What EtA Looks Like When It’s Done Well

Scaling an Outsourced Finance Business - Lessons from System Six

Welcome back to The Small Business Mentor!

A quick message before we jump in:

  • If you haven’t already, be sure to check out the Small Business Mentor Podcast wherever you listen to your podcasts

  • If you’re reading this online, subscribe HERE and join thousands of business owners and professionals receiving these emails every week.

Let’s dive in…

This week, we're taking a look at the world of outsourced finance services with Chris Williams, owner of System Six, a financial services business that does bookkeeping, payroll, bill pay, and invoicing.

System Six’s goal is to serve as the day-to-day finance team for small businesses whose owners don't have the time or inclination to manage those tasks themselves. 

The Story:

Chris acquired the business in July 2021 when it was doing $2.5 million in revenue with 18 employees.

He was the textbook searcher. Chris came from a finance background in investment banking and private equity and got his MBA before going out to buy his own business.

It’s the dream that has launched a thousand MBA acquisition ships and in Chris’s case the dream has been realized. 

As of early 2024, the company has almost doubled to $4.5 million in revenue with 38 employees.

Some of the key reasons have been Chris’s focus on developing a marketing strategy to identify new clients, building the management team, and keeping the company on track as it grows quickly.

He has also done a good job of cultivating a nice customer niche. 75% of System Six’s clients are from the small business acquisition community (search funds, independent sponsors, self-funded searchers) otherwise known as the Entrepreneurship through Acquisition (EtA) community.

Their average client does $5 million in revenue and has 30 employees.

The Small Business Mentor’s Take:

There’s a series of lessons I think we can learn from Chris’s acquisition and the growth of Systems Six : 

  1. He bought right. Systems Six does something all companies need but few want to spend a lot of time doing.

    Being 10% better at bookkeeping isn’t going to make your Heating, Ventilation, and Air Conditioning (HVAC) company or marketing agency that much better so you don’t really want to do it yourself but you absolutely need it. As long as the price is competitive you’ll keep outsourcing it.

    That makes it steady recurring revenue with no real customer concentration. There’s only so much bookkeeping that can be done at any one company.

  2. He developed a defensible marketing channel. Chris was able to grow his business as a member of and participant in the EtA space. He posts frequently on X and goes to lots of EtA conferences. He was able to bring that channel to the business.

    I love acquisitions where an owner can keep an existing base of customers but then layer in new kinds of customers based on a unique set of connections or skills the owner has.

    That has also led to more in depth knowledge of industries like HVAC that have a high concentration of EtA owners. Systems Six can specialize in integrating with an industry dominant software like ServiceTitan as a selling point against the competition.

  3. He invested early in leadership. Chris hired a dedicated sales person at $3.2 million in revenue and a full-time HR person at 25 employees. These are tough near-term decisions. Those kinds of employees reduce margins in the short-term but set the stage for further growth.

    I usually don’t recommend that companies at System Six’s level hire a full time sales person. In my view the owner should really do that job until the company is past at least $5m in revenue and it usually requires more like $10m. Chris has me challenging that assumption. 

    I think it works at System Six for two reasons. First Chris has a robust marketing channel so he isn’t relying on a sales person to generate leads, just to close them.

    And second, many bootstrapped owners have a sales background. Chris is more of a financial guy so I see the justification for a sales person early on.

  4. He uses a pod-based delivery system. System Six uses 5-7 person "pods" to serve clients, each with a team lead, client leads, and junior bookkeepers. That’s in contrast to a typical system that would have separate teams for each function ie a bookkeeping team, a client lead team, etc.

    I think this kind of set up ensures client coverage and better service. But listen to the podcast to hear us talk about the trade offs.

  5. He’s beginning to explore global talent. System Six is just beginning to hire internationally for junior-level work to address capacity constraints. I see this as a key to keeping Systems Six’s offering competitive as it scales.

Chris's journey with System Six demonstrates the potential of the EtA path in service businesses. By acquiring a solid finance services company and making smart investments in people and processes, he's positioned the company for continued expansion. 

As small business owners, we can learn from his willingness to take short-term profitability hits for long-term growth. I can’t wait to see where Chris can take this company.

Keep growing,




  • If you’re reading this online, subscribe and join thousands of execs, business owners, and working professionals receiving these emails every week.

  • Listen to the Small Business Mentor Podcast on Apple or Spotify.

  • Be sure to follow me on X/Twitter and LinkedIn for my most up to date content.

1  (Sources: https://invedus.com/blog/outsourcing-statistics/; https://www.weareamnet.com/blog/outsourcing-statistics/; https://explodingtopics.com/blog/outsourcing-stats)

Join the conversation

or to participate.