The Bowling Alley Moment

Do you know you're a founder yet?

Hi all —

Whether you’re hiring for your early-stage startup, giving advice to founders, or considering investing… you have to figure out whether the person on the other side is “pre- or post-bowling alley moment.”

The Bowling Alley Moment is the moment you realize that being at a startup is nothing like other kinds of work experience.

Traditional work experience - whether in corporate, consulting, banking, etc. - is like bowling with bumpers on:

It’s not easy, sure, but we’ve got guardrails.

We assume, then, that starting or joining a startup is like taking the bumpers off, and facing the dreaded gutters:

So we show up with our bowling ball and clown shoes to start our entrepreneurial journey. Nervous, sure, but mentally prepared to bowl without bumpers.

We arrive and we’re confronted with this:

There isn’t even a fucking bowling alley. It’s a vacant lot. We’ve got to somehow buy the lot, build a bowling alley, and THEN we get the chance to bowl. And we’re standing here holding our bowling balls, wearing our clown shoes, looking like total idiots.

Every success founder (& every successful early-stage employee) has their Bowling Alley Moment.

It’s the moment you realize that what you’ve learned in your big career won’t help you (yet). You finally understand the challenge you face. You realize you need a different set of skills and a different way of thinking, acting, and being.

Many founders never realize this. They LARP, building products nobody wants, doing whatever successful companies do with no results. They stand in the cold wind of a vacant, ugly parking lot pretending to bowl.

And worse: Most of the advice you receive (and nearly all the business knowledge that exists) applies once the bowling alley is built. Even founders who have gone through this stage tend to “memory-hole” it: They forget what it was like to look at an empty lot while wearing clown shoes.

If someone has not yet experienced their Bowling Alley Moment, there’s not much you can do to help them.

A good friend said about a startup he met: “I’m worried about them. They still have hope and light in their eyes.” What he meant: They’re pre-Bowling Alley Moment, and haven’t yet come down to earth.

Everything that’s real about business emerges after your Bowling Alley Moment. While it’s brutally painful, you learn what matters, how to operate, and how business actually works.

Do you remember your Bowling Alley Moment?

—

PS - If you want to support early-stage B2B founders (who, IMO, are bombarded with bad advice):

1. Share this newsletter - especially in founder communities & slack groups!

2. Connect me with founders who want help finding PMF & navigating $0-$1M ARR - I work with a few at a time to help them “figure it out”