Habits and Hustle Episode 491: Jay "Jeezy" Jenkins: The $4M Bet That Built an Empire + His 7-Question Mentor Method
Oct 7, 2025
Jay 'Jeezy' Jenkins, a Grammy-nominated rapper and successful entrepreneur, shares his journey from cutting lawns to building a multi-million dollar empire. He reveals the bold decision to invest $4 million in his own career before getting signed, emphasizing the importance of betting on oneself. Jeezy discusses his unique method for securing mentorship from industry giants like Tony Robbins, and the transformative power of pain in leadership. He also previews his upcoming Vegas residency with a 101-piece orchestra and his philanthropic work through the Street Dreams Foundation.
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Humble Hustles Laid The Foundation
- Jeezy started earning by cutting lawns and selling watermelons in his teens to make about $20 a day.
- He used family networks to build a cash-based local business and early entrepreneurial skills.
Spent Millions Before His Break
- Jeezy spent millions funding artists and studio projects before focusing on his own music career.
- He went broke supporting others, then pivoted to invest in and build his solo music path.
Use Seven Focused Questions
- Use focused questions to access high-level mentors; Jeezy uses a seven-question method to get direct, practical answers.
- Prepare concise, well-chosen questions and respect the mentor's time to build meaningful advisor relationships.
