Episode 491: Jay "Jeezy" Jenkins: The $4M Bet That Built an Empire + His 7-Question Mentor Method

From cutting lawns for $5-$10 each to building a business empire worth millions, Jay Jenkins has never played it safe. In this episode of Habits and Hustle, I sit down with the artist better known as Jeezy for a raw conversation about betting everything on yourself. We discuss why he spent $4 million of his own money before getting signed, and the unconventional way he built relationships with mentors like Tony Robbins and Robert Greene. We also dive into his transition from music mogul to business empire builder, his upcoming Vegas residency with a 101-piece orchestra, and why he believes pain is a prerequisite for leadership. Jeezy is a Grammy-nominated rapper, entrepreneur, and New York Times bestselling author. He's built million-dollar businesses including Avion Tequila, launched his own energy drink Edge, and is known for his mentorship programs and philanthropic work through his Street Dreams Foundation. What We Discuss: (03:00) From lawn mowing to watermelon entrepreneur: His first business ventures (07:00) Why he spent $4 million of his own money before getting a record deal (14:00) His secret "board of directors" including Tony Robbins, Robert Greene, and TD Jakes (20:00) The seven-question strategy that gets him face time with billionaires (27:00) Building and selling Avion Tequila: The $100M+ exit strategy (35:00) Why he gave away half a million mixtapes for free (46:00) Mental health, self-development, and finding peace after chaos (51:00) The Vegas residency with 101-piece orchestra that's making history (54:00) Why Tony Robbins doubles his charity donations every year ...and more! Thank you to our sponsors: Therasage: Head over to therasage.com and use code Be Bold for 15% off Air Doctor: Go to airdoctorpro.com and use promo code HUSTLE for up to $300 off and a 3-year warranty on air purifiers. Magic Mind: Head over to www . magicmind.com /jen and use code Jen at checkout. Momentous: Shop this link and use code Jen for 20% off Manna Vitality: Visit mannavitality.com and use code JENNIFER20 for 20% off your order Prolon: Get 30% off sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit https://prolonlife.com/JENNIFERCOHEN and use code JENNIFERCOHEN to claim your discount and your bonus gift. Find more from Jen: Website: https://www.jennifercohen.com/ Instagram: @therealjencohen Books: https://www.jennifercohen.com/books Speaking: https://www.jennifercohen.com/speaking-engagement Find more from Jay “Jeezy” Jenkins: Instagram: @jeezy