How to Hack It at a Startup

On the first day of new hire training at Stitch Labs, I ask everyone the same question: “Why work at a startup?” We all joined Stitch because we either needed or wanted a job—but why a startup job, specifically?

Behind this question is a deeper one: does this new hire know what a startup is?

I’d wager that most people at most startups don’t know what a startup is, which helps explain why most startups fail.

What makes a startup?

To paraphrase Steve Blank, a startup is an organization trying to figure out what its product is, who its customers are, and how to make money.

A venture-backed startup isn’t a business, at all; it’s a group of people racing to build a business that no one’s ever built before.

When I think about those who understand and thrive in these environments, two particular qualities come to mind: a high tolerance for ambiguity and an unrelenting desire to build.

Tolerance for ambiguity

Ambiguity is uncomfortable, but it’s the price we pay for change. To choose a startup is to say yes to ambiguity—as something worth exploring because of unknowns, not in spite of them.

It’s tempting to think of success as an exponential curve, but the journey is rarely (if ever) so direct. I like Tien Tzuo’s switchback metaphor:

On switchbacks, you get to the “end” only to turn around and trudge back in the opposite direction. Every foot of gain requires many steps forward, and the only way you make it to the top is by switching back and forth, back and forth, over and over again.

All those “about faces” can really fuck with your rhythm, but they’re what get you to the top.

Desire to build

Grit keeps you on the mountain, but to go up, you have to build.

You can work very hard and for long hours, but if you’re not finding ways to make yourself, your team, and your company more effective, you’re not building.

You get the most out of grit when you balance it with ingenuity, impatient iteration, and straight-up refusal to do the same tasks over and over again.

Doing the same things over and over again is what widgets do. Big companies hire widgets. Startups hire builders. At a startup, building is everyone’s job, every single day.

These qualities can be learned

These qualities come naturally to some, but they can be learned.

I definitely had to learn. I had to put chaos into context as the best place to make change happen. I had to accept that progress was often a game of inches. I had to say yes to those things and commit to all that they entailed. From there, the doing became much easier.

I’d like to see startups be more open and explicit about their economic purpose and why someone should choose a startup job. The playhouse veneer of Nerf guns, beer in the fridge, and ping pong tables hurts everyone. A more honest portrayal of startup culture would help the right people choose startup work, find success in their role, and help their companies reach their objectives.