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EPISODE · May 27, 2025 · 19 MIN

The Mindset That Separates Winners from Losers

from The Playbook · host David Meltzer, Entrepreneur.com

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.

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The Mindset That Separates Winners from Losers

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This episode was published on May 27, 2025.

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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...

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