My guest on this episode is Chris Williams. I was introduced to Chris via Justin Vogt about a year ago. And since then, Chris and I have talked monthly about his search, thoughts on running a small company, the podcast, and all things work and life. I've really enjoyed getting to know him, and I'm thrilled to have him on the podcast finally. Chris recently bought a bookkeeping and accounting outsourcing business in California called System Six, which had 24 employees and around a million dollars in EBITDA at the time of acquisition. As Chris has spent more time in the CEO seat, it's been fun hearing about his ideas, challenges, and new growth plans for the company, and I'm excited to share them on the podcast.

Over the course of this episode, Chris and I talk about why he chose to buy a small company versus continuing in private equity, the daily life of being a CEO, building a team around flexibility, and growth opportunities ahead. Also, Chris is looking to build a specialty in searcher owned companies for bookkeeping and accounting. If this is an area you need help in, definitely reach out to Chris at chris@systemsix.com and tell him you heard him on Think Like an Owner.

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Links

SystemSix

Alpine Investors

Emporos Systems

Topics

(5:27) - Chris’ background and career

(7:15) - Was there a specific moment where you realized that you wanted to run a business yourself?

(8:28) - Did you find PE to be focused less on People?

(10:36) - Were there any opportunities for PE firms to recruit you to work directly within portfolio companies?

(12:32) - Chris’s search and the emotional journey

(17:13) - Are there any high-level takeaways you would share with other searchers?

(19:30) - What is the business you bought?

(21:29) - How much interaction did you have with the owner during the process?

(24:43) - What kind of questions did the owner’s wife ask you?

(26:23) - How has the team received you?

(28:20) - What are the biggest differences in your day to day compared to your time spent in PE?

(31:24) - Is there a specific moment or memory you’ve had since operating that has made it all worthwhile?

(33:44) - What’s an operating rabbit hole you’re going down right now?

(36:12) - Profit Sharing

(39:28) - SystemSix’s interesting flexibility offerings

(42:50) - What are you most excited for over the next 6 months?

(44:34) - What college class would you teach if it could be anything?

(48:00) - What’s a strongly held belief you’ve changed your mind on?

(49:36) - Have you found any interesting or reliable ways to experiment with different paths?

(51:02) - What’s the best business you’ve ever seen?

(52:51) - Is there a reason you didn’t focus more on software businesses during your search?

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