From Street Smarts to CEO Savvy: Steve Stoute on Culture, Conviction, and Breaking Through Barriers

“You have to have a belief in yourself that’s so maniacal people think you’re crazy.”

– Steve Stoute, Founder & CEO, UnitedMasters

In a wide-ranging and raw conversation with Aspire host Emma Grede, music industry executive turned cultural strategist Steve Stoute pulled back the curtain on what it really takes to turn cultural capital into business impact. Whether you know him as the founder of UnitedMasters, the architect behind Jay-Z’s Reebok deal, or the man Fortune 500 CEOs call for advice, one thing is clear: Stoute has spent his life translating culture into commerce — and doing it on his own terms.

The Real Inflection Point? Relationships.

Born in Queens, New York, Stoute was surrounded by the pulse of hip-hop long before it became a global industry. LL Cool J, Run-DMC, Salt-N-Pepa — these weren’t just names on a screen; they were neighbors.

But proximity alone wasn’t enough.

“I knew a lot of people who had the idea. But they couldn’t convert that idea because they never learned the relationship part,” Stoute said. “They got caught up in proving they were right instead of figuring out how to bridge the gap.”

Stoute’s superpower became clear early: pairing unshakeable cultural intuition with elite relationship skills. That combination — knowing something others don’t and being able to sell it to the right rooms — became his edge.

From Real Estate to Hip-Hop Theme Songs

His entrepreneurial path wasn’t linear. At 19, Stoute used a $45,000 profit from flipping a house (seeded by his mom refinancing their home behind his dad’s back) to enter the music business.

His first big break? Producing the Martin show theme song — thanks to a young, then-unknown comedian named Martin Lawrence.

“It wasn’t like I thought this was going to be a career. I was just chasing what I loved,” he explained. “But once I got in, I started to see the power of connecting culture with brands.”

The Business of Being the Bridge

Jay-Z once called Stoute "the bridge" between hip-hop and business. And it’s true — Stoute helped usher in a new era where artists became brands and sneakers became status symbols.

He recalls the early days trying to convince white corporate America to bet on hip-hop.

“They didn’t need us. That’s what made it hard,” Stoute said. “So I had to learn how to talk their language, understand their cadence, and find the common ground.”

One of his earliest wins? Will Smith’s Men in Black soundtrack — a moment that revived Smith’s music career and opened Stoute’s eyes to the power of product placement. Ironically, nobody (not even Smith) got paid for the sunglasses that blew up from the video.

That “unclaimed upside” was the lightbulb moment. “That honestly got me down the path of trying to figure out who did the product placement. That curiosity led me to leave music and start an ad agency.”

That agency? Translation. A pioneer in helping brands authentically connect with culture.

“Everyone Can Start a Business. Period.”

One of the most viral moments in the conversation came when Grede asked what separates those who should pursue entrepreneurship from those who shouldn’t.

Stoute didn’t flinch.

“Everyone can start a business. Period,” he said. “But unless you’ve got a dream in your head you can’t get out of your head — it might not be worth it. The math doesn’t work. The failure rate is high. But if you can’t not do it, then I get it.”

His warning? Don’t get seduced by the trendiness of the word “entrepreneur.” If it’s not something you’d be willing to go broke over, it’s not for you.

No, You Can’t Just Microwave a Mentor

Another mic-drop moment came when the topic turned to mentorship.

“People running around asking ‘Will you be my mentor?’ — I’ve never heard of that shit before,” Stoute said. “Mentorship isn’t a transaction. It’s a recognition. It’s something that happens over time, not because you ask for it like popcorn.”

His advice instead? Ask great questions. Be around people you admire. Let the relationship evolve.

Culture Isn’t a Buzzword — It’s a Strategy

Stoute is tired of “culture” being tossed around like marketing ketchup.

“Don’t use the word unless you know what it means,” he said. “Culture is about rituals, shared language, common values. It’s not a hashtag.”

His job — through UnitedMasters and Translation — is to translate what’s happening in the streets into something Fortune 500 CEOs can understand. And that only works if he removes his opinion from the equation.

“You don’t have to like the trend. You just have to understand it. And hire someone who does.”

Leadership Is Telling the Truth — Even When It Hurts

Stoute believes one of his most important leadership values is "challenge and respect."

That means creating a workplace culture where people can disagree directly without being disrespectful — a rare thing in today’s remote, Zoom-heavy world.

“I went back to a four-day workweek because conflict wasn’t happening on Zoom,” he said. “And conflict is necessary for growth. You have to find people who can hear the truth. The best artists, the best employees — they all want the truth.”

Legacy Isn’t About Likes. It’s About Impact.

When asked what motivates him today, Stoute didn’t talk about money or fame.

“I’ve taken so much time away from my family. At least I want something to show for it,” he said. “I want to put a dent in the culture. Whether it’s creating the first Black beauty brand in Sephora or helping artists go independent — that matters.”