The Best CEOs Don’t Punish Failure, They Encourage Risk

I said to my wife, “Heads up, I’m probably getting fired today.”

She offered some encouragement. I hung up, sweating, and walked to the CEO’s office.

Back up.
I was a marketer at a startup. I had pitched a massive direct mail campaign—$200k+ on one bet. The CEO approved it. I ran with it.

Months of work. Big spend. Huge expectations.

Result? Four leads. Yes, four.

I dug in. The problem was obvious: our list select was garbage. And I owned the decision.

I knocked on CEO Yonatan Stern’s door. Told him it failed. Told him it was my fault.

To my surprise, he said (paraphrasing):
“I’d rather you take big swings and fail than play it safe. We’ll move on.”

That lesson stuck. As did the kindness of Yonatan at that moment.

We went on to sell CardScan, and Yonatan then built ZoomInfo. You’ve probably heard of that one.

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Leaders: when your people take risks and blow it, do you back them? Or bury them?