August 10, 2026
Winning & Learning
@anthonycorletti

The idea of "what one is willing to trade off in order to win" has been on my mind lately. In some corners of the internet, you'll find the tradeoff framed as being liked versus winning:

I've also found that the original sentiment is often attributed to Nelson Mandela: "I never lose. I either win or I learn."

In the world of early-stage company building and scaling, I don't think winning has to come at the cost of learning β€” or of being "liked." It doesn't have to be only win or learn. Why not both?

This little 2x2 illustrates my point.

Most shots on goal you take end up in the bottom-left corner if you're not careful. These could be jobs or life stages filled with constant churn and no traction internally or externally.

The top-left and bottom-right quadrants are halfway there, each with their own pros and cons. Some efforts leave you with incredible learnings but less "winning," or what some might call external validation.

Conversely, you might join a rocket ship at the right time and find yourself winning left, right, and center. But if you haven't been the growth driver, you're learning secondhand β€” from proxies, a few layers removed from where the real action is happening.

Both are great, but they come at a cost. Really, it comes down to your personal preference and it's worth considering both sides. Fixate on winning or learning alone, and you might miss the kind of opportunity that could land you in the top right.

I think leaning into your perspective and capability is more likely to send you there. I like to think about it like a market advantage β€” you have a perspective on the market that no one else has. Use it!

Once you're there, the only tradeoff left is whether you're ready to hold on for the ride.