The Founder of Pinterest on What Surprised Him Most About Starting a Company

Ben Silbermann says the biggest surprise of building Pinterest was just how long it takes to create something meaningful. After reading stories of overnight successes like Facebook or Instagram, he expected things to move quickly. Instead, reality looked very different. “It can take a really, really long time to build things that are worthwhile,” he reflects.

Pinterest launched in March 2010 with only 3,000 accounts—discouraging enough on its own, but even more so given how long he had already been at it. He’d started building Pinterest in late 2009 and had left his job back in 2008. The slow early traction wasn’t just disappointing; it was demoralizing.

People often compare startups to a marathon, but Silbermann thinks the analogy is wrong. A marathon has a clear path and a finish line. A startup, he says, feels more like a road trip in a barely functioning car, with bad headlights, little fuel, and no reliable map. You think you’re headed to one destination, only to discover you’re supposed to be somewhere else entirely—and if you need gas, you may have to get it from someone who could kick you out of the driver’s seat.

That combination of uncertainty and constant decision-making with imperfect information was the hardest lesson for him to learn. And he notes that even today, running a startup still feels like navigating in the dark, trying to make the best choices without ever truly knowing what’s ahea