You’ll Always Miss Being in the Basement

We were tucked away in the corner room of a damp, musky basement.

A walking cliché, really: a handful of basically kids, working on The Next Big Thing, getting paid practically nothing, in a startup on University Ave in Palo Alto. We’d see the Facebook kids across the street dress up for their toga parties and hundred million user celebrations. Listen in on VCs courting people like us at lunch. Go to the never-ending list of meetups every week.

The founder and the CEO had done it all before in the previous boom, growing the company to billions. They knew what growth actually meant for a company; they had lived it.

One day, in-between talking about our obviously bright and inevitable future and where we wanted to take the fledgling company, the founder stopped and said something that sounded like a lightning bolt to me, even back then:

One day this company will get huge. You’ll help hire your replacements, and they’ll hire still more people under them. We’ll be making tons of money, we’ll IPO, we’ll be famous, we’ll move into bigger and better offices.

As great as that’s going to be, I guarantee you one thing: you’re always going to miss being down in this basement, with these people.

Like many things he said, this was true at face value, but it just wasn’t in the cards for our particular company itself. The company was perpetually just about to close the one massive sale that would make us rich, at least according to our sales team.

But he was right. Even now, parts of me want to be back in that basement. I want to be working with that team, on a product we thought would be the next big thing, laughing with each other on the walk to lunch. Feeling like a part of something.

Most decent companies have a basement. Even if the company isn’t successful, or rich, or famous, or doesn’t even have a physical basement, they have a basement. Even if the work itself was grueling and underappreciated… a lot of pride can come from within a team’s frustration, at times.

I’m stretching the metaphor, but money can’t buy basements. My favorite memories from my five years at GitHub are simple and cheap. Having our weekly small-sided lunchtime soccer game against Atlassian. Passionately arguing the style of music required for us to finish Pull Requests. Organizing drinks with Square back when we both could fit into one tiny bar. Debating scaling of our respective sites with Heroku friends (“it’s just a fucking Git repository, that’s easy!”, we would inevitably learn). Literally every one of our office dogs.

Look: there’s plenty to worry about in a growing company. Product, trajectory, hiring. At the end of the day, a company needs to make money. That’s how you pay the employees that contribute so much to your success.

But at some point, you’re going to want to end up back in that basement.

Probably the folly of being human, maybe. You remember the good times and forget the bad. You take to glamorous reinterpretations of history. But it’s a nice comfort nonetheless. It’s why I do things, anyway.