Confessions of a small time CEO

You wake up before dawn to workout, you come home to quiet, the world still. You’ve been here before, sitting at the kitchen table, drinking coffee, eyes on the clock and the cat staring back at you. Everything looks calm from the outside, but inside? It’s chaos. The adrenaline of excitement, risk, all jumbled together just trying to hold the center together while the edges fray this is the real confession of a small-time CEO.

No one tells you how lonely it gets. You smile at your team, nod along at meetings, and at the end of the day, all the weight comes crashing down when you’re alone with your thoughts. The sleepless nights aren’t from fear of failure anymore—failure’s been staring you in the face for years now. It’s the unknown, the endless loop of "what's next?" or "can I pull this off in time.”

There’s a constant dance between hope and pragmatism. People look at you and see confidence, direction, purpose. But every decision? It feels like playing poker with no cards, just a bluff you hope no one calls. Sometimes, it's less about survival and more about winning or losing your way. Keeping the lights on another month, avoiding the call from that client that represents 20% of your revenue.

You get good at making excuses, rationalizing choices that, in your gut, you know are right and are willing to die on that hill. You tell yourself it’s just this month, just this quarter, just until the next client signs. But when is it ever truly one more client? You’ve been saying that now for 17 years, 286 customers and growing finally.

There's an odd satisfaction, though. A sort of gritty pride. It's the satisfaction of knowing you've built something—even if it's small, fragile, and on the edge of collapse. You're still standing. And in the quiet moments, there's a clarity that emerges, a tiny pin hole of light, an understanding that success isn't always about scaling to unimaginable heights. Sometimes, it's about getting to play the game one more day and keeping your vision alive, no matter how small.

And maybe that’s enough. Maybe being a small-time CEO is about being content with the struggle, with the endless cycle of risk and reward, because that’s what keeps you going. It's not the dream of being the next Amazon or Apple—it’s the knowledge that you’re still here, still fighting.

And for now, that’s enough.