Expert workshop: Buy smart, a holistic guide to business acquisition
How to grow faster, reduce risk, and prepare your business for acquisition success
There is a version of business growth that takes years. You build relationships one client at a time, expand your team gradually, and wait for revenue to compound through organic effort. And then there is acquisition, which can double the size of your business overnight.
That speed is exactly why Holly Clawson, founder of Sum of All Numbers, pursued it five times over 20 years. In this month's expert workshop, Holly joined Michelle for an unfiltered conversation about what business acquisition actually looks like in practice, not the glossy version you read in case studies, but the real one, complete with toxic employees, unexpected timing, COVID-era miscalculations, and the moment Holly was offered a buyout for her own company and realized she was not ready.
What followed was one of the most practical conversations we have had in this series. Here is what Holly shared.
Why would you acquire instead of grow organically?
Holly's honest answer: she moves fast. In service businesses where revenue is built on relationships, organic growth is inherently slow. You cannot manufacture trust on a timeline. Acquisition gave Holly speed that organic development simply could not match.
But speed is not the only reason to consider acquisition. Depending on your goals, you might acquire to eliminate a competitor, to bring talent in-house, to expand geographically, or to enter a client segment that would take years to develop from scratch.
The starting point, before you look at a single deal, is being clear on why you would acquire. That clarity shapes which opportunities are worth pursuing and which ones just look attractive on the surface.
What does the acquisition process actually look like?
Holly walked through each of her five acquisitions, starting with a straightforward solo practitioner handoff in 2007 and building from there. Each deal doubled the size of the business. Each one also came with its own set of surprises.
One consistent theme across all five was timing. None of them arrived when Holly felt fully prepared. Opportunities came through relationships and referrals, not listings, and usually before she had finished whatever she was already working on. What made integration possible despite the unexpected timing was not perfect readiness. It was having documented systems, a team with capacity, and funding sources already identified.
Holly's takeaway: you will never feel completely ready. The infrastructure you build before a deal presents itself is what determines whether you can move when the moment arrives.
What is actually harder, the financial due diligence or the cultural fit?
Financial due diligence is straightforward. You run the numbers, verify profitability, calculate EBITDA including owner perks, identify which costs can be eliminated through economies of scale, and analyze individual client profitability. It is detailed work, but it follows a logic.
Cultural due diligence is harder to evaluate and more critical to the outcome.
Holly shared three distinct examples from her own acquisitions. One seller became a 20-year friend and continued collaborator. Another walked away immediately after the deal closed. And one brought employees who actively sabotaged the transition through toxicity and resistance. The financial profile of that deal was sound. The human element nearly undid it.
The question to ask yourself before closing any deal is not just whether the numbers work but whether the people, the values, and the way that business operates are compatible with what you have built. A misaligned culture does not fix itself after the contracts are signed.
What is the J-curve and why does it matter?
Plan for 30 to 40 percent client fallout in the first year. That is not a worst-case scenario. That is a pattern Holly observed across her acquisitions and one she now budgets for deliberately.
The J-curve describes what typically happens after an acquisition: revenue dips initially as some clients resist the change, then recovers and grows as relationships are established and trust is rebuilt. The dip is real and it is normal. The mistake is not preparing for it financially and then panicking when it arrives.
The COVID-era acquisition Holly reflected on honestly was the exception. That one did not follow the J-curve like the previous four, and she attributed it to timing. Small business owners who had been through years of pandemic-era upheaval had depleted their tolerance for change entirely. It was a reminder that even a well-structured deal can be affected by external conditions no playbook fully accounts for.
How does seller financing work and why does Holly prefer it?
Across all five acquisitions, Holly's preferred financing method has been seller financing rather than SBA loans or hard money lending. The reasons are practical.
Seller financing typically comes with better interest rates. It also keeps the seller engaged in the outcome. When the seller has a financial stake in a successful transition, they have a real incentive to support client relationships, answer questions, and help with integration rather than depositing a check and disappearing.
Holly also insists on performance-based purchase price adjustments in her contracts. If revenue comes in higher than stated, the seller receives more. If clients are lost or revenue falls short, the purchase price decreases accordingly. This protects both parties and accounts for the gap that can exist between what is on a spreadsheet and what is in the actual books.
What did Holly learn about her own blind spots?
One of the most valuable parts of this workshop was Holly's willingness to name her own tendencies. She described herself as a yes person, someone who jumps at opportunities before asking enough hard questions. Over time, she has built a team that balances her optimism with the analytical skepticism she does not naturally bring to the table.
The story of Eowyn and Britta illustrated this well. When a seller insisted that two employees come with a deal, Holly's initial reaction was that the business did not need them. She agreed reluctantly. Those two employees became the most valuable part of that acquisition and instrumental to the growth of Sum of All Numbers beyond the purchased client base.
The lesson she took from it: when a seller advocates hard for something that seems unnecessary to you, it is worth slowing down to understand why.
What should you have in place before you pursue an acquisition?
Holly was consistent on this point throughout the session. Before you can integrate someone else's business, you need your own house in order. That means documented systems and standard operating procedures that do not depend on any single person to execute.
Without that foundation, integration becomes guesswork. You are trying to absorb chaos into chaos, and the result is that both businesses suffer.
After her most challenging acquisition, Holly and her team deconstructed everything that had happened, documented the lessons, and built a formal SOP for future acquisitions. She now has a playbook built from 20 years of experience and five real deals. The instruction she offered to this workshop: start building yours before you need it.
Where do you start if acquisition is on your horizon?
A few concrete next steps from the workshop:
Get clear on your purpose. Know why you would acquire before you start looking at what. The reason shapes every decision that follows.
Document your current operations. Your SOPs need to be solid before you take on someone else's complexity.
Start monitoring the market. Holly receives daily emails from business brokers about available companies in her region. Find the brokers and marketplaces relevant to your industry and start building awareness of what is out there.
Build your advisory team now. Holly works with business attorneys and relies on her team's analytical strengths to balance her own tendencies. Identify the people who will ask the hard questions you might not think to ask.
Let your network know you are open. All five of Holly's acquisitions came through relationships, not listings. The best opportunities often find you when people know you are looking.
A final thought from Holly
At one point during the session, someone offered to buy Sum of All Numbers. Holly's reaction surprised even her: she was not ready. The business she had built felt like her own, and the thought of sending it off felt like a loss rather than a win.
It was a reminder that the psychology of acquisition runs in both directions. Understanding what motivates a seller, how attached they are to what they built and what they need from the transition, is just as important as understanding the financials.
Successful acquisition, as Holly put it, is not about finding a good deal and securing financing. It is about cultural fit, operational readiness, honest self-awareness, and the discipline to protect value while you capture growth.
Want to keep learning from sessions like this one?
This workshop is part of our ongoing monthly series where we bring in experts to cover the financial and operational topics that matter most to service business owners. You can watch previous workshop replays and sign up to be notified about upcoming sessions on our monthly financial workshops page.
Thinking about acquisition as part of your growth strategy?
A fractional CFO can help you evaluate the financial side of a deal, pressure-test the numbers, and make sure your own operations are ready before you move. Book a consultation to start the conversation.