
Hosted by Bill Gallagher · EN

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 successThe four accountabilities that define a real CEOThe CDNOW story: from IPO to near-bankruptcy and a last-minute acquisitionWhat bankruptcy and shutting down a startup teach you that winning never willWhy most companies have a comfort problem, not a culture problemHow AI multiplies great people but doesn't replace the need for themConnect with Mike:Trajectify: trajectify.comLinkedIn: linkedin.com/in/mkrupitYouTube: Building Better BusinessesConnect with Bill:Website: ScalingCoach.comLinkedIn: linkedin.com/in/billgallagherFree Q20 Growth Diagnostic: ScalingCoach.com/Q20Busy is Broken — Bill's new book, coming September 2026. Sign up at busyisbroken.comKeep scaling.Mentioned in this episode:Busy Is BrokenHave 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.

There's a healthcare CEO Bill coached — smart, driven, impeccable résumé — who ran a national company the same way they ran eighth-grade group projects: by doing everyone else's work. Episode five of the Busy Is Broken series is about the moment that reflex stops being a strength and starts being the bottleneck. The overachiever who took over the group project in middle school got praised for it. Decades later, the same instinct shows up at the C-suite, and it doesn't scale — it suffocates.Lee came into a healthcare empire valued in the hundreds of millions. From the start, Lee second-guessed the leadership team, reworked slide decks at midnight, edited marketing copy mid-flight, and jumped into facilitation exercises Bill was running — not to collaborate, but to control. Not cruel. Not incompetent. Just an overachiever reflex from school that had never been updated. The result: people stopped presenting detailed plans because they knew Lee would reshuffle them. They stopped proposing creative solutions because Lee would override them. They learned helplessness. The best ones left.The gap is the giveaway. If you asked Lee, Lee was "protecting the company." If you asked the team, Lee was suffocating it. That gap — between how the leader describes the behavior and how the team experiences it — is the micromanager's blind spot. Lee eventually got it. Replaced wrong hires with right ones, stopped covering for empty seats, started letting go. The company stabilized. But it took years of damage and talent loss before the reflex broke. This week's invitation: when someone brings you a draft, a plan, a decision, notice the impulse to edit. Before you touch it, ask: "Is this good enough to ship, even if I'd do it differently?" If yes, let it go.Links:Busy Is Broken book and free diagnostic: https://busyisbroken.comQ20 Growth Diagnostic: https://scalingcoach.com/Q20Mentioned in this episode:Busy Is BrokenHave 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.

Suneet Agarwal joins Bill Gallagher on the Scaling Up Business podcast. Tune in to hear Suneet share insights on growth, leadership, and building scalable businesses.Mentioned in this episode:Busy Is BrokenHave 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.

What kind of castle are you running?In this solo episode, Bill Gallagher breaks down two fundamentally different leadership styles: command-driven and culture-driven. One scales. The other burns people out.Most founders default to the command style because it feels productive. You tell people what to do, they do it, problems get solved. But as your company grows, that approach becomes a bottleneck — and a trap.Culture-driven leadership is harder to build but far more powerful at scale. It means creating systems where people make great decisions without you in the room.In This Episode:This episode is drawn from Bill's upcoming book Busy Is Broken.Connect with Bill:Mentioned in this episode:Busy Is BrokenHave 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.

What if the biggest tax on your business isn't coming from the government — it's coming from your management style? In this solo episode, Bill Gallagher digs into the research showing that micromanagement alone can strip 28% of a team's productive output. He connects the dots between chronic overwork, toxic busyness culture, and the massive hidden costs that never show up on a balance sheet — from skyrocketing turnover to plummeting quality and customer loyalty. This episode will make you rethink everything about how you're running your team.Mentioned in this episode:Busy Is BrokenHave 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.

Jason Wild has built a reputation for identifying and acquiring companies that can become category leaders. In this episode, he joins Bill Gallagher to share his approach to strategic acquisitions — from finding the right targets to integrating teams and scaling operations post-deal. Whether you're considering your first acquisition or your fifteenth, Jason's framework for building through M&A will change how you think about growth.Mentioned in this episode:Busy is Broken bookOur new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.comQ20 Diagnostic OfferStuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

How did "busy" become the ultimate badge of honor in business? In this solo episode, Bill Gallagher traces the cultural and historical roots of our obsession with busyness — from the Protestant work ethic to Silicon Valley hustle culture. He makes the case that constant busyness isn't just unproductive, it's actively destroying your ability to lead, think strategically, and scale your company. If you've ever worn your packed calendar as a point of pride, this episode will challenge everything you believe about hard work.Mentioned in this episode:Busy Is BrokenHave 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.

Suneera Madhani built Stax (formerly Fattmerchant) into a billion-dollar fintech company, landing on the Inc. 5000 list and earning recognition as one of the most influential leaders in payments. In this episode, Suneera joins Bill Gallagher to share her journey from startup founder to CEO of a high-growth company — and the leadership lessons she learned scaling through every stage. If you're building something big and wondering how to keep your culture and your vision intact while you grow, this one's for you.Mentioned in this episode:Busy is Broken bookOur new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.comQ20 Diagnostic OfferStuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20

I learned the most important lesson about leadership on a small sailboat in San Francisco Bay. Overpowered and fighting the tiller in a building westerly, an older skipper said five words: "Put in a reef." We reduced sail. The boat flattened, the helm went neutral, and we locked into a clean groove. Less canvas, more speed.That's the thesis of my book Busy Is Broken, and this is a solo episode where I walk through the ideas, stories, and data that can change how you lead and how you live.In this episode: the sailboat metaphor for leadership, why your effort might be the bottleneck, and the three shifts every scaling leader needs to make.This week's invitation: find one meeting you can cancel tomorrow. One decision you can hand off. One hour reclaimed for something important — not just urgent.Key Takeaways:An overpowered boat heels, drags its hull sideways, and the rudder fights you. The fix is counterintuitive: reduce sail, balance the boat, let the wind do the work.The three shifts: micromanagement to empowerment, superhero identity to self-awareness, always-on to rest and recovery.This is episode one of thirteen — a solo series from Bill's book, Busy Is Broken.Links:Book: Busy Is Broken by Bill Gallagher (coming August 2026)Podcast: The Scaling Up Podcast — scalingcoach.comBill Gallagher: scalingcoach.comMentioned in this episode:Q20 Diagnostic OfferStuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20Busy is Broken bookOur new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.com
How do you succeed in a world that demands your attention 24/7 ?In this episode, Bill Gallagher sits down with Fred Marshall, CEO, investor, and author of Thrive: The Antidote to Future Shock, to explore how to navigate anxiety, information overload, and rapid change. Fred shares practical ways to restore your attention, simplify your life, and build a meaningful future using intentional habits.(06:13) Why We’re All Feeling Overwhelmed*We’re living in an age of constant input.*The average person checks their phone dozens of times a day, fragmenting focus.*This makes it difficult to think deeply, build meaningful work, or feel in control of your life.(16:04) When Change Outpaces Our Ability to Adapt*Future shock happens when the pace of change exceeds our ability to process it.*Technology, economics, and social systems are shifting from linear to exponential growth.*This creates anxiety, uncertainty, and a sense of constantly “falling behind.”(21:01) Take Back Control*Instead of stressing about global uncertainty, focus on what’s within your control.*Build a weekly rhythm of small, consistent actions toward your desired future.*Choosing where to invest your time and energy is the antidote to overwhelm.(25:20) Shift from Consumption to Creation*Most people are stuck consuming content instead of creating value.*Endless scrolling leads to distraction, anxiety, and lack of meaning.*Creating, whether in business, relationships, or personal growth; builds fulfillment and momentum.Thanks to Fred Marshall for being on the show!Connect with Fred on LinkedIn: https://www.linkedin.com/in/fredric-marshall-1984bb/Learn more about his work: https://thrivefutureyou.com/Bill Gallagher, Scaling Coach and host of the Scaling Up Business podcast, is an international business coach who works with C-Suite leaders to achieve breakthrough growth.Join Bill in the Growth Navigator Coaching Program: https://ScalingCoach.com/workshopBill on LinkedIn: https://www.LinkedIn.com/in/BillGallBill on YouTube: https://www.YouTube.com/@BillGallagherScalingCoachVisit https://ScalingUp.com to learn more about Verne Harnish, our team of Scaling Up Coaches, and the Scaling Up Performance Platform, which includes coaching, learning, software, and summit. We share how the fastest-growing companies succeed where so many others fail. We help leadership teams with the biggest decisions around people, strategy, execution, and cash so that they can scale up successfully and beat the odds of business growth.Did you enjoy today’s episode? If so, then please leave a review! Help other business leaders discover Scaling Up Business with Bill Gallagher so they, too, can benefit from the ideas shared in these podcasts.Subscribe via Spotify: https://spoti.fi/3PGhWPJSubscribe via Apple Podcasts: https://apple.co/3PKe00uBill on Facebook: https://www.facebook.com/billgall/Bill on Twitter/X: https://x.com/billgallMentioned in this episode:Busy is Broken bookOur new book, Busy is Broken, coming this September. Sign up for the release at busyisbroken.comQ20 Diagnostic OfferStuck? Q20 Growth Diagnostic will give you a fresh perspective and it's free. ScalingCoach.com/Q20