Chris Whelan was a practicing emergency room physician who, after a 2009 conversation with MedExpress at a conference, got involved in urgent care. After conditions in Massachusetts became more friendly to the urgent care model, he and a partner opened their first Health Express in 2011.

"We were just thinking of it as an alternative to the ER, not really thinking about growing a business at first," Whelan says. "We probably woke up on day one when a gentleman from a hedge fund called us and one of his proteges walked in and they wanted to buy us and we're like, what are we doing? And we did it fast. We had three by the end of the year and we got up to eight, entered the sale process in and out a couple times, and then did it properly at the end and sold in 2018."

The determination that he had the right buyer when he sold to South Shore Health System, and that it was the right time, developed organically. Knowing his partner was passing away, he says it seemed like the right time to get out of the game and ensure some stability for his partner's family. However, he says he didn't have an investment banker or connection with an M&A law firm, so the deal went sideways.

"And it had been going sideways for months but I tend to be a guilty Irishman — it was just like, I got to continue this process, we started it," he says. "And then it became evident to me that it wasn't tenable the first time; that was around 2016."

The business kept growing. They opened more centers and its volume was improving, so it seemed the right time to try a sale again.

"I had a goal of who I wanted to be the buyer and I was lucky enough that that's who we had," he says. "It was a hospital system and I wanted them because, at the core of this, I was just trying to deliver what I knew would work, which was the patient experience. Board-certified ER doctors or nurse practitioners with experience in emergency rooms was very essential to us."

While he was clear that he wanted a hospital system to be his buyer, he says he couldn't just tell the hospital to buy his business.

"That's where you need grown-ups in the room that have done this," he says. "I picked an investment banker that operated in the health care fields, as well as many other fields, and had experience. And I got a legal team that had done many of these deals before. It was so amazingly important as you were going through the process that way — multiple bidders and you get lucky enough to have the bidder you really wanted — you'll take less, I took less, because it was really important, and it feels that way now."

It was a great buyer and a great outcome, he says. It was important for the maturity of the company. It was also a relief to be able to shift gears after the sale.

"At the beginning you wear many different hats," he says. "I was doing 50 hours clinical and 50 hours of management in any given week and that's just how it had been for years, and I accepted it. But it was certainly nice to get to the other side."

For entrepreneurs who are trying to figure out when it's the best time to sell, Whelan says it starts by being true to your business. In his case, he says a sale helped deliver better patient care. The aim can also be to make a profit, move on in life or leverage the sale to grow and improve the business.

"I got to hit maybe all three of those actually," he says. "But selling it to someone where the business would grow and not just be to another company was important to me, not necessarily important to everybody. You got to be true to your business. What is your product? What were you trying to do when you started this. If we all come at it organically to solve a problem, you better keep solving the problem."

Whelan talked about selling his business at the Boston Smart Business Dealmakers Conference. Hit play on the video above to hear more about his experience.