Ep 304 From Bankruptcy at 24 to $35M: Building Profitable Business Through Discipline and Purpose with Mike Chaput

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From Bankruptcy at 24 to $35M: Building Profitable Business Through Discipline and Purpose with Mike Chaput

What if the worst business failure of your life became the foundation for 26 years of unbroken profitability?

At 24, Michael Chaput bought a business that went bankrupt. At 50, he runs a $35 million company that hasn't had a single unprofitable month in 26 years—not through 2008, not through COVID, not ever. In this episode, Michael shares the hard-won lessons from hitting rock bottom and how financial discipline, tough decisions, and the right philosophy about profit built a business that never bleeds red.

In this episode, you will learn:

• Why "caring too much" kills deals: How poor due diligence and bad leases destroyed Michael's first business and the bankruptcy lessons that changed everything.
• The 17% margin discipline: How Michael uses peer benchmarking to spot expense ratio problems (like rent at 20% vs. industry standard of 3-6%) and maintains profitability every single month.
• Why keeping poor performers is cruel: The science of play vs. economic pressure and why letting underperformers go is the kindest thing you can do for them and your team.
• Profit as constraint, not purpose: Michael's philosophy that profit is like staying in bounds in basketball—necessary, but not the point of the game.
• How operating systems create alignment: Using Rockefeller Habits and EOS to turn vision into action and inspire "play" instead of toil.
• The 1,000-book advantage: Why reading one business book per week for 20 years built the foundation for every major decision.

Key Takeaway:

Profitability isn't luck—it's discipline and hard decisions made quickly. Michael Chaput's 26-year track record without a single red month proves that success comes from three non-negotiables: (1) knowing your numbers cold (benchmark expense ratios, target specific margins like his 17%), (2) making tough calls fast (letting poor performers go is kindness, not cruelty), and (3) treating profit as a constraint, not your purpose. Bad deals have long tails, so care enough to walk away. Build a clear vision that inspires "play" instead of just paychecks. And never stop learning—Michael read 1,000+ business books over 20 years. That's how you build a business that never bleeds red, no matter what the economy throws at you.

Bio:

Mike Chaput bought his first company at 24 with borrowed money and no experience, a move that led to early failure and bankruptcy, but also ignited a lifelong drive to understand what makes businesses succeed. He took those hard-won lessons and built a new company from the ground up, scaling it to $35M in revenue with 140 employees, best-in-class margins, and a values-driven culture. With degrees from Columbia Business School and UC Berkeley's Haas School of Business, Mike blends top-tier strategy with real-world execution. As a founder and the CEO of Endsight, as well as a board member and trusted advisor to multiple high-growth companies, Mike brings a grounded, operator's perspective to leadership, sustainable growth, and building resilient teams with purpose.

Links:

Website: https://www.endsight.net/

LinkedIn: https://www.linkedin.com/in/michaelchaput/

Instagram: https://www.instagram.com/thechaputperspective/

YouTube: https://www.youtube.com/@thechaputperspective

Conclusion:

Michael Chaput's journey from bankruptcy at 24 to building a $35 million company with 26 years of unbroken profitability isn't just inspiring—it's a masterclass in what separates businesses that thrive from those that merely survive. The lessons are clear: financial discipline beats hope, tough decisions beat comfort, and a uniting vision beats just working for a paycheck.

If you've been struggling with profitability, tolerating poor performers, or feeling like you're constantly firefighting, this episode gives you the blueprint to break free. Start by knowing your numbers, set your margin target, benchmark against your peers, and have the courage to make the hard calls. Remember: profit is necessary, but purpose is what makes the game worth playing.

#ProfitAnswerMan #Profitability #BusinessGrowth #Entrepreneurship #SmallBusiness

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Music provided by Junan from Junan Podcast

Any financial advice is for educational purposes only and you should consult with an expert for your specific needs.