Reid, today we’re going to talk about something that’s important in life and work: friendship—our connections with people in our lives and how they benefit us.
And in this conversation, this episode is gonna be a little different. We’re going to start with riffing a little bit on friendship, and then we’re going to transition, and we’re actually going to play for listeners at commencement speech you recently gave at Vanderbilt University.
Tell us what the speech was about.
You know, mine—and I think, you know, other folks like me—as I’ve gotten kind of more established in, you know, kind of my network and what I do, is obviously started by being really
Commencement speeches are these things where you try to honor this huge change in people’s lives. And many of us have gone through them—
Some of us have graduated from institutions, yes.
And some of us have been smarter and left earlier. And so the—you know, you try to figure out how to contribute something that’s both personal and original to this.
So, personal in terms of like: why are you the person speaking about it? Why do you bring this to it? And also original, as opposed to the, you know, there’s generally some themes and commencement speeches like, you know, “Stay young, stay foolish, stay ambitious,” etc.
And I was like, “Well, actually in fact, friendship’s a super important part of our lives that kind of has that implicit thing for most people.” It’s like, “Oh, isn’t it just what you do naturally? It isn’t something that you actually can focus on, be thoughtful about, be reflexive, have skills, improve on?”
And actually in fact, all of those questions I just asked…you can. You can focus on it—just like, for example, you can focus on being a better partner by going to therapy; or going to marriage counseling; or couples counseling; or read books about how to deal with conflicts; and how to think about which of the conflicts that are serious—and maybe you shouldn’t be in this nature of this relationship with a person—and which are the ones that actually, in fact, make you better by giong through them…make you both, you know, stronger…both people you more want to be: wiser, more compassionate, etc., and so wise.
And that’s why we decided to do it. And so then, of course, the commencement speech is a particular format where you have thousands of people in the audience, generally speaking, who are massively distracted by, “Oh my God, the intensity of what was my life for the last three, four, or five years is now completely going.”
“What am I going to do with my career?”
“What am I going to do with my career?” etc. And so you distill it to some stories—some friendship stories from my life about how they were, like, really transformative to my career and to my life—and also to some principles that to remember that your friends are a part of your life.
And there is a very much of Startup of You, which is: life is a team sport, and actually, in fact, some of your real key friends—and just about I think everyone who spends any amount of time, you know, at a college—builds some really great friendships there, and that those are part of your team as you go forward in your life and in your work.
And some ways to approach it—and to approach it thoughtfully, intentionally, build rituals around it; kind of talk explicitly about the friendship, about, “Here’s what our friendship not just means to me, but here’s how I want—I personally want to have this dance of our friendship and make it better as we do—”
So let me ask about that ’cause I think that’s super interesting, which is the explicit conversation. Is your view that two friends should sit down and talk about the state of their friendship: what’s working, what isn’t, where they want to go together? And, if so, how often should that check-in happen?
Part of the reason why it’s hard to give as crisp is ’cause it really matters between each specific friendship. Generally speaking—even with me, who has this principle—I don’t think that any of us spend much time being as…call it‘gracefully deliberate’ about it as you should be. Which is to say, “Hey, I really value this friendship. I value these parts of it. Let’s let’s do this dance a little differently. Let’s do this dance a little bit better.”
Now, sometimes people experiment by like, “Oh, let’s go do a trip together,” which is great. “Let’s go see the Taj Mahal. We both—remember we wanted to go to India and do that, and experience the sunrise of the Taj Mahal? And we’ll have this whole trip, and that’ll be part of it.” That’s great.
But also like, you know, for example, you know, one of the things about yours and my friendship is we challenge each other intellectually. We have things that we have kind of different weightings on, different risks on. We both really value the ‘think differently about this’, not necessarily ’cause we will think differently, but because someone else we really care about who think seriously about it pushes us on it, causes our own thinking to envolve.
And it’s like one of the things that—like whenever I check in with you, I’m always asking about like what, kind of, counterculture, counter-mainstream thoughts have you encountered recently? ‘Cause it’s really valuable—and you do that and that’s part of who you are.
Those kinds of things should be brought more lightly, explicitly—like thinking of friendship as a dance. Saying, “Hey, look, we can get better at it, we just—”
And we can do it in not-awkward ways, like, “I really want you to ask me about my feelings more, Ben. You know, please do that.” Like that’s a ham-handed way of getting into something, but it could very well be the—like, for example, “Hey, you know, your journey with the dharma of dogs, and your dog is actually something I really benefit from derivatively; I’d love to hear more about it.” Like that would be something that would be a nice, graceful nudge that I would add in to our conversations.
I love ‘gracefully deliberate’.
I love that—as sort of to capture the emphasis of deft touch, which is needed on this topic.
Couple things. Number 1: one point of stress that I see sometimes in friendships is someone’s looking for too much out of one person. It tends to be that certain friends give you certain types of things, and other friends give you other types of things.
So, for example, there are friends of mine who are very intellectually stimulating; really fascinating people to talk to; reading constantly—I love their writing…They’re not the kind of person that would check in with me at an emotional level.
And then there are friends with whom I share perhaps more emotional history, or, in other ways, they are just more—the higher EQ—and it feels like I’ll have deep life emotional conversations with them. Sometimes it’s the same person. But, seeking emotional depth out of intellectual friends or wild intellectual stimulation out of someone where you have true emotional depth—sometimes that’s expecting too much.
Curious how you think about the package deal versus sort of segmenting your friends.
So, I think that it’s best to think about friendship as a pantheon. We have a—I think an overemphasis in—at least our American culture—of having a best friend. Like, it’s your best friend is—
Yeah, I think it’s a terrible idea. Yeah.
Yeah, maybe it comes from childhood. Like, you know, your 5-year-old: “Who’s your best friend?” It’s like, you know, “Have a friend.”
And actually I think, just like having a richness of experience, or richness of different paths, or richness of creativity, and exploration—it’s good to have a pantheon of friends in different ways. And it doesn’t necessarily mean always narrow them to a box—which some people would have a reflex to.
One of the things I think is delightful about friendship—and part of the reason why we have difficulty talking about it—is because the ambiguity around friendships are like, “Oh, well where are we on that friendship path?”, and so forth is actually in fact a feature—not just a bug—right? Because it’s like—well its potential. It’s becoming. It’s a path that we are walking and journeying together, sometimes more often, sometimes less often.
And so, you don’t want to go, “Oh! This one’s only intellectual, and that’s it.” But you go, “Well, I know that the intellectual thing really works, so I have that expectation, that’s when I might seek that friend out, etc., you know, as a pattern.” And I think that having a pantheon is very good.
Now, one of the other things in your question that’s really important is: a friendship is a two-to-tango thing, whether it’s a journey or a dance. And the part of being graceful or deft is it can be a place where one friend really wants a bunch of things from another person, where that’s not the right dance and you have to maintain that kind of grace on both sides.
So, when I’m expanding my friendships, I do it lightly. I do it through some exploratory—like, think of it as a morning trip or a, you know, a few extra dance, or a little bit of improv—to kind of see where it goes. Sometimes it comes upon you unexpectedly, and someone you thought was just a deep, intellectual friend turns into a real, kind of, emotional and personal-life friend because they’re having a moment, or you’re having a moment, and all of a sudden a bridge is built.
Yeah, sometimes it just takes one powerful shared experience.
You know, like you’re flying somewhere together, and your flight gets cancelled or something. You end up spending 7 hours in the airport—or something like that can actually create that bridge.
Exactly, and so—so staying open to that and so forth—even as you have these different things.
And then when you’re thinking about how should it develop, it isn’t necessarily only work on the things that are less, like, so for example, this person might be just spectacular on the intellectual side, and you are great for each other on that. And, you know, your emotional, or personal, or how you feel that you—what your tactile sense of being a human being is…less obvious about how to do that dance. Like, this person you’re really, really good at a polka with, and this person is jazz improv. It’s fine.
There’s a economist, Robin Hanson, who had this great piece once on the virtue of the ambiguity of the phrase, “I love you.”
Because sometimes when we say “I love you” to somebody, we mean, “I love being your companion.” Sometimes we say “I love you” because we feel an obligation due to a genetic relationship. Sometimes we say “I love you,” meaning, “I lust after you.” Sometimes we say, “I love you” actually when we’re angry, but it’s the thing we say just to get over our anger.
And if we forced ourselves to be ultra precise in every one of those interactions—so instead of “I love you,” you’d say, “I lust after you,” or, “I like being friends with you, I like being comrads with you”—that would actually undermine a lot of what’s magical about love. And so the ambiguity of the word ‘love’ allows for the oscillation over the arc of the relationship.
What you’re describing, I think, is this delicate framework of intentionality and precision—while also allowing sort of the ambiguity and serendipity to unfold. Because, you know, one thing that’s funny about your and my networks—people in tech, in the valley—it’s like there’s so many tech entrepreneur types that are super into quantified self personal development—self-improvement.
You know, we are as well, but they get hyperprecise about every aspect of their life, including friendship and romance. You know, they’ll create Google spreadsheets, and survey people, and assign 1-10 numbers on everything. “How are we trending? Hey Reid, are we better friends this week than last week?” You know, that kind of thing.
And that really can be detrimental. Too many people actually think that they don’t have to actively invest. But like a flower that’s not watered, the flower will wither if you don’t actively attend to it. So, many of us underinvest—are underframeworked on the topic of friendship, but there is such a thing as being overly…yeah, specific on this.
And the other thing to amplify—’cause you didn’t use it in the “I love you” definitions, but you got to it in your exposition—is the “I love you” also can be a dynamic, kind of, intention and path to the future, which is, “I love you because I want to continue getting closer, continue going down this journey with you, continuing deepening…”
And actually, in fact, that expression of path togetherness is, I think, really, really important in this.
Yeah, our mutual friend Brad Feld has a thing called ‘friendship love’. Do you think the word ‘love’ has a role in friendship? Can you love your friends, or is that just for people you romantically are involved with?
I think it’s good to do that. Some people find that weird because they find the love that they’ve kind of grown up with—like these words or dances that we do these things, they’re also, you know, word games…you know, kind of following in practice.
And so some people are like, “No, no, no, love is—”. Like, if I say, “I love you,” it’s like, “Oh, wait, are you bisexual?” Like, you know, like what’s going on?
And I actually think it’s worth understanding that there is that depth of emotional feelings. I would be of the camp to say: if it isn’t using the word ‘love’, we should have another word with also that depth and resonance that also applies within friendship, because I think it’s important to recognize that’s a component of it.
Language tends to be the word-game dances that we all agree on. If most people say, “Uh, I’m kind of uncomfortable. I’d rather have that be just a romantic and family side…” Great. Let’s have another word that does that, too.
And sometimes a close friend today is not a close friend in five years. I mean, sometimes these friendships fade over time, which is something I personally—I don’t know if it’s contrarian to you or contrarian to others—I think sometimes friendships are meant to be only for a season of life.
A hundred percent.
And you have to sort of let them fade. And that’s okay, right? And you might have five close friends today; maybe only three of them are close friends in five or ten years from now. And that doesn’t mean you did something wrong. It just means that’s how life unfolded.
And it might be that neither of you did something wrong. And it’s—again, that’s the kind of the metaphor of journeying. ‘Cause, like, well, this person really wants to go climbing those mountains, and this person wants to go sail in that sea.
There—you know, it’s just like, “Okay great! And, by the way, send me postcards!”
Awesome. Let’s go to the speech.
Thank you so much, Chancellor Diermeier; Provost Raver; members of the Vanderbilt board. And congratulations, Vanderbilt Class of 2022. It’s my privilege to join you today at such a proud moment in your lives.
Okay, that’s enough of that.
Hey everyone! It’s such an honor to share this day with you. It’s a magnificent stadium you’ve got—but I do have a suggestion about air conditioning.
Anyway, when I got this invitation, I was excited because you all have such enormous potential to improve the world. So I thought, I’d talk about, you know, entrepreneurship and technology—how we all need to be the entrepreneurs of our own lives.
But then I thought there was something even more important to me, which is foundational to our aspirations for the future, to the goal of “stay young, stay foolish.” And what I realized I most wanted to talk about was: friendship.
Not the Hallmark kind—not all sunshine and roses and bunny rabbits. I mean real, substantive friendship—that’s sometimes really hard, and that shapes and changes our lives. In fact, alongside your family, making and cultivating and keeping close friends may be your life’s most important work.
Yes, to help your career—I’m the LinkedIn guy, I’m not going to tell you otherwise: your network’s important. But more than that, friends will be absolutely central to your sense of happiness, connection, and meaning.
Also, friendship’s a conversation. So I want to try something that feels a little bit more like a conversation. It’s an odd conversation, since I’ll be the only one talking. But I’ll try to explain the importance of friendship with four brief stories from my own life’s path, each with a learning that’s been valuable to me in every part of my life.
Starting with one back from before many of you were born—in a prehistoric haze of the 1980’s. What I learned then was: when there’s something important that you need to know, your real friends will tell you about it.
I went to college at Stanford—or as you may know it, “The Vanderbilt of the West”. When I got to campus my freshman year, I thought what many of you might have thought arriving here a few years ago: that what would matter most, you know, about college was “the college”—the teachers, the skills, the degree, the institution.
But within a month, I knew I was wrong. Don’t misunderstand me; college was awesome. Like you, I was able to get a great education, with brilliant faculty teaching enlightening classes. Yet right away it was clear to me what would matter much more to me, were my fellow students. After a high school where, frankly, it wasn’t always easy to find friends who shared my interests…now, I was surrounded by them.
And through some of my classes, I met this one woman, Kyndaron, who seemed to like talking to me. We started out discussing our coursework in World Civilization. Over time, we got to learn about each others’ families, our disastrous dating experiences, we saw each others’ flaws. In other words, we became friends.
And one day, after we’d known each other a while, Kyndaron said one of the kindest things anyone’s ever said to me. She said, “Reid, you seem to have no understanding of half of humanity.” She meant women. And she didn’t actually say it that way, ‘cause she’s too nice. But it’s what she meant. Because like a lot of young men, I got to college with approximately zero comprehension of women. And no one else had ever cared enough to tell me I needed help.
And that’s what’s great about Kyndaron. She didn’t just say it; she did something about it. She had lined up a few friends who were game to let me come listen to some full-on girl talk, and learn. If I’d be interested. “If?!” Of course I was interested!
So one afternoon, Kyndaron told me to meet her and her girlfriends at a picnic table by her dorm, and they got right into it. Discussing their friendships—way more intensively than I ever did with my male friends. Openly talking about their sex lives, in ways that still make me blush. And especially, going over some of the crap they had to deal with, routinely, just for being women.
You know—“There was this guy at the party following me, hitting on me…I had to figure out how to make him go away, but I didn’t want to be rude, or make him mad…” And that was hardly the worst of it. And I was like, “Wait, what? You have to live like that?” Naïve, obviously, but if you don’t know this about me, I am a white man.
So there was a lot I didn’t know about a lot of people’s experiences. And of course, there still is. But before Kyndaron, I didn’t even know that I didn’t know. And after, I started to clue in years before I would have otherwise, to approach relationships of all kinds understanding that your experience may be very different than mine. It’s an imperfect awareness, to be sure, but it’s helped me be a better friend, boss, spouse, investor—really every part of my life.
So to reiterate: when there’s something important you don’t know, real friends will tell you about it. They might even help you learn it. And, like me, you may be deeply grateful.
My next story comes from the year after I left college. When I was more or less at the point where many of you are now. What I learned then was that your friends can help you see what you can’t see.
So I’m 22. What did I want to do with my life? I wanted to make the world a better place, at real scale. And I thought a good way to do that would be grappling with the big questions of values and ethics—who we should be as a society.
So, I headed to Oxford to study philosophy. And within months—and yes, this is a theme—I knew I’d made a mistake. While Oxford’s philosophy department was one of the world’s best, the professors there seemed only to want to talk about esoteric theories, with hardly any interest in, you know, “actual people”.
Clearly not what I wanted—because it wasn’t connected to that mission: expressing values in a way that would have a big, broad social impact. So philosophy wasn’t my path. But I had no idea what to do instead, and I was kind of lost and miserable.
Fortunately, I had a friend, Stefan. He knew me well. And when he saw me struggling, he asked me this one question that was so simple, it changed my life completely. He said, “You want to put good values into society, at real scale.” I was like, “Mhm. Yeah. Mhm..”
“Why do you think philosophy is your only path to do that?”
And I was like, “Ohhhhh.”
And Stefan said if academia wasn’t getting me there—well, I should choose a different path that would! Don’t sit here feeling you don’t know what to do. Go do something! I’d never stopped to think of it like that. Of course, there must be paths that were more about making change.
So with no savings and less clue what I’d actually end up doing, I took the leap. I went back to where I grew up—northern California—to look for entry-level jobs in a field that valued change at scale: the tech industry.
Now, spoiler alert, that worked out okay. But I didn’t know that then. And I wouldn’t have done it without friends backing me up, and egging me on. We all have dreams for what we’d like to do in this life. A meaning we want our life to have. It’s not always clear right away what that is. And if you’re not sure yet, that’s ok.
And that’s where this lesson comes in. Your friends can help you see what you can’t see. They’ll help you, you’ll help them, and you’ll all do better and go further.
So that was my twenties. It wasn’t until my thirties that I started to absorb this next lesson about friendship: friends will tell you not what you want to hear, but what you need to hear.
It’s a decade later, 2002, and I’m part of the executive team at this thing, PayPal. And after several years of 100-hour weeks, a lot of luck—and a few scrapes with federal banking laws—we’ve just sold PayPal to eBay.
I was 35. Completely exhausted. And so I was planning on taking a year off, get out of Silicon Valley, and just travel. Everyone congratulates me on this excellent decision, and so off I go—first stop Australia—to hang out with my grad school friend Ned, who’d recently moved there.
Ned and I had grown surprisingly close over the years. I say ‘suprisingly,’ because on paper we weren’t cut out for that: he was a West Point graduate, former Army ranger, athletic, kinda badass. And I was, well, me. And as a couple of Americans studying abroad, we bonded, and grew to know what made each other tick. And we’d made a point of keeping up in the intervening years, making sure to have regular meals and stay in touch.
So he takes a few days off and we drive down the south of Sydney to this beach bungalow for some catch-up. And Ned’s like, “So, post-PayPal, what are you thinking about?”
I said, “Well, I’ve been watching this website, Friendster, transforming peoples’ social lives.” Facebook didn’t exist yet. “And I have this idea for a different kind of social network, one to help people’s economic lives.” It was exciting because I thought it could really help a lot of people have more satisfying careers; impact their families, their communities.
But first, yeah: I’m gonna do this travel year that everyone, including me, is so jazzed about. But not Ned. Ned thought I was blowing it. He and he alone told me: “I hear you’re tired, dude—but this next thing sounds super important, and you know how the tech industry works. The time to do that idea isn’t six months from now; it’s now. Cancel the trip and get back to the Valley ASAP. It’s too important to who you are.”
And as I started to picture my vacation spiraling down the drain—in the opposite direction, of course, this being Australia—deep down I knew Ned was remembering what I’d momentarily forgotten: that mission I’d defined a decade earlier. Because Ned had been around when I first arrived at that. He knew about me, and as a good friend, he wasn’t going to let me off the hook.
You can guess the rest. Changed my tickets, flew back home, got to work at starting what became LinkedIn. Which was good, because Ned was correct: the time was right then. Lots of other people were already working on ideas for professional networks. If I’d taken my vacation and delayed pitching LinkedIn even a few months, they’d have too big a head start. I don’t get funded; the whole thing doesn’t happen. No long friendship with Ned, no frank talk, no LinkedIn.
To be clear: the point of this story isn’t, “Never take vacation, always work more!” That would be dumb. And I try not to say dumb things. But there is this myth of the “Entrepreneur as Solo Genius”. It’s a good story, but it’s not usually true.
In fact, I have found just the opposite. You have a team. Some of your key teammates are your friends. The ones you share your dreams, and fears, and hopes with are the people most able to help you get where you should be going. Because, again, friends will tell you not what you want to hear, but what you need to hear.
Okay, here’s the last lesson I’ll share. It’s maybe the most subtle—but in a way, the most important—and something I’m still learning. Paradoxically, your friends help you the most by letting you help them. Let me see if I can get this one across. I’m sometimes asked if I’ve had any mentors. The truth is, I’ve had a hundred—most of them, friends.
And in turn, I’ve been fortunate enough to help and be a mentor to many of my friends. Some profoundly. But to be clear, I say this not from pride, but gratitude. Because having friends who have trusted and permitted me to help them has brought me greater joy than nearly anything else in my life.
I mean, of course we also hang out, have dinner, play games, go on vacation—all those good things. But it’s when I’ve helped the people I know best, towards goals and values I know them to have, that I’ve most felt, “Ah. This is why I’m here.”
I’m thinking of a particular late-night talk that I had with my friend Oscar, whom I’d known for a decade to be a smart, thoughtful, honorable man, but who at that time was being a friggin’ jerk—clearly trying to passive-aggressively provoke his wife of six years into divorcing him.
And so one night we sorted through what Oscar was doing, why he was doing it. And that whatever was driving that passive-aggressive garbage, he needed to confront it head-on, and either re-connect or disconnect from his wife, cleanly.
Long story short, that conversation made a big difference in Oscar’s life. They stayed together. A family with kids. Very happy. But that’s not why I’m mentioning it here today. For one thing, Oscar’s not here, and besides: his real name isn’t Oscar. What kind of friend would I be if I took a private talk and shared it with an auditorium full of people in Nashville?.
I’m mentioning it because it was also one of the key experiences in my life. Because for Oscar and me even to have that talk, he had to put his full trust and faith in me. Which was a great gift to me. Because by doing that, he showed me that I was the kind of person who was worthy of such trust. He showed me I was worthy. And I’ve never forgotten that feeling. And that’s how your friends help you most by letting you help them. And I want you to experience the same thing.
Luckily, there are simple things you can do to cultivate this essential part of your life. First, decide to make friendship a priority. Because it isn’t a side hustle, it’s the whole game. Make an active choice that friendship matters to you is your best first step to ensure its place in your life.
Number two: make friendship a conscious practice. Because it’s something you can work on—this is something I learned from Kyndaron; we did this all the time. Establish rituals: have a weekly call, a monthly breakfast, an annual fishing trip. Talk with your friends about what the friendship means to you, and how you’d improve it.
Yes, that sounds awkward—friendship’s supposed to be easy, right? But trust me, talking about it it will deepen your connection and you will be glad for it.
And third, as you go forward, realize: less time doesn’t have to mean less friendship. Life is going to make a lot of demands on you, including many good things: lovers and partners; careers; hobbies; kids.
But if you and your friends share what you want from your life—if you know each others’ dreams—you will support each other along the way, no matter how busy you are.
Vanderbilt Class of 2022, when you’re my age now—a third of a century from today— the world will be a very different place. Partly because each of you will change it. But in what direction? What will be your mission?
Graduating from a place like Vanderbilt, your possibilities are vast—for more than nearly any other group of people in history. And you want to make it count. You want to make it meaningful.
So I’ll leave you with this: life is most fulfilling as a team sport. We achieve more, and feel better—together. It’s why we rejoice at being here, now, present with one another. Our connections, and especially our friendships, are where we thrive, and how we move forward, and upward.
You will help each other grow, and figure out hard choices, and feel less alone in the world, and part of something bigger—as successful, and as fulfilled, as you deserve to be. So as you prepare to scatter, to different places and paths, take a moment to look around.
Because you may think, here at commencement week, that your life is all ahead of you. But actually you’re already in it. And many of the people who will be the most important to you are probably sitting around you right now.
Thank you for being here, and congratulations, Class of 2022.
This has been a great conversation. I’m glad to call you my friend, Reid.
Our friendship has led to many paths of growth and understanding, and so I’m deeply appreciative.
Alright, everyone. Hope you enjoyed the speech, and that it got you thinking about your friendships—what you give your friends, and what they give to you.