Like every crank who has been in the startup world for awhile, I’m starting to appreciate experience.

Tech’s disruption fetish

The tech industry pushes such a youngin’s narrative: take kids fresh from their second year of university, shove them into a venture-backed position, and kaPLOWEY! Money and fame rains from the sky! Money party time!

It makes sense, though: their half-semester course in undergraduate sociology definitely qualifies them to manage their employees’ livelihoods.

Most of this focus is on disruption, which, come to think about it, used to be a negative word back when it happened to your water supply or the regional power grid. Now it’s good to disrupt old industries, and we throw a lotta bright-eyed bushy-tailed kids on magazine covers to promote that. And some extent of it is true: younger perspectives lend themselves toward being ignorant enough to try something new, to rethink unchanged processes. Granted, that can go hand-in-hand with the “most startups fail” narrative, but who am I to get in front of a good cliché.

It’s different

The thing that kills me — and I hear it every few months — is when young startup founders make dumb decisions because they don’t have any historical context to inform their decisions. They haven’t been there before. And yeah, that tends to work for product, where you’re inventing something new, but there’s a really good chance you shouldn’t be experimenting with your people.

Time and time again, the young startup promotes their longest-tenured young engineer to become CTO of their 20-something startup. And it makes sense on the surface, because it’s their “best” engineer. And why not? They’ve been there for so long that they know the system they’ve built more than anyone else.

But now they have two problems: they lose their “best” engineer, and on top of that, they gain what’s probably a shit manager.

I’ve heard startups tackle this in all number of manners. One startup was confident when they said, “Yeah, we’ll send him to take management classes and spin him up to speed in no time; he’s a super fast learner”, neglecting to realize that he’s a fast learner when it comes to new programming languages, not understanding humankind.

Do you know who the best managers were early on at GitHub? The ones who had done it before, preferably for years, and preferably at companies who had a strong management culture (think Microsoft, for example).

Yes, you can A/B test managers and employees with satisfaction surveys to optimize over time. Yes, you can learn management on the job, starting from nothing. But you’d also be a fucking moron to rely upon that for the whole organization.

With product, if you deploy a breaking change, you can also usually roll back in minutes. Unless you’re building heart EKGs or something similarly mission critical, you can afford to be a bit cavalier. Okay, I’ll even say it: you can be disruptive. And disrupting product is lit, or whatever the kids in Brooklyn say these days.

Disrupting people is not lit. If you deploy a breaking change to your organization — i.e., hire an incompetent manager who is a huge dickbag — you can’t rollback the number of people who quit, go through real emotional issues, or are otherwise become dysfunctional in the organization.

The fresh-outta-college thing

This isn’t a young-versus-old issue, although that can inherently play a part. It’s a matter of experience, and being exposed to these things, either directly or even indirectly.

I’ve gotten asked a lot over the years whether someone should drop out to instead pursue their dreams of starting a startup. I kinda had some wiggle room initially in my responses, but now the question itself seems kinda mind-boggling to me.

Of course spend at least a couple years working for someone else. There’s such a bonkers amount of lame shit that you learn that will serve you in spades down the line: how does insurance work? How are salaries dealt with? How do good companies deal with firing people? Bad companies? How does product get built competently? What did you like about your experience, and what did you hate? A little bit goes a long way.

Follow people who have that experience

One of the tweets I’ve referred back to over and over again in conversation is this reply from Startup L. Jackson (may he rest in peace):

@MikeIsaac @ryanchris anyone who has previously been screwed. Nobody else. — Startup L. Jackson (@StartupLJackson) December 23, 2015

Sometimes you gotta fuck up — or get fucked up — to learn how to avoid making those same mistakes in the future. And then you’ll make more mistakes, and a few of your employees will run off and start their own thing, vowing to never make the mistakes you made. And then they’ll make their own mistakes.

It’s a wonderfully shitty cycle. 💖