Knowing which one is right for you starts with two questions most advisors will never ask.
For the better part of a decade, the DSO sale was the exit strategy. Aggregate up, find a private equity-backed group willing to pay a premium multiple, roll equity, collect again when they recap. A lot of your peers took that deal.
For many, that fairy tale has not had a happy ending.
Several of the largest DSO platforms are in bankruptcy or restructuring. Others are frozen — unable to deliver the recapitalization they promised, leaving doctors who rolled equity in a waiting room with no checkout time. The golden exit became a lesson about what happens when private equity takes over an industry.
So if you were watching that play out — or living it — you’re asking the right question: If not that, then what?
There are other pathways.
Though they have endless variations, they broadly, they fall into two categories. Neither requires a private equity sponsor. And the right one comes down to two simple questions.
Your Freedom Number Is the Only Honest Advisor in the Room
Most practice owners thinking about an exit have done the vague math. We should probably be okay. They’ve glanced at valuations, had a few preliminary conversations, maybe run a loose projection or two.
But they find themselves facing a nagging question… “will it be enough?”
That question is impossible to answer without knowing your Freedom Number.
Your Freedom Number is the amount of monthly cash flow you need (post tax) to sustain your lifestyle needs without trading time for dollars.
Not some reduced or austere “retirement” lifestyle. Built on your real expenses, your real vision for how you’re going to enjoy this season of your life.
Without it, every exit conversation is abstract. You’re comparing two vehicles without knowing your destination. And when the destination isn’t clear, most people don’t choose — they drift. One more year. Let me grow it a little more. Maybe after I find the right associate.
That drift is its own decision. It compounds. The years you could be building a second engine of income outside the practice become more years trapped inside it.
Calculating your Freedom Number and working towards it gives you a clear goal and a defined measuring stick for progress. Reaching your Freedom Number with confidence is the secret ingredient of successful practice exits.
that’s the first question. I’ll address the second in a moment. But first…
Back to the two categories of practice exits.
The Associate Pathway: A Succession, Not a Transaction
Dr Cree Hamilton just finished a transition that started in 2014.
He didn’t find his successor through a broker or a job posting. He found him through mentorship — years before the idea of a formal transition ever came up. They spent a full year in due diligence before any agreements were signed. Not financial due diligence. Personal due diligence. What kind of dentist. What kind of man. Whether the values that built the practice would survive in someone else’s hands.
They were right for each other. Phased buyout began in 2017 — first half, then second half last year. When Cree and I spoke last week, he had five days left.
That’s what this pathway looks like when it works. Not a transaction — a succession. The team stays. The patients never feel the ground shift. The culture survives the handoff because it was embedded in two people, not just one.
But here’s what Cree would also tell you: it worked because he had something specific to give. Not just time — investment. Genuine, sustained investment in another human being’s development. He wasn’t white-knuckling his way to the finish line. He had the energy to mentor, to lead, to hold the vision while someone else grew into it. And critically — his financial foundation was already built. The practice sale was a milestone, not a lifeline.
That distinction matters enormously.
The associate pathway done right asks more of you during the transition than the five years before it. You’re running a practice and developing a successor and protecting the goodwill that makes the whole thing worth something at closing. If you’re genuinely spent after decades of giving this everything, a multi-year commitment to someone else’s growth won’t restore you. It will finish the job.
So ask yourself honestly — not aspirationally: Is there real investment left in you for this? Do you want to mentor someone through ownership, or do you want to be done?
Both are legitimate. You just need to be honest with yourself.
The Walk-Away Sale Deserves More Credit Than It Gets
Dr Rick Ostler sold his practice in two weeks.
Scratch start. Long-tenured team. A practice he’d built from nothing and could have spent another decade in. When the right buyer came along — qualified, hungry to own, decent enough that Rick wasn’t handing his patients to someone he’d regret — he and his wife had the real conversation and made the call.
Good run. Next person’s show.
No extended runway. No watching whether the associate was developing fast enough or winning the team over. No second-guessing a handoff measured in years instead of weeks. The check cleared, and Rick left — genuinely, visibly at peace with it.
His wife was smiling too.
That is not a lesser exit. It is a clean one. And in a profession that has spent years romanticizing the graceful succession, the clean sale doesn’t get nearly enough credit.
Here’s the honest arithmetic: the associate pathway is a bet. You’re wagering years of continued engagement on a relationship that may or may not hold under real pressure — clinical gaps, production shortfalls, personality friction, financing complications at closing. Any of it can unravel a deal that looked right. And when it does, you don’t get the years back.
One of the most experienced transition advisors I know put it plainly: I don’t have time for do-overs.
The walk-away sale removes that exposure. It asks you to find one qualified buyer who’s ready now — not someone who might want to own someday, but someone already looking, pre-qualified, hungry. That’s a different search than posting for an associate. Broker relationships help. So does announcing your intentions openly — your own team will often surface candidates you’d never find through a formal channel.
If your Freedom Number is within reach of what the practice will sell for today, don’t let the story of how an exit is supposed to look talk you out of a clean finish.
Certainty, at this stage, is worth more than elegance.
Stop Defaulting. Start Deciding.
There’s no formula. But there is a framework.
Question one: Does the capital from this sale, invested well, fund the life you actually want? That’s your Freedom Number doing its job. If the answer is yes, you have a real choice. If no, you have a timeline problem no transition structure solves on its own.
Question two: Do you have genuine desire and capacity to invest in a successor’s development over years — or do you need a clean close and the freedom to build what comes next?
Most doctors never ask either question directly. So they stay. Not by choice — by default. More years in a practice they’ve mentally left, waiting for a clarity that only comes from asking what they’ve been avoiding.
The DSO promised a specific kind of ending. For many, that script has changed without warning.
But the goal was never the vehicle. It was what comes after — a life where the practice no longer owns your time, your energy, your identity. Exit-Optional living. The freedom to stay because you want to, not because you have to.
There are endless variations on these pathways. with a little creativity, and a willingness to create your own path and not be defined by what others have done, you can create a pathway that creates the outcomes you really want.
You have permission to do that.
Choose deliberately. And take action.
Don’t waste your life living someone else’s definition of success.
You get to decide. You get to build. You get to live the life you want to live.
At Freedom Founders, we help dentists and practice owners get clear on their Freedom Number and build the investment foundation to make a real exit possible — on their timeline, not someone else’s. Learn more at FreedomFounders.com.
