One of the most important lessons I’ve learned in business

I never went to business school. My business education was a startup accelerator called Momentum.

Patterned after TechStars, Momentum gave entrepreneurs a $20,000 investment and placed them in a 12-week bootcamp, which was intended as a crash course in everything needed to start a tech business and raise venture capital. As a part of that bootcamp, every Thursday night all the entrepreneurs would gather around for a “fireside chat”, where we would have the opportunity to listen to a business leader tell their story. Out of 12 of those chats, one moment sticks with me to this day.

We’ll call the business leader Bob, although that’s not his real name. Bob was the type of guy who flies a helicopter to work, and so obviously had a different perspective on life and business than I had. Bob was incredibly successful, but also went out of his way to be accessible in that conversation, which I really appreciated.

Someone asked him: “If there was one lesson you’d hope that these entrepreneurs would learn in starting their businesses, what would it be?”

Bob thought about it for a moment. He took a beat longer than normal as, we had learned that evening, was his way.

“I’ve worked with companies all over the spectrum,” he said at last. “From Fortune 100 companies to pro sports teams to two-person startups. And across all those companies, there’s only one thing that all of them have in common.

“Nobody knows what the hell they’re doing,” he said.

“The difference between successful companies and unsuccessful companies, is that with the successful companies you can’t tell.”