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Toxic Optimism

Without meaning to, cofounders fall into default roles: the optimist and the realist.

The gas pedal and the e-brake.
The dreamer and the doomsayer.
The firestarter and the firefighter.

It works at first. You balance each other out.

Over time, however, these roles harden, until one of you becomes the default bearer of enthusiasm and the other becomes the default bearer of caution.

And it starts to feel like a burden.

I was the optimist. The opportunist. The guy with the grand vision.

Every obstacle, every rejection, every setback was simply “part of the journey.” I thought I was doing my job, as the CEO, of keeping morale high.

But somewhere along the way, optimism stopped being a gift.

Personally, it became a shield. A safety blanket.

If I was constantly optimistic, I didn’t have to admit I was scared.
If I was constantly optimistic, I could protect my team from anxiety.
If I was constantly optimistic, I wouldn’t scare away investors or customers.

If I kept saying “we’re fine,” I wouldn’t have to ask, “are we actually?”

My smile was a cry for help.

At some point you do have to face the truth ↓

Meanwhile, one of my cofounders became the designated downer.

I thought they were being negative.
They thought I was being delusional.
And we were both right.

And this is where I fucked up.

Optimism feels like a leadership trait. But left unchecked, it becomes a wall.

When one person is always “up,” the other learns to stay quiet. They stop bringing concerns, risks, or doubts. They don’t want to be “the problem.”

They don’t want to kill your vibe.

Even worse, it’s easy for you to mistake doubt for disloyalty.

Here’s what I wish I’d known about optimism the first time.

How You Know It’s Toxic

• You brush off concerns as fear-based thinking.

• You avoid hard conversations by faking positivity.

• You’re pressured to keep everyone pumped even when you’re not.

Optimism must be real. Not a performance. Not a deflection.

What Helped

Eventually, I had to slow down and ask myself:

• Am I making space for the hard stuff?

• Do people feel safe telling me when something’s wrong?

• Am I being genuinely optimistic or avoiding reality?

The surprising thing is that my cofounder got more optimistic. They didn’t feel like they had to carry all the doubt alone anymore.

Turns out the most powerful kind of optimism isn’t loud.

That kind of optimism doesn’t silence doubt. It welcomes it. Listens to it. Uses it.

And if you’re the realist,

• Don’t hold it all in.

• Say the hard stuff before it becomes resentment.

• Your fear might be the only thing keeping the ship from sinking.

The best cofounders don’t split into roles and stick to their corners. They share the weight. They trade seats. They face hard things, together.

That’s all for now,

BTW — The Cherrytree cofounder community is now open. Join here →

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