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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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In this episode of Ben Thinking, host Ben Nevares sits down with serial entrepreneur and business broker Chad Peterson to talk straight about what separates real entrepreneurs from the rest. Chad shares the no-BS reality of building businesses, burning the boats, and why having a backup plan might be the worst decision you can make. From blue-collar beginnings to elite business exits, Chad breaks down why most people aren’t built for the entrepreneurial grind—and how he helps those who are sell their companies for top dollar.
This episode is a must-listen for business owners, solopreneurs, and anyone considering starting—or ending—their entrepreneurial journey.
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⏱️ Chapter Markers:
01:45 – The Blue-Collar Start: Roofing, Paper Routes, and Work Ethic
04:30 – Why "Job People" Can’t Handle Business Ownership
07:10 – Defining Real Entrepreneurs: No Safety Net, No Excuses
10:00 – Burn the Boats: The No-Plan-B Mindset
12:50 – What Makes a Business Sellable?
15:15 – Selling Yourself vs. Selling a Company
18:30 – Emotional Challenges of Selling Your Business
21:00 – Why Most Businesses Never Get Sold
23:45 – Stories from the Brokerage Frontlines
26:00 – The Role of Grit in Success
28:10 – Getting Real About Risk and Pain
30:30 – What Chad Looks for in a Sellable Company
33:15 – Advice to Business Owners Approaching Burnout
36:00 – Closing Thoughts: Know Who You Are in the Game
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