In this process over the last 10 months, the biggest thing that I probably realized is just how impermanent all of this is. My dad was 72, he was sick, he was diabetic… We were expecting it. My friend Dave, we were not expecting. In both of those things, what I realized is, if I were to die today, I’d feel pretty good about my life.

I’ve tried to do everything that I wanted to do. I want to do a lot more, but I’d see what’s on the other side of all of this.

We’re a speck of dust in time.

We’re 80 years over 80 years times 9 billion on this earth, times a billion years of the earth.

It approaches zero.

I feel comfortable that there’s an impermanence to things, we’re here for a little while. You’ve got to keep pushing. What’s the point in stopping? (25:45)

Often Wrong, Never in Doubt

I make a lot of mistakes, but to be honest with you, this may sound so sick, I don’t really think about them that much. I don’t have that great big thing that I regret. Shit happens. I get a lot of stuff wrong. Most of the time I’m wrong.

“Often wrong, never in doubt.” That’s what I say. And I say it to remind myself because it’s okay. And I don’t get caught up, you don’t need to be right.

I’m not ashamed of being wrong. I don’t know what my biggest mistake was. I know that I’ve made a lot of them. I should be making more in the future, if I don’t, that’s death. (59:12)


That was a perfect example of me expressing my bias. Part of my bias came from my insecurity about not having a grad degree. Part of my bias was just feeling inferior [to people with MBAs], that I’ve felt for huge amounts of time.

What I said at the HBS thing was me spouting off, making myself feel better about my biases. It can matter, it doesn’t matter. I would rather say that there are ways of figuring out how valuable you are that are independent of those traditional signals, whether you have them or not.

Changing your mind is so powerful.

It makes for really bursty, difficult, marriages at times. My wife will tell you. But man, is it powerful in business: Change your mind all the time.

Really good, scaled, leaders want the right answer and they’re fine with capitulation, they’re fine with change. They really are, because they just want the right answer.

You can get so invested in an answer, and you build up all this superficial logic to reinforce it, versus saying, “I don’t know, let me — you know what? I changed my mind.” (50:00)

Deciding What You Do

There’s all this psychological burden around failure which is self-inflicted. Nobody actually looks to put you down. And so it’s you really internalizing that that’s actually true and as a result there is literally nothing to lose. There’s nothing to lose. All you end up doing is self-actualizing. I mean it’s crazy — this is like psychological first principles. I’m not saying that that part’s easy. Because you have to basically remind yourself of that every day because then you have all these other people who are like, “Oh, I have a job at Deloitte, look at my condo” and you’re like, “Oh, I’m still poor.”

So I get it. But you have to see past the superficiality of those decisions. And I’m not saying those are easy either. I was in a horrible financial state. I grew up on welfare my whole life. I was not in a position where I could not make that decision initially. And when I went to Nesbitt Burns, I was taking a job for money. And so I did it, and when I quit it was a real punch in the gut for our family because I was the oldest kid and I was the one paying for everything. So, I’m not saying it’s easy, but I didn’t have much to lose, actually.

I think everybody has to have a set of experiences that get them to that point. And everybody’s time horizon will be different. Mark [Zuckerberg] can drop out of Harvard. I mean think of how hard it is for you to drop out of Harvard. Like, that is way harder than dropping out of San Jose State, I must imagine. Right? Or Laurier. It’s Harvard, you know? Or Waterloo. It’s like, dropping out of Waterloo’s hard. Right?

So he got there really early, he got there when he was 18 years old. I got to my point in life when I could make a decision like that at 23 years old. Some people make that decision at 38 years old. The question is, are you giving yourself a chance to be introspective enough to get to that place in your life?

Where you’re willing to take a shot and work for yourself, do the things that you like, independent of how people judge you?

That’s a big deal. No matter however that manifests and whatever you end up doing. And that’s what I mean by box-checking. I was listening to this podcast. There was a woman who was telling this story about how she was sent to Catholic School, first day, grade one, she’s like, “Oh my God, don’t ever send me to Catholic school, I don’t want to be told what to do. I want to read what I want to read,” etc.

The story goes full circle where she ends up teaching first grade in Catholic school, falls in love with that whole process, ends up becoming a nun. And then lives out her entire life, in this whole thing. What was amazing to me is that you can make all kinds of decisions that seem box-checking, but for her that was not box-checking, that was living her truth. For other people, being a teacher may be box-checking. Do you see what I’m saying? So it’s not the superficial manifestation of what you do, it’s how you got to that decision. (37:55)

Find Your Path and Stick to It

If you would have asked Mark [Zuckerberg] what he thought Facebook would be he would have gotten it totally wrong. There’s an honesty here, that there’s a lot of luck that was between literally finding a version of a Facebook which was a product in US colleges, to now this global force that unites the world.

This idea that all of a sudden at a super young age you have a sense of all this stuff is bullshit. It’s hindsight, and it’s romanticizing something that was frankly a lot of serendipity.

Why that’s important is that right now I think the culture, particularly in Silicon Valley is so mercenary around talent and people. People hopscotch from job to job, they try to get every single little checkbox they can. It’s a very dangerous time in many ways because you’re much better off gaining some sort of perspective. That’s not a function of time, but it’s a function of experience. I look back at the years that I spent at AOL which were quite frustrating if you thought about it because here I am languishing at a place like AOL while my friends are working at Google and this and that, and it’s all working and nothing that we were doing was working. And they had equity and we were worthless.

But I got real experience. And I refined a point of view. And I really think, why can I do what I do? It’s because I have a extremely precise and very specific and unique world view. I got that through those experiences. The idea of being a founder is not the goal. It’s the byproduct of a point of view. And then the question is, how do you get to a unique point of view? And you get it through experience. And you can have them in totally different ways.

There’s the superficial manifestation, the notion of being a founder today is like what, yesterday, you would have said the notion of going and getting an MBA. It’s just bullshit. It doesn’t mean anything.

You either have really invented a really unique nanomaterial, or you’re bullshitting. Do you know what I’m saying? You either are really capable of designing something really clever, or you’re bullshitting.

You’re either really gaining a perspective because you’re doing something super interesting at a smaller company, but you care about what they’re doing, or you just go back to Facebook, or you’re bullshitting. You know?

Your entire life is going to be based on this idea of introspection, self-actualization, and blocking out the outside and noise. Everybody is trying to put you in a box. Every single person is trying to figure out a little way of just attaching a little label to you, so that you become incrementally more predictable to them.

You have to find a set of experiences that allow you to push back against that. And so you should focus on those. That’ll come through your friends, which is why you need to have an eclectic group of friends, by the time you spent [at school], where you go to work, having the courage to do things that are a little uncomfortable for you, force you to push back on the societal infrastructure that’s telling you to do the opposite. That’s what you need to be doing. That’s the roadmap.

And then the output of that will be all the other stuff that is superficial around it. Maybe you do start a company. Maybe you join a company, and then you start a company. Who cares? Those are, again, byproducts of a path. You’ve gotta find your own path, and have the confidence to stick to it. (43:05)


It was incredible. At the time, it was horrible! Lived above a Laundromat, in Ottawa, Ontario, in a little French ghetto called Vanier. But I went to a really good high school, Lisgar Collegiate, every little rich muckity muck went there. I didn’t. And so I secretly hated all of them. But what it really was doing was lighting this unbelievable fire, this nuclear reactor inside my stomach, where I’m just like, “I am just going to win.”

And, you know, it wasn’t really until Waterloo where it really started to really unlock, particularly in these work terms where I was in the work environment, I’m like, “I can crush.” I just knew that I could do it.

Yeah, so in hindsight it was the best thing. Now, part of it, why is was the best thing is I’ve now taken enough time to be introspective, to self-actualize, and to deal with it. But it came with immense amounts of baggage. And for a while, I just needed to be rich, because I was so poor.

And then you get there, and you’re like, “Wow, this is really going to amplify either the best parts of my character or the absolute worst parts of my character.” And there’s probably a year where it was the worst parts of my character, but I, again, it’s like, for me it’s been a journey of self-learning. And it was a hugely instrumental thing. Like I look at my children and I’m like, “Wow, what boundary conditions could I possibly even remotely give them that will allow them to struggle in a way that makes them want to achieve great things?” (21:25)


Work at a Place that’s Not Working

I think everyone needs to work at a place that isn’t working. And the reason is because you’re forced to actually really be good. When things are really working, it’s like a combination of luck — a lot of luck, a lot of really good momentum, and pejoratively you can also call it inertia. But when things aren’t working, and literally like, nothing was working, you know, the merger was a disaster, there was all these inquiries among all these European antitrust guys, the DOJ was still looking at the AOL Time Warner merger…

All the good people were being fired, all the other good people were retiring, and so there was nobody left. And so you just had to figure out how to do something. And when you’re forced to do that, then you’re actually forced to try to be good at something.

And the thing that I latched onto was these kinds of businesses that all had these kind of interesting similar social-type properties, which was just about building really good features for individual users. Which, at the time, was not a paradigm that people understood. You built products at people. And this was the first time you started to build products for people. And now it’s kind of the norm. It just seems like a comical thing when you wouldn’t think about it that way, but at the time that wasn’t true. And making that phase shift was really interesting. (0:48)

Discern Between Luck and Skill

I was really young. The best thing that happened to me was, AOL was in a period of deep decline, and they were firing everybody in sight. They would obviously fire the people that were getting paid the most, which roughly equated to the people that were the oldest, and doing the least. And what was left over were all these young people, and we would just get increasing responsibility because they just didn’t have an alternative.

I tell people now that was the luckiest thing that happened to me in many ways. When things work, I think a lot of people pretend they know what happened, but you actually learn more when things aren’t working. You know what your effort hasn’t done, versus, what could have been a whole bunch of things has done.

Was it your effort? Was it timing? Was it skill? Was it an accidental PR thing?

Twitter blew up — if you remember, I mean literally, and no offense to Ev and those guys — but not because of those guys, I mean that team has done more to retard the progress of Twitter. It blew up because Fred Wilson and those guys decided to blow it up at South by Southwest.

We had the fail whale constantly, and infighting. All you do in success is conflate luck and skill, but in failure you learn why all of these things aren’t working. You learn how to build a better team. A small, lightweight, fast, nimble team.

You learn how to try and iterate and test stuff. You learn how to celebrate failure because most things aren’t working. And you keep trying stuff, and trying stuff, and trying stuff, and you just dispense with the ego.

I was surrounded by these people that were credentialed. They had all these degrees, they were just able to check all these boxes. They had a name that was pronounceable. Like all this shit, and they were fucking morons. You just realize, that’s just not what it’s about.

I look at this [room] and I see an unbelievably diverse group of people. You people are gonna take over the world, you people are what I was 10 years ago. And there’s this establishment change that is happening now.

And so for me, what I learned was that establishment change has to happen.

And so that’s what sustained me, because I was like… I’m a little frustrated, but I’m learning. And I’m getting self-confidence to realize what the old parochial white man tells me, is not right: “He don’t know what the fuck’s going on.”

That’s a huge realization, and everybody’s realizing this in their own, sort of, personal shape and form now. And so we’re unlocking different parts of people’s brains to be able to think they’re capable of anything. I felt that at AOL. But the problem was, I didn’t feel it enough of a way. So when I got offered a job to go and work at Mayfield, I took it because I went back to the same patterns that I was exhibiting when I took that job at Bank of Montreal.

It’s the job that people wanted. It’s what society tells you is important. It’s the hardest seat to get.

But I walked in there and I thought within two months, “Wow I made a huge mistake.” I played to the rules of the man.

I didn’t listen to my own gut. I didn’t have a way to tell my parents why something else I was doing wasn’t the right [thing.]

Today, it’s the easier it’s ever been for you guys to be independent, you know, because you can point to success cases that validate the choices you’re making.

Six years ago, there were fewer of those. Ten years from now there’ll be even more, because a bunch of you guys will be crushing it. So it’s gonna get easier, and easier, and easier. But at the time, it was hard for me.

I grew up on welfare. How do you tell your parents, “Listen. I had a job making a lot of money, and I quit.” And I was making not that much. Then I finally got promoted at AOL, I’m making a couple hundred thousand dollars a year, I quit again.

So every time they’re like, “Okay, economic light right around the corner, right around the corner,” I left!

It just seemed like that’s not what you do. You get in a seat… and for them, the idea that you’re an executive, I was 27 years old. “You’re an executive, at this company, that’s known. That’s everything!” And to me, it was nothing.

And I just didn’t have the courage to do anything about it. And then, this Facebook thing, I finally just said, “I just gotta follow my gut.” My instincts were telling me this is it. Something is here. And I made the most important and the best investment of my life, which is I made a choice of my time. (14:14)

Accidental Luck

I got accidentally lucky. The great thing about Silicon Valley right now is there’s a lot of companies where you can get accidentally lucky. You have to have a thematic sense of what you like, and then you just have to sort of give yourself one or two iterations to get to the place you want to be.

While Winamp was great, I ended up at AOL for a while, which was okay, not that great. But then that allowed me the platform to then get to Facebook, and that was amazing. (9:34)

Success and Failure Through Luck

One of my general life principles is, people conflate luck and skill all the time. The things that work are actually not that meaningful, because you don’t really know, in the moment, why something is working. Oftentimes when things don’t work, you have a very good sort of trail of breadcrumbs, that that thing is not the right thing in that moment, for a bunch of important reasons.

And so I have to tell people a lot, I’ve learned more when I worked at AOL — which was highly dysfunctional, extremely political, archaic, decaying organization at that time — than I’ve learned in many other situations. You’re in a situation where you have to unpack why all of these things aren’t working, and then tell yourself, if I’m ever in this position again, these are all the things that I’m never gonna do.

That was probably the most instructive team situation that I was in. And then when things really work, like at Facebook, you’re kind of just like, “Is it working because I showed up today? What if I didn’t show up today, would it still be working?” Probably most of it’s working because Mark showed up in 2004. You have to approach it with just a tremendous amount of humility.

When things work, longevity comes because you don’t take yourself too seriously. When things don’t work, it’s a perfect opportunity to do what most people don’t spend enough time doing, which is actually trying to gain true knowledge because society’s incentives just aren’t built that way.

Society’s incentives are built to wrap a bunch of nonsensical BS and terminology and verbiage on top of things that are working, so you can basically pretend that you know what you are doing. And society undervalues things that don’t work because we want to lionize winners and we basically throw away people that don’t win.

That’s why Silicon Valley, by the way, is so special. The value system is actually inverted. The people that have started things that were spectacular flame-outs actually get more respect than the people that have actually built something that worked. And the reason is that we appreciate that ambition. And we’re like well, if but for the grace of God, we as well.

The line between that failure and success is so minute that you see a lot of these folks that get on the right side of that, and all of a sudden it’s like you know, their… I was gonna say their shit doesn’t smell but I know we’re on TV. So, their poop doesn’t smell. And you just laugh at them because they’re just complete clowns in real life. (3:20)

The Most Valuable 1%

I am an elitist. I’ve always been an intellectual elitist, I’ll be honest with you. I was never an elitist about where you went to school, I was always super insecure. I’m this kid from Canada, I grew up in Vanier, poor. Blah-blah-blah… I’m working with all these people that went to Harvard, Stanford, Yale. It’s hard to go into a place like that every day and not feel a little insecure.

Everybody went to Harvard at Facebook. I mean, like, everybody. And whoever didn’t go to Harvard went to Stanford. And so you feel kind of schleppy. But, over a number of years of working, then you’re like, “Actually, no, I’m good. And not only am I good, I’m better than all these guys.” And then you think to yourself, how many people are like that? That grew up in Ottawa, that grew up in Toronto, that grew up in fucking Karachi, and can kick ass?

There’s a ton of these folks, and the problem today is that the framework for how society assigns value is dated. It’s based on a degree, it’s based on a school, it’s based on a lineage, it’s based on a pedigree, it’s based on your gender, it’s based on all this fucking bullshit that doesn’t matter.

And so, for me, I was really interested in what does the world look like if you can capture the top 1%. And most people think when you say 1% you mean the rich people. Who cares about those people?

What about the most valuable 1%? The smartest 1%. The most ambitious 1%. Those people drive 99% of the gains in the world. They do. They do it at every company, they do it in every state, in every province, in every city… everywhere.

And I wanted to start a company that built an index of those 1%ers. (35:40)

The Importance of a Degree

If you go to Carleton or Ottawa, and you feel insecure because you didn’t go to MIT, you shouldn’t. Or you went to Algonquin and you didn’t go to wherever — you shouldn’t. None of us should. All of that stuff doesn’t matter. (45:15)

A Different Kind of Education

For all of you who are going to get a lot out of school, there’s a lot of folks that you probably know who will not. And who will have benefited from a different kind of education. All we needed to do was give them enough self-respect, and respect, to say that’s okay and equivalent to me, even if I graduated from a B.Sc in electrical engineering from Waterloo. (1:09:40)

Passion and Ambition

You have to have passion and you have to have ambition. And ambition is important. You have to be willing to fail at big things. You have to. And it may not be that you do that right away.

I wasn’t in a position, frankly, to have the courage or the psychological underpinning where I’d… It took me 13, 14 years to not give a shit what other people thought. Everybody takes their own amount of time to get there.

My framework was: I’m making enough now, I can give money to my folks, I can help my sisters, it’s great. I never thought, “Oh, well let me just go and totally throw all of it to the wind, let me double down on the equity…”

I don’t regret it. I made the decision when I was capable of making the right decision, and I had enough ambition where the scope of what Facebook’s potential represented to me overcame the remaining insecurity that I had.

But if I tried to make that decision in 2002 or 2001 or something else, I would not have made, maybe, the right decision. And so everybody has their own path. This is why I’m saying, it can’t now be all about you dropping out and you finding your 20-year-old buddy and starting something and going into an accelerator. It can’t also be about working at a company the rest of your life.

The point is, everybody has to find a different path, and I just think that right now, what we do is, we focus on one model at the exclusion of every other model. Instead what you need is you just need a diversity of different ways of getting to the right place.

But the thing that you need to have is ambition, and then you need to give a shit. And most people just don’t give a shit.

If you do anything important, in any field, it will initially not be understood. What’ll happen is, people will think you’re either crazy or stupid, and you will think you’re not good. (45:40)

Naïveté and Fearlessness

I don’t think people have to be good speakers, I don’t think they have to be good presenters. I think people have to care about whatever it is that they’re talking about, that has to be demonstrable. You want to see a little sense of naiveté and fearlessness. (38:40)

The Possibility of Winning

I was a little overweight, people called me a Paki… I fucking dealt with that shit for 15 years. I meet these amazing women that talk about how they’ve felt, you know, maligned as they’ve tried to — my other partner is a Pakistani Muslim, what he’s gone through — and I fucking empathize with that. And it gives me energy because it’s like, these are the people that should win. I want to win with them. They should win, you should help them win. And then other people like them will feel better about winning. And that it is possible to win. (37:20)

Two Paradigms for Careers and Entrepreneurship

The problem with that hyper-mercenary culture is all of a sudden you’ve completely divorced yourself of any sort of passion and a reason why you’d want to work at a company. The end result of that is that you’ll not do as good of a job, and you won’t make as much money.

When I went to Facebook, it was kind of a joke thing, that people didn’t totally understand. Most of my friends thought it was kind of comical that I would even go there, because I didn’t have to go there. But I believed in this idea, at the time, I described it as a White Pages for the world. And it just grew, and grew, and grew into something that had such massive impact.

And then the ramification, the end of it, was, to be very blunt, was just extraordinary wealth. But I think if I had tried to seek it out that’s not what would have happened. And I worry that a lot of people are just in the grind, you know, trying to jump into this thing, try to arbitrage, trying to make a little money…

I just don’t think, particularly in technology, it’s the goal, because there’s just such a vicious cycle. There’s just so much churn. It’s hard. Most of these things don’t work. If you come in motivated by the wrong things, you never achieve anything, and then you just end up jaded and disappointed.

I think unfortunately a lot of incubators are very problematic in that way because they just create a bunch of very jaded young folks who are just acquisition fodder.

That would be my advice: you have to take a step back and try something that’s defined in one of two paradigms.

One is, you yourself want it. Madly want it, need it. Travis, when were driving, I was on the phone with [Travis Kalanick]. He started it for himself. Zuck started Facebook for himself. Ev started Twitter for himself. Larry and Sergey started Google for themselves. So, that’s one category.

There’s this other category which is there’s this market-defined opportunity that’s screaming for a solution. But if you can’t basically jump into something because of those two things: you’re attracted by a market solution or you’re attracted by a product you want to use yourself, you’re just a scheme-scammy arbitraging fuck, and you’re just gonna get left behind. You’re gonna get found out by people like us, and you’re gonna get fired.

That’s raw, real advice. Don’t do it. You’ll make more money doing something you love, trying to have impact, than you will trying to make money. (4:05)

The prevailing wisdom, all of this blathering rhetoric about, oh, everything starts as a trivial thing… people laugh at trivial things. I get it, but I think that language is fraught with a lot of hindsight bias.

The reality is, I’m not sure if people are thinking about whether it’s trivial or not trivial. Again I go back to, someone built something for themselves that they needed.

That language is a very convenient way of trying to explain something that I think was much harder to explain and much more innate. I think you’re either gonna build something you really like, or you should go into this other category.

I transitioned myself from building something, and helping build something that I wanted for myself, to building something for the market. And the reason I did that was a very simple view that I had, which overpowered this. I felt like I had everything I needed. I didn’t need anything else. Nothing was really bothering me. Except this idea that the right people weren’t getting to the starting line. And what do I mean by that?

People die and of those people that died, one of those people could have been the next Steve Jobs. And when you unpack why are they dying, there’s many reasons that should have a reasonable explanation.

Or, people are undereducated or miseducated. You need a degree from blah-blah-blah university to get in the door at blah-blah-blah place. Why? And so now you’re locking and shutting people out. You’re not getting money to the people that you should get money to, that have the good ideas.

So, to me, those problems now dominated the way that I thought about what I wanted to do with my time. (30:40)

Code and Confidence

I would really encourage a couple of things. One is, we all need to know how to code. All of you people just demonstrate the fact that this is the lingua franca, this is it. Half of you can probably speak English.

English doesn’t matter, it’s inefficient.

But this is the lingua franca of the 21stt century. So knowing to code is a critical skill.

Having an internal sense of confidence that the things that may have isolated you as different are now the strengths that make you powerful.

You guys are coalescing. This is a power dynamic. This is the new establishment. You are it. You’re deciding. How sick is that? That’s sick! And so, once you realize that, what you have to figure out is, how you can now be more true to that inner voice?

That’s a really big challenge. But I think that’s a skill, figure out that. (27:00)


I grew up so frustrated chasing this ideal. It just doesn’t amount to much. Once you get into the veiled curtain — now I’m in this position, I get to fly around, meet anybody I want, and so many times, I’m so disappointed. Because the image of what I thought that person represented was just so much higher than the reality of what that was.

And then when I come back to the Valley, I feel at peace, and I feel challenged again. I feel like these people are real and they’re trying to do stuff. When I’m here [at Waterloo], I feel the same thing. And so that’s what we all have to realize.

You people have to take over. Otherwise the world is fucked, you understand? You have to take over. (29:10)


I went to a very good high school, the rich high school — not the high school I should’ve gone to. I would be so ashamed that I worked at Burger King. At some point, there was this release moment where it was just, this is my life. I can’t do anything about it. This is what it is right now. I had a sense that I could figure some stuff out later, but I didn’t really know. So I just accepted it. The minute I accepted it, I wasn’t ashamed of it. When I wasn’t ashamed, I could start to be inside my head, like, “What really matters?”

The Canadian government didn’t want the Rodney King riots, so I was able to take all of my dad’s rejection letters and call every single one, and one of them gave me a job. I worked at this well-known telecommunications startup in Ottawa. They had a really burgeoning tech scene at the time.

I worked at this organization that was run by this really iconic guy, Terry Matthews. And he was a “billionaire.” I was like, what the fuck is that word?! I didn’t even know a fucking “thousand-aire.” What is a billionaire?!

[Terry] was risk-on. He was so dynamic, on the businesses he started and how he viewed his place in the world. I was enthralled. (4:20)


What does grit and resilience come from? Well, it has to come from a personalized struggle of something that you care about. And so for me, what I’ve been spending a lot of time with is, what is the context that I need to set for my kids? I think I can do a lot of context setting in the construct of healthcare.

In an educational world, I really do believe I’m going to give my kids complete freedom to be able to want to go and achieve, anything they want, even in the absence of a degree. I want them to step off the bridge and fall flat on their face. And I don’t have a toolkit of what the tactics are. It all comes back to this idea of grit and resilience.

Oh, by the way, like, the educational system has a huge role to play, too. Like we have coddled, and diapered, kids all the way up through high school now, where you don’t really put them in a situation, where they can overachieve or underachieve with any meaningful consequences.

Everything’s managed to the middle. Our sports infrastructure’s all about everybody gets to score a goal, everybody gets to get on the field. It’s not just a parental thing, because even if you try to do something and punch your kid in the face and kick him out in the snow, it doesn’t matter because everybody else will be there with 19 blankets and a warming hut, and the police. So there’s nothing you can do by yourself. (23:12)

Betting the Farm

I live by a very simple philosophy, and it’s not mine. I was flying home from Vegas with Vinod Khosla on his jet. VK says, “Chamath, look over here.” We’re flying into San Jose, and he says, “Look over this side.” It’s all this land. He says, “See all that land?” I’m like, “Yup.”

And this was like, eight years ago, ten years ago, something… and he says, “I own all that land. You know how much that land is worth?” I say, I don’t know. He says, it’s probably worth $200 million. And I say, okay. And he said, “You know how much I’m worth?” And he said some number, three or four billion… and he said, “I’m gonna take that three or four, and it’s either gonna be worth 40, or it’s gonna be worth zero. And if it’s worth zero, I got that [land].”

And he went and funded alternative energy, genetics — just amazing, amazing, groundbreaking, risk-seeking stuff. I was not in a position to think, or act, or do any of that. Until about three or four years ago. I want to try to live like that.

A lot of the money that I have is gonna come back to [Waterloo], and this place is gonna be the nuts. Like, it’s gonna keep getting better, and better, and better. The rest of it is going to go into genetics work. It’s not going to my kids, it’s all gonna go away.

I’m just gonna free roll it all, and I’m gonna end up with a ton of it that’ll go back into the world and do a lot of good, a lot of it in hopefully folks like your hands.

And so that’s how I view it; I’m a risk-seeking individual.

You know this from poker. The best thing that my parents taught me about growing up poor is they were never ashamed about being poor. I was ashamed about being poor, they were not. (46:30)

Validity and Authenticity

It doesn’t have to be successful. I’m just myself. I can be authentic. All of this money that we’ve been lucky enough to accumulate, and make, and compound and all of this stuff, it could vanish tomorrow. Will you say everything that I’ve said is invalidated? (19:25)

An Exceptional Learning Organism

A lot of how we invest is in a process that we call, becoming an exceptional learning organism. Now that may sound gobbledygook-y, but let me just unpack it for a second. Today’s world is so incredibly dynamic. Everything is changing. And the rate of change is so rapid and it’s so multidimensional. To think that one knows the answer, a priori, is really, really, really scary to me.

It’s my job to coach [companies] that not knowing is okay. And then it’s my job to coach them on a framework that allows them to learn, on the presumption that they will react quickly enough to the things that need to be fixed as they learn it.

So across all the investments that we do, whether it’s cancer, or diabetes, or education, or rockets, or social media, that’s the goal. Because nobody knows what’s going to be around the corner in three months, six months, a year.

We have a bunch of these interesting social media investments because we want to be learning, to try to answer the question. I don’t know what the answer to the question is. (5:49)

Live Your Life

It’s funny, and this is going to sound flippant, but I don’t particularly care. Now, that’s taken me a long journey to get to a place where I can comfortably tell you that answer. But I don’t care. I don’t care what they think.

I’m on a path. I have to do what I have to do. I’m at a point in my life, now, where I have to be very inside-out motivated, and so it would be disingenuous for me to give some glib answer about what I want them to think of me because honestly, at some very, very, basic level I just don’t care.

Everybody grows up in these social hierarchies that pound into you certain ways of behaving and certain value systems. That happens if you’re born a woman instead of a man, that happens if you’re born black vs. white, or if you’re born Muslim vs. Catholic… All of these things basically have, in unfortunate ways, these predefined expectations of you as an individual. And so in many ways a lot of people, despite their best intentions to break away from that, get beaten down into a system where that’s what they end up living out.

And so, you know, in my example, my parents emigrated to Canada. We grew up on welfare, I’m kind of like, very honest with it now, because I’ve accepted it and lived it. I was deeply ashamed of it when I grew up. I was a pathological liar about it when I grew up, and all my friends knew that I was lying. I’d have them drop me off like 18 blocks away from where I actually lived and I would walk home. And I pretended I lived in a house that I didn’t live in, I mean, it was crazy.

I was deeply trying to live out… because I went to this rich high school, and I was like the only not-rich kid, and so it just created all these things that it’s taken me a long time to unpack.

And when I went to school my parents were like, “Oh you have to be a doctor or an engineer or a lawyer, because that’s the only way we’ll feel socially validated for all the sacrifices we made to be here.” And I did it. I checked the box. And then when I graduated they were like, “Oh you need to do the thing that’s most respected; I went to work at an investment bank for a year.”

So for many years, I was living my parents’ life, and I was basically getting outside-in validation. And then at some point, it just started to chip away where there was this little circuitry break, and I just kept saying, “I just don’t feel right about the decisions that I’m making.” And that culminated, ultimately, after I went to a place like Facebook that gave me tremendous confidence in my own abilities.

I was just always telling myself, “I just don’t feel like I’m living my life.” And look. I have it much easier than other people, because I think that the struggles that they go through are much deeper and much more psychological. I mean, I didn’t deal with like tremendous abuse in that way. It was just more of a constant Chinese water-drip torture of like this is what you should do, this is what you should do. It’s just very hard to push back and say no, because there’s no counterfactual to measure it against.

It’s taken me a long time to unpack all of this, and to be truly comfortable with who I am as a person, to not care as much… It’s helped that I’ve been successful because it validates my own internal sense of self-worth. All these things are precursors. I’m not saying there’s some magic formula, and you read a book, and all of a sudden you have this great self-confidence. I’m just saying that, I think that a lot of people want to live their own life, inside-out, and I think that they’re all looking for ways in which they can get, an amount of success that validates the choices that they really do want to make in their life.

I go back to, well what if there were systems that actually created a more democratic way for a different class, and a broader class of people to run the race and be successful? You’d probably have, in broadly-speaking terms, a more self-actualized, confident society. There’d be less bravado. As a result, I think at a very macro scale, there’d just be a lot less bad things. And I think that’s probably, generally good for all of us. (14:25)