At the peak of COVID, I interviewed for a head of marketing role at a large company. The founder was a billionaire. Self-made, bootstrapped, had a reputation for being challenging and a bit of a rebel.
He had a policy: anyone interviewing above a certain level had to sit down with him. My role would have been three layers below him. The fact that he made time to interview people that far removed from his direct reports told me something about how seriously he took the people on his team.
He also had a policy that interviews with him had to be in person. Social distancing was still a thing back then, so logistics were interesting. There we were, sitting in a boardroom with 15 chairs on each side, 20 feet apart, trying to have an engaging, intimate conversation without shouting or resorting to microphones.
It was one of the most unique interviews I've ever had. He barely glanced at my resume. Instead, he wanted to know who I am. What shaped me. Why I am who I am now. He was trying to figure out whether I'd be the right new addition to his team.
He asked about my background. He was intrigued that I was an immigrant. He asked about my schooling. Then he asked about my grades. I was honest: my college grades were abysmal. Not because the subjects were hard, but because I didn't care enough to show up to class. I preferred to pick up an extra shift waiting tables at Red Lobster than show up for "Health" class lectures. He found that funny.
That honesty seemed to interest him more than the grades themselves. He wanted to know how someone with terrible grades still got into a good MBA program and still had strong career progression. Hard work and grit, obviously. He wasn't looking for polish. He was looking for something else.
Then he said the thing that changed my trajectory.
"My hesitation with you is that you've never run something where you were invested."
He was saying: you've done corporate roles, good for you, but I don't see the entrepreneurial heart I need. You've never had real skin in the game. Not like he'd always had.
This was coming from someone who had stood up multiple businesses from scratch and handpicked the leadership team for each one. He wasn't being dismissive. He was being honest. And he was right.
I don't remember my exact response, but it was something like: I think of myself as an entrepreneur at heart. I haven't done it yet, but I'm not afraid of it.
Saying that out loud, to a billionaire who had actually done it, something clicked. It's one thing to think of yourself as an entrepreneur. It's another to say it to someone who knows what it takes to be a good one.
I think about that conversation a lot. Not because he gave me permission. He didn't. But because he named the path I feared to follow. I had never put real skin in the game. I had never bet on myself with my own sweat, my own time, my own name on the masthead. Now I have.
My results will be different from his, but those results will come from putting it all on the line and doing the work.
Disclosure: I write these posts. AI helps me edit them.