https://www.youtube.com/watch?v=UZn8MEsQwOg (19:25)

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.

https://www.youtube.com/watch?v=UZn8MEsQwOg (14:25)

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.

https://www.youtube.com/watch?v=7TOnKXBabpM (5:49)

https://www.youtube.com/watch?v=1dUbrL8b9l8 (1:09:40)

“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.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (59:12)

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.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (46:30)

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.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (29:10)

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.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (27:00)

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.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (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.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (30:40)

https://www.youtube.com/watch?v=Njj6HZvixK8 (37:20)