In this episode of What's Your Deal?, Matt sits down with longtime client and friend Chad Cook—a true serial entrepreneur who has started, grown, and sold 12 businesses over the last 34 years. From his humble beginnings running a paper route and selling donuts to owning large-scale Family Fun Centers and a statewide Dippin' Dots distribution business, Chad shares the real stories behind his business ventures, including the wins, the lessons, and the near-bankrupt moments. Matt and Chad discuss the strategic mindset required to build sellable businesses, the importance of family support and faith, and how Chad's ability to maintain calm and rhythm through both recession and rapid growth has led to a fulfilling life—personally and professionally. Whether you're an aspiring business owner or seasoned operator, Chad's story is a blueprint for creating legacy, freedom, and peace through entrepreneurship.   00:16 – Meet Chad Cook: 12 businesses, 34 years, and one donut-selling paper route   01:13 – How Chad built trust and relationships with buyers over the years   02:51 – Why Chad started his first business without a safety net   03:41 – Navigating weekends and family time in a Family Fun Center business   04:45 – A rundown of Chad's business ventures over the decades   06:49 – Building and operating Castle Golf and Freedom Station   08:21 – Making big financial commitments in capital-heavy businesses   10:40 – What is a game route business and why it's nearly passive   12:17 – Why game routes are one of the most passive models Chad's found   13:15 – Involving the kids: How Chad built family into his businesses   14:40 – Strategy or opportunity? How Chad chose his businesses   18:20 – Designing businesses to be sellable assets   19:18 – How Chad and Brenda decide when it's time to sell   20:50 – Why selling a business takes years—not months   24:38 – Treating businesses like kids: Chad's approach to growth and exits   25:44 – The importance of relationships in business and family   27:41 – Chad's toughest business challenge: The Great Recession   30:40 – Surviving on credit cards—and the decision to go debt-free   33:15 – How income-producing debt differs from consumer debt   35:50 – Selling a business to his son—and watching him scale it fast   39:00 – Balance or rhythm? Chad's approach to work-life integration   44:01 – Who gave Chad a hand up? The mentors and loved ones who believed in him       Resources & Links   Want to be a guest on the show, or have a deal that you would like for us to evaluate? Apply here   Follow Us on Social Media   Instagram: @AmpedSuccess   LinkedIn: Amped Success   Tiktok:  @Ampedsuccess   YouTube: @AmpedSuccess 📧 Contact Us: For inquiries, reach out at [email protected]

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