Jermaine Dupri, Hall of Fame songwriter, Grammy award winner, and producer, knows that his ‘next’ will require even more effort if he is to succeed. Dupri has worked with the Mount Rushmore of hip-hop, R&B, and pop for over two decades, and a fateful conversation with the artist Babyface served as the ignition point for him to try something entirely different: JD’s Vegan, a line of vegan desserts. We spoke at length about his company and how he approaches challenges whether he is in the boardroom or the recording booth.

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Something in the ATL water

Dupri says he always felt the drive to make an impact — and was never afraid to put in the hard work. Like many future entrepreneurs, he began cutting lawns as a kid and was quickly enamored by the financial freedom it provided. He confidently sold his services and then went about securing the necessary equipment to get the proverbial job done.

This run before you walk approach to life seems to have always been accompanied by a beat, a rhythm – taking Dupri to the ends of the entertainment universe and back.

Early success in finding and producing the no. 1 record for ’90s rap duo Kris Kross shouldn’t have been a surprise for those who knew his unapologetic nature and innate ability to spot gaps in the market. Dupri recognized that rap and hip-hop were celebrated by youth without representation. At the respective ages of 12 and 13, the Kris Kross duo became the youngest hip-hop artists to have Gold and Platinum albums.

Famed musician Kenny ‘Babyface’ Edmonds took notice and told a younger Dupri in part, “You’re the guy with the ‘little’ Kris Kross record, right?” Dupri openly admits how this perceived slight challenged his inflated, youthful ego. But, like any good entrepreneur, he wanted to find out why an icon like Babyface would abruptly silence the industry cheers. Dupri quickly learned that Babyface meant no disrespect, but rather a cautious and audacious reminder that while getting your first number 1 record might feel good, it’s even cooler to have multiple number 1’s.

From that day forward, Dupri stopped celebrating the success of Kris Kross and began thinking and working like an entrepreneur.

Entrepreneurism requires vision

“I’m a guy that wakes up every day, and I look around to see what’s missing? Automatically. With Kris Kross, I looked around, and I saw what rap meant to kids and the younger generation, says Dupri.

Culture is part of it and understanding the connection a city has with music defines the opportunity, according to Dupri.

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“In many ways, nobody thought of Atlanta as a successful hip-hop city until Kris Kross. No other rappers in Atlanta were selling millions in records. Kris Kross often doesn’t get the credit for putting Atlanta hip-hop in the space that it is in today, but many people in the rap scene of Atlanta say that Kris Kross was their first tape. It then becomes intertwined in their lives and a part of the larger culture.”

Education on the road

“At 12 years old, I knew I wanted to be something but didn’t know what the word entrepreneur meant. I went on tour as a dancer and had a tutor for school. Unfortunately, the Atlanta school system at the time (1983-84) wasn’t prepared for that kind of setup and refused to accept my grades. So when I was told that I would have to repeat 6th grade, I immediately flipped from age 12 to 21. I had been on tour and knew it was what I wanted.

Dupri continued his pursuits and decided not to return to school. “I was taught so much through my relationships with Run DMC, Houdini, Grandmaster Flash, and these New York guys in hip-hop,’ he recalls. “It put me dead in the face of hip-hop in an era where you can never be taught by better people. I learned DJ-ing, graffiti, emceeing, and everything. I learned it all.”

The art of celebrating success

“You don’t get to celebrate it the way other people do in other fields. When people win the Super Bowl or the NBA finals, they go to Disney World the next day – not in the music business,” says Dupri.

“There’s also a pattern of people struggling to keep up with success in my business. It’s sort of written in, but I wake up every morning with the mindset that it’s not going to happen for me. It’s go, go, go.”

Last night, for instance, I was in the studio working, trying to finish this new Usher album, and during the conversations about the record, I started getting very nervous. I could feel the anxiety and the uneasiness carrying over to other areas, triggering worry about JD’s Vegan and other areas of my life. It’s just part of it.”

“Keeping success is harder than achieving success,” he says.

“I remember being a cocky young producer with a no. 1 song. Then, I met Babyface, who said, ‘You’re the guy with the little Kriss Kross song.’ It disturbed me at first, but then he told me, ‘It’s cool to have a number one record, believe me, but it’s cooler to do it multiple times.’ He taught me to listen and learn and not get caught up in the moment of success.”

Building the muscle to succeed

“Pay attention to what made you feel good. You will have more moments that will make you feel bad than good. In your search as an entrepreneur to feel better, remember the things that made you feel good in the process of the journey and keep it moving forward.”

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“You might forget things that happened 10 to 20 years ago, but try and remember what made you feel sane and happy. It’s like training your muscles in the gym, but for your mind. Train to find the win regardless of what’s going on.”

On trust

Dupri says that regardless of the situation, he struggles to trust those meant to support his efforts. “It’s hard for me to find people I trust. I don’t always believe that people will do what I think they should be doing. They might do something good for them through me.”

He continues, “I admit my lack of trust in others might be one of my bad traits. I struggle to hand off a lot of things. I’m pretty much hands-on with everything that’s going on in my life.”

Can’t slow the beat

There is a rhythm to Jermaine Dupri in the cadence of his statements and the pauses of his inflection that leave one wondering what’s around the bend. Music appears to serve Dupri as his driving force and the underbelly of every path he takes. “You have to keep the metaphorical beat up because slow music feels like you’re losing ground for many in the business arena. People automatically believe that you can’t sustain success if you slow the beat or slow the music down just for a second.”

“It happens in many other areas. LeBron James went to the playoffs eight years in a row, but people wonder about the slowdown when he doesn’t. Quincy Jones made Thriller at the age of 50. I believe that although I’m a million steps behind Quincy, I’m also trying to chase that energy that he had when he was 50. People should understand that mindset.”

Changing the narrative with JD’s Vegan

The music icon turned food entrepreneur understands the whiplash reactions he gets when people hear of his venture into vegan. But he sure isn’t surprised. Dupri’s been vegan for years, and this is an extension of the man identifying a gap and tearing through the opening.

“The beat changing for me is JD’s Vegan because it comes from left field, he says. “Some might feel like I’ve transferred my energy from music into something else, but it’s only chatter.”

Dupri notices that no one is paying attention to the fact that JD’s Vegan changes the narrative in hip-hop. “For the first time in hip-hop, JD’s Vegan offers a healthy choice, but I want to make sure I’m clear. I’m not attacking anybody in hip-hop, but I do want people to understand that a majority of things that are sold through hip-hop are not always good for you as a person,” he says.

“I want to counter the alcohol, gun violence, and unhealthy choices by showing JD’s Vegan is healthy. There are people in my community with high blood pressure, bad eating habits, and some dying before 70 because of poor diet. I can help in that area based on what I’m doing with JD’s Vegan, and it’s definitely a different challenge.”

Embracing the “New”

“I’m new. I was inducted into the Songwriters Hall of Fame. Jay Z was the first rapper to be inducted, which was mind-blowing. The year after, I was inducted as the second rapper.

No one has ever written a number one Rap, Pop, and R&B record. I’m 100% New compared to whatever people think about me. Even with JD’s Vegan, it’s completely new compared to what you’ve seen before, and I believe I have marching orders to continue to stay new. Trying to stay new might be the hardest job in the world, but that’s who I am. New.”

No end in sight

JD’s Vegan frozen dessert offering has already achieved a level of success most would aspire to with exclusive distribution through Walmart. JD’s Vegan affords Dupri an opportunity to introduce healthy living options into his community, and by all accounts, this just might be his ‘why.’

A man approaching 50 with the same level of anxiety any young entrepreneur can recognize. Dupri openly admits his limitations along with his drive to embrace his, “I’m New” in everything he tackles.

Maybe this time, he’ll be able to celebrate and do so, feeling healthy.