$1,700 to $4,800: The First Bet I Made on Myself

In 2007 I was 25 — broke, about $5,000 deep in credit card debt, and walking down a hospital corridor I’d walked a thousand times before. Somewhere along that corridor, something landed on me. Not a voice. More like a picture: if I kept doing exactly what I was doing, nothing was going to change. … Read more

The Most Expensive Mistake I Made as an Operator

Outwork the competition. Outlast them. Out-grind everyone in the room. …was trying harder. You’ve heard it. I didn’t just hear it — I built my early years on it. When I was younger, I was certain that breakthroughs were a function of force. Work harder. Pray more. Push, and push, and push again. Out-hustle every … Read more

Finish or Let Go

(Previously named The Battle To Finish) There are two ways to never finish — and they look like opposites. Everyone celebrates the start. You announce the business and people cheer. You launch the thing, open the tab, pitch the idea, plant the flag. Starting feels like progress, and it photographs well. Almost nobody throws a … Read more