Episode 688

full
Published on:

27th May 2026

From IPO to Bankruptcy and Back — Scaling Across Full Lifecycles, with Mike Krupit

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:

Connect with Bill:

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

Keep scaling.

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About the Podcast

Scaling Up Business with Bill Gallagher
Do you dream of an easier way to scale and grow your business? Do you wish you didn’t have to work so hard and put in as many hours? Do you find growth too slow, or hard to sustain?

This podcast—Scaling Up Business with Bill Gallagher—can help you achieve and maintain the growth you want.

A message from your host: “I’ve been in your shoes as a founder, CEO, and executive leader. I’ve coached and trained many leaders just like you over more than 15 years to grow their businesses successfully and profitably. But more than that, I’ve helped give them their time and sanity back. My core strength is making the growth process easier, faster, and way more fun.”

A dynamic thought leader, Bill talks with fascinating and brilliant guests each week, including visionary CEOs, trailblazing entrepreneurs, best-selling authors, renowned business strategists, and more.

Broadly, each episode focuses on one of the four major decision areas every entrepreneur and company must get right: People, Strategy, Execution, and Cash. More specifically, the show explores topics such as:

* Business Growth & Scaling.
* Customer Experience & Marketing.
* Innovation & Differentiation.
* Leadership Development.
* Delegation & Accountability.
* Vision & Strategy.
* Team Dynamics.
* Hiring & Talent Management.
* Company Culture.
* Employee Engagement.
* Crisis Management.
* Effective Communication.
* Influence & Persuasion.
* Business Strategies.

Running a business is ultimately about freedom. Subscribe to this podcast to learn how leaders like you can get your organizations moving in sync, create something significant, and still enjoy the ride. Subscribe if you want to elevate your business to unprecedented heights by tuning in to a masterclass in business excellence.

For information on Bill Gallagher’s coaching and training programs, and Scaling Up Workshops, visit www.ScalingCoach.com
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William Gallagher