For years my plan was simple. When I was ready to retire, my associate would buy Mountain Springs Dental. He had been with me for several years. He was a good dentist and the patients liked him. It felt like the natural handoff.

It didn’t happen. I told part of this story in What I Wish I’d Known Before I Sold to a DSO. This post is about the part I skipped: why the associate sale fell apart, and what I could have done years earlier to give it a real chance.

What happened

I had been telling my team for a couple of years that I wanted to retire and sell. The sale didn’t sneak up on anyone, including my associate.

When the time came, the financing wasn’t there. By then I already had a strong offer from a DSO on the table.

That DSO wasn’t a stranger. I had known the principals for years. They had approached me years before about buying a portion of my practice. Back then I was a solo practitioner with no associate, and it didn’t feel like the right time. When I decided it was time to sell, I called them to see if they were still interested. They were.

My associate had worked for a DSO in another state before he joined me, and it hadn’t gone well. Staying on under a DSO wasn’t something he was willing to consider. He moved on to another practice nearby. I understood his choice.

The honest part

I could stop there and say the financing fell through and that was that. But that isn’t the whole truth. Looking back, I see two options I didn’t fully explore.

The first was financing the sale myself. A seller can carry the note and let the buyer pay it off over time. I wasn’t financially prepared to do that, and it didn’t feel right to me at the time. When your retirement depends on the sale proceeds, waiting years to be paid is a real risk. I wasn’t set up to take it.

The second was keeping ownership. I could have brought on a second associate, stepped out of the chair, and stayed the owner. That might have been a good option. I didn’t look at it as closely as I should have, because I wanted to retire sooner rather than later and the DSO’s offer was a good one.

I’m not sorry I sold. The DSO offer fit my timing and my financial needs. But saying I had no other options wouldn’t be accurate. I had options. I just hadn’t prepared for them.

What I’d ask about if I were five years out

If you hope an associate will buy your practice someday, these are the questions I’d be asking now, not in the year you want to leave.

1. Has your associate talked with a dental practice lender? A conversation years ahead shows whether the numbers can work, and what would need to change if they can’t.
2. Have you talked through the details with your associate? Telling your team you plan to retire is one thing. Sitting down to talk about price, terms, and dates is another.
3. Could you carry part of the note if you had to? If seller financing is the bridge, your own savings need to be ready for it. That takes years to set up.
4. What would it take to stay the owner and step out of the chair? Who runs the business side? How many doctors would you need? Could you live with it from a distance?
5. Would a gradual buy-in work better than one big sale? Ask your advisor whether buying in over several years would be easier for your associate to finance.

Where I landed

The DSO was a good outcome for me. But I chose it partly because it was the only door I had prepared. If you’re a few years out, prepare more than one.

I wrote Exit Strong for exactly this stage, when you still have time to build your options. And if you’d rather talk through your own situation, book a free 20 minute call with me.