winning = fun

Ambitious people are happiest when they're winning. Why? It's because ambitious people love to build things, and you get the right to build things when you're winning.

That's what struck me most about doing YC this summer, and it's why I think YC continues to work many years later.

When you're winning, investors tend to like you, and you get more resources to build.

When you're winning, people like to talk about you, and that makes it easier to continue winning (provides social proof for hiring, grows brand recognition with customers, etc).

YC puts a magnifying glass on all of this when you're in the batch. The same ingredients — investors, customers — are intensely amplified. The heat is stronger; momentum builds faster.

What's more, ambitious people love working with ambitious people, and that makes the YC program especially powerful. The program is engineered for compounding ambition. Consider:

• Ambitious Founders × Ambitious Peers = Energy
• Momentum + Accountability (Peers, Partners, Demo Day) = Winning

At YC, all you focus on for three months is growth and momentum, perhaps to a fault. But that intensity is the point, and the alternative (not doing everything possible to reach escape velocity as quickly as possible) seems less likely to work, especially in the early days. Sam Altman writes in Startup Playbook:

Growth solves all problems, and lack of growth is not solvable by anything but growth… The prime directive of great execution is 'Never lose momentum.'

Winning creates energy, and energy is fun. Momentum is addictive.

Notably, not all fun = winning. There are lots of distractions in start-ups that are fun but don't contribute to winning, and there are lots of things that look like work but are actually distractions.

But one thing's definitely true: winning = building = fun. To have fun in life, keep winning.

september 13, 2025
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