Editor's Pick

How to Keep Winning


I've always been fiercely competitive. I enjoy everything about it—from training to get better, to building and developing teams, to the stress, pressure, and intensity. And while I love winning, there are very few things I dread more than losing. It just feels awful. This meant that I had to get good at constantly not losing. Here are six tactics and principles I learned along the way to protect against failure and keep winning.

Almost everything else you can come back from except death. I'm using "death" both literally and figuratively to mean the point of no return. First, know the death boundaries, and obsess over the extreme downside scenarios and prioritize survival. Visualize all the ways you could die—all the time. In that way I'm very careful, almost paranoid. I ran Replit for eight years with little commercial success, but at no point did we ever get to the red zone when it came to runway—we always had plenty of cash on hand. You'd be surprised by the number of brilliant founders that reach out to me for advice when they're three months from death.



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