Champagne Problems

How Storytelling can Prevent a Culture of Entitlement

There is a moment, if you are lucky enough to have a successful startup, where an incredibly significant but nearly invisible transition occurs.

It starts with the first hire you make after achieving success, and it’s vital that you understand what has just happened.

You’ve hired the first person who doesn’t know what you had to do to achieve success.

The problem here is that as a founder or early employee of a startup, you all remember being hungry. Sometimes literally. You remember long days and nights working at a dining room table. You remember wondering whether you should have bought that sandwich, or gone for the ramen instead. You remember every agonizing decision about money and time, and how to best spend it to work towards success.

Every early employee also understood that you were not yet successful and that to become successful, you had fight for it. You all fought together for a common cause. And finally, after months, or years, of struggle, you’ve achieved something amazing. You’ve made it.

And so you hire that next person. Whoever they are. Whatever they do. And they come to the company, and they see this successful thing, and they see the perks you offer, and the atmosphere, and they think, “Hey, this is a great place to work! See all these happy people? See how fulfilled they are? We’re successful!”

But they didn’t see the hard work. They didn’t see the long nights. They didn’t see the times you wondered where tomorrow’s paycheck was going to come from, or the bitter fights that emerged from being under unimaginable stress.

They just see success. And that makes their perspective on their job radically different than yours. Because when you’ve lived the panicked life of a startup, it never really leaves you. You stay hungry. You stay vigilant. You stay careful (or paranoid, whatever you want to call it). But the new folks — there’s something missing. Something off. They’re not hungry, and they’ve never been hungry. They’re less vigilant. They’re not careful. Time doesn’t have that pressure that you constantly feel.

It’s easy to be resentful of the new folks. To think that the culture is clearly deteriorating, and that “these kids” are just not as motivated as you are.

And you’re right. But you’re also wrong. If you’re still vigilant about hiring (and you’d damn well better be), then the problem isn’t that you’re now hiring worse people — the problem is that they can’t possibly know what it’s like to have been in the situation that you were in. And more importantly, you shouldn’t assume they can.

Yes, it’s easy to say that the burden should be on them. But why should it? How should it? Is there any way for even the most diligent, committed employee hired into a successful company to understand what it’s like to not yet have achieved that success? Of course not.

You have a disconnect between the people that worked to achieve success, and the people that will hopefully propagate that success. How do you bridge that gap? I can’t tell you a foolproof way to do it — there’s really nothing that compares with experience. But there is a simple thing that you can do that’s really easy to forget:

Tell them the story of your success.

Sounds simple, right? It is. Tell them the stories of how you almost failed. Tell them the stories of the awful hacks you had to pull to get things working. Tell them about the false leads and the failures and the pain and the misery and the hope and the passion and the success. These are great stories. These are stories that people love to hear, because you know they end well, they involve interesting people, and there is a beautiful narrative arc through hope to despair back to hope, and good triumphs over evil in the end. That’s why you’re still here.

At my last company, we had a very distinct transition point, where people started taking our success for granted. I was pissed. We’d worked so hard, and now we had these slackerly hangers-on who weren’t busting their ass the way we did “back in the day.” A huge amount of resentment built up inside of me, and it was only after a moment of reflection (walking the dog, where these things often happen) where it became clear that the problem wasn’t with them.

The problem was that I wanted them to have knowledge that they didn’t have and couldn’t get.

So the solution was to start telling stories. To tell people of the days before we’d achieved success. To tell people the days when we worked out of a storage room, or a living room. Where ten dollars in revenue was a cause for celebration. Where a server fire meant we thought we were going to lose our whole audience. To tell them of the things they cannot possibly know, in the hopes that they can understand the meanings of those stories and carry them forward.

This is how we used to learn, in the days before the internet. It is how we can still learn the things we have not experienced ourselves. But it is up to the people who lived in the time before success to share those stories with the people who were hired after.

And the first step is understanding that these stories need to be told.