Pinterest

How Fear of Embarrassment Turned into a $11 Billion Dollar Valuation

How Fear of Embarrassment Turned into a Billion Dollar Valuation

Ben Silbermann had wanted to make a difference. He didn’t just want to be another doctor in the family following the footsteps of his parents, or his parent’s parents. He wanted something more. Someone more.

He had been inspired by the movie “Pirates of the Silicon Valley” and had decided to move to California. He replayed in his mind, over and over again, the scene when Bill Gates had announced “there might be something going on in California”.

He really didn’t know what to expect in California but he didn’t care. Moving meant a new start and a new future but it was different and what he wanted.

“I remember I had this feeling that this was the story of my time and I was in the wrong place.”

He needed the change.


California was everything Ben had imagined it to be.

He started working at Google designing display advertisements and he loved it there — the culture, the vibe, the people, everything.

“I thought Google was the coolest place. People there were so smart and they were all doing these really interesting things. I just felt really lucky to be a a part of it even in a small way.”

But there was a problem.

He couldn’t build any products at Google. He wasn’t allowed to, because he wasn’t an engineer.

It was either continue working at Google or quit and do what he had come to California to do in the first place, to pursue his dreams.

He had to quit.

“I left, not because I didn’t love the company, but because of my particular background, it would have been really hard to built products.”


He took a few months off before starting to build iOS apps with his college friend Paul. He pushed out several, but all of them had failed. He knew nothing about the market he had been building for and it was something he wasn’t passionate about.

So he thought. He thought about what he had learned from building those apps and what he really wanted to do. What was he passionate about? What was something he really cared about?

He loved to collect things even as a kid- was that something he could do? To Ben, collecting something “tells a lot about who you are” and the place to share that side of who you were simply didn’t exist yet on the internet. He asked himself:

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How do we best share things with three or 10 people or 20 people?”

This was an idea that made sense. It was something that he could be passionate about. This was what he really wanted to build.

So he did decided to build it with two co-founders. For the next 6years, Ben would continue to work on the idea.

That idea? It was Pinterest.


Most of us look at Ben’s story and think: Holy shit, that’s amazing. Pinterest is an overnight success.

But was it really? Had Pinterest always been that successful?

No. In fact, for the first 9 months, growth had been steadily declining. Ben had done everything he could think of, but people just didn’t get it. They didn’t ‘see’ Ben’s vision. They didn’t see the concept behind Pinterest.

“I sent Pinterest to 200 of my friends and I think 100 of them opened the email. It was catastrophically small numbers”

The site had less than 10,000 users at the time, most of whom weren’t even using it.

Still, Ben never gave up. He persisted.

People asked him why and Ben responded:

“The idea of telling everyone we blew it was so embarrassing. I thought, Google is never going to take me back- they barely hired me the first time!’”

To Ben, the fear of embarrassment was what had kept him going. But that wasn’t really the reason why he succeeded.

The reason was because Ben simply chose not to give up. Pinterest was his passion, and for that reason alone, despite all obstacles, he continued to work on it even things had been bleak.

And that’s where most of us differ from Ben. How many times have we given up when faced with a seemingly difficult obstacle? How many times have we gave up on our passions simply because we didn’t try? How often do we look back at what we could’ve done, should’ve done?

Unlike Ben, we’ll never know because we gave up too early.


For entrepreneurs and founders, challenges are a part of what we face each day. It’s inevitable. It’s a part of life. It’s a part of business.

If business were that easy, we’d all have a few extra million dollars in our pockets.

Anything that’s ever been worth doing will take effort. And that’s the thing — business isn’t meant to be easy. By building a business, following your passions, you’re creating something that doesn’t exist. You’re creating something out of nothing. That, in itself is a challenge.

What if Ben had decided to give up? Can you imagine if, at 9 months, Ben had decided that it had already been too long? Would Pinterest still exist?

The underlying lesson of Ben’s story is to remind you to not give up so easily on things you’re passionate about. The moment you give up, you lose the chance to make it in the first place. You’ll never know whether or not you might’ve succeeded.

The only thing we can do is believe in ourselves. We have to believe, for the sake of what we’re passionate about, that we can push forward and overcome our obstacles. To be determined and believe in our own abilities. The obstacles we face today are building blocks to tomorrow’s success. From overcoming these obstacles, we gain perspective, perspective into building a better future for ourselves, perspective into creating a better story to tell.

The key is finding passion for what you do. You don’t have to love what you do. Just be passionate about the problem that you’re solving, why you’re solving it, and the potential of the solution. When you build a business, you’re in it for the long haul and if you’re not passionate about what you do, you’ll give up for all the wrong reasons. — Excerpt from Overnight Success is possible.

Overnight success is possible. Just don’t be surprised if it takes years.

Pinterest’s valuation is at $11 billion as of 2015.


If you’ve liked this post, I’m writing another one featuring 50 of the most successful founders and entrepreneurs I know with their most embarassing “Oh I fucked up” moments so you can see for yourself how they overcame those challenges.