The Most Honest Thing I’ve Said in a Boardroom

A note to founders on conviction without bullshit

My Take:

We met with an early-stage founder recently.
Smart. Thoughtful. Obsessed with the problem. Maybe we'll join up.

We were going through the regular rounds of diligence and I asked about pricing.

At this stage, I expected a range.

Instead, he came back with two decimal points, wrapped in absurd confidence that suggested his pricing schedule had been handed down via stone tablets.

And I remember thinking: there's no f*****g way he can know that.

He just didn't have enough customers, enough usage, or enough data to be that precise with that much confidence.

Now look: I have compassion for the guy. I used to be that guy.

Entrepreneurs are stuck in a bind. You have to show up with conviction while managing real uncertainty. If you speak too plainly about the uncertainty and the unknowns, a lot of VCs and board members (even the ones who profess to be comfortable with the rough-and-tumble of early stage) will run for the hills. So most founders resolve the tension the same way: by wrapping themselves in the mantle of false certainty.

I did that for years.

Old me would've launched into the routine:

"Calibrating for X, Y, and Z, and accounting for A, B, and C, it's clear that..." Blah blah blah blah blah.

A lot of words. A lot of posturing. A lot of saying what people wanted to hear so they'd stay off my back.

Then one day, in a board meeting, I got asked a question there was no possible way I could answer.

What came next wasn't my better angels swooping in. I was irritated, and I smugly blurted out:

"I'm sure I don't know the answer to that question. But here's my theory of the case."

And weirdly, it landed. The room didn't collapse. If anything, the conversation got better.

Now this isn't about shrugging and saying, "Who knows, aliens could swoop down, the moon could turn into blue cheese. Your guess is as good as mine!" That's not useful either.

Here’s what it is. And feel free to repeat after me:
“I don't know. But here's my theory of the case.”

Have beliefs. Have reasons. Be ready to revise them fast.

Turns out people don't need you to know the answer.

They just need to trust that you'll figure it out and are learning at the speed of light.