The right way to start a company

Sam Gerstenzang
4 min readNov 27, 2015

Three times in my life I thought I would start a company. After Stanford, after a16z and after Imgur I thought that this was my moment. But each time, I went through my spreadsheet of ideas and found some reason none of the ideas would work. Or sometimes there wasn’t a reason, just a “meh.”

My most recent attempt, a few dedicated months after I left Imgur, was really hard. Everything felt like it was lining up: a great cofounder, potential first hires, funding, a few ideas that seemed promising. But I kept searching for that feeling, a click that made it obvious. And I never found it. I began to question a core part of my identity that was built around being a future founder.

I’d see some fundraising headline and think “she raised this much for THAT?” Or speak to another founder about the silly thing he had spent three years of his life working on. What made it click for them? Had they done it without true conviction? Or were they simply more easily convinced than I was? Or worst of all: maybe I just didn’t have what it took to be a founder.

I wondered what would keep me going, like Ev, after my cofounder quit and I had no traction. How did I know if I had, as Noam calls it, “stamina” for that idea?

“Work on something you’re passionate about” ends up being fairly useless advice. You can be passionate about building teams or closing sales, and it might turn out that horses or makeup or gourmet food aren’t nearly as interesting when you’re running out of money and your best employee just quit.

Alok once said to me that passion comes from success, and I think that’s right. You need to somehow get yourself to a point where you have someone who loves your product but just wants this one more feature. Numbers going up and to the right are very motivating.

But how do you pick that thing before it’s the thing? If you take on a big, important challenge, it’s hard to figure out where to start. If you take on a small challenge, it’s hard to see how to make it big. With an important challenge, no one will think you can succeed. With a small challenge, no one will think it matters if you do.

You read stories about Airbnb or Whatsapp and you realize there is no magic moment, or at least that magic moment doesn’t come at the beginning: it only comes after a lot of hard work. Even the Facebook team worked on Wirehog after Facebook had launched and was growly quickly: they still hadn’t realized how unusual Facebook was.

Here’s Brian from Airbnb:

We didn’t have this flash of inspiration that Air bed and breakfast was going to be huge. In fact we started building a different product — a roommate search tool. We worked on this for 4 months and then realized “” had already built this service. I couldn’t believe how much time we wasted on this before checking the URL

Airbnb, Whatsapp, Facebook: it took each of them time to realize how big each of their ideas truly were. What kept them going? Determination, sure. But also small nudges from others. In my own search, it was startling to me how one coffee or a casual word from a friend could turn my day up or down. I think that’s one of the things that makes Silicon Valley work so well: fewer haters.

Whatsapp would have died had this exchange just gone a bit differently:

The following month after a game of ultimate frisbee with Acton, Koum grudgingly admitted he should probably fold up and start looking for a job. Acton balked. “You’d be an idiot to quit now,” he said. “Give it a few more months.”

Perhaps Jeff Bezos’ “regret minimization framework” is the right way to do it, but it doesn’t make it any easier to choose between a bunch of different fragile, barely born ideas. Maybe the best thing to do is to delay the choice just a bit longer, or maybe that’s the way you justify never starting anything.

I think it’s okay to start a company “just to start a company”, and I don’t think there’s one right way to do it. Silicon Valley loves the mission-based startup and retroactively constructs a founder mythology. But big companies get started because someone takes the leap, she listens to encouragement, and ignores the haters until the company reaches product-market fit. That part is always the same.

I haven’t taken the leap yet, but someday, I will.


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Sam Gerstenzang

Building @askumbrella. Previously building products, teams, and companies at @sidewalklabs & @imgur, investing at @a16z