Chapter 7 of 11
Selling

The Six-Hour Walk

On January 14th, 2017, I left for a walk on the beach in South Florida to figure out how to double my company's revenue. I planned to be gone an hour or two.

I came back six hours later having decided to sell it instead.

The Plan I Left With

I say double revenue "again" because we had just done it. December 2016 closed the books on a four-year goal: revenues doubled, profits tripled, the whole transformation that had started when my best employee quit and told me the truth on his way out. The machine was running better than it ever had.

So naturally, the question I carried onto the beach was: how do we do it again? New office space? Was the management team right for the next stage? What capital would it take, what product lines, what hires? I wanted quiet to think it through properly, and a long walk along the shore seemed like the right tool. I headed south with a head full of logistics.

I walked for three hours before I turned around.

Somewhere on the way back, the honest thought finally got loud enough to hear over the planning: I didn't want to do it again.

The Thought I Came Back With

It had been 26 years. And for 26 years I had genuinely loved the challenge. But standing on that beach, I was tired in a way that a vacation doesn't fix. Tired of managing people. Tired of the daily weight of cash flow and marketing and sales and staff and customers. Nobody was forcing me to keep doubling the company. I could have coasted. But coasting wasn't fun either, and I have never been able to do things that aren't fun for very long.

And there was something else, the thing underneath the tiredness that I had not been letting myself look at. Two months earlier, in November 2016, my wife's closest friend had been diagnosed with brain cancer. She was our age. Until that fall, I don't think I had ever seriously contemplated the fact that I was not going to live forever. It sounds absurd to write down, a 48-year-old man discovering mortality, but that is what happened. The diagnosis didn't give me an answer. It gave me a clock.

By the time I could see the hotels again, the question had changed shape entirely. It was no longer how do I double the company. It was: what are the things in life that will feed my inner soul? What do I actually want the years to be?

I walked up to one of the hotels along the beach, ordered a beer, took out my phone, and started typing notes for what would become the next stage of my life. Three things: more time with my family. See the world. And find a way to help other entrepreneurs build what I had built, because business was the thing I knew and loved, and I wasn't ready to stop loving it, only to stop carrying it.

That Monday I called the M&A advisors and said: it's time. I'm ready to sell.

The Letter

I flew back to Toronto with one more thing to do, and it was the part I was most nervous about.

It was my wife's birthday. I wrote her a long letter, everything from the beach, all of it on paper: the decision, the plans, the travel, the years I wanted us to have. And at the end of the letter I asked her to renew our wedding vows. Twenty-plus years in, I asked her to marry me again.

She said yes.

The sale closed that fall, in 2017, one year before my 50th birthday. Twenty-seven years, ended by a walk I had intended to spend on a growth plan.

What I'd Add Now

I believed I had found my "why" on that beach. Help entrepreneurs. Write, teach, share what I knew. And in a real sense I had; it produced most of what I have done since. But nine years later I can tell you the why did not hold still, and the wanting that walked south with me that morning walked back north with me too. It just changed clothes. That part of the story took more years, and eventually a heart attack, to understand, and it gets its own chapters. The walk was still the best decision I ever made. I just no longer confuse it with an answer.

Deciding to sell took six hours. The selling took a year, and cost more than anyone tells you.

Jeff Wiener
Jeff Wiener

Jeff Wiener founded Digitcom, a Canadian telecommunications company, in 1991 at age 23 and ran it for 27 years, growing it into an eight-figure business named one of Canada's fastest-growing companies five years running. He sold it to a private equity firm in 2017 and semi-retired at 49. He now invests in multi-family real estate and writes about building wealth, selling a business, and the second act.