A few years ago, I received a call from a fine young man I’d advised for about nine months about ten years ago. During that nine month period when I advised him, he wanted to start a company and we explored what that entailed. He was a very smart person and diligent in his work. First rate mind and education. Winner.

“What keeps you from starting a company?” I would ask him.

He would variously give me the following excuses:

“I just bought a car.

I’m evaluating two different ideas trying to figure out which one is the better idea.

I just don’t know if I have what it takes to start a company.

I need a tech co-founder and can’t find anybody.

My mother hates the idea.

I am taking a graduate school course and I want to finish it before I start a company. The course was in some software subject.

I have a new girlfriend and I won’t be able to date her because all of my time will be spent on the new company.

It’s bird hunting season and I always go hunting with my Dad.

I’m broke.

I’m taking flying lessons.

Should I go to law school?

The prior girl wasn’t the one, but there’s another one and she wants to have kids.”

He had a “good job with high pay” and while he wanted to start a company to create wealth, amongst other things, he had no short term financial pressure in his life.

At about that time, I advised him thusly, “You need to sit down and define when you think you will be ready. Make a list of the ten things that have to fall into place to signal you it is GO TIME.”

He nodded and told me he’d do it.

I called him a week later and told him I was going to pull the plug on our advisory arrangement until he was sure he was ready. No reason to waste his money and my time. In essence, I was firing myself. He was quite incredulous.

I told him to spend the money he’d been paying me on whittling down the list and then I did something borderline cruel.

I told him that there was never, ever going to be a time when the list was all accomplished. It was unrealistic to expect that to ever happen. 

There was never a time when anybody was ever “ready” to start a company.

I told him that was what risk felt like and that uncertainty, that anxiety, that awkwardness was fuel — the fuel that would drive him through the hard times when it looked nigh onto impossible, but he would find the way.

I told him the fire in his belly to start a company had to be hotter than the scary ache in his gut about the risk. Right now I didn’t see or hear that.

I told him — I DON’T THINK YOU CAN DO THIS AND I DON’T THINK YOU HAVE WHAT IT TAKES.

We did not speak again until he called me a few years ago, but I would check on him through mutual friends. I always knew what he was up to.

When he called me, he was the co-founder (with a tech co-founder) of a successful startup that was out of the cradle and already scaling nicely. It took him several years to become an overnight success.

He was the CEO and while the value of the company in a liquidation scenario was not where he wanted it to be just yet, there would be a celebration at the pay window if it went in that direction.

He started to tell me this, but I cut him short, “I know all of that. Congratulations. I never doubted you would be successful . . . . . if you would only take the leap.”

He laughed. I laughed. They were ironic laughs.

“Do you recall what you told me when we parted company?” he asked me.

“Yes,” I said.

“So, do I,” he said. “I’ve reflected on it often and it stung. I guess I needed to hear that.”

I apologized as I had not intended to hurt him, but I did intend to jerk a knot in his rope and try to get him into the batter’s box.

“So, was I right?” I asked.

“Yes as to the litany of  excuses I made as to why I wasn’t ready, but no as to my not having what it takes to be a founder and successful at it.”

There was enough space between each of those words that I knew he had rehearsed it and that it was important to him and he delivered the line perfectly and with conviction. I wonder if he had written it down and was reading it.

We were on the phone, so I didn’t see his face, but I imagined he was rubbing the bridge of his nose, glasses in hand, eyes closed, heart beating a little more than normal.

“I always knew you had what it took,” I said, speaking the truth. “I always knew you would be successful if you just took the leap. That’s why I said what I said. You didn’t know it. I did. Now, you do.”

We put some softer words around the end of the conversation to ensure we were both members of the same human race and we wished each other well. He married the girl who wanted a lot of kids and they had them. We did not become great pals.

I read some time thereafter he’d sold the company and hit a good lick. He sent me a very nice gift and a heartfelt note.

I consider that to have been one of my most successful CEO/founder advisory assignments in the last thirteen years.

Nobody is ever ready. YOU have to take the bloody jump and hope your parachute works. It’s risky out there. But, you can do it. Sometimes, you need a jump boot in your ass to take the leap.

But, hey, what the Hell do I really know anyway? I’m just a Big Red Car.