‘We Don’t Forget Where We Come From’: Real Estate Mogul Don Peebles Reveals His Best Entrepreneurial Lessons With 2-Time NBA All-Star Andre Drummond

The famed real estate developer explains how he got his start, and Drummond shares what he wants his future to look like beyond basketball.

By Jessica Thomas • edited by Brittany Robins • Aug 12, 2025

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Key Takeaways

Peebles shares how a setback led him to become the first African American to own and develop a major hotel.
Drummond shared plans to venture into real estate to help support his hometown.
They emphasize the importance of using their platforms to give back to society.

On every episode of The Playbook, produced by Sports Illustrated and Entrepreneur, we pair a business titan with an elite athlete to discuss their approaches to business and success. In this episode, real estate mogul Don Peebles sits down with Philadelphia 76ers center and two-time NBA All-Star Andre Drummond.

Peebles got his start as a real estate developer in Washington, D.C. But when a major deal went south, he headed to Miami, where he won a bid to develop the Royal Palm Hotel. In doing so, Peebles became the first African American businessperson to own and develop a major hotel. Several years later, he purchased the members-only Bath Club.

“It was a barrier-breaker for Black entrepreneurs,” Peebles says. “I realized at that point that the business side could be used as a transformer and an energizer.”

It eventually led Peebles to launch a $500 million fund for minority developers in 2019. “It’s important we don’t forget where we come from, and we don’t turn our backs on the rest of our society,” Peebles says.

The message resonated with Drummond, who runs an annual free basketball camp in his hometown of Middletown, Connecticut. But Drummond has even bigger plans for the future. “I want to bring money into my town,” he says. “It’s a really small town; not much is really out there. I want to start building the economy out there to start getting people jobs.”

^{Photo Credit: 108 Leonard, developed by The Peebles Corporation with Elad Group}

Drummond, who’s played in the NBA since he was a teen, has seen fellow athletes face hurdles once they retire from the sport. He wants to set an example for young athletes that it’s okay — and even beneficial — to have passions and projects beyond the court.

“We always get knocks for doing things outside of our sport,” he says. “If I can help the next person watching this and let them know that it’s okay to do things outside of your sport and to expand your mind [beyond] the game, so we don’t have that large number of guys that are struggling to find out what to do after basketball’s over.”

Peebles agreed with that mentality of using one’s sport as a jumping-off point to create a fulfilling career – one that will support athletes until they decide to retire, and that they can pass down to their children to build generational wealth.

“You can’t give your kids your skills, but you can give them your business,” Peebles says. “And that’s where the relay is. It’s that next generation. If we can get everyone to think that way, we transform our society.”

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Key Takeaways

Peebles shares how a setback led him to become the first African American to own and develop a major hotel.
Drummond shared plans to venture into real estate to help support his hometown.
They emphasize the importance of using their platforms to give back to society.