Chris Williams – Running a Search and Acquiring and Operating a Small Business – Ep.95

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 [email protected] and tell him you heard him on Think Like an Owner.

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Links Mentioned:


Alpine Investors

Emporos Systems


(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?

Think Like an Owner Sponsors:

Live Oak Bank — Live Oak Bank is a seasoned SMB lender providing SBA and conventional financing for search funds, independent sponsors, private equity firms, and individuals looking to acquire lower middle-market companies. Live Oak has closed billions of dollars in SBA financing and is actively looking to help more small company investors across the country. If you are in the process of acquiring a company or thinking about starting a search, contact Lisa Forrest or Heather Endresen directly to start a conversation or go to

Hood & Strong, LLP — Hood & Strong is a CPA firm with a long history of working with search funds and private equity firms on diligence, assurance, tax services, and more. Hood & Strong is highly skilled in working with search funds, providing quality of earnings and due diligence services during the search, along with assurance and tax services post-acquisition. They offer a unique way to approach acquisition diligence and manage costs effectively. To learn more about how Hood & Strong can help your search, acquisition, and beyond, please email one of their partners Jerry Zhou at [email protected] 

Oberle Risk Strategies– Oberle is the leading specialty insurance brokerage catering to search funds and the broader ETA community, providing complimentary due diligence assessments of the target company’s commercial insurance and employee benefits programs. Over the past decade, August Felker and his team have engaged with hundreds of searchers to provide due diligence and ultimately place the most competitive insurance program at closing. Given August’s experience as a searcher himself, he and his team understand all that goes into buying a business and pride themselves on making the insurance portion of closing seamless and hassle-free.

If you are under LOI, please reach out to August to learn more about how Oberle can help with insurance due diligence at Or reach out to August directly at [email protected].

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