^{Forwarded this email? Subscribe for more.}

The Naughty List

Last weekend: Movie night. Friends. Ice cream. Pirates of the Caribbean.

Halfway through, my girlfriend goes, "Jack Sparrow is such a founder."

He’s reckless. But not careless.
He breaks rules. But not values.
And he always finds a way.

Imagination with a rebellious streak.

Jack Sparrow — I mean Captain Jack Sparrow — cares about the big things: loyalty, freedom, doing right by those who trust him. But he couldn’t care less about protocol, paperwork, or playing nice with the gatekeepers.

That’s the essence of startups. The tension between being good and being obedient.

With that, no pirate sails alone.

Forget trust, loyalty, and all the deep, serious themes from the movie for a second.
Let’s talk about something a little more fun...

Naughtiness.

We all know that willingness to color outside the lines is necessary for being a founder.

But how does it relate to cofoundership?

It’s this almost mischievous sense of shared defiance. When one of you says, “What if we just...,” and the other says, “Let’s do it.”

People rarely mention that cofounder compatibility often means rejecting the same script at the same time.

Psychologically, that’s not trivial.

Because rebellion is risky. It breaks social norms. People scrutinize. It threatens stability.

So when someone joins you in that risk (and not just tolerates it) it gives you a special kind of trust.

Not the trust that comes from professionalism or shared experience.

Sociologists call this transgressive solidarity. Bonds form when people go against the grain together.

Underground movements. Jazz duos. Teenage friendships that last a lifetime because of a prank they pulled in middle school.

That’s why naughtiness isn’t a distraction from the work.

It is the work.

(Here’s the Pirates theme song because we all need to hear it once in a while).

That’s all for now,

BTW — Grab yourself some dumbfound coffee. Our grind fuels yours.

_{Our Sponsors}

Cherrytree is free. Always has been, always will be. That’s all thanks to our amazing sponsors. Show them some love. ⤵️