Lessons from Ben Silbermann, Founder of Pinterest

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. Here’s a writeup of some of my favorite nuggets that Ben shared. And below is a video with some of the highlights…

 

The School of Life Conference

I’ve been following Alain de Botton and his wonderful School of Life content for years. When I saw that they were hosting one of their weekend conferences in San Francisco, I signed up immediately.

The conference — best described as philosophical self-help programming focused on emotional intelligence — took place over Friday afternoon, Saturday, and Sunday morning. It was mostly Alain de Botton himself lecturing charismatically from on stage, interspersed with short video clips, pair-up exercises with someone sitting near you, and line-up-at-the-mic exercises where one person in the audience spoke to the full of audience of 500.

The pervasive word of the weekend was pessimism. None of us is normal. A degree of loneliness is the norm. No one can fully understand anyone else. So walk through life, Alain said, with a kind of “cheerful despair.” Of all the topics covered, from self-knowledge to meaning, from work to sex, the topic that received the most airtime was romance and relationships. Love is the source of our deepest happiness and our deepest despair. Pessimism pervaded all discussion of romance at the event.

There’s an obvious alignment between Buddhism and the School of Life. Life is suffering. Life is unsatisfactoriness. The inevitability of death was remarked upon as frequently at this conference as at a Buddhist meditation retreat.

For the most part, I was in violent agreement with the ideas Alain laid out, and utterly captivated by the breadth of topics explored. Where I part ways intellectually, I think, is the School of Life’s intensive focus on psychotherapy, particularly as understood by childhood experiences. Many of the frames they use involve analyzing your parents. Childhood experiences matter, of course, though I’d submit not as much as psychoanalysts would have you think. Even then, there are a range of childhood influences beyond strictly parental.

One of the most poignant exercises of the weekend involved this prompt: “On a piece of paper, write down something rather personal and vulnerable that you are longing, in a way, to share with someone, if only they were trustworthy and kind.” People wrote down sometimes stunning confessionals. And then the confessionals were read aloud on stage anonymously.

One of the most difficult exercises was to pair up with a person sitting next to you in the audience — a complete stranger — and describe your sexual fantasies. Yes, your uncensored sexual fantasies.

One of the most amusing exercises involved writing down a long-held life dream you’ve maintained — perhaps to achieve a certain kind of change in the world, finally marry a soulmate, accomplish a professional goal — and then throw the piece of paper containing the dream in an oversized trash can that had been rolled on-stage. Relinquish your dreams!

Other nuggets I wrote down in my notebook:

  • “I’m a little broken” should be the first words on a first date with someone. “Hello, my name is… And I’m suffering because…”
  • Let’s all strive for “sane insanity.”
  • There’s no such thing as overthinking; only thinking badly.
  • Kierkegaard quote, which could be the modern Stoic manifesto: “If you marry, you will regret it; if you do not marry, you will also regret it; if you marry or if you do not marry, you will regret both; whether you marry or you do not marry, you will regret both. Laugh at the world’s follies, you will regret it; weep over them, you will also regret it; if you laugh at the world’s follies or if you weep over them, you will regret both; whether you laugh at the world’s follies or you weep over them, you will regret both. Believe a girl, you will regret it; if you do not believe her, you will also regret it; if you believe a girl or you do not believe her, you will regret both; whether you believe a girl or you do not believe her, you will regret both. If you hang yourself, you will regret it; if you do not hang yourself, you will regret it; if you hang yourself or you do not hang yourself, you will regret both; whether you hang yourself or you do not hang yourself, you will regret both. This, gentlemen, is the sum of all practical wisdom.”
  • Manic cheeriness is an ill of modern society.
  • Many people’s #1 problem is they are too hard on themselves.
  • Think through the worst case scenarios
  • When lusting after someone new from afar, stare into their eyes, and think about all the ways s/he could annoy you over time.
  • Good sex involves decadance, roughness, immediacy, vulgarity. Good relationships involve respect, responsibility, patience.
  • Tip on humor to lessen the fights with your partner. Exaggerate the annoying tendency of your partner to make him/her laugh. For example, if your wife is obsessed with cleaning, try to out-clean her to such an extreme degree that she can’t help but laugh at your newfound obsession. If your husband is always panicked about getting to the airport early, pack your suitcase and propose leaving for airport the night before the flight–just to be safe. Make him laugh.
  • True love is the forgiveness of weakness; not the admiration of strength.
  • Interview question at job: In what particular ways are you crazy?
  • Hang a sign at the office that says, “No one who works here is entirely normal.”
  • Over-obedient adults are more problematic than under-obedient ones.
  • What are you most afraid of? Who are you afraid of letting down?
  • Frustration + Surprise = Anger. Frustration + Expectation = Sadness.
  • When you encounter a local frustration, instead of maintaining “local pessimism” around whatever happened try enveloping your feeling into a kind of “global pessimism.” For example, if your kid spills rice all over the floor, the local pessimist would say: “My kid isn’t neat.” The global pessimist would say, “Children are lifelong punishment for a few moments of sentimentality.”
  • As a child you cry when angry or wronged. As an adult you often cry at tender moments or when encountering profound beauty.
  • To have a meaningful life, become skilled at cultivating meaningful moments. Hardship can be meaningful when it’s a byproduct of your search for something meaningful.

Thank you, Alain, for all you do. And thank you to the School of Life for being a fount of ideas and inspiration.

“That Doesn’t Surprise Me”

I’m always on the lookout for how people try to signal high status.

Here’s a subtle example I’ve discovered recently. Tell someone a fact they don’t know, and listen for the answer: “That doesn’t surprise me.”

The other day I told a guy who’s well connected in tech: “Did you know that Joe had a falling out with his cofounder, and so he has moved on to a new project?”

The other guy’s reply: “That doesn’t surprise me.”

The alternative answer would have been: “Huh, I didn’t know that.” By saying “That doesn’t surprise me,” he conveyed that he did not, in fact, know the thing that was just said to him, but rather than stop there — which would have lowered his status relative to me in that moment — he simultaneously conveyed the fact that he would have guessed the fact to be the case had he been asked. All done in one tidy sentence.

As another example, Donald Trump’s first quoted response to the Harvey Weinstein news was: “I’m not surprised.”

Signaling status in this way is not necessarily good or bad or even that important. It’s fun to notice it. And, sometimes, it can be a useful data point as you build psychological models of how the people around you operate, and in particular, as you predict how status-oriented a person might be.

What’s the Reward for Uncovering Truth?

A friend emailed me the below excerpt from Mark Nepo’s The Book of Awakening. The closer we get to the core of all being, the more synonymous the effort and its reward.


So often we anticipate a reward for the uncovering of truth. For effort, we expect money and recognition. For sacrifice and kindness, we secretly expect acceptance and love. For honesty, we expect justice. Yet as we all know the life of experience unfolds with a logic all its own. And very often, effort is seen, and kindness is embraced, and the risk of truth is held as the foundation of how humans relate. However, the reward for breathing is not applause but air, and the reward for climbing is not a promotion but new sight, and the reward for kindness is not being seen as kind, but the electricity of giving that keeps us alive.

It seems the closer we get to the core of all being, the more synonymous the effort and its reward. Who could have guessed? The reward for uncovering the truth is the experience of honest being. The reward for understanding is the peace of knowing. The reward for loving is being the carrier of love. It all becomes elusively simple. The river’s sole purpose is to carry water, and as the force of the water deepens and widens the riverbed, the river fulfills its purpose more. Likewise, the riverbed of the heart is worn open over time to carry what is living.

All this tells us that no amount of thinking can eliminate the wonder and pain of living. No wall or avoidance or denial – no cause or excuse – can keep the rawness of life from running through us. While this may at times seem devastating, it is actually reassuring, because while the impermanence of life, if fixed on, can be terrifying, leaving us preoccupied with death, the very same impermanence, if allowed its infinite frame, can soothe us with the understanding that even the deepest pain will pass.

Hiring a Head of Content

In September 2017, we announced Village Global, a new type of venture capital fund that is networked at its core. From who we have as financial backers, to how we invest, everything we do is about empowering and connecting people.

So far we’ve been heads down, focused on generating outcomes worth writing about. We’re finally ready to start telling some of the stories of the Village network, and, as such, we’re hiring a Head of Content and Marketing.

The Role

You’ll spread ideas and insights that matter to the tech community. You’ll pull out the best gems from our events, podcasts, and other media and repurpose them across different social media channels.

You’ll interview Village Global luminaries, network leaders, and founders — some of the most talented people across fields, disciplines, and companies — and create original, compelling content based on their stories.

You’ll join the ground floor of a new kind of venture firm and build our content and marketing strategy with us from the ground up.

You’ll go from 0 to 100,000’s of monthly readers/followers/subscribers, and aim to become one of the most recognizable brands in venture capital.

You’ll join a small team where you’ll learn about all aspects of venture capital. We want this to transform your career.

Interested? Here’s what we’re looking for:

You’re a writer, editor, and curator at heart. Maybe you run content for a startup or do marketing for a big company. Maybe you’ve been a founder who loves to write on the side. Maybe you’re starting off your journalism career but want to explore a different way of applying your skill set. You understand storytelling, narrative hooks, and you know a catchy idea when you hear it.

You understand online marketing and want to get better. You already have experience and good instincts when it comes to social media, VC and entrepreneurship Twitter feeds, email marketing, and running experiments to build brands. You geek out on audience building and engagement and use metrics to keep score.

You’ve always wanted to build something from the ground up. We’re looking for someone who can help architect a high level content strategy but who can also execute on it from start to finish on their own. Over time, you might even build a team around you to help fulfill our potential as a firm.

Venture capital and Silicon Valley fascinate you. You don’t necessarily need deep knowledge of all things technology and VC, but you should be wanting to learn fast to become a domain expert.

We’re based in San Francisco, but we’ll accept remote.

To be clear, this role is not:

  • General PR — If your dream job is pitching the New York Times and spinning out press releases, this isn’t that.
  • General marketing — This is not about designing corporate schwag, booths at conferences, etc.
  • Event management/production — We’re already covered there.

Does this role at Village Global sound like something you’d be terrific at?

If so, we want to talk to you. Email us and include a link to your LinkedIn profile: [email protected]

Do you know someone who’d be great for this job? If you refer the person we hire, we’ll pay you, the referrer, $5,000 as a thank you!

What I’ve Been Reading

Books, books, books.

1. Manhattan Beach by Jennifer Egan. Great historical fiction authored by a Pulitzer Prize winning writer who has command of every page. Set in Brooklyn during World War II, I learned a bunch about New York at that time, the mob scene, and scuba diving. The main character becomes the first female diver working on the Brooklyn docks.

2. Kafka on the Shore by Haruki Murakami. My fifth or sixth book by Murakami. Kafka is totally engrossing. I read 200 pages of it straight through, in the middle of the night on a 12 hour flight. Kafka On the Shore, while set in modern day Japan, is as strange as any of his novels: cats who talk, fish fall from the sky, alter egos take on their own named characters, and characters enter others’ dreams. Murakami is peerless in his ability to create rich worlds that leave you in a trance. Critics often refer to Murakami’s novels as “dream like.” That phrase captures my reading experience 100%.

This is not a book with dozens of highlightable one-liners. But here are a few of my highlights:

“Actually, I don’t have any memories either. I’m dumb, you see, so could you tell me what memories are like?” Miss Saeki stared at her hands on the desk, then looked up at Nakata again. “Memories warm you up from the inside. But they also tear you apart.”

I’m free, I think. I shut my eyes and think hard and deep about how free I am, but I can’t really understand what it means. All I know is I’m totally alone. All alone in an unfamiliar place, like some solitary explorer who’s lost his compass and his map. Is this what it means to be free? I don’t know, and I give up thinking about it.

“The pure present is an ungraspable advance of the past devouring the future. In truth, all sensation is already memory.”

3. Homo Deus: A Brief History of Tomorrow by Yuval Harari.

The first 60% is a rehash of Sapiens. The next 40% is good (I highlighted 110 sentences!) but not great. Still worth reading if you’re a fan of Sapiens (as I am) if for no other reason than to get the refresh. A few random highlights:

If and when computer programs attain superhuman intelligence and unprecedented power, should we begin valuing these programs more than we value humans? Would it be okay, for example, for an artificial intelligence to exploit humans and even kill them to further its own needs and desires? If it should never be allowed to do that, despite its superior intelligence and power, why is it ethical for humans to exploit and kill pigs?

The technological solution to such dramas is to ensure we never have uncomfortable desires. How much pain and sorrow would have been avoided if, instead of drinking poison, Romeo and Juliet could just take a pill or wear a helmet that would have redirected their star-crossed love towards other people.

We just don’t know what to pay attention to, and often spend our time investigating and debating side issues. In ancient times having power meant having access to data. Today having power means knowing what to ignore. So considering everything that is happening in our chaotic world, what should we focus on?

4. Red Notice: A True Story of High Finance, Murder, and One Man’s Fight for Justice by Bill Browder. Surprisingly gripping true life account of a hedge fund manager who makes a fortune in Russia by being contrarian, and then ends up making enemies with Putin. Timely, given the state of U.S.-Russia relations.

5. My Life on the Road by Gloria Steinem. An engaging memoir from the legendary feminist and social activist. Stories from her travels, especially her visits to college campuses across the U.S.

Musings on Philanthropy After Hosting Refugees

For much of 2017, we had LGBT refugees from Iraq and Uganda living at our house in the Bay Area. I sent out some private reflections and anecdotes about the experience to some friends. For those especially interested in the topic, feel free to email me and I can share with you.

Here are the thoughts on philanthropy that I’ve been mulling over after the tremendously fulfilling experience of hosting refugees.

Maximizing Philanthropic Utilitarian Impact vs. Emotional Satisfaction

My favorite charity to support is Give Directly. Give Directly sends money directly to some of the poorest people in the world with no strings attached. Backed by research, I believe Give Directly is one of the most efficient ways for your dollars to help those who need it most.

The challenge as a donor to Give Directly is that you don’t feel anything when you give. The money leaves your bank account and ends up in some stranger’s bank account. Then you move on with your life. Whereas when you host refugees, you feel very emotionally involved in the experience. But helping one refugee in the Bay Area is not making a dent in the global refugee issue in general, arguably one of the most important humanitarian issues of the next decade. The “systems”/impact part of my brain struggles with this.

What I realized this past year is that our experience hosting the men was a perfect 1-2 punch. By being extremely hands-on with three refugees, we generated the emotional propulsion to care deeply about the refugee issue more generally. We then used that emotional energy to engage at the systems level: learn how the systems work, research which organizations are helping, and begin to take steps to engage in philanthropy that would be more scalable.

Doing only Give Directly or any other type of super utilitarian and analytical but ultimately feeling-free giving would be emotionally unsustainable. Doing only refugee hosting or food bank handouts, or any other type of non-scalable, super local volunteer activity would undershoot on our potential to maximize impact. Do both — that’s what we learned.

Are the Financially Poorest People the Absolute Neediest?

When I donate to charity, in my own small way I try to prioritize helping the financially neediest on a global scale. For this reason, I haven’t given much to America-centric non-profits.

That said, the refugee experience has prompted me to re-evaluate an element of this belief. To what extent is financial poverty the truest proxy of neediness? The LGBT refugees from Iraq had phones, Facebook and Snapchat accounts, and exposure to most modern technologies that we have in California. In financial terms, they were/are richer than teenagers living in, say, the slums of India. At the same time, they’ve been disowned, indeed had their lives threatened, by their own family. And exiled from their country. And rejected by their religious community because of their sexual orientation. Who’s needier?

You Can Care About Complete Strangers. You Can Love People who Aren’t Biologically Related to You.

Complete strangers walk into your house. From a different culture, speaking a different language. They shack up with you. You help them. They help you. You argue with them. You laugh with them. You begin to care about them. You begin to love them.

I now have a glimpse, I think, into how and why people adopt children. You really can love people who aren’t biologically related to you. In our own ways, we truly grew to love the refugees who lived with us.

Scuba Diving the Great Barrier Reef

It was a blast living on a boat for two nights (a “liveaboard”) and diving 10 times in the warm waters of the Great Barrier Reef off the coast of Cairns, Australia.

Our schedule was: Wake up at 5:30am, dive, eat breakfast, read a book on the sun deck, dive, read, dive, eat lunch, read, dive, read, go to sleep. Repeat.

It was my first time diving post certification. My ears still aren’t fully equalized, but beyond that, I had no issues and was able to really relax into the experience. Swimming amidst the fish and coral is really something.

Here’s a ~1 minute video I created with photos/videos from the dives. My iMovie for iPhone directorial debut…

Do You Love Making Connections and Thinking About Networks?

I recently co-founded Village Global, a new early stage venture firm. We’re hiring!

Here’s one position we’re actively recruiting for. It’s a unique role. Please email [email protected] if you’re interested. And if you refer a candidate we hire, we’ll pay you $3,000!

Title: GM of Network

We are looking for someone to help us build our network-driven platform strategy.

This will include helping design the events, programs, and systems by which we help portfolio companies with hiring, distribution, fund-raising, advice, key introductions, and other network needs. You will help figure out the best possible introductions to make across our vast network.

You should possess a deep passion for connecting people and also sweat the details. You should love connecting people and love thinking about the systems for how to make those connections more efficient and effective.

Ideal background, experience, and personality

  • Demonstrated ability to connect with everyone from LPs, VCs, and portfolio founders. Knowledgable about VC industry.
  • Experience creating value-add initiatives or events for entrepreneurs or investors
  • Experience working in a venture capital firm, incubator, accelerator or small startup tech company
  • Comfortable with uncertainty and fast-changing conditions
  • Self-starter and self-motivator — able to work independently and with little oversight
  • Experience using a CRM system or eagerness to become totally fluent in one
  • Preferably located in the Bay Area, though open to Los Angeles or New York if willing to travel
  • Comfortable interfacing with professionals from different countries and planning events outside the U.S. (You would not need to physically staff events outside the U.S.)
  • Able to attend at least a couple events per month in the Bay Area
  • Service-oriented, knows how to add value — wants to focus adding value to companies rather than investing.
  • Think big and execute small; detail-oriented but can also do strategy. Willing to do whatever it takes — no task too low or high

Learning to Scuba Dive

A couple months ago, a friend and I were wading out in the Mediterranean Sea, looking to body surf some of the light waves that were crashing down on the beach. I’m a strong swimmer, I body surfed a bunch in New Jersey as a kid, and the water temperature in the Mediterranean was pleasant. No big deal. After 15 or so minutes of bobbing up and down in the water facing out toward the sea, fruitlessly trying to surf the waves that lost power just as they crested, my friend yelled over, “Hey, I think we’re a bit far out from the beach. We should probably swim back in.” I turned around and looked back at the beach. We were indeed way further out from the shore than I would have expected, given it had only been 15 minutes and we hadn’t swum out too far. I hollered back that I agreed, and we both turned toward the shore.

I swam hard back toward the shore for about 30 seconds. I was definitely moving through the water. I figured I’d be at the sandy beach in no time. When I pulled my head back up to stay directionally oriented, I glanced toward the shore, and I felt a jolt of panic: I was further from the shore than before. Despite swimming strongly towards it, I was now further from the shore than I was 30 seconds prior. My heart began beating quickly and my breaths became shorter. For a few moments, I contemplated whether I’d make it back to shore at all. I’d never had the experience of swimming as hard as I could in a certain direction but being pulled in the exact opposite direction at the same time. There was no one else swimming in the ocean who could lend a hand, and we were far enough from the beach that yells for help may not have been heard.

After a pause, my friend yelled out to me that we needed to swim parallel to the shore to escape the rip tide. Apparently there’s fairly common knowledge, but I had never heard of it. Thankfully, I was with someone who knew what to do when caught in a rip tide. I moved parallel, and indeed, within a couple minutes, we were back in easy water, and I swam easily toward the beach. I was happy to have made it back in one piece, but disappointed that my “panic mode” activated so quickly.

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As it turns out, managing your panic impulse — not freaking out too much when something goes awry or when you feel claustrophobic — is key to becoming certified for open water scuba diving. (In the certification, they also train you to swim parallel to the shore in a rip tide!)

Prior to last weekend, I had never scuba dived, and snorkeled only a few times in Hawaii. But I had heard that the coral reefs are dying due to warming ocean temperatures. I figured I better go see the reefs while they’re still alive.

Scuba training is intense. Several hours of online training, Friday night orientation, all day Saturday and Sunday at the pool in the Bay Area, then another Saturday and Sunday at freezing cold water ocean in Monterey to attempt certification. Through it all, you’re being told to remember different safety acronyms that represent safety checklists, sign language (to communicate underwater), and a multitude of instructions for how to configure and operate the equipment. Along the way, you’re supposed to get comfortable breathing through your mouth underwater and figure out how to make sure your ears stay comfortable as you descend into water. Finally, you’re taught 10-15 specific skills that you have to successfully demonstrate in the pool and ocean: how to do an emergency ascent on breath alone, how to give your buddy oxygen, how to demonstrate neutral buoyancy in the water, how to clear your mask of water, and others.

Much of the skills training involves emergency situations that you will likely never encounter. The purpose of these skills is obvious at one level: on the off chance you do have an emergency underwater, you’ll know what to do. Otherwise you’ll die, as plenty of people do. The more interesting other purpose of these skills is to stress test you: to get you comfortable with things going wrong and to train you to just keep breathing in and out, and calmly figure out how to solve the problem.

One of the skills they train you to do in the pool is how to take off your BCD under water. The BCD is the life preserver backpack that has the oxygen tank, weights, and all your equipment attached to it. It’s hard to do, and not something you’d ever want to try in a real ocean dive. Almost all the students failed in their first and second attempts. When I took off the BCD at depth, I began flailing about in the water, trying to stay on the bottom of the pool even though the weight had been taken off my back. Meanwhile, I was trying to keep the oxygen line in my mouth the whole time. The purpose of the pool-only skill is to induce stress and build confidence. The students who dropped out of the class too frequently panicked and jumped to the surface. Removing and then putting back on your BCD under water was a big confidence booster…even though I’ll likely never have to use the skill in real life. It’s interesting to contemplate other stress tests we should be running in our personal and professional lives…

Some other quick observations on my experience:

  • I was one of the weaker students in the class. It was a good experience to struggle at something genuinely new and hard for me. In addition to all the scuba-specific training, I was also a newbie at putting on a thick wetsuit, using a compass under water, and other random tasks. And, in general, any activities that require fine physical motor skills — buckling and harnessing and clipping and tying knots — are not my strong suit, especially if I’m wearing wearing thick gloves and operating in cold water. For all these reasons, it was especially gratifying to learn the skills, complete the four open water dives, and become certified.
  • Diving opens up new travel options. I’m excited by the prospect of being able to add a day or two to a trip somewhere in the world, and go diving. A whole new world of travel opportunity might be opening up.
  • Diving is a dangerous sport. Our teacher recounted multiple stories of people who have died while diving. With danger comes adrenaline. I don’t do many physically dangerous things in my life.
  • Learn to scuba dive when you have a life partner or go-to friend. It’s a buddy sport — beginners never dive alone. Learning with your partner is a blast.
  • My ear equalization is still a little messed up. If anyone has tips on clever ways to equalize, let me know. For me to stick with diving, I’ll need to be able to equalize effectively and not have my ears clogged up for the week+ after diving.

Next up: The Great Barrier Reef in Australia. And New Year’s Eve in Sydney. My first time to Australia!