The Pain of Knowing Your Future Self
What David Berg Taught Me About Being a Founder
I work in venture. Every day I sit across from early-stage founders and try to understand what makes someone worth betting on. Most of what gets written about them is either too early or too polished. This series is my attempt to tell the real story — from the inside, while I’m close enough to see it. Not the highlight reel. The real thing. My hope is that within each of their stories, you find something that belongs to you too.
The best founders I’ve met aren’t more logical than everyone else. They’re more certain.
Not reckless. Not delusional. Certain in a way that lives somewhere deeper than the spreadsheet, deeper than the market analysis, deeper than what makes rational sense. It’s the thing that makes someone move anyway — toward something they can’t fully explain yet, away from something they can no longer stay inside.
David Berg is the clearest example of this I’ve ever seen up close.
I’ve known David since kindergarten. We grew up together, lost touch when he moved to New York in ninth grade, and rebuilt the friendship as adults — a few times a year, holidays, whatever windows life gave us. But every single time I saw him, I saw the same thing: someone whose values were as strong as his instincts, and a trust between us that didn’t need to be explained. We could always talk about the hard things. Where we were trying to go. What it meant to actually succeed and find our place in the world.
That closeness is why I can tell this story. And why I think it’s worth telling.
———
Before Commander AI, David was one of the top-performing salesmen at Battle Motors — selling trucks in the waste management industry. Traveling all over America, sitting across from company owners, learning their world from the inside. He was good at it. Really good.
But David Berg was never born to sell garbage trucks. That was never his essence. And somewhere in him, he always knew it. The gap between where he was and where he was supposed to be — that gap has its own specific kind of pain. The pain of knowing your future self and not being there yet.
That’s what I believe built Commander AI. Not just a market insight, not just a clever idea — though those were real too. It was the pain of a man who couldn’t stay where he was.
———
I started to really see it when David moved to Miami toward the end of his time at Battle Motors. I used to visit him there, and we’d work out together, sit in the sauna in his building, and talk for hours. He was in the early stages of ideation — what could this startup be, who would build it with him, how would it work. And I was in my own version of the same leap, early in my time in venture, meeting five to six founders every day, trying to understand what made someone worth betting on.
We were both standing at the edge of something unknown at the exact same time. And I think that’s part of why I could see him so clearly.
One afternoon, we’re sitting on the beach. It’s a couple hours before Shabbat — that night, we’re helping host 30 to 40 young professionals for the Kabbalah Center’s new location in Miami’s Design District. And David is on the phone with the person who would become his CTO. I’m sitting right next to him, watching him essentially will this man into a co-founder. Not with a pitch deck. Not with data. Just with pure, unshakeable conviction that this was going to be the next big thing, and that this person needed to be part of it.
And I felt joy. Real joy. Because I was watching someone who didn’t just believe in himself — he could transmit that belief. In waste management, of all things. There’s no glamour to hide behind in that industry. You can’t seduce anyone with the vision of revolutionizing garbage trucks. You just have to be that certain. And David was.
———
After the pre-seed, David opened an office on the 3rd Street Promenade in Santa Monica. The same street we used to hang out on as kids. And I remember hearing about it and thinking — of course. Of course that’s where he landed.
But the romance of that image fades quickly when you’re in it. Because what followed was the real education — hires, fires, something breaking, something threatening to break, every single day. I used to tell David he was a glorified firefighter.
And here’s what I noticed during that time: I stopped feeling the need to give him advice. Every time we spoke, every time he laid it all out, I already knew that he knew what to do. My job wasn’t to fix anything. My job was just to be there. To witness it. To be the person who saw him clearly while he was in the middle of it.
———
Then came the seed round. And before the $5,000,000, there was a gauntlet.
No. No. No. No.
Rejection after rejection.
From the outside, David was stoic through all of it. But I knew him well enough to see underneath that. He was carrying a lot. And the way I understand how he kept going is this: the pain of those rejections was real — but the pain of not building this thing was greater. The pain of giving up would have been more unbearable than any no. So he kept going. Not because it was easy. Because stopping was simply not an option his identity would allow.
Here’s what doesn’t get said enough, especially about non-technical founders: what David did, consistently, is genuinely rare. He had the vision. He had the sales instincts. He didn’t have the technical background. And he went out and built it anyway. Found the right people. Convinced them. Raised the round. Built the team. Put out the fires. Day after day after day. Most people with his profile would have waited until the conditions were perfect. David understood that the conditions were never going to be perfect. So he moved anyway.
He raised $5,000,000. He built Commander AI into what it is today. And he’s just getting started.
———
The throughline of David’s story — and I think the throughline of every founder worth watching — is this:
A life lived entirely by logic is a life not fully lived.
David woke up every day with certainty beyond logic. With the belief that no matter what was in front of him — as hard as it was, as painful as it felt — what needed to happen would happen. And he would will it into existence.
That’s not blind faith. That’s not naivety. That’s a person who understood something most people don’t: the distance between where you are and where you’re supposed to be is not closed by logic. It’s closed by conviction. By movement. By refusing to let the gap between your present self and your future self become permanent.
———
More founder journeys coming soon. Each one a different story. Each one with something in it that belongs to you.