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

 

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