EPISODE · Apr 16, 2026 · 35 MIN
Don Peebles III | The Long Game w/ Jay Roberts #12
from The Long Game · host Prosper Group
On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Don Peebles III, Chief Operating Officer of The Peebles Corporation, the largest Black-owned real estate development company in America.We dive into his origin story—growing up at the dinner table learning cap rates before long division, being immersed in the family business from an early age, and building his own credibility inside one of the most respected development firms in the country.Our conversation explores how The Peebles Corporation has built a four-decade track record across major U.S. cities by targeting both ends of the market—ultra-luxury and affordable housing—while most developers compete in the middle. Don breaks down the story behind the Bath Club, one of Miami Beach’s most historic private clubs and now a cornerstone asset in the firm’s portfolio.He also shares why off-market relationships are the only deals worth doing, what the next generation of real estate development looks like, and the mindset that has kept The Peebles Corporation at the top for over 40 years.This episode reveals what it looks like when legacy, credibility, and the right market thesis compound across generations.🎯 TAKEAWAYS:Why The Peebles Corporation targets both ends of the barbell—ultra-luxury and affordable housing—and why chasing the middle is a losing strategyThe full story behind the transformation of the Bath Club into one of the firm’s most iconic assets as it approaches its 100th yearWhy a 12-seat omakase restaurant inside the club could be on the verge of a Michelin starHow nearly 5,000 affordable housing units could define the firm’s next chapter—and why affordability should be a stepping stone to ownershipHow Peebles wins deals by going directly to sellers and avoiding marketed listings entirelyWhy information is more valuable than money—and how transparency builds long-term investor trustHow AI is reshaping real estate and why interpersonal skills now matter more than technical expertiseIf you’re interested in investing with Prosper Group, visit https://prospergroup.com/invest/Stay up to date with Jay Roberts:Instagram: https://www.instagram.com/jayrobertsFor more information about Don Peebles III and The Peebles Corporation:https://peeblescorp.com
What this episode covers
On this episode of The Long Game by Jay Roberts, CEO of Prosper Group, we sit down with Don Peebles III, Chief Operating Officer of The Peebles Corporation, the largest Black-owned real estate development company in America.We dive into his origin story—growing up at the dinner table learning cap rates before long division, being immersed in the family business from an early age, and building his own credibility inside one of the most respected development firms in the country.Our conversation explores how The Peebles Corporation has built a four-decade track record across major U.S. cities by targeting both ends of the market—ultra-luxury and affordable housing—while most developers compete in the middle. Don breaks down the story behind the Bath Club, one of Miami Beach’s most historic private clubs and now a cornerstone asset in the firm’s portfolio.He also shares why off-market relationships are the only deals worth doing, what the next generation of real estate development looks like, and the mindset that has kept The Peebles Corporation at the top for over 40 years.This episode reveals what it looks like when legacy, credibility, and the right market thesis compound across generations.🎯 TAKEAWAYS:Why The Peebles Corporation targets both ends of the barbell—ultra-luxury and affordable housing—and why chasing the middle is a losing strategyThe full story behind the transformation of the Bath Club into one of the firm’s most iconic assets as it approaches its 100th yearWhy a 12-seat omakase restaurant inside the club could be on the verge of a Michelin starHow nearly 5,000 affordable housing units could define the firm’s next chapter—and why affordability should be a stepping stone to ownershipHow Peebles wins deals by going directly to sellers and avoiding marketed listings entirelyWhy information is more valuable than money—and how transparency builds long-term investor trustHow AI is reshaping real estate and why interpersonal skills now matter more than technical expertiseIf you’re interested in investing with Prosper Group, visit https://prospergroup.com/invest/Stay up to date with Jay Roberts:Instagram: https://www.instagram.com/jayrobertsFor more information about Don Peebles III and The Peebles Corporation:https://peeblescorp.com
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Don Peebles III | The Long Game w/ Jay Roberts #12
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