The Hardest Thing for Founders To Be Comfortable With

This is a cringey post

Hey y’all — it’s cool to be cringe.

Being comfortable being cringe is actually a secret weapon for founders.


It communicates that you have confidence in the thing you’re building (and selling). You’re all in on it. You believe it can make a difference.

But it’s hard to reach that comfort especially if you’ve never done sales or marketing before.

For many founders it’s the hardest part of building and growing a startup.

It’s natural. I had to overcome it too.

Let me show you how!

Founders & Cringeyness

What Is Cringe?

You might think about being cringe as something like being awkward.

There’s a good (short) book by Adam Kotsko about how the predominant driver in pop culture humor morphed in the early 2000’s from irony to awkwardness. The switch is best explained as the difference between the mid 90’s, Larry-David-written Seinfeldian humor and later-career Larry in Curb Your Enthusiasm.

They’re not the same.

You know this because of how each makes you feel.

Awkwardness gives you a general feeling of discomfort about being present for something, whereas witnessing cringe gives you a more personal and specific I’m-embarrassed-for-you feeling.

So what is cringe?

In a world where everyone keeps their options open in everything from who to date to who to invest in, cringe is refreshingly single-minded.

It’s a willingness to go all-in on something you believe in, no matter how it makes you look.

For founders being cringe is shamelessly shilling your product to anyone who might get value from it. Not because you’re trying to trick them into paying you, but because you genuinely believe you can help them.

Cringe does whatever it takes.

It’s me posting a fourth founder bio thread on X in a little over a week because the first three added $2,000 in MRR to Megaphone:

Even when your friends troll you:

Overcoming the Fear of Cringeyness

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