Pinterest’s Unlikely Journey To Top Of The Startup Mountain

Editor’s note: Derek Andersen is founder of Startup Grind. Follow him on Twitter @derekjandersen.

Over the past 12 months, I’ve had the pleasure of interviewing some of the Valley’s best entrepreneurs and investors at Startup Grind. People like Naval RavikantKevin RoseTony ConradMG SieglerJeff Clavier, and others have inspired us with stories and trials they have overcome to get where they are.

In February we hosted Pinterest co-founder (and now officially CEO) Ben Silbermann in Palo Alto. He is one of the most humble entrepreneurs I have met in my seven years in Silicon Valley. The story of Pinterest’s founding is more valuable to me than most startups because it is a reflection of what a lot of founders who regularly read TechCrunch go through in the everyday startup grind.

Pinterest’s founders are smart guys, but they’re not prodigies. The product is huge now, but no one liked it when it launched. They weren’t well funded and for a very long time. These are things that normal, non-rock star entrepreneurs like me (and maybe you) can relate to.

Founder Background


Raised by doctors in Des Moines Iowa, Ben assumed he would follow the same path as his parents. He attended Yale University starting in 1999 and soon realized that he didn’t want to be doctor. After a consulting gig in Washington DC, he headed to Silicon Valley in 2006 to join Google working in customer support and sales.

“I felt the story of my time was happening in California,” he said. “I didn’t have a specific plan I just wanted to be closer to something that felt really exciting. Google was the first company I worked for that was thinking really big.”

As a non-engineer at Google, Ben felt there was only so far that he could go in that culture. He kept talking about doing a startup but it was his girlfriend (now wife) who pushed him saying, “You should either do it or stop talking about it.”  After leaving Google he spent time working at places like the Hacker Dojo, and every coffee shop in the valley.  Sound familiar to anyone?

To Pivot Or Not To Pivot


Four months after launching, Pinterest only had 200 users.  Ben has said their product was “in stealth mode but not because we wanted it to be.” The first major pockets of users were in Iowa and Utah and the company wasn’t on any radars in the Valley.

It didn’t pop in California for the first year and a half. Ben believes the typical market fit philosophy for technology of having to get early adaptors on board is no longer required. There was no press coverage on the site, but the early users really liked it, and more importantly they used it a lot. “The site grew by the same percentage (40%-50%) every single month. It’s just that the number started so low that it took a while to get going.”

The team attempted to raise money, but the non-engineer driven founders had little success. Despite dozens of meetings with “everyone” in Silicon Valley. Most passed on the deal. They worked with a lot of engineers most of which weren’t near the Facebook and Google level of talent they’re getting access to today.

Remarkably the Pinterest team maintained their original vision despite the Valley’s pressure to be successful quickly or pivot (aka: admit failure). Pinterest’s early traction wasn’t positive. But the Silicon Valley culture and community of being helpful and not giving up kicked in to push the team to keep pressing forward. While feeling the pressures of possible embarrassment if he had to go to Google to ask for his old job back, Ben never seriously considered giving up.

Focus On Product


Much of what you see on the site today was in the product at the very beginning. They were one of the first sites to do the grid-like layout and they over invested in design. They spent months working on it. “We were obsessive about the product. We were obsessive about all the writing and how it was described. We were obsessive about the community. I personally wrote to the first 5,000-7,000 people that joined the site.”

Pinterest was about getting you offline to do all of these things you’re talking about online. Pinterest was also integrated with Facebook from the very beginning. All the founders were aligned on building something that they were really proud of. “I think we knew from the beginning that we were building a very different kind of product.”