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Exclusive: Pinterest’s mastermind departs for Jony Ive’s new design firm. Here’s why

We sat down with cofounder Evan Sharp to look back on a decade of work at Pinterest, and what LoveFrom holds for him next.

Exclusive: Pinterest’s mastermind departs for Jony Ive’s new design firm. Here’s why
[Photo: courtesy Pinterest]

Back in 2010, Barack Obama was president, smartphones were in their infancy, and the future was bright for the internet. A website called Pinterest went live, transforming text-heavy URLs into beautiful, collectible cards.

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Some 11 years and 200 billion pins later, Pinterest cofounder Evan Sharp—the trained architect behind Pinterest’s watershed design—is leaving his company to join Jony Ive’s highly secretive creative collective, LoveFrom.

I’ve met with Sharp several times over the years, and have found him to be an introspective executive who is willing to work through nebulous thoughts aloud—a rarity in the C-suite. As he prepared for his departure from Pinterest, and the journey that’s made him a design leader, a father, and a billionaire, Sharp sat down with me to discuss where he leaves the company, and where he’s going next.

This interview has been edited for length and clarity.

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Fast Company: How does it feel to leave Pinterest after 11 years?

Evan Sharp: When you found a company, and you’re such a part of it, it’s sort of like leaving yourself. It’s like, “What does that even mean?” There’s just the fear of the unknown. Then, as soon as you start talking about it, it triggers a lot of other legal requirements and reporting. And so I think it was tough for me, and very scary, to think about leaving. The biggest fear for me has been stepping out of the story that I have, that I’m the founder of this company that’s pretty successful—and that story gives me so much emotional security. It staves so many of my Am I good enough [thoughts]. It’s just the natural human condition of being self-conscious and an imposter and all that.

What was it like telling your cofounder Ben Silbermann the news?

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Ben and I have been talking about what I’m going to do next for a long time. We really are partners. He’s such a brother to me, really. I think this is true of most [co]founders: You’re bonded with them, like siblings, in that even if you have a fight or something, there’s just this relationship that’s always there. But I’m still very involved, and I’m on the board, and I’m advising quite a bit and planning to work with him on some product stuff moving forward, so it doesn’t feel as binary a change as it might.

Evan Sharp, left, with Pinterest cofounder Ben Silbermann [Photo: Pinterest]
I imagine that because you built Pinterest and saw it grow for so long, there’s something about the platform that other people can never understand quite like you can.

I think you’re exactly right. I mean, I do feel like I’ve earned over the last 11 years, or 12 years even, just this deep understanding of what we’ve built, why it resonates, where it can go, and that’s really valuable.

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OK, let’s play a game. It’s 2010. You’ve just launched Pinterest in beta. You arrive from the future to meet your past self.

Wow.

I know! It’s intense. What do you tell him?

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It’s kind of cliché. A lot of it’s about just personal journey stuff, it’s like, “Be confident in yourself, trust your intuition, be more decisive, spend less time worrying about if you’re right or wrong. Focus on the user.” I think I spent the first many years of Pinterest trying to be a really good leader, like what I thought a good leader should be.

We hired all these great execs from Google and Facebook, and when I compared myself to them, [they were] incredibly accomplished, very professional, very solid managers. I’m this real creative guy who was really good at design and coding stuff, but wasn’t that kind of manager. I spent too much time in self-doubt and limiting my impact because I was trying to be somebody I wasn’t.

And it wasn’t until I met Jony [Ive, about six years ago] and realized, “Wow, this guy has a lot of the same sort of personality traits that I do.” Not that I’m the same or comparing myself to him as a designer, but meeting him really gave me incredible permission to just be myself and really leverage the things I’m good at in the organization without having to become what I thought a leader needed to be. If I could have done that earlier, well, I think it could have been even more impactful as a business.

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Looking back at 2010, what strikes me the most is just how optimistic technology was. The challenge was bringing design to the table, but we didn’t imagine this dystopia of misinformation and toxicity to come.

ES: Well, first of all, it’s an era now when you look back at it, isn’t it?

For sure.

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[Photo: courtesy Pinterest]
I studied history at college, so I always think that way, historical periods. My experience of it was I moved out [to Silicon Valley] around 2009 to work at Facebook. I was just there for, I think, a year, and then Pinterest. But in the beginning, it seemed like there was all this hype around tech, right? The “disruption!” A disruption isn’t good. On Star Trek, a disruptor is like the thing you shoot people with. There was all this idolization of that, and then very quickly that tipped, and now there’s all this demonization.

The mission of Facebook had been to make the world more open and connected. I think it’s way more connected now [because of] the internet; it’s not just Facebook.

But if you think about the role of connection? Think of the wires of the internet like pipes. If you’re a plumber, you have to know what the sewer pipe is, and what the water pipe is. You have to know what you’re carrying, a little bit, so that you don’t mess things up. And I think to your question, there was way too much assumption that everything was going to be positive, and that people would use these tools for good. I think everybody who was involved is guilty on some level of that, of that thoughtless optimism.

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This reminds me that for a long time your goal for Pinterest was to make people do things in real life: If you collected images of decks, success to you was to get someone to build that deck. But you shifted that thinking over time a bit, to be less about inciting action than making sure people had positive emotional outcomes from Pinterest. How far do you feel like you got down that path?

I think we’ve gotten 5% to 10% of the way down what’s possible. But the struggle in doing that, I found, is there’s not a good playbook for [how you measure emotions].

If you’re in the ER, everyone measures vital signs, right? Heart rate, blood oxygen. In the emotional world, there seem to be similar hyper extremes, like depression. Oh, there are real measures for that! And some levels of anxiety. But when you go ask psychologists the question, “What framework could we use to understand emotional outcomes and measure them ourselves?” you get a lot of conflicting answers.

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We need those disciplines to push and innovate and continue finding ways to translate what they’re learning into measures and frameworks so that they are really actionable for these scaled tech services. It’s not just about building technology, it’s about understanding what to measure.

The thing I’m actually the most interested in, in a way, when I think about what to build in the world, is to try and help the experts put together a clearer framework around our inner experience and how to relate to that, and how to bring that to people at scale.

You’ve pivoted at Pinterest a bit recently, embracing influencers as Creators, which are a select few people who can post content like videos. Obviously Pinterest has never seen itself as a social network, and it’s sidestepped so many issues endemic to them. But how do all these emotional outcomes you’re after relate to this new direction for Pinterest? Because influencers can make people pretty unhappy!

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[It goes] back to 2017 when we really started to think about and institutionalize the emotional outcomes of the product experience. One of the things we realized is, it wasn’t just about our users feeling good or bad, it’s that a lot of the reasons people use Pinterest, to say the obvious, are emotional, like [inspirational] quotes or cute animals. And the way that we were measuring so much of what people were doing, it was based on clicks and click-throughs.

And so Ben and I spent quite a bit of time that year focused on, what is the impact for Pinterest with users? What’s good, what’s bad? What do we need to do? And that led to a whole bunch of decisions around taking down medical misinformation [like anti-vax content] and banning political ads entirely. And then starting to work on positive things . . . leading to how we built Creators.

If you click on a recipe, or you buy something for your house, it’s really easy for us to say, “Oh, this is the value the user is getting.” But if a user looks at 20 quotes, it’s a little less obvious without more digging in, and so we actually changed the mission of the company. It had been to help people discover and do what they love. And we shifted it to be an emotional mission, to bring people the inspiration to create a life they love. It’s a little bit weird, if you think about it. But then if you think about the fact that Pinterest is a digital media company, it’s not weird, because media is an emotional thing.

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But when you think about what an inspiration platform should be, it is about action, right? It’s about doing. And it just makes sense that the way users should be able to respond to an idea pin is by sharing what they do, or by sharing a visual. There should be almost like a community around that piece of content. [Editor’s note: The Pinterest Creator platform allows just this behavior today; users can post their own work underneath a Creator project.]

Imagine an image of a beautiful pie on Instagram. It was posted by someone, and so when you look at that image, the context of Instagram, or whatever, Facebook or TikTok, it’s really about the person and what they did. So as a user I’m kind of staring at it, “Oh, this person made this beautiful pie.” On Pinterest it’s always been, “That’s a pie I could make.” It’s the exact same media. Because of the context of the environment, it’s a completely different experience for the user.

Pinterest was in the first wave of design-fluent startups, alongside companies like Airbnb and Instagram. But is design still the differentiator it once was? Because I do feel like design across the board is light years from where it was in 2010.

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I think the idea that things should look nicer, and be easier to use, that’s come a long way. [But] I think there’s a really poor understanding of what the word design truly means.

There’s way more awareness that design can drive business value, and that’s largely thanks to Apple, obviously, and the example that they’ve set. But the essence of design is about tuning everything to have integrity through itself, so if you’re building a company, in theory, to manifest design, it’s the culture of working there, the way we treat and relate to employees, the way you treat and relate to users. To me, that’s what design is. . . . Tuning everything to be in harmony with itself and to be in harmony with your consumer or user.

The way you talk about design almost makes me think of biophilia or our ecosystem. The way the natural world works, where there’s an inherent balance—some definite injustice—but things sort of work themselves out, and it’s just a holistic system.

This may sound weird, but when my daughter was born three years ago, I wrote this little kid’s story for her. It was called The Gardener and the Builder.

When I started working in 2010 on Pinterest, I really thought of myself as like a construction worker, metaphorically, building like you build a shed. You put the brick on top of a brick, and then you’re done. And I think one of the biggest shifts for me with the company has been [realizing] you are not building this company, you are growing this company. And you have to create the right conditions, and you have to prune.

If you think about industrial design, there really is a moment of like, “This thing is done.” And whatever happens, it can sit on that shelf for 100 years, and it is what it is. But with software, it’s constantly shape-shifting. And so relating to what you’re building in that four-dimensional gardening way, it’s never done.

Do you have ideas that you just can’t manifest at Pinterest? Is that a reason to leave now?

It’s more that my fantasy for years . . . is that I want to go apprentice. I really value the people who really know how to build product, who actually do that. There aren’t that many people who really understand how to do it really, really well, and I think I have a capacity for that. Being in these these executive roles, it takes you away from that craft. And I’ve been away from that craft for quite a while.

It’s been amazing to be in this role and to learn things, but I’m called to develop that and to get better at building things, and to learn. That’s really the thing that’s led me to this point. My hope is that I will learn all sorts of soft skills about teams and creativity, and then also literally craft things that will make me a much better partner for Ben and for Pinterest down the road.

So on to LoveFrom! What do you want to do there?

I just want to learn! I’m sorry if it’s not interesting. Jony’s putting together this team of some of the best talent in the world, in all these different disciplines, and I’m so hungry to learn how to build, how to be a better designer, really. I mean, it’s a really precious opportunity if you think about who he is and what he’s learned, and who he’s learned from, and who he’s worked with. But it’s not just about him. I’m just really excited to be in an environment where I’m exposed to such different ways of understanding how to be excellent in what you do, and how to be curious and how to be uncompromising in what you’re building. I just want to learn and grow and contribute, and that’s my focus for now, in that world.

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About the author

Mark Wilson is a senior writer at Fast Company who has written about design, technology, and culture for almost 15 years. His work has appeared at Gizmodo, Kotaku, PopMech, PopSci, Esquire, American Photo and Lucky Peach

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