When Success Starts Costing More Than It Pays: Dr. Michael Filosi on Selling, Stress, and Starting Over

Michael Filosi bought a dental practice nobody wanted. It had possums in the walls, no website, and not even an answering machine. Ten years later, four private equity firms were competing to buy it from him. On paper, that is the whole story. Worst to first, a builder who backed himself and won.

The part that doesn’t show up on paper is what it cost him to get there.

In this episode of Success, Rewritten, Michael walks through the full arc with host Emily LoMenzo Washcovick, from the coffee that led him to a run-down building, to the 3am nights hunched over a toilet, to the 81 days it took to sell the whole thing and walk away at 41.

The builder who fell in love with the problem

Michael is quick to tell you he was never going to be the best technical dentist in his city. He struggled with the hand skills early, watched his wife, also a dentist, do work he could not match, and made a decision that reshaped everything. If he could not be the best clinician, he could try to build the best practice.

So he did. He knocked on the door of a run-down clinic, negotiated his way in, pulled trees out of the ground with his bare hands, and grew the place from two surgeries to ten. He calls the drive behind it an “incandescent lack of acceptance,” a refusal to believe things had to stay the way they were. When his wife asked whether the second renovation was a vanity project, he sat with the question honestly and realized it was not. He would have done it even if nobody was watching, because, as he puts it, “you’ve gotta fall in love with the problem you’re trying to solve.”

For a long time, the benefits outweighed the costs. Just barely, and just enough.

When success starts showing up in your body

The stress did not announce itself. It showed up physically, and Michael assumed that was simply the deal.

“At 3:00 in the morning for a lot of nights in a row, I’d be in our en suite, dry retching into the toilet,” he says. His wife would hear him from two rooms away. And still, he thought it was normal. “This is just the price you pay for doing what you do. This is the cost, and you pay the cost, and you get on with it.”

The reframe came from someone else. Over coffee, Michael mentioned the retching almost as a joke to a business colleague, a person who likes business and is good at it. The colleague looked at him with something close to alarm and said, “Michael, if that happened to me, I’d sell tomorrow.” It landed because it came from someone who understood the game and still thought this was too much.

The lost decade

Michael is a systems thinker, so he did what systems thinkers do. He wrote a list of every reason a person does anything. Things you have to do, things that are good for you, things you enjoy, things you do as an act of service. Then he looked at his own life against the list and could not tick a single box.

He kept returning to a term from finance. “There’s this term called the lost decade, which is when you get no returns. And I kind of felt like if I kept going doing what I was doing, it would be the lost decade of my life.” He was 41. He did not want the next ten years to look like the last ten.

Once he saw it, the decision was fast. He wrote the email to his accountant, let it sit for a couple of hours, and knew that hitting send was the first domino.

Eighty-one days

From that email to money in the bank was 81 days, with no buyers lined up when he started. Michael sought them out himself, flew them in, ran the numbers, negotiated, and pushed the process faster than the buyers had ever moved. He negotiated no earn-out and no retention period. He walked out on his last day and kept the property, which the practice now rents from him.

The stress vanished the moment the sale cleared. A few days later he stood outside and, in his words, shouted at the sky, a Shawshank Redemption kind of moment. His wife later told him it was phenomenal how quickly he dissociated from something that had been such a large part of who he was. He does not miss being needed. He could not wait to delete Slack.

Directionless, but not lost

What comes after is the harder chapter, and Michael is honest that he is still in it. He describes himself as “directionless but not lost,” a distinction that matters. He talks about the difference between exploiting, going back down the same mine shaft you dug yesterday, and exploring, kicking the top of the ground to figure out where to dig next.

Some of it has surprised him. Things he was sure he would love have fallen flat, and things he never expected have started to click. He has enrolled in a barista course, floated the idea of playing guitar in a pub, and started helping on a passion project with people whose intentions he trusts. He is a believer in “increasing your surface area of luck,” saying yes to small things because fortune turns on small moments. And he is learning something that does not come naturally to a person built like him. “You can’t pursue happiness. It needs to ensue.”

The honest version of a success story

Michael is clear that he is telling this story as a counterbalance. He is tired of the laptop-on-the-beach version of entrepreneurship. “I won. I got to the top of Everest. I did it. I was enormously successful. It was so hard, like so hard, and it took such a toll.” And then the line most people will not say out loud: “I’m not convinced it was worth it.”

Asked what his younger self would say to him now, he does not reach for hold on tight. He thinks the younger version would ask why he pushed so hard, and point out he could have gone at 75 percent and still done well. That is not a tidy ending, and Michael does not try to make it one. He got out before it took what it could have taken. Whether the whole climb was worth it is a question he is still turning over, and he is comfortable leaving it open.

Check out the interview with Michael on YouTube, or on your favorite listening platform (here’s Spotfiy, and Apple Podcasts)