Skepticism vs Optimism
Read time 2.0 minutes.

The best founders I know have a peculiar habit; they often talk about their business as if it were terrible.

They’ll tell you how brutal customer acquisition is, how scattered the market feels, and how risky every decision looks. From the outside, it almost sounds pessimistic.

But here’s the twist: that skepticism is their superpower.

Because when you understand just how hard it is to win even one market segment, you don’t waste time chasing five. You get disciplined. You cut options. You make choices that stick.

Now compare that to the founders who think they’ve already hit the jackpot. They see their startup like a winning lottery ticket waiting to be cashed. That optimism is intoxicating — but dangerous.

It’s why they over-hire before finding fit.
It’s why they over-build before finding demand.
It’s why they think “we’ll just turn on marketing” is a strategy.

The result? Paralysis. They don’t actually decide anything. They just say yes to everything.

And here’s the thing about positioning: “yes to everything” is really “yes to nothing.”

Great founders survive because they know how bad the odds are. Average founders flame out because they believe the odds don’t apply to them.

Optimism makes you start. Skepticism keeps you alive.

Onwards and Upwards,

Liam Gill