Ben Silbermann and the things we keep

A boy in Des Moines collects dried insects and pins them to cardboard. Years later, a founder watches people use his shopping app to save pictures of products instead of buying them. Ben Silbermann has encountered the same impulse twice: the pleasure of choosing something, keeping it, and putting it beside something else. A collection begins with an object. Given time, it becomes a description of its owner.

That is a useful place to begin with Pinterest. The company launched its desktop product in March 2010, with Silbermann, Paul Sciarra and Evan Sharp as its co-founders. It offered an online space for a familiar activity: gathering things you liked. The proposition was simple enough to sound small. Its difficulty lay in making the gathering feel worthwhile, then persuading people to try it.

Three months after launch, Pinterest had about 3,000 users. There were people who loved it, including Silbermann himself. There were also friends who responded with the gentle enthusiasm usually reserved for a colleague’s experimental haircut. He had made something he wanted to exist. The public had yet to agree on how urgently it needed to exist.

The story that follows is full of unglamorous actions: answering support calls, visiting boutiques, watching people use a screen. It also contains an Apple Store stunt, a carefully considered grid, a public listing and uncomfortable questions about the company behind the pictures. The cardboard collection explains an idea. It cannot, by itself, explain everything that happened once that idea became an institution.

An Iowa collection, a westward detour

Silbermann grew up in Des Moines and attended Roosevelt High School. He graduated from Yale in 2003 with a degree in political science. His eventual business was built around pictures, but his formal training supplied neither a design credential nor a computer science degree. The route into technology took him through a consulting job in Washington, D.C., before he moved west.

Google employed him from 2006 to 2008. He worked in advertising customer support, close enough to the internet business to see it operating, without being one of the engineers creating its products. There is something appealingly literal about that position. A person interested in how people use the internet spent his working time hearing from people who needed help using it.

Leaving Google in 2008 brought him into partnership with Sciarra, a Yale contemporary. Their early shopping application, Tote, struggled to gain traction. Yet the people who did use it were doing something interesting: saving images of products for later. The intended transaction was a purchase. The activity they were choosing was collecting. A disappointing business could still contain a promising observation.

Evan Sharp brought another set of skills to the developing idea. He was studying architecture at Columbia when he met Silbermann in 2009; they shared an interest in infographics. Sharp’s design and coding work helped turn the collection into something people could see at a glance. The partnership mattered because an appealing premise still needed an interface. A digital cupboard is only useful if you can find what you put inside.

The customer who never bought anything

A shopping app gives its maker an obvious question to ask: what did someone buy? Tote’s saving behavior suggested a question further upstream: what did someone want to remember? That difference allowed Pinterest to accommodate a much wider range of intentions. You could assemble a room before furnishing it, gather recipes before cooking, or collect the ingredients of a project whose shape was still uncertain.

In 2013, Silbermann described collecting as a way to reveal who you are. That belief gave the service a reason to exist beyond moving images around a screen. A saved object was evidence of taste. A board made those individual choices legible together. The user could express something without having to write a clever introduction to themselves.

The visual arrangement was part of the product’s argument. Pictures of differing heights sat together in columns; a collection could be browsed rather than read from beginning to end. Beauty gave users a reason to return to their own work. Someone taking the trouble to arrange ideas deserved a result that looked considered. Even a board devoted to shelves needed somewhere respectable to live.

This makes Silbermann’s childhood collecting more than a charming anecdote. Keeping an insect involves attention to the individual specimen and to the collection it joins. Pinterest translated that relationship into an everyday digital habit. The analogy has limits, of course. A pinned recipe can become dinner. An insect collection is less accommodating on that front.

“Collecting tells a lot about who you are as a person.”

Ben Silbermann / 2013

Three thousand people, and a shop full of Macs

Faced with slow growth, Silbermann looked for more people like the users who already enjoyed Pinterest. The early community included people he had grown up with, using it for their homes and their meals. Bloggers and local boutiques offered places to reach them. The “Pin It Forward” campaign spread invitations through bloggers introducing the service to their audiences.

That was a different map of adoption from the one a founder might draw around technology conferences and venture capital offices. A person planning a living room could be an early adopter. So could someone following a favorite craft blog. Their interest in the task counted for more than their interest in startups. Pinterest had to meet those people where their attention already was.

Some efforts were rather less formal. Silbermann recalled stopping at an Apple Store, bringing up Pinterest on the computers, then hanging around to suggest that it was catching on. The stage was a retail showroom; the promotional budget was largely nerve. Years later, he told the story with an awareness of how desperate it sounded. It is reassuring that a company’s origin can include such thoroughly amateur theater.

He also made himself available to users and watched them try the product in coffee shops. Support calls gave him immediate access to complaints, particularly when the service went down. This was a demanding way to learn. A founder’s affection for a product is abstract until someone rings to say their carefully saved pictures have disappeared.

The practical lesson is narrower than the usual instruction to persevere. Pinterest had an identifiable group enjoying a specific activity. Silbermann kept looking for that group’s neighbors. Persistence had something to investigate: a pattern of use, a community, a reason to return. Without those details, patience is difficult to distinguish from waiting.

Teaching a search engine to browse

As Pinterest grew, Silbermann kept returning to discovery. Search works particularly well when you can name what you want. Collecting is useful earlier, while you are working out what to want. His ambition for a personalized catalog placed Pinterest in that unsettled interval between an inclination and a decision.

In 2014, Guided Search added suggestions that could help people move from a broad query toward related ideas. A search for a scooter could lead through vintage styles and helmets. Each step made the next choice easier to describe. The product gave a wandering thought some handrails, without requiring the user to know the destination at the start.

Lens, introduced in 2017, extended that idea through the phone’s camera. The company was developing image recognition technology underneath a service often associated with decorating and wedding planning. A picture could become a way into search. For Silbermann, the connection was consistent: make it easier to discover an idea, then help someone do something with it.

Commercial possibilities were present throughout. Rooms contain furniture; recipes contain ingredients; inspiration can end in a purchase. A catalog of things people hope to use has a plausible advertising business inside it. The editorial question is how comfortably those interests sit together. A recommendation has to serve the person collecting it, even when someone else pays to put it in view.

Pinterest began trading on the New York Stock Exchange in April 2019 under the ticker PINS. Its IPO raised more than $1.4 billion. The small collection service had become a public company, with investors expecting financial results as well as an attractive product. There are many things one can arrange beautifully on a board. Quarterly expectations are less cooperative.

The people behind the pleasant pictures

During Silbermann’s CEO tenure, the workplace came under scrutiny. Former employees Ifeoma Ozoma and Aerica Shimizu Banks alleged racial and gender discrimination. Former chief operating officer Françoise Brougher brought a lawsuit alleging gender discrimination and retaliation. These complaints challenged the comfortable picture of a company whose public product revolved around inspiration.

In December 2020, Pinterest announced a settlement of Brougher’s case: $20 million for her and her attorneys, plus a $2.5 million commitment to advancing women and underrepresented communities in technology. The company did not admit liability. A settlement does not resolve every disputed account, but the complaints belong in the history of the business Silbermann led.

They also complicate the appealing early image of a founder taking every customer’s call. Direct attention can work in a small community. A large workplace needs fair processes, clear responsibilities and ways to raise concerns that survive distance from the founder. The qualities that help a product find its first audience do not automatically settle the questions of power inside its maker.

Silbermann’s story is more useful with that tension left visible. Taking care over a screen is one kind of responsibility. Taking care over an organization is another, involving people whose experience may differ sharply from the founder’s intentions. The two demands grow together as a company gains influence.

A founder makes room

In June 2022, Silbermann handed the CEO role to Bill Ready, moving into the newly created position of executive chairman. His note to employees described a yearly habit of writing down ideas and aspirations for Pinterest. This time, thinking about the company’s future led to a decision about his own place in it.

He wanted to spend time with users, support new products and advise on long-term strategy. The description reached back toward the early work that had interested him: learning what people wanted to make and helping shape the tool. Ready’s background in commerce also suited a business with a growing need to connect inspiration and shopping.

In August 2023, Silbermann became non-executive chair. Pinterest’s 2026 proxy continues to list him in that role. The distinction matters: the founder remains involved in board leadership, while the chief executive runs the company. His biography now includes the act of transferring responsibility, alongside the act of starting something.

Return to the original collection and the idea still feels recognizable. People save things because they might become useful, because they please them, or because they hint at a life they want to try. Silbermann helped build a place for that ordinary, unfinished business. A board leaves room for the next addition. So, eventually, must its founder.