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The Mindset That Separates Winners from Losers

The Mindset That Separates Winners from Losers

In today’s episode, Kevin O’Leary breaks down what he looks for in founders, why most people fail with money, and how freedom really works.

The Playbook With David Meltzer

May 27, 202522m 24s

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Show Notes

In today’s episode, I sit down with Kevin O’Leary to talk about what separates true entrepreneurs from wannabes. He explains why passion, not profit, is the real driver of success, and why most of his top-performing investments have come from founders who treat time like their most precious asset. Kevin shares why honesty beats politeness when giving feedback, how he spots resilience in a pitch, and what most people get wrong about financial freedom. We also talk about his views on work-life balance, the dangers of debt, and the surprising power of saving early and consistently. His candor is sharp, but it comes from experience—and results.