Best Business Partners

From Checkers to Chess: Brian Shapiro on Luxury Real Estate & Innovation

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In this episode of The Best Business Partners Podcast, Jess and Erin sit down with Brian Shapiro, Managing Partner of the Miami Portfolio Collection—one of only three licensed Portfolio offices in the country. With over $3 billion in Miami real estate sales through his family team, Brian brings unmatched expertise in luxury, strategy, and leadership.

He opens up about the lasting inspiration of his late mother, whose influence continues to shape his approach to business and life. Brian also shares why running a boutique Portfolio office is like “playing chess while others play checkers,” breaking down how elite agents anticipate moves, think long-term, and elevate every transaction.

Beyond real estate, Brian is now spearheading a cutting-edge AI real estate technology company, positioning himself and his team at the forefront of industry innovation. Packed with insight, personal stories, and fun analogies, this episode is a masterclass in playing the long game in both business and life.

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