Pinterest Founder Ben Silbermann’s Lessons on Decision Making, Values, and Taking Time for Yourself

Village Global Team
Apr 3, 2018 · 7 min read

Ben Silbermann is co-founder and CEO of Pinterest, one of the world’s most successful consumer internet companies.

Ben is also a Village Global luminary — a group of tech industry founders and executives who are backing the next generation of amazing entrepreneurs.

At a dinner recently with a small group of Village Global’s Network Leaders, Ben shared stories and lessons from the Pinterest journey. Below are some of our favorite nuggets.

Focus on the “who” more than “what” when solving complicated problems

When reflecting on what he wish he’d known at the outset when founding Pinterest, Ben emphasized the inadequacy of a habit he learned as a product manager. When you’re a CEO, you gotta think people-first:

I’m a product person so I’m always like, “Oh, you know, we’re going to solve this on the whiteboard.” But if the problem is of any complexity, you’re not going to solve it yourself. Who is going to solve that problem? And then how will you know whether they succeeded?

Starting out, I think I would’ve told myself to focus on the who as much as the what in every decision. I think if you put the right person in the right job at the right time, you’re almost halfway there. I wish that I would’ve learned earlier how fundamental this is.

Be you. Don’t blindly emulate Apple or Google (or whomever your hero companies happen to be.)

There’s serious hero worship in Silicon Valley. Be like Zuck. Be like Page. Be like Jobs. Ben spoke against this sort of thinking. Be the best version of yourself.

For a long time we had this complex where I thought I really need to make [Pinterest] as much like the iconic companies as possible. And I was always trying to force fit all of these things that actually are amazing for other companies. I think I would’ve earlier celebrated the things that made our company weird because those ended up actually being the things that make it special and successful versus just trying to like make everything slowly look more and more like kind of my company heroes.

Make better decisions by remembering these four tips

Ben shared several tips on one of the most important topics in business: decision making.

  1. Consider how this decision will set a precedent

I think a perspective to adopt, without being too inflexible, is, “What if this decision is a precedent? If this decision becomes the new baseline, what would you do in the next situation?” It’s good to think, “If I joined the company tomorrow and heard about this decision and it was stripped of all context, what would it symbolize?”

2. Think about the consequences of a decision beyond the immediate person obviously affected

For a while I would make decisions and I’d think, “It affects this person so I’m going to communicate it to that person.” Instead I should have been thinking: “Who are the two rings of people around the person? And what is the context that they need to understand that rationale?”

3. Write down decisions you make — and your rationale at the time — into a “decision journal.”

Next time you hire someone, cut a partnership deal, decide on a key product spec — or make any hard decision — write down your reasoning in a journal. Later, you can see how the decision played out relative to your reasoning at the time you made the decision. You can learn whether you should have trusted your gut at the time or not.

Ben has been doing this for awhile and swears by the technique:

I feel like if you don’t write down a decision you made and why, there’s so many things going on that it’s very hard to remember exactly what you were thinking at the time, because you have this kind of running dialogue that’s being updated along the way. So that’s been really helpful for me.

4. Act quickly. A timely decision can be a good decision.

There does need to be a time constraint on decisions. It’s something I have to remind my team: sometimes a good decision is a timely decision.

Avoid the “tyranny of the articulate”

In many engineer-driven startups, world-class debaters end up making many of the decisions. Ben talked about why this is problematic:

There’s this tyranny of the articulate that happens at companies…But there’s only a loose correlation between how good people are at communicating and how good they are at actually building stuff.

I personally think debating is a horrible way to get to any solutions. There’s this idea that vigorous debate yields results, but in my experience, vigorous debate yields people who vigorously defend what they think. As a result, they’re unwilling to compromise at some point because it’s a debate and the objective is to win.

When it is necessary to have a debate, Ben offered this important reminder:

Most debates never get anywhere because there’s no clearly agreed upon goal. So scope what the actual problem is; articulate the goal.

Clarify your unique company values

Pinterest is known in the Valley for being incredibly values-driven. Ben shared with the group how he and his co-founder set and reinforced the company’s core values and how important that was given the challenging road it’s been to get here:

Our culture is extremely aligned with the mission of the company and the product. Evan and I built the product because we wanted to build a product that helped people discover and do their passions. And because the company was not on an amazing trajectory early on, the people that selected in to joining Pinterest really believed in that. They weren’t getting paid, there wasn’t an office. Bring your own computer! So obviously they were bought into the mission.

We ended up articulating a set of values. One value is called Knit and it’s really about the value of collaboration. It’s this belief that if you get highly divergent perspectives you’ll yield a better answer. And that started because at the time it was very unusual to have a design founder. We were recruiting a lot of top flight designers and they just have a fundamentally different problem solving tool kit. It’s about balancing a set of variables versus deductively chopping them off.

The second value is a very simple one, it’s: Put Pinners First. It forces a conversation that’s extremely sharp on whether something actually pushes forward the emotional value proposition or the functional value proposition of the company.

There’s a third value, it’s just: Be authentic. It’s the counterbalance on getting a lot of pretty nice people. It gives people permission to be pretty direct about things and it’s an aspirational value. I think it’s one that we’re always working on.

There’s the last value which is really a reminder of time bound decisions. It’s called: Go. It keeps us very aware of when it’s time to analyze and when to go, because I think that gets confused at companies all the time. People are getting very marginal increases in certainty at the price of speed.

Track your health. You’ll burn out because of social isolation and poor health before you run out of money

Good founders track their cash flow burn obsessively. Running out of money is a very real risk for early stage founders. Ben pointed out that running out of health is as important a risk to track:

Working all the time at the expense of your health and then cutting off all of your friends and family is probably not a good strategy because if you’re actually going to go after something for a long time as an entrepreneur, having your health and your relationships in tact turns out to be really important. And a lot of the folks who have burned out did so not because they ran out of money. They burnt out because they became socially isolated and really unhealthy.

Direct your board members with specific requests for help

Many founders only contact their board members when there’s a problem. Or when their corporate legal charter demands it. This creates a funky expectation in the minds of board members — i.e. “Oh, that CEO is calling me, there must be a problem or paperwork to sign.”

Ben pointed out that boards can be helpful on actual strategic challenges. You can use them proactively. But they need to be directed:

I think a lot of boards really want to help, but they’re afraid to overstep. Now I’ll just be like, “I need to hire these three people — you need to help me.” Or, “I have this hard decision, who can you connect me with to help on those?” And the more prescriptive, the better the feedback and actually the better the board feels. When boards want to be helpful, but they don’t know how, bad things happen.

Take time for yourself to think about your future.

Pinterest is not really a social network, Ben said. There’s a very real single-user use case — one person can assemble boards and pin photos and keep it all to themselves, no sharing expected. This solitary use case is something Ben believes is important for people:

I think that solitary time to think about your future, your dreams, your aspirations is really important for people and I think that it’s been crowded out by pervasive high quality entertainment. People actually need this as part of their basic identity.

It’s also a very vulnerable thing to do, to think about, “What do I want to be in the future? What is my dream? What does my dream home look like?” The internet hasn’t really been that thoughtful about creating environments to let you explore other dimensions for yourself. I think it’s really important. And I think if you could actually help people with that, it would play a really positive role in their life.

To stay in the loop on the entrepreneurial lessons that emerge from future Village Global events, sign up for our occasional email newsletter here.

Welcome to a place where words matter. On Medium, smart voices and original ideas take center stage - with no ads in sight. Watch
Follow all the topics you care about, and we’ll deliver the best stories for you to your homepage and inbox. Explore
Get unlimited access to the best stories on Medium — and support writers while you’re at it. Just $5/month. Upgrade

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store