My first boss was the CEO of the company. I was young, hungry, and looking for someone to learn from. He wasn’t a genius—I never thought that. But I needed to learn, and he was the one in front of me.

At first, I thought he was just a little eccentric. Later, I became convinced his entire playbook was pulled from some clandestine operations manual—like if the CIA wanted to slowly demoralize a startup from within.

I remember the first time I met him. He was giving a crooked, confusing pitch. I jumped in and straightened it out. I didn’t wait to be invited. I just started performing—and that’s when I realized something strange: that’s how he did all his work. Not by contributing. Not by guiding. But by sitting there, silently, while someone else figured it out in front of him.

I built the pitch decks. I built the pro formas. I ran Excel until my eyes stung. And he’d be there the whole time—not giving feedback, not adding value—just… there. Like a cardboard cutout of a CEO that had somehow learned to blink.

It only clicked for me after a few months. Any time the team had a breakthrough—any time real progress or honest discussion broke out—he’d say, “All right, awesome guys,” and walk out of the room. He wasn’t uninterested. He was unprepared. He had no tools to engage with success.

Then came the moment I brought in a serious investor—someone I had built trust with, someone real. I was proud of that introduction.

So what does the CEO do? He starts the first word of a sentence, takes a long, theatrical drag from his heavily modified electric vape, breathes out like he’s on stage in a high school play, then finishes the sentence.

I thought it was tobacco. The investor thought it was marijuana. And who in their right mind tries to raise capital like that?

The only mistake I learned was when there’s no one worth following, the best thing you can do is learn by filling the vacuum. In the field, this works, in the business environment there are more men like him than I could, I’ve ever expected in my last 10 years building companies.

He didn’t teach me how to lead. But he taught me what happens when no one does.