Matthew Baron | The Long Game w/ Jay Roberts #32

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Sign up for The Long Game newsletter at ProsperGroup.com.On this episode of The Long Game, Prosper Group CEO Jay Roberts sits down with Matthew Baron, founder and president of Baron Property Group, a vertically integrated development and investment firm building across New York City and Miami.

Matthew shares lessons from more than two decades in real estate development, from navigating complex financing and market cycles to building a pipeline totaling nearly 4 million square feet, more than 3,600 residential units, and over $2 billion in value.He takes Jay inside the refinancing of Metro parc, a 559-unit rental development in Hialeah, including how a lender pulled out just days before a $225 million refinancing was expected to close and how his team was forced to replace hundreds of millions of dollars in capital.

Jay and Matthew also discuss the Amazon HQ2 deal in Long Island City that could have generated substantially over a quarter of a billion dollars for Matthew and his partners before Amazon abandoned its plans for New York City in 2019.

The conversation explores the challenges facing real estate development in New York, the impact of rent stabilization and proposed rent freezes, why capital and developers are increasingly looking toward Miami, and the dramatically different experience Matthew had developing in South Florida.Matthew explains why he prefers rental developments over condominiums, how long-term ownership can help developers withstand market downturns, and why successful real estate development requires patience, resilience, strong relationships, and the ability to constantly adapt.

He also shares lessons from one of the worst deals of his career, why entering unfamiliar markets without deep local knowledge can destroy a project, and why failure and experience remain two of the greatest teachers in business.

🎯 TAKEAWAYS:

• How Matthew built a real estate development pipeline valued at more than $2 billion

• What happened when a lender pulled out days before a $225 million refinancing

• The story behind Matthew’s Amazon HQ2 deal in Long Island City

• Why Matthew believes failure is an unavoidable part of long-term success

• Why relationships, communication, and transparency matter during difficult deals

• Why Matthew believes New York has become increasingly challenging for developers

• How Miami’s approach to development and investment differs from New York

• Why Matthew prefers rental developments over for-sale condominiums

• How market cycles and long-term ownership can create opportunities for developers

• Why local knowledge is critical when entering a new real estate market

• Why resilience, adaptability, and the ability to pivot are essential in development

• How Matthew thinks about playing the long game in real estateStay up to date with Jay Roberts:Instagram: @jayrobertsWebsite: ProsperGroup.com