Rollover Equity: A Business Owner’s Guide to Negotiating Terms and Maximizing Exit Outcomes
Rollover equity occurs when you reinvest a portion of your sale proceeds into the acquiring company’s new ownership structure instead…
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When the owners of a concierge medical practice began thinking seriously about retirement, they knew the time was right to explore a sale.
They also knew it wouldn’t be easy.
The business operated in a highly specialized corner of healthcare, and like many lower middle market companies, it fell into an awkward zone: large enough to attract buyer interest, but small enough that many traditional investment banks might not prioritize the opportunity.
At first, they didn’t hire an advisor. A search fund had approached them directly, and they decided to run the process themselves.
They negotiated, executed an LOI, but the deal fell apart in the final innings.
After months of time and emotional investment, they were back where they started. But with stronger knowledge of what they needed to succeed, and a determination to persevere.
That’s when they turned to Axial for Owners.
This business is a founder-led concierge medical practice providing personalized healthcare services, including advanced testing, wellness coaching, nutrition guidance, and functional medicine. The company operates on a membership-renewal model and a lean physician team designed to deliver a high-touch patient experience, with smaller doctor panels and same or next-day appointments.
The owners had already experienced the realities of the M&A process firsthand.
They reached an LOI with the search fund that had approached them, but the deal ultimately fell through. While the experience was instructive, it left them at a crossroads: either pause indefinitely or restart the process with new representation.
But they were confident that they had nailed down the primary learnings from their first experience:
Because of this, when it was time to restart, the owners were leaning heavily toward hiring an M&A advisor. At the same time, they found that identifying the right advisor was harder than expected.
As the owner explained:
“It’s a bit of a wilderness out there. There are many contenders in the space, and ours is even more specialized. It has a special structure, and we were looking for advisors who did not have to undergo an extensive learning curve.”
They needed an advisor with relevant healthcare transaction experience and, ideally, someone who had successfully sold businesses of a similar size.
The owners originally discovered Axial through an online search. What stood out immediately was the efficiency and structure of Axial’s Advisor Finder process.
Instead of spending weeks calling firms, collecting references, and guessing at fit, Axial quickly identified a shortlist of relevant M&A advisors with proven experience in healthcare services.
The owner noted:
“Finding Axial was exhilarating… because they solved a lot of these difficulties.”
Axial introduced the business to four advisors, each pre-vetted for fit, experience, and an active interest in taking on the engagement. Axial also helped coordinate meetings and stayed involved as the owners narrowed their shortlist.
“Axial gave us four contacts, explained why they were chosen, made sure that they were interested in us, and then set up the appointments.”
From there, the owners narrowed the list to two finalists and ultimately selected a boutique advisory firm with strong experience in concierge and healthcare services M&A.
While all of the advisors introduced through Axial were qualified, one firm stood out for two key reasons:
As the owner described:
“The reason we chose our advisor in the end was that they were able to move quickly. And they were very convincing about other sales they had managed in exactly the space that we occupy.”
With the right advisor in place, the owners launched a new go-to-market process.
Within 2.5 months, they executed an LOI with their first buyer from the new process. A few weeks later, that too fell apart – after all, Axial data suggests that LOIs break 50-60% of the time.
But this time was different. Because they had run a broader, competitive process, they already had a good sense for who would be their first alternative. They reached back out to the next-best buyer, and a month later, had an LOI executed with them.
The result was a successful transaction with a private equity firm that has a portfolio company in the space, and a 283-day process for a team that was able to handle the turbulence.

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For the owners, the greatest value Axial provided wasn’t simply introductions; it was eliminating the time, labor, and stress of sorting through a crowded, unclear advisor landscape.
As the owner explained:
“We’re involved in running the business. When we’re contemplating a sale, it’s not as if we can staff up for that.”
Instead of spending months searching for the right partner, Axial helped them move immediately to qualified conversations with M&A experts that could maximize their likelihood of success.
“Axial’s network of advisor relationships was extraordinarily valuable… knowing just the right people to talk to and being very efficient about deploying that expertise.”
In a process where momentum matters, that efficiency helped them restart after a broken LOI and regain confidence in their ability to reach the finish line.
When asked what he would tell another business owner considering a sale, the owner emphasized how much time and stress can be saved by working with the right advisor.
“If you have a lot of time to spend, you can just walk around and explore for a long time. It was great instead to have a guide to get us through the jungle and get us to our destination as quickly as we could have hoped.”
In the lower middle market, deals fall apart all the time.
Sellers get cold feet. Markets tighten. Diligence uncovers surprises. Even signed LOIs break more than half the time.
For owners, especially those without an experienced M&A advisor and backup options, this isn’t the exception. It happens more often than not.
What separates stalled or failed processes from successful exits isn’t avoiding setbacks altogether. It’s how owners build the deal team that can succeed in spite of them.
After a prior deal fell through, these owners didn’t retreat. They reset and leaned on experts. They targeted an M&A expert with deep experience in healthcare, and they partnered with Axial to leverage an expert in finding the right advisor.
Compounding expertise in this way is how owners maximize their chances of a successful transaction.
