Ep. 482 — Matt Curry: He Sold His $18M Auto Repair Empire, Regretted It, and Built It Back Better

6 min read

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Episode Summary

The offer letter is on the table. The number is real money. Your spouse is tired. You’re tired. You start doing the mental math on what life looks like after the wire hits and the family office takes the keys. That’s exactly where Matt Curry was at 47 when he sold Curry’s Auto Service: ten stores, $18M in revenue, voted #1 auto repair shop in North America by Motor Age. Eight months later, he was looking at his account, more money than he’d ever seen, and realizing he had no place to go. Within twelve months, he watched the private equity buyer lose every employee but one and cut revenue in half. In this conversation, we got into why he sold (and shouldn’t have), what he never normalized on his own personal spending, how he came back at 51 to build Craftsman Auto Care into 8 stores doing $36M with technicians making over $300K, and the discipline that did it: two-minute daily meetings, the “say yes” system that took monthly revenue from $1.4M to $1.9M without a single new store, and the painful exercise of sitting in a Vail ski condo listening to his own phone calls and hearing every way his team was saying no. If you’re sub-60 with a cash-flowing business and an offer on the table, this is the episode.

Top 10 Takeaways

  1. The freedom you’re trying to sell for is freedom you might already have. Take six months off first and find out.
  2. Your business pays for cars, insurance, travel, meals, and trips you’ve never actually priced. Normalize that number before you wire out.
  3. Private equity cares about stock price. Your team cares about whether they’re appreciated. That buyer will burn your culture in six months.
  4. ADD energy is the entrepreneurial superpower. The trade-off is forcing yourself to delegate every detail you don’t want to touch.
  5. Sub-60 with a cash-flowing business you’re not sick of? The default answer is don’t sell. Solve the operator trap instead.
  6. Get advisors with no skin in the deal. Three attorneys with billable-hour eyes will all tell you to sell.
  7. Two-minute daily meetings beat quarterly off-sites. Enforce and reinforce the message every day, every store.
  8. Listen to your own phone calls. “No” is killing your top line faster than any market headwind.
  9. Saying yes is a system, not a slogan: is it good for the company, good for the customer, and good for the rep personally?
  10. As your valuation grows, you can’t just hand the business to your kid. The estate plan can’t wait until you’re ready to retire.

Sound Bites

“I could have done what I’m doing now without ever selling. I had the freedom, I had… I didn’t realize what I had.” (@00:19:56) — Matt Curry

“It was weird, waking up the next morning, looking at your account, and you got a lot of money in your account, more than you had money than you’d ever seen before, but you had no place to go.” (@00:49:00) — Matt Curry

“I didn’t realize how much freaking money I spent. I thought I could live off a half a million dollars a year, and you know what? I can’t.” (@00:54:24) — Matt Curry

“I was listening to all the ways we were saying no. It was the absentee owner not paying attention.” (@01:15:54) — Matt Curry

“If you’re still in good health, and you’re not 65 or 70 years old, really be intentional about it. What does your life look like after that? I don’t think I put enough thought into that.” (@00:50:30) — Matt Curry

About This Episode

Matt Curry is the founder of Craftsman Auto Care and the author of The ADD Entrepreneur: How to Harness Your Superpowers to Create a Kick-Ass Company, a Wall Street Journal bestseller. He started Curry’s Auto Service in 1998 on $103,000, 13 credit cards, and a $35,000 loan from his father-in-law, in a four-bay garage in the back of a Northern Virginia industrial park. He grew it to 10 stores and $18M in revenue before selling to a strategic buyer in 2014. He started over in 2017 with Craftsman Auto Care and has opened 8 stores in 8 years, projected to do $36M this year, with one of the most reviewed auto repair operations in the country. This conversation sits squarely in the regret-after-sale canon Ryan keeps returning to: the owners who sold for freedom they already had.

Resources Mentioned

  • The ADD Entrepreneur by Matt Curry — Wall Street Journal bestseller on harnessing ADD as an entrepreneurial superpower.
  • Craftsman Auto Care — Matt’s current operation. — craftsmanautocare.com
  • Finish Big by Bo Burlingham — Ryan referenced this as the book he read after his own sale. The 75% regret stat that shaped his work.
  • Small Giants by Bo Burlingham — Referenced in the conversation about privately held businesses choosing not to sell.
  • Delivering Happiness by Tony Hsieh — Ryan referenced the Zappos culture playbook and the famous 2am pizza customer service story.
  • Cadre DC — Derek Coburn’s entrepreneur network in the DMV area.
  • Mavericks — Networking group Matt is involved with.

Connections

Phase + Module:

  • Module 1 — Ownership Goals — Matt’s regret traces directly back to never doing the work of defining what he actually wanted. “You gotta really ask the why.”
  • Module 7 — Leadership Team — The 25-year-tenured core team and the “enforce and reinforce” discipline that scales without him.

Milestones:

Concepts referenced:

  • The Owner-Operator Trap™ — Why Matt sold for freedom he already had, and how most owners can solve the trap without a transaction.
  • Normalized EBITDA — The personal spending coming out of the business that nobody normalizes until the wire hits.
  • Owner’s Scorecard™ — Time, cash flow, and wealth as the three constraints that drive every ownership decision.
  • Independence by Design™ — The alternative path Matt is now living: 8 stores, $36M, and the freedom to leave for a year.
  • iBD North Star™ — “What problem are you actually trying to solve?” The question Matt wishes he’d asked at 47.

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