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. Mike shares the CDNOW story straight: a planned merger with Columbia House that fell through at the last minute, the dot-com bust hitting at the same time, preparing for Chapter 11 while also running a sale process, and a late acquisition by Bertelsmann at $3 a share when the stock had once peaked near $39. He also opens up about his last startup, where he chose to return capital and shut it down rather than take more money and put a team in greater jeopardy.

In This Episode:

• Why people — not ideas or products — are the real driver of company success
• The four accountabilities that define a real CEO
• The CDNOW story: from IPO to near-bankruptcy and a last-minute acquisition
• What bankruptcy and shutting down a startup teach you that winning never will
• Why most companies have a comfort problem, not a culture problem
• How AI multiplies great people but doesn't replace the need for them

Connect with Mike:

• Trajectify: trajectify.com
• LinkedIn: linkedin.com/in/mkrupit
• YouTube: Building Better Businesses

Connect with Bill:

• Website: ScalingCoach.com
• LinkedIn: linkedin.com/in/billgallagher
• Free Q20 Growth Diagnostic: ScalingCoach.com/Q20

Busy is Broken — Bill's new book, coming September 2026. Sign up at busyisbroken.com

Keep scaling.

Mentioned in this episode:

Busy Is Broken

Have you ever had a week where you're completely slammed but somehow nothing actually moved? Is this one of those weeks? That’s not really a time problem. It's a busyness habit problem. My new book, Busy Is Broken: Do Less, Scale More, is about growing by doing less, not more. Read or listen to a sample chapter, over at busyisbroken.com. That's busyisbroken.com. Also on amazon and other booksellers.