I gave a commencement speech at Vanderbilt earlier this month. It’s an honor to share these transitions in life, so I try to share transitions from my own life’s path.
Along that path, many of the most impactful lessons that shaped my perspective, decisions, and ultimately the actions I took came from my friends.
That’s why I decided to share stories of some of those key moments between friends with the graduating class of 2022. Each story represents a core truth about friendship:
- When there’s something important you don’t know, real friends will tell you about it.
- Your friends can help you see what you can’t see.
- Friends will tell you not what you want to hear, but what you need to hear.
- Your friends help you the most by letting you help them.
My first book, the Startup of You, came from the commencement speech I gave to my high school – the Putney School. When I was talking about this with my partners at Greylock, we thought this most recent speech was also applicable to the entrepreneur community. I pared the speech down slightly, taking out some of the comments that were specific to the Vanderbilt community, but the key elements are all the same.
You can listen to the pared-down version on the Greymatter podcast by following the link below, and you can watch the video from my full speech at Vanderbilt here.
I am so very glad to be here.It is really an honor to share this day with you. When I got this invitation, I was excited because you all have such enormous potential to improve the world.
So I thought, Oh I’ll talk about 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 I realized what I most wanted to talk about was friendship.
Not the Hallmark kind – not all sunshine and roses and bunny rabbits. I mean real, substantial friendship – that’s sometimes really hard, and that shapes and changes our lives.
In fact, alongside your family, making, cultivating and keeping close friendships may be your life’s most important work.
Yeah, to help your career; building a network is more critical than ever. (I’m the LinkedIn guy, I’m not gonna tell you otherwise). But more than that, friends will be absolutely central to your sense of happiness, connection, and meaning.
Also, friendship is a conversation. So, I want to try something today that feels 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 from back before you were born – in the prehistoric haze of the 1980s.
What I learned then was: When there’s something important you don’t know, real friends will tell you about it.
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 about college was, y’know, “the college” – The teachers, the skills, the degree, the institution.
But within a month I knew I was wrong.
"When there’s something important you don’t know, real friends will tell you about it."
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 that what would matter much more to me, were my fellow students.
[Compared to] 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, cuz 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. But no one else had ever cared enough to tell me that I needed help.
And what’s great about Kyndaron was, 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 out 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 get 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 – I don’t know if you 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. 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, 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 you are now. And what I learned then was that your friends can help you see what you can’t see.
So at 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 and 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. Because while Oxford’s philosophy department was one of the world’s best, The professors there seemed only to want to talk about esoteric technical theories, with hardly any interest in, y’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.
"Your friends can help you see what you can’t see."
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 large scale.”
I was like, “Yes.”
“Why do you think philosophy is your only path to do that?”
And I was like, “Ohhhhh.”
And Stefan said that if academia wasn’t getting me there – well, 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.
Went back 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. 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. (If you’re not sure yet, that’s ok.)
And, that’s where this lesson comes in. Again, your friends can help you see what you can’t see. They’ll help you, you’ll help them, you’ll all do better and go further.
So that was my 20s. It wasn’t until my 30s 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 the company PayPal. And after several years of 100-hour weeks, a lot of luck, and a few scrapes with federal banking rules, we’ve just sold PayPal to eBay.
I was 35. Completely exhausted. So I was planning to take 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).
But as a couple 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 south of Sydney to this beach bungalow for some catch-up.
And Ned’s like, “So, post-PayPal, what are you thinking about?”
I say, “Well – I’ve been watching this website “Friendster, transforming peoples’ social lives, (Facebook didn’t exist yet). And so I have an idea for a different kind of social network, to help folks’ 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.
"Friends will tell you not what you want to hear, but what you need to hear."
Because Ned had been around when I first arrived at that. He knew that about me, and as a good friend, he wasn’t going to let me off the hook.
You can guess the rest. I changed my tickets, flew back home, got to work 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. [In that scenario], I don’t get funded, and the whole thing doesn’t happen. [Similarly], no long friendship with Ned, no frank talk… no LinkedIn.
Now 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’ve found it’s just the opposite.
You have a team. Some of your key teammates are your friends. And the ones you share your dreams, 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.
OK, here’s the last lesson I’ll share. It’s maybe the most subtle. But also 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 from 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, and have dinner, and play games, go on vacations, all those good things. But it’s when I’ve helped the people I know best, towards the goals and values I know them to have, that I have most felt: “Ah. This is why I’m here.”
I’m thinking of a particular late-night talk 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 with his wife, cleanly. Long story short, that conversation made a big difference in Oscar’s life. They stayed together. A family with kids and very happy.
But that’s not why I’m mentioning it today. For one thing, Oscar’s not here (and besides, his real name isn’t Oscar, and what kind of friend would I be if I took a private talk and shared it on a podcast to the internet?).
I’m mentioning it because it was also one of the key experiences in my life.
"Your friends help you most by letting you help them."
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.
1: Decide to make friendship a priority.
Because it isn’t a side hustle, it’s the whole game. Making an active choice that friendship matters to you is your best first step to ensure its place in your life.
2. 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 it 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.
3. 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, and anyone starting their work journey, 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 today your possibilities are vast – more than for 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, 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.