developing as a Leader & a Student

Timestamp: 45:54 – 49:50

• On Self-Help: Jeezy’s curious nature leads him to voracious reading, listening, and seeking growth: “If I could quit my job, I’d be a student for life.” (Jeezy, 46:25)
• World-View Comes from Military Upbringing: Early exposure to life abroad shaped his drive and perspective.
• Personal Evolution: Focus shifted from changing the world to changing himself: “I had to realize one day ... I can’t fix nothing if I don’t fix myself.” (Jeezy, 49:04)

Best Advice from Mentors

Timestamp: 50:04 – 52:30

• “Education costs, like it costs money, it costs pain.” — Dave Gibbons via Jeezy (50:04)

• On Leadership and Pain: “You’re not a leader if you’re not in pain, because it takes pain to lead.” (paraphrased, 50:30)

• "Nobody's coming to save you. I'm like, okay, I gotta get out here and just do what I gotta do." (Jeezy, 50:52)

• Tony Robbins: "There's nothing he does that he doesn't call me personally ..." (Jeezy, 50:26)

• Describes Tony’s generosity and belief, e.g., doubling bikes for charity events.

Final Reflections and Future Plans

Timestamp: 52:30 – End

• Potential One-Man Show: Jen Cohen encourages Jeezy to try a Broadway-style “one man show” akin to Mike Tyson, blending stories, business advice, and personal development.
  • “I receive that. I'm gonna give Mike a call.” (Jeezy, 53:33)
• Distribution Focus: New ventures like energy drinks, keeping company independently run in Georgia, while planning for wider distribution.
• Legacy Mindset: “Just so you know ... come witness it, but also come be a part of history.” (Jeezy, 55:03)

Timestamps for Important Segments

• Jeezy’s Early Hustle Tales: 01:08 – 05:32
• Music as Escape/Education: 06:15 – 09:48
• From the Streets to the Boardroom: 09:48 – 12:18
• Mentor Method / 7 Questions: 17:31 – 23:41; 19:03 (origin)
• Avión Tequila Story: 26:28 – 29:02
• The $4M Bet and Mixtape Hustle: 34:19 – 35:55
• Obama/“My President is Black”: 37:04 – 39:17
• Vegas Residency/Orchestra Plans: 32:53, 42:11, 55:03

Episode Tone

The conversation is candid, packed with stories, practical wisdom, and both strategic and soulful life advice. Jeezy’s approach is bold yet reflective; he’s humorous, unfiltered, and deeply authentic about both mistakes and triumphs. Jen Cohen brings energetic curiosity, drawing out tactical insights that any aspiring entrepreneur, artist, or leader can apply.

Recommendations & Takeaways

• Dare to Invest in Yourself: Betting big—with money, time, or reputation—can yield exponential returns if combined with relentless work.
• Structure Your Learning: Approach mentors with intention (like Jeezy’s 7-Question Method) to maximize impact and respect time.
• Do Not Measure Success by Stuff: True quality of life is about peace, personal growth, and meaningful relationships—not external markers.
• Legacy Over Hype: Leadership is about lifting others and making moves that outlast one’s own timeline.
• Curiosity Is a Superpower: Stay teachable, open, and committed to evolving.

This episode will inspire listeners to hustle smart, live with intention, and redefine their own path to fulfillment—regardless of starting point.