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In this “Lessons” episode, Robert Croak, the creator of Silly Bandz, breaks down the critical decision every entrepreneur faces: when to sell and when to keep building. Learn why selling for life-changing money can offer security and freedom—but also why the journey of building can lead to even greater long-term fulfillment and success. Croak shares hard-won lessons from turning down $50–60 million offers, overspending on rushed investments, and learning the difference between being a great operator and a smart investor. He emphasizes the importance of building a solid financial base before diversifying, warns against premature angel investing, and explains why staying humble and strategic—especially after a big win—is key to lasting wealth and impact.

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