219: From Bankrupt to Bestseller: How Mike Michalowicz Used His Own Failures to Empower Other Entrepreneurs

219: From Bankrupt to Bestseller: How Mike Michalowicz Used His Own Failures to Empower Other Entrepreneurs

Mike Michalowicz appeared to have everything an entrepreneur could want—big companies and lots of revenue coming in. But things aren’t always as they seem. As Michalowicz was high on fleeting indicators of success, his businesses were leaking profits. “I got caught up in the vanity metrics…how big my business was revenue-wise and how big my business was people-wise,” Michalowicz says. After feeling the sting of and two failed investments and losing millions, Michalowicz found himself struggling with depression—along with a realization that ignorance and arrogance were a deadly combination. Thankfully, with support from friends and a rekindling of his love of writing, Michalowicz was able to pull himself out of the ashes and rebuild his career—this time with heart and soul. Michalowicz used writing as a way to find solutions to all of the biggest challenges he faced as a founder. His books Profit First, Pumpkin Plan, and Clockwork tackle managing cash, business growth, and automating a company, respectively. His next book will focus on how entrepreneurs can serve a greater purpose and make an impact on the world. Listen in and get inspired as Michalowicz gets brutally honest about his own struggles, and shares years of lessons learned to empower other entrepreneurs. Key Takeaways The actions that led Michalowicz to lose millions and hit rock bottom How Michalowicz found his niche and rebuilt his career after 10 failed companies Why working too hard can signal a lack of efficiency How to manage cash and avoid spending money you don’t have

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622: (Solo) The Truth About Founder-Led Content in 2026

622: (Solo) The Truth About Founder-Led Content in 2026

Founder-led branding isn’t dead — but it is evolving fast. Showing your face and posting “day in the life” content is no longer enough to stand out. The bar has risen, audiences have matured, and what...

13 Jan 8min

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

621: We Bet $200K on Bras Before Making a Single Sale — Sold 400,000 in 2 Years | Nala

Nala was built by two founders with no fashion background who invested $200,000 before making a single sale and went on to sell over 400,000 pieces in just two years. In this interview, Chloe and ...

8 Jan 49min

620: (Solo) The Secret to Making Bold Business Moves With Confidence

620: (Solo) The Secret to Making Bold Business Moves With Confidence

One of the biggest challenges founders face — especially at the end of the year — is knowing what to do next and feeling confident that the move you're about to make is the right one. Certainty feels ...

6 Jan 11min

619: Airline Charged Me $65 - So I built a $250M Competitor | Adam Ewart

619: Airline Charged Me $65 - So I built a $250M Competitor | Adam Ewart

Adam Ewart turned a £50 excess baggage fee into a global bootstrapped logistics company operating in 145 countries and staying profitable for 15 straight years. In this interview, Adam breaks down ...

1 Jan 47min

618: (Solo) What 5 World-Class Founders Taught Me This Year

618: (Solo) What 5 World-Class Founders Taught Me This Year

Every year I sit down with some of the world’s most fascinating founders — but this year’s interviews hit me harder than most. Reinvention, resilience, copycats, failure, loneliness after exits, scrap...

30 Dec 202511min

617: How A Failing Skincare Brand Became An 8-Figure Makeup Empire | Aliett Buttelman

617: How A Failing Skincare Brand Became An 8-Figure Makeup Empire | Aliett Buttelman

Aliett Buttelman spent eight years grinding in the dark before a single viral moment with Taylor Swift turned Fazit into an overnight seven-figure brand. In this interview, Aliett breaks down the ...

25 Dec 202552min

616: (Solo) 5 Honest Business Lessons I’m Taking Into 2026

616: (Solo) 5 Honest Business Lessons I’m Taking Into 2026

2025 has been one of the most eye-opening years of my founder journey — personally, professionally, and strategically. Instead of sharing a highlight reel, I want to share the real lessons that moved ...

23 Dec 20258min

615: Stop Chasing Sexy Businesses - This Boring One Made Me $500M+ | David Royce

615: Stop Chasing Sexy Businesses - This Boring One Made Me $500M+ | David Royce

David Royce went from a broke college kid in a door-to-door pest control job to building and selling four service businesses for nine-figure exits by applying Silicon Valley systems to an unsexy blu...

18 Dec 202558min

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