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

Habits and Hustle

Jen Cohen

Education, Health & Fitness, Business, Self-improvement, Entrepreneurship

4.4 • 800 Ratings

🗓️ 7 October 2025

⏱️ 56 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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

Transcript

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0:00.0	Hi, guys. It's Tony Robbins. You're listening to Habits and Hustle. Crush it.
0:06.5	All right, you guys. Today we have a special guest on the show. He goes by GZ, right? Young GZ. Right? That's what my husband told me. Yeah. Right. And first of all, thanks for coming on the show. We're going to talk about all your business ventures, your new biggest project in Vegas. So thank you for being on the show. Thank you for having me. Of course. We do this thing on the podcast. We take healthy performance shots. They're called Magic Mind, and they're like kind of to keep you like focused and they're, it's all healthy stuff. So it's like Ash Waganda. Are you into health at all? Yes, for sure.
0:37.7	Okay.
0:38.1	Do you exercise?
0:39.0	You're a big workout person?
0:40.2	Okay.
0:52.8	So then you'd like these. So they're very, basically we just like shake them. We like do a quick cheers and then we're off to the races. Let's do it. So it's just a bunch of like healthy ingredients to keep you like on point. You're going to know in two seconds. It tastes good.
0:53.8	It's actually really good.
0:54.8	It is good.
0:56.2	It is good. It's actually really good.
0:55.0	It is good, right?
0:56.0	Yeah, it's good.
0:57.0	It is good, right? Yeah, it's good. And now you're going to be super alert and super focused for the rest of the show. Let's do it. All right. So I wanted to ask you, where did you even get the name GZ from? Well, growing up, there was an era where a New Orleans rap syndicate that was called
1:14.4	Cash Money was taking over the world. And it was like where Little Wayne came from and all these
1:19.8	guys. And they had these nicknames like BG and Jizzle and all that stuff. And around that time,
1:26.0	I was becoming a hot boy because I was actually
1:28.7	like hustling and getting my first entrepreneur job on. And the people in my neighborhood used to
1:34.7	call me Jeezie because of my voice. Like my name is Jay. They call me Jeezzy because that was like
1:39.5	my hood slang name. And it just kind of fit when I started to do music because it's like, well, what
1:45.3	did they call you? I'm like, Jeezy. And I just, and at the time, people were putting young on their rap names. Right, right, right. So I put young Jeezy together. And that's how I came up with young Jeezy. I love that. Okay. What, like, you are, you're kind of known for being very entrepreneurial, right? So you kind of have, you have the music side to you and you have the business side.
2:04.6	Can you talk about, like, what was your first entrepreneurial endeavor that you ever did? I think I had one job before where I actually worked with my uncle. I had a job at McDonald's for like five hours. They put me on the fries and I was out of there.
2:20.1	Really? Yeah, no, I'm serious.
	...

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