Last year I had a series of meetings with a billionaire, which was a fascinating opportunity. This individual did not work in dentistry but in finance. He and his family owned a diverse portfolio of companies, including several in tech. He said something that stuck with me: “We are very contrarian in our investments. But if you’re going to be contrarian, you have to be right. Being contrarian without being right is called being an idiot.”
Funny. And accurate.
Recently, that quote has come to mind when thinking about practice ownership exits in the current marketplace. The biggest problem isn’t the strategy — it’s the order of operations. And the conventional order is backwards.
Here’s how it usually goes. A dentist “feels ready to sell” and calls a broker. The broker appraises the practice, and that appraisal is where the owner first learns how attractive their practice actually is: unfavourable lease terms, patient numbers and behaviour, trends across the legacy years — the last three years of your career that determine your business’s value. Because this happens only once the dentist feels ready, rather than while there’s still time to influence these variables, attractiveness “is what it is” instead of being a starting point you could have shaped.
If the appraisal leads to a letter of intent you like, you move into due diligence. Now you’re digging up documents you haven’t thought about in thirty years — X-ray floor plans filed with the Ministry of Health, tax returns and bank statements from three years back, signed staff contracts, a DPC minute book you didn’t know existed. This is when sellers discover how “ready” their business really isn’t. And to a buyer’s accounting and legal team, none of that scrambling looks like the thing of beauty your broker promised the buyer it was.
Then comes the last piece: personal readiness. In the conventional order, this gets sorted out after closing — once the seller has to figure out what comes next. For smart, hardworking, career-driven people, discovering your sense of purpose after ownership, in real time, without a plan, is dangerous. It’s a big reason 75% of business owners regret selling their business within a year of doing so.
None of this is anyone’s fault. The broker, the advisors, the seller — everyone did their job within their own silo. But that leaves you with a 75% chance of regret, plus the risk of lower net proceeds and a rocky execution. You’ll survive this order. But the goal was never to survive. It was to thrive.
So as an exit planner, I run it in reverse.
We start with personal readiness. Before anything else, we work through what you want, what you need, and who you’ll be after ownership ends. This is what puts you in the power position — confident, clear, able to execute — instead of leaving your emotions and identity to be sorted out after the fact. No one is used to having less control than a dentist who just sold their practice. Selling first and figuring out the rest later is backwards.
Next comes business readiness. If the business isn’t ready, a valuation is premature — either it’s futile, or you’re leaving equity on the table. This is also where we make sure net proceeds can actually be maximized. It’s not what you sell your practice for that matters. It’s what you keep. Skip this scrutiny and Parliament Hill wins. You lose.
Only then do we get to business attractiveness — decorating the cake. With you ready and your business ready, we can build maximum demand and maximum value into the sale.
This order matters more than ever in today’s market, which is full of scared, risk-averse, indecisive buyers and lenders and advisors who scrutinize everything. Great buyers compete aggressively for organized practices. Average practices compete aggressively for great buyers.
The order of operations isn’t a technicality. It’s the difference between surviving your exit and thriving after it.
