Can Ben Silbermann Turn Pinterest Into The World’s Greatest Shopfront?

Pinterest, the social media phenom, has created the web’s new design paradigm–and maybe the greatest selling engine ever devised. We sit down for a rare interview with Ben Silbermann, Pinterest’s CEO.

For a guy running such a beautiful website, Ben Silbermann looks like hell: He has prominent bags under tired, watery eyes; his shoulders hang heavy; his shirt is wrinkled; and his dark hair is uncombed. When he speaks–with the open-vowel inflections of his Iowa upbringing–his voice is so slight that it often gets lost beneath the din of other conversations. When he moves, it is with the economy of a marathon runner trying to conserve every last bit of energy on the eve of a big race.


“I’m tired,” says the 30-year-old CEO of Pinterest, the social scrapbook that’s the hottest website on the planet, as he prepares to shovel down a bowl of noodles a few feet away from his desk. Silbermann leaves for the office at 7 a.m. most mornings and works nonstop until dinner. His only respite, if you can call it that, comes in the predawn hours when he takes his newborn son, Max, into his arms and fires up his laptop to check email. Just a few weeks before Max was born in early July, Silbermann declared a companywide lockdown, ordering his 35 employees to come early and stay late in order to build new iPad and Android applications. The goal: to stoke growth. He ordered commemorative T-shirts with the phrase summer of apps printed across the chest, and he cut off almost all contact with anyone outside the company, including potential business partners.

Such is life at what earlier this year was declared the fastest-growing web service in history. In January, Pinterest surpassed 10 million monthly unique visitors in the United States; by April, that figure had nearly doubled, according to Internet measuring service comScore.

This schedule is the price of running a site as beloved as Pinterest, which has won its fans thanks to its breakthrough design. Think of Pinterest as a giant digital catalog filled with the web’s most beautiful images. Users–“pinners” in the twee parlance of the site–copy images they find elsewhere on the web and store them on one of their personal Pinterest pages, called pinboards. (Everything in the company’s office, down to the Wi-Fi password, has the word pin in it.)

Ben Silbermann, Pinterest cofounder and CEO, rendered in 22,765 pins by Eric Daigh. Click here to see how it was made.

On first blush, Pinterest may sound like a hundred other social media websites where people share images and comment on them. But the design choices of Silbermann and his cofounder Evan Sharp, based on a new way of browsing that dispenses with the web’s rigid rules of presenting content, have made the service incredibly addictive. To create a pinboard is to say to the world, Here are the beautiful things that make me who I am–or who I want to be. Young women use Pinterest to plan their weddings, men collect watches and bikes into de facto gift registries, and couples assemble furniture sets for their new homes. Pictures of attractive men and women in various states of undress abound. The sum of each user’s choices is displayed in an ever-changing pastiche on each person’s home page. “When you open up Pinterest,” Silbermann says, distilling his vision, “you should feel like you’ve walked into a building full of stuff that only you are interested in. Everything should feel handpicked for you.” In other words, it’s a store in which every single product has been tailored to your needs, ambitions, and desires.

Pinterest’s combination of elegant design and smart social networking dynamics has made it the Internet’s latest Great Revenue-Generating Hope, at a time of extreme skepticism about newfangled ad-based business models. While Facebook’s 1 billion users seem stubbornly resistant to the entreaties of marketers, the Pinterest set has already been opening their wallets. “This is going to be an alternative form of e-commerce,” says Greg Fant, chief marketing officer at One Kings Lane, the design-centric home-decor web retailer. Pinterest users who find their way to One Kings Lane are three times more likely than the average One Kings Lane shopper to make a purchase; referrals to One Kings Lane from Pinterest have nearly surpassed traffic from Facebook. Across the web, the average sale resulting from a Pinterest user following an image back to its source and then buying the item is $180, according to research from e-commerce firm RichRelevance, compared with $80 for Facebook users and $70 for Twitter users.

Pinterest gets none of that. The company is in what’s known artfully in Silicon Valley as a pre-revenue phase. But that doesn’t mean Silbermann hasn’t thought about how Pinterest is eventually going to get its share of all that e-commerce. “We talked about it a lot,” says an early employee who asked to remain anonymous because he was flouting Silbermann’s wish to keep the focus away from dollars and cents. “There was never a doubt in our minds that we could make a shitload of money.”


By the time Silbermann and I meet in late July, midway through the Summer of Apps–it’s the first time he’d let a reporter inside Pinterest for more than 45 minutes, and the first time he’d spoken to any journalist in several months–he has added another 25 employees and Pinterest was just weeks away from releasing its new apps. The company had just moved into a new office, an expansive loft in San Francisco’s SoMa district, and Silbermann was already negotiating to lease an additional 60,000 square feet next door to accommodate hundreds of new employees. “It’s a busy time, but it’s good,” says Silbermann, a sensitive, deep-feeling man with a boyish face and a gentle demeanor who couches even his harshest criticisms in a sea of qualifiers and who often uses the word gosh without irony. As in, “I’m not going to lie. There are really stressful days when I feel like, gosh, I just want to make the most of this.”

What Pinterest has done is solve the problem of discovery on the web. And it has been a problem for a while. Let’s say you want to buy a gift for your mother. Nothing specific, just something nice. A search for “nice Mother’s Day gift” on Google–or even “very special, very expensive Mother’s Day gift”–isn’t going to be much help. Google depends on finely tuned queries in order to yield useful results. (This makes Google a great advertising platform, because it delivers customers who have already expressed an intention to buy something.) But talk to Google the way you might talk to a clerk at a department store, and it won’t know where to begin.

You could go to the web’s superstore, Amazon, but that’s not much better. To browse, you have to go back and forth through a detailed system of menus, categories, and merchants while constantly being tempted by thousands of competing products at thousands of price points. “You spend three hours buying a $20 toaster,” says Barry Schwartz, a psychologist at Swarthmore College and the author of The Paradox of Choice.


“Browsing in e-commerce is a more difficult problem than search,” says Leland Rechis, a director of product experience at Etsy, the marketplace for handmade goods. “Amazon and Google pretty much stink at browsing.” These failings of the two great Internet moneymakers are not entirely their fault. The structure of the Internet is partly to blame. The web was laid out not in human terms but as a series of ever-more-specific menus, making the kinds of free-associative leaps that routinely happen in a shopping mall–Niketown to Gap to Yankee Candle–nearly impossible. Contrast this with the fact that many of the world’s most profitable retailers–Apple and Trader Joe’s, to name two–succeed by curating a smaller selection of products for their customers.

Pinterest is the first site to succeed massively by bringing that curated vibe to its user experience. Schwartz decries how the web exacerbates the choice problem, but he gets excited when I mention Pinterest. “People who can afford it shop in boutiques. Pinterest strikes me as the same, except that the selectors of the merchandise are your friends. I’m not surprised it’s exploding.”

Click here to see a time lapse.

Silbermann’s path to solving the problem that has bedeviled two generations of web designers fits so neatly into Silicon Valley’s American dream machine that the story should be handed out to kids when they land at SFO to stake their fortune. Born into a family of doctors in Des Moines, Iowa–his parents run an ophthalmology practice, and both of his sisters are physicians as well–Silbermann went to a large public high school where he played cello and was a nationally competitive debater. As a high-school junior, Silbermann earned a spot at the prestigious Research Science Institute, a free academic program affiliated with MIT and the Department of Defense that is perhaps the country’s most selective summer camp. He figured he’d be a doctor as well.


Silbermann was accepted into Yale and spent the next two years taking science classes and prepping for the medical-school entrance exams. Then he changed his mind and decided that a career in business was the thing. He bought himself a leather portfolio, put together a resume, and spent his last year of college applying for consulting jobs. After graduation, he found himself at the Corporate Executive Board, a large Washington, D.C., management consultancy.

He tried to be a good consultant, but his interests started to drift again. It was the mid-2000s, the beginning of the social web boom, and Silbermann began obsessively reading tech blogs and following the startups of the day–Digg, MySpace, YouTube, and Facebook. He was especially taken by the Internet’s potential to bring people together around new interests or ideas. “So many things that I was excited about as a kid were about proximity,” he says. “The idea that somebody could grow up in rural Iowa and be into break dancing because of YouTube–that was a really simple, profound idea.”

The more he read, the more Silbermann became convinced that he was missing the story of his generation. His peers were building world-changing companies. What was he doing? “It was this burst of frustration,” says Silbermann, who recalls thinking, I just gotta get out there. Silbermann and his girlfriend quit their jobs and moved West. At the end of 2006, he landed a gig doing customer support for Google’s advertising division–a minor miracle as far as Silbermann was concerned, considering he had no technical background. He spent two years at Google before striking out on his own in 2008.


Silbermann’s first product, which he launched with a college friend, Paul Sciarra, was a shopping app called Tote. The partners managed to raise a small bit of seed funding, and Silbermann spent a year refining the app. Tote failed to take off, but it did reveal something interesting: Rather than buy things, people used Silbermann’s app to email themselves pictures of products to view later.

This struck a chord with Silbermann, who had been a collector all his life. Ask him to explain the origins of Pinterest and he’ll inevitably bring up his boyhood hobby of collecting bugs. “I really liked insects,” he says. “All kinds: flies, grasshoppers, weevils.” He’d pin them to a piece of cardboard, dry them, tag them, and put them in little shadow boxes, creating his own private museum of natural history. I suggest that this sounds like a slightly ridiculous stab at a creation myth, but Silbermann only smiles and then, by way of explanation, adds, “I grew up in the Midwest.”

In the fall of 2009, while Silbermann was still struggling to turn Tote into a business, he had a drink with Evan Sharp, a student at Columbia’s Graduate School of Architecture. They bonded over their mutual love of infographics–another one of Silbermann’s improbably nerdy interests–and then they started talking about collecting. Silbermann suggested that a digital collection–of books, clothes, or even insects–could be a powerful medium for self-expression. Silbermann abandoned Tote, and he and Sciarra began working with Sharp on the new idea.

Click here to view the infographic in more detail.

Perhaps he owes it to his Midwestern background or the fact that he was, in the words of one early investor, “a nobody” at Google, but one of Silbermann’s great strengths as an entrepreneur has been an ability to look beyond the sometimes narrow-minded world of Internet entrepreneurship. So much of the social web is built upon the assumption that people want to be creators–Facebook and Instagram make everyone a photographer; YouTube makes everyone a filmmaker; Twitter makes everyone a broadcaster. But Silbermann didn’t think regular people would always want to express themselves that way. He certainly didn’t. “Most people don’t have anything witty to say on Twitter or anything gripping to put on Facebook, but a lot of them are really interesting people,” Silbermann says. “They have awesome taste in books or furniture or design, but there was no way to share that.”

As they sketched out Pinterest, Silbermann and Sharp cast aside many then-predominant orthodoxies of web design. Facebook, Twitter, Tumblr, and many other content-driven websites were organized around “feeds,” lines of text or images that ran from top to bottom by time. The two young men wanted to create a design that allowed users to browse multiple images at once. “We were really excited about bringing something that wasn’t immediate and real time, something that wasn’t a chronological feed,” says Sharp, who is serious, bearded, and armed with a history degree from the University of Chicago and a habit of starting sentences with phrases like, “This is going to sound a little pretentious.” The idea was to remove the rigid organizational strictures that the web imposed–directories, time stamps, pagination–and replace them with a grid of images that would feel more like visiting a store or a museum.

Sharp coded much of the site sitting in a Whole Foods on the Upper West Side of Manhattan while Silbermann, Sciarra, and a single engineer worked from a dingy apartment in Palo Alto. They spent four months batting versions back and forth. “This was the first one,” Sharp says, pulling up a grid of images whose borders turn a rather garish shade of royal blue when a mouse hovers over each image. “I must have been trying to give Ben a heart attack.” Whereas most designers start with mock-ups, Sharp developed and coded 50 working versions of the site, experimenting with various column widths, layouts, and ways of presenting the pictures. “From the beginning, we were aware that if we were going to get somebody to spend all this time putting together a collection, at the very least, the collection had to be beautiful,” Silbermann says. As Sharp puts it, “The grid was everything.” His final version displayed interlocking images of a fixed width–192 pixels–and varying heights. When new images were pinned, the entire site would rearrange itself, meaning that users rarely saw the exact same home page twice.


Pinterest’s design overturned conventional wisdom in a number of other surprising ways. Silbermann rejected the idea that entrepreneurs should hack something together, open it up to the public, and tweak, iterate, and pivot. At a time when “gamification” was hot, Silbermann and Sharp declined to feature any elements that might encourage pinners to compete with one another. Pinterest offered no leader board or any other way to find the most popular pinners, and unlike Twitter, which makes a person’s follower count the focal point of the site, Silbermann did not include it on the home page.

Most web companies design their sites to generate lots of page views, which helps them show momentum to investors and, in theory, makes them more attractive to advertisers. This frequently means producing extra page views by any means necessary. A central element of Pinterest’s design, though, was the then-novel “infinite scroll,” automatically loading more images as the user expands the web-browser window horizontally or goes toward the bottom of the page. The decision meant that Pinterest would generate fewer page views than most websites, but it also meant that users spent almost no time clicking buttons or loading pages.

“The thing that appealed to me was that it was never-ending,” says Chris Culley, a Dallas-based designer who joined Pinterest in 2010. “I would sit there and scroll for an hour. I was pretty much addicted.” As were millions of others.


Pinterest’s traffic has come from demographic groups not normally associated with fast-growing websites. Nearly 80% of Pinterest’s users are women, most between the ages of 25 and 54, according to Google Double Click Ad Planner. Whereas most social services rely on early adopters on the coasts and then hope to break through to the masses, Pinterest’s growth has been driven by such unlikely cohorts as the “bloggernacle” of tech-savvy young Mormons. One of the first celebrities on Pinterest was Ann Romney, wife of Republican presidential nominee Mitt, and before the site caught fire on Silicon Valley’s tech blogs, it received a laudatory write-up in the Deseret News, the Salt Lake City newspaper. “Practice moderation in your pinning,” the article advised, “but enjoy the crafty, creative spirit of Mormonism.”

Silbermann and Sharp’s grid has since proliferated across the web. It has inspired numerous copycat sites that mimic its look and feel down to the font selections, and it has informed the design of Lady Gaga’s social network, the question-and-answer site Quora, and even Facebook, which began testing a Pinterest-like layout in July. A Mashable article last February, full of favorable quotes from designers, declared, “Pinterest Is Changing Web Design Forever.”

Click here to view the infographic in more detail.

When the site launched in March 2010, Sharp dropped out of architecture school. With Pinterest’s fortunes uncertain, he took a job at Facebook, which allowed him to move to Palo Alto and pay his rent as Silbermann raised VC funding. Sciarra, who declined to comment for this article, left Pinterest earlier this year to join Andreessen Horowitz, the venture-capital firm, as an entrepreneur in residence. Silbermann says that he and Sciarra remain friends. “Everyone finds his own path,” Silbermann continues. “I think he was interested in doing other stuff.”


With Pinterest live, Silbermann spent the next 12 months designing the character of its community. The grid itself is only as beautiful as the pictures that fill it, and Silbermann worried that Pinterest would be inundated–and rendered useless–by party pictures, porn, and all manner of Internet weirdness. (A hilarious animated short produced by dramatizes this struggle, portraying Pinterest as a Magic Kingdom-like castle whose princess denizens are put under siege by “the trolls, the memers, the Facebook bros.”)

To fend off the Facebook bros–and to prevent the site from turning into another online photo album–Silbermann prevented early users from uploading pictures directly from Facebook, and he initially limited new sign-ups stringently. Many of the early invites went to a group of design bloggers whom Silbermann recruited personally. He gave each new user a limited number of invitations, urging them only to invite others whose taste they respected. A “welcome” email congratulated new pinners on being selected to the site and added, “You must have good taste!”

In Pinterest’s early days, Silbermann gave out his cell-phone number, attended blogger meet-ups, and personally composed weekly emails that were sent out to Pinterest’s tiny, but growing, community. “It’s like you’ve built this little city with nobody inside of it yet,” he says. “And you want to fill it up with the right kinds of people who are going to teach future people what they should be doing when they move in.” Most Silicon Valley types look at early users as viral marketers; Silbermann saw them as role models. (Until recently, Pinterest’s welcome email advised users to “pin carefully” because “your pins set the tone for the community.” The site bans nudity and discourages users from posting images of too-skinny models, otherwise known as “thinspiration,” after the phenomenon became a problem.)


Silbermann’s view of design as social engineering was on display when I sat in on Pinterest’s weekly design review. “We start with what we want people to feel and what we want them to do, and there’s a design that feeds into that,” he says. The focus of the two-hour critique was the company’s forthcoming iPad app, which Silbermann believes is critical to Pinterest’s ability to change the way people discover new things. “You can use a tablet in places and at times when your mind is free to explore stuff–like having a beer or sitting on the couch,” Silbermann says. “Pinterest was made for tablets.”

The app, which I tried as a beta version in July, includes a new feature called “sheets,” which allows users to seamlessly trip through Pinterest pages in the same way one might bounce around a shopping mall. (The Summer of Apps concluded in mid-August when they went live. The iPad app was No. 1 in the App Store within a day.) With a finger flick, users can quickly cycle back and forth through pinboards, user profiles, and pages for topics like gardening or travel without ever returning to the home screen. “Most apps assume you have this navigation tree,” says Sharp, as he shows off the new app. “But that’s not the way you discover. It’s not the way you shop. It’s not the way you go through a museum. That’s our interaction model.”

For all the talk of Pinterest’s promise as a business, it is currently generating no revenue whatsoever. The fact is far from a secret. Go to its website, click on “Help,” and then click on the frequently asked question, “How does Pinterest make money?” The answer is, in short, that it does not.


In 2010, Silbermann began experimenting with a service called Skimlinks that paid it a small fee for referring customers to the websites of some retailers–roughly 6% of the sale price of every item sold as the result of a pin. Last February, he turned off that revenue stream. So far, the company has not attempted advertising sales.

This too is by design. “At a small company, so much of the trick is focus,” Silbermann explains, repeating “so much” for emphasis. “Not only can you only do a finite number of things, but you have to do them in the right order. So we actively try to remove things that take away focus from things that are really important.”

Investors seem perfectly happy to let Silbermann take his time in developing a business model. To date, Pinterest has raised $138 million from an A-list roster of investors that includes Andreessen Horowitz, ueber-angel Ron Conway, Yelp cofounder Jeremy Stoppelman, and Shana Fischer, the former head of mergers and acquisitions at Barry Diller’s IAC. In May, Pinterest raised $100 million, led by the Japanese e-commerce giant Rakuten, a funding round that valued the company at $1.5 billion. Rakuten’s founder and CEO, Hiroshi Mikitani, told The New York Times that if Pinterest had been for sale, he would have bought the whole thing.

Silbermann, left, and his cofounder and chief designer, Evan Sharp, used their status as Silicon Valley outsiders to break all the rules of social media web design. | Photo by Art Streiber

Some of Pinterest’s most popular users–and the brands that want to reach their followers–are not waiting for Silbermann to create commercial opportunities, choosing instead to create ones for themselves. For example, certain brands pay Satsuki Shibuya, a 31-year-old designer with more than a million followers, between $150 and $1,200 every time she pins an image of their product. She refused to tell me which brands she’s worked with and, because paid pins look identical to unpaid ones, it’s hard to guess. “A lot of brands are getting into the game,” she says. “It’s a smart move. They’re already putting ads in magazines and there are 10 times as many people looking at Pinterest.” Earlier this year, she said no to an advertiser because the items seemed too far removed from her personal style. “For three or four pins,” she notes, “I could have bought a car.”

I heard similar stories from other prolific pinners. “The power pinners are really wrestling with what to make of this opportunity,” says Su Wu, who works in the research communications department at the University of Southern California and, as a sideline, pins to an audience of 300,000 followers. One notable exception: Jane Wang, who has the largest follower count on the service–3.4 million–and happens to be Silbermann’s mother. “My mom does not get paid to pin things,” Silbermann says with a chuckle.

She probably gets offers, though. Greg Fant of One Kings Lane says that earlier this year, his company began experimenting with paid-for pins, offering a hundred of the top home-furnishing pinners a substantial percentage of the proceeds that their pins generate. “We’re still figuring out how best to scale the program,” he says.

So what happens when amateurs who are not Silbermann’s mother are offered fat checks from marketers? Should Pinterest try to stop it? Or take a cut?

Silbermann stares at me blankly. “We’re just trying to preserve the authenticity,” he says. “Pinterest is a young platform.”

It’s sometimes hard to tell whether Silbermann is being sincere or coy when he says things like this, but one thing is for certain: He is not callow.

Earlier this year, Silbermann hired Tim Kendall, an engineer and Stanford MBA, to serve as the company’s head of product management and partnerships. Kendall is credited with creating Facebook’s monetization strategy in 2006, and he helped Tumblr develop its recently launched advertising platform. He told me that he took the Pinterest job because Silbermann impressed him and because he saw a huge opportunity. “What’s unique about Pinterest is that as you go through these streams of content, some of that content will be purely organic and noncommercial and some of it will be commercial–and you’re not able to discern between the two,” Kendall says. “That’s pretty awesome for future business potential.”

For a sense of what he’s talking about, look no further than Pinterest’s competitors, which are already moving their companies aggressively in this direction. Earlier this year, Joseph Einhorn, CEO and founder of Fancy, Pinterest’s New York-based rival, began selling products and travel bookings directly on its site, while offering users who share for-sale items a 2% affiliate fee if a post results in a sale. “We looked at Amazon and saw a $100 billion company that has never changed and has no competition,” Einhorn says. As of June, Fancy, which has just 213,000 monthly U.S. visitors, according to comScore, was already booking $10,000 a day in sales. A crude back-of-the-envelope comparison of user bases suggests that Pinterest, which boasts 100 times Fancy’s traffic, could be earning nearly $1 million a day just by following the same approach.

But as Kendall himself suggests, selling products might be just the beginning for Pinterest. Jess Lee, CEO of the fashion-focused Pinterest rival Polyvore, says, “E-commerce 1.0 was driven by digital cameras, electronics, hard goods–things with technical specs that you can plot on a chart. But why does someone pay $25,000 for an Hermes handbag? It’s not rational. It’s based on taste; it’s totally amorphous and not trackable. That’s e-commerce 2.0.” Polyvore, which is profitable and attracts 5 million users a month in the United States, makes about half of its revenue from taking a cut of what its users discover on its site and end up buying elsewhere.

The other half of Polyvore’s revenue, though, comes from magazine-style advertising campaigns by the likes of Nordstrom and Mercedes. “I want the entire sales funnel,” she says, meaning both the ad revenue that creates the desire and the sales that fulfill it.

A clue that Pinterest might be aiming for this approach: the investment by Rakuten, a $5 billion online retailer. “We share a vision with Pinterest,” says Mikitani, Rakuten’s CEO. “Our theme is that shopping is entertainment. If everybody bought everything on Amazon, it would be a dystopia.”

Pinterest could continue to refine the way it encourages the discovery of new products–incorporating splashy (and expensive) ads–and it could sell goods on pinboards on behalf of retailers. Or it could turn itself into a giant affiliate marketer, albeit one that charges a lot more than 6% of each sale. Whereas electronics, the bread and butter of most e-commerce sites, has painfully narrow margins, the categories that dominate Pinterest, like apparel and home furnishings, can have initial margins of 50% or more. “Look at the content on the site,” an early investor told me. “It’s all stuff with a high price tag. They’re all massive categories and they’re offline categories.”

I try some of these theories out on Silbermann, who demurs, obfuscates, cracks wise, and generally prattles on about the need to focus on his product. Finally, perhaps out of frustration, I suggest that perhaps he hasn’t yet figured out how his beloved grid will actually make money.

Silbermann smiles, looks me in the eye, and–suddenly the perfect Midwesterner–ever so politely tells me to stuff it: “We have a pretty good sense.”

A version of this article appears in the October 2012 issue of Fast Company.