Scaling Up Business with Bill Gallagher · 2026-05-27 · 46 min
What does it take to go from startup all the way to exit, multiple times, across different sectors? Mike Krupit has done it. He's been part of three IPOs, including CDNOW, where he served as COO and helped take the company public. He's also been through the harder side: building, growing, and winding down companies when the math stopped working. In this conversation, Bill and Mike dig into what 30 years of building companies actually teaches you. The most surprising lesson, in Mike's words: it's not about the idea, the product, or the timing. It's about having the right people in the right seats. And in the AI era, that hasn't changed; AI is a multiplier on top of people, not a replacement for them. They get into the founder-to-CEO transition Mike has lived multiple times, the four accountabilities a real CEO holds (vision, fiduciary, people, outside face) and why everything else needs to be someone else's job.
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