- Ali Rougani from Y Combinator interviews Ben Silberman, the co-founder and CEO of Pinterest
- Ben grew up in Iowa and initially thought he would become a doctor
- He developed a love for the internet during college and became excited about the potential of technology
- Ben started experimenting with different projects while working at a consulting firm in Washington, D.C.
- He eventually left his job at Google to pursue his own ideas and started building various products, including an app called Tote
- Ben faced challenges in raising money for Tote during the 2008 economic collapse but eventually secured funding through a college business plan competition
- With the funding, Ben hired engineers and began developing the Tote app, but faced delays in getting it approved for release
- Ben then met Evan, and together they had the idea for a tool to collect things online, which eventually became Pinterest.

- The founders of Pinterest initially created a toy called Tote, which later evolved into Pinterest.
- The motivation behind creating Pinterest was to build a tool for collecting things online that they themselves would find useful.
- Initially, Pinterest had slow growth and struggled to find users, but they found a small group of people who enjoyed the service.
- The founders actively sought out users by attending conferences and targeting bloggers who were interested in the product.
- They learned the importance of taking care of users and gathering feedback to improve the service.
- As Pinterest grew, they built a research team to better understand users and their needs.
- There was no specific moment when they realized Pinterest could be big, but when seeking funding, they were forced to consider the potential scale of the company.
- The early days of Pinterest were financed through small fundraisings and the team was kept small to minimize expenses.
- The goal of fundraising is to obtain the necessary resources, not just to raise money.
- When attracting people to the startup, the founders focused on offering an adventure rather than a guarantee of success.

- The founders of Pinterest used their apartment as a way to recruit people by throwing barbecues and attracting like-minded individuals who were builders at their core.
- The company's ambition has grown since its early days, with the goal of creating a personalized catalog of ideas that helps users discover what is right for themselves.
- The founder reflects on moments of discouragement and the importance of learning from mistakes and taking risks.
- Mentors have played a significant role in the founder's journey, offering support and guidance.
- As the company has grown, the founder's role has shifted to creating and managing an organization and communicating effectively.
- The founder is still involved in product decisions, but focuses on asking the right questions and unifying the product vision.
- The culture of the company is based on values such as being obsessed with users and having a passion for building things.

- The speaker emphasizes the importance of prioritizing the users of their service
- They believe that diversity in skills and backgrounds leads to a better product
- They value engineering, design, writing, and marketing
- They actively seek to hire people with different backgrounds, including women, underrepresented minorities, and those from outside the United States
- The goal is to bring together diverse ideas to create a unified product
- The speaker is grateful for the opportunity to discuss Pinterest and its future.

- Ben Silberman, co-founder and CEO of Pinterest, started his career in Iowa with the intention of becoming a doctor but developed a passion for technology during college.
- He faced challenges in raising funds for his app Tote during the 2008 economic collapse but eventually secured funding through a college business plan competition.
- Ben and his co-founder, Evan, came up with the idea for Pinterest while working on their initial app, Tote.
- Pinterest initially struggled to find users but actively sought them out by attending conferences and targeting interested bloggers.
- The company's ambition is to create a personalized catalog of ideas to help users discover what is right for them.
- The founder emphasizes the importance of learning from mistakes, taking risks, and having mentors for support.
- The company values diversity in skills and backgrounds and actively seeks to hire people with different perspectives.
- The founder is still involved in product decisions but focuses on asking the right questions and unifying the product vision.
- The culture of the company is based on values such as being obsessed with users and having a passion for building things.

It's called the Accommodator Continuity Fund.

And I couldn't be happier to be here today to conduct a fireside chat with Ben Silberman, who, as you guys all probably know, is the co-founder and CEO of Pinterest.

Ben has a fascinating background and a set of diverse experiences with entrepreneurship.

So we're thrilled to have him here and I want to welcome him here today.

A lot of people and it's very bright light.

Ben, let me just start first by asking you to tell us a little bit about Ben before Pinterest.

Sort of what you were interested in growing up and through college and what you graduated college and then went and did and how that kind of all led to today.

And a lot of the time when I grew up, I thought I was going to be a doctor.

Both my parents are doctors, both my sisters are doctors, and so it didn't even feel like really a choice.

But as a kid, I loved all kinds of things.

And then when I went to school, I went to Yale and I was pre-med, but I didn't really have a specific plan other than maybe I should be a doctor.

And then somewhere along that line, I thought, geez, I don't know if medicine is for me.

And I feel like medicine's 1 of those professions where if you think that, you actually know that.

And so I just, you know, I started taking other classes.

I ended up getting a major in political science.

But the other thing that happened was, you know, college was the first time that I had, like, my own laptop with high-speed Internet, which makes me sound super old, but Things change fast.

But I remember actually that being a really transformative experience, just being able to get on, get access to all kinds of information.

And I just became, this sounds really corny, I just kind of fell in love with the Internet.

I loved the idea that everyone could access the same information no matter where you were in the world.

And I would always play these kind of what if games.

Like whenever I saw a problem, I'm like, what if the internet could help solve this problem?

And so I think that's how I really got excited about technology.

So you didn't drop out, you got your degree, you graduated, and then you didn't start a company right away, is that right?

No, I decided not to be a doctor, my parents were like, okay, better figure out something to do to make money.

And I took that job mainly because they offered it to me.

And then along the way, I was kind of working with friends and building these toys on the Internet.

And I say toys because they weren't really intended to be these serious businesses or anything.

I was just really curious about what we could do.

So I remember 1 of the first things that I had started making in college, it was a tool that let you try on glasses online.

Because my parents, I spent a lot of time, they're ophthalmologists, and they had an optical shop attached.

And people were there because they couldn't see.

And so I would watch all these people go in and try on these blanks of glasses and then they'd try to look in the mirror but they couldn't see.

And so then they'd ask like, how do these look?

And I was thinking, oh, you know, maybe we could build software to help people see that.

So instead of having like 12 pairs of glasses that were available, you could have the whole access.

So that was an example of 1 of these toys.

I worked with a friend of mine named Altai, and we made a tool to help his band promote themselves all over the country.

This is all on the side, while you had a day job.

And so, yeah, that's how I kind of got started, more playing with things than just sort of focusing on building a serious company.

Now you're clearly creative, you clearly had a sense of like the internet could be something interesting to solve various problems, But you weren't technical.

So how did you overcome that in the early days, in terms of actually being able to create the things you wanted to create?

Yeah, well, I would always start off thinking about an idea.

And I had some friends that were technical.

And then none of us were super technical.

So we'd always just chip in and learn what we needed to do to get the next part.

So learning about things like product design, you know, I would do like simple like front-end coding and just, you end up learning like little bits at a time.

And for me at least, it's a lot easier to learn things when there's something that you want to build than doing it in a very abstract classroom way.

When did you, or how did you decide, okay, I'm going to now leave my job and jump and commit fully to starting a company?

When I was in DC, I was always reading these blogs.

I remember typing in TechCrunch, I was like, whoa, something is going on on the internet.

And I just really wanted to be part of it.

So I didn't feel like I could start a company, but I thought maybe a good half step would be to try to work at a company that I really respected.

And so I really wanted to work at Google.

So I moved out to California, and I got a job at Google.

And the only job I was qualified for at the time was online sales and operations, which is kind of like customer support.

And I worked there for about a year and a half.

And all the while, I'm like, oh, trying these little projects on the side.

And it was actually my girlfriend at the time, who's now my wife.

She was the 1 that kind of gave me the kick in the pants.

I was like, oh, wouldn't it be cool, I should build this.

And she's like, you know, Ben, maybe you should either do it or stop talking about it.

That turned out to be really good advice.

What was the first thing you tried to build?

Well, immediately when I left, I hooked up with some friends of mine, and I was still interested in medicine.

I had this latent interest in medicine, so we wanted to build a tool that would help people gather your medical records across your family.

You could kind of build a family tree and everyone could update it.

And I started it with these friends that were kind of on a break period before they got their PhD.

But in a few months, then they got their PhD and they're like, hey, you know, we have PhDs.

And then, you know, I was kind of like in the void.

Yeah, like 1 guy went on to become an extraordinarily successful researcher out at MIT, another guy went to medical school.

It was just like, just not doing that much.

But I hooked up with a friend of mine from college, and at that time, the iPhone had just recently come out.

And actually, I remember so vividly watching that keynote on this laptop and being like, holy cow, this thing's gonna change everything, I hooked up with a friend to build products for the iPhone, and 1 of those products, our idea was like, why don't we take all those catalogs in your mailbox and put them on the phone?

Because catalogs suck and phones are great, but people still want to shop.

And that was our first idea that we really formed into that company.

And we knew that to build that, we would have to raise a little bit of money.

And we set out to raise money on that premise.

And that was, was that the first time you'd raised money for Tote?

It was the first time that I'd been in charge of raising the money and done it really formally and it was a total shit show, to be honest.

You know, the other part of this was, this is 2008, so the economy is just like collapsed.

And we would just like go to these meetings and these folks would just be like, why are you even here?

I'm like, I don't know, you took the meeting.

And so we went through the full West Coast investors, we went to the East Coast.

Struck out on the West Coast, and not for lack of effort.

I think that everyone who could have gotten called got a call.

We would cold call people out of alumni directories, like whether we went to the school or not.

We were like, this looks like a wealthy individual.

And we ended up doing something quite desperate, which is I ended up finding all the college business plan competitions that had loosely written rules about attendance in that school.

And I entered 1, and we got second place, and the prize for second place was a meeting with a venture capitalist who was an alumni of the school, and they were able to give us our first couple hundred thousand dollars, which to me felt like all the money in the world.

I was, like, looking at the bank account.

We paid The awesome engineers that were helping us out.

But at the time, iPhone development was really slow.

And not only was it slow to develop, it was also slow to get approved.

And so even after we had built this app and we were ready, I thought it was going to be like in the movie, like you push, like, release, and then, like, all these people use your thing.

And so at the same time, you know, I had met another friend in New York named Evan, and we had this other idea that was, again, it was kind of like 1 of these toys.

You know, looking back, there were elements of all these other projects we'd worked on, but it was this toy, and the toy was like, you know, what if there was a tool to let you collect things online?

You know, It had some of these elements of this catalog on the phone.

It had some things that I just loved as a kid.

I was a big collector as a kid, and Evan was too.

And ironically, that toy is what would later become the whole company.

So Tote then sort of morphed into Pinterest.

Yeah, I mean, I think morphed is a generous word.

It was getting done, and we thought it was really cool.

And so we thought, hey, let's put this thing out into the world.

And that was sort of how the switchover happened.

So when you reflect back and think about the early days of Pinterest, what was the problem that you're trying to solve out there?

Was it something you're building at the time for a narrow group of people or for everyone?

And what was the thing that you were trying to solve?

Well, I'm gonna sound like kind of the worst business person, but we just thought it would be cool for ourselves at first.

He was studying in architecture school in Columbia, like buildings, not computers.

And we thought, gosh, if you had this tool to collect things for yourself, that would be really useful.

And not only that, you know, those collections could kind of give you a window into how other people saw the world.

And we just thought that would be a really fun product that people might be interested in.

And so I think what initially motivated us in that early team was we really enjoyed using the product for ourselves.

And when we released it, it actually was not a runaway success.

It grew really, really slowly, but part of what kept us going is we thought it was a really cool product that we enjoyed, and we thought, well, maybe there are people like us that would also enjoy it.

Like, how did you, you know, you've talked a little bit about like, trying to market it and being scrappy about that.

Yeah, so we released it and you know, I did probably what everyone does.

Like the first thing you do is you email all your friends and you kind of hope that it's gonna, and no 1 really got it, to be totally honest with you.

Neither the people on the East Coast that Evan knew, nor the people on the West Coast, they just didn't really get it, and they were really polite.

They were like, oh, it looks interesting.

But there was a small group of people that were enjoying it.

And those folks were not who I think stereotypically you think about early adopters.

They were folks that I grew up with, people that were using it for regular stuff in their life.

You know, what was my house going to look like?

You know, what kind of food do I want to eat?

And we really thought, where are those people congregating?

And I ended up going to a conference where a lot of the blogs that people were reading about those things, a lot of those bloggers gathered, and I met these bloggers, and they seemed like the kind of people that would really enjoy it.

So we organized a marketing event with those bloggers, where we had each of them introduce the service to their audience.

Jonathan Levy This is like a few hundred.

But in between, we did all kinds of, honestly, pretty desperate things.

I used to walk home, and I was in Palo Alto, and I'd walk by the Apple store.

And I would stand in the Apple store and just like change all the computers to say Pinterest.

And then like kind of stand in the back and be like, wow, this Pinterest thing.

And but you know, slowly we started to get folks who really loved the service.

And then since it took us so long to get those users, we cared about them so much.

I used to have my cell phone on all the customer support emails.

I would take customer support calls all the time.

So when the service would go down, I had this problem where everyone would start calling me, be like, hey, I can't get my pins, you know.

And I don't know, I think that for me there were these 2 lessons.

In 1 it's that there's a stereotype of where early adopters come from and they should be these technology forward folks.

I just think that that idea is really outdated now.

I think that so many people have these amazing computers in their pockets, So many people have data that early adopters are coming from everywhere, and it could be taxi cab drivers in India, or Midwestern folks who are planning their home.

And I think if we had been really dogmatic about wanting kind of cool Silicon Valley people to like it, we probably wouldn't have made the service that we made.

I mean, I think there was a lesson in really taking care of users.

And so all the time, I would sit in coffee shops and ask people to try the service and just try to watch them and see what they were doing to see where we could smooth out the edges and improve the service.

And what did you, would you ask for user ideas and user feedback, and would that inform what you were building?

Or was it more the case that you would observe and continue to build something that felt good for you?

You know, 1 thing is that what people say they want and what people mean can sometimes be different.

So a really common thing that I would ask people sitting in a coffee shop, I'd be like, hey, Why don't you try to create a board or try to pin something?

And then I would ask them to do it, or I'd ask them to look at a button and push it.

And right before, I'd say, what do you expect to see on the other side of that?

And then right after, I'd be like, is that what you saw?

And if it was different, I'd be like, we should fix that up.

And so I do think that listening to the people that use the service is incredibly important, but you have to use judgment to decide, you know, what parts of the product you really want to invest in.

I mean, Pinterest now has millions and millions of users.

How do you still carry that forward in terms of caring for users and you personally kind of observing or getting feedback from them?

Yeah, I mean, when we started growing and we realized there were users that we couldn't fully understand in a first-person perspective, because maybe they were in a different country or they were on a different infrastructure, we started to build out a research team.

And today we have researchers that go around the world and bring people into the office to do that kind of work.

But after you have all that, there's still these pieces where you have to use your judgment you take all these signals and you put something out and sometimes it works sometimes it doesn't and you have to go go figure that out

right so from those early days how long did it take before you thought you were on to something that could be really, really big, that you'd built something that could be useful for lots and lots of people?

You know, what's funny is like, I don't think there was this 1 moment, like, we were growing every month.

And I think it wasn't until we went out to go raise some more money, because we felt like things were going well, we want to use money as a tool to grow the business, that we were first forced to say, how big do we think this can be?

And I remember feeling kind of this dual feeling.

1 is like my nature isn't to be like, this thing is gonna be really grand.

But I remember talking to an investor who became a mentor of mine, he said, you know, why not?

And if you thought about it that way, how would it change?

You know, today when I talk to the company, I say, we want to build the world's catalog of ideas, the tool that everyone uses to discover things in their everyday life.

And in a weird way, sort of raising the bar on what the company can be ends up attracting people who are more ambitious and are more creative in solving big problems.

So, between the time of kind of launching Pinterest, you're working on TOW, you decided that's not getting much traction, let's launch Pinterest, something that feels great to us.

Did you, between that time of sort of launching Pinterest and growing it as you mentioned, and getting to your series A, did you have multiple small kind of fundraisings, or how did you finance the company?

We did a little bit more money from some of the angel investors, But we also were not spending very much money.

It was in a two-bedroom apartment where 1 of the rooms was rented to a guy who didn't work at the company.

And I think that's because we'd been without money for so long, and we just didn't really know.

We didn't really know how long it would take.

So everything was kind of through that lens of how do we make sure that we just have what we can to keep going.

And for us, I don't think fundraising has ever been a goal.

It's just this tool that you use to get to the next step.

And actually, I think a problem that's happened sometimes recently is people confuse money, the tool, with the goal of the company.

And the goal is not to raise a bunch of money, the goal is to get the resources you need, whether they're talented people or whether they're users or whether they're pieces of technology, to then achieve and build the product and service that you want.

1 of the things that you've said, or you've been quoted as saying, is that when you're trying to attract people to your startup, great people to your startup, people are attracted, they don't want a guarantee of success necessarily, they want a guarantee of an adventure.

And that was a sort of approach you took in recruiting people in.

Yeah, you know, really early on, I didn't have a network of engineers in Silicon Valley, so we did all kinds of things, similar to marketing.

The first engineer, 1 of the first ones we hired, I put an ad on Craigslist and he replied.

And then as we started to get a little bit of momentum, we would try to just use the assets we had.

And what we had was this shitty apartment on California Avenue with a patio.

And we were like, our asset is going to be this apartment, because if people see it, they're definitely going to know that we haven't made it yet.

But if we throw barbecues there, they're going to know we're cool people.

I mean, so we would throw these barbecues every Friday, and it was like, bring your own food, and then we would bring beer.

And actually we recruited a lot of people there and I think that the people that we loved recruiting kind of intuitively you kind of recruit people that are a little bit like yourself.

When you get bigger you want to recruit people that are very different from yourself.

But I loved people that at their core they were builders.

They wanted to be known for what they built, not what they said.

They tended to be curious about a ton of different things, but then deep in something.

And so, you know, our first engineers, you know, 1 of the guys, in his first interview, I'm like, what have you built?

He built, like, magic tricks for his kids.

See all Y Combinator transcripts on Youtube

Ben Silbermann at Startup School SV 2016