Built to Sell: How Chad Cook Turned 12 Businesses into a Life of Freedom and Balance - Chad Cook
What's Your Deal? | Buying Businesses, Business Acquisitions, Investing & Exit Strategies
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Show Notes
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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