Navigating the Complexity of Judgment

David Osborn built a $200 million net worth from the ground up, becoming the largest franchise owner in Keller Williams history and founding a nine-figure private equity firm. But that’s not the whole story. In this conversation, David breaks down how he made his first $100M, the trap of chasing more, and what it really means to live a wealthy life. From 15-hour days and hiring disasters to building empires through people—not hustle—David shares what most millionaires won’t. This episode is a masterclass in mindset, leadership, leverage, and the shift from success to significance.

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