Digital Mayors Podcast

Ep 53: 20 Years in Business With My Brother: The Wins, Mistakes & Stories We’ve Never Told

August 29, 2026·1h 10m
Episode Description from the Publisher

Twenty years ago, Michael Nathanson walked into Dan's real estate office with a license Dan didn't know he'd gotten and announced, in his own unique way, that they were apparently going into business together.Twenty years later, we're turning the microphones on ourselves.In this special episode of The Digital Mayors Podcast, we look back at the early days of The Nathanson Brothers, difficult markets, first transactions, mistakes, career changes, starting new businesses, community involvement and what we've learned from working together for two decades.The biggest takeaway surprised even us: the best part wasn't the transactions or businesses. It was the people and relationships.HighlightsThe unexpected moment everything startedWhat working with your brother really looks likeLessons from the housing crashThe coin flip that changed our careersOur best and worst business decisionsWhy South Florida community involvement became so importantWhat we want the Nathanson Brothers name to mean 20 years from nowVisit LoveWhereYouLiveFL.com for the episode, our South Florida community hub and more from The Digital Mayors Podcast.

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