https://www.youtube.com/watch?v=Njj6HZvixK8 (21:40)

And that’s what we did. And what happens is that when you do the first few key interesting investments along that premise, those people tell their friends, who also tend to be these crazy, eccentric, blighted people because they don’t represent the canonical sense of what is a great venture investment anymore in Silicon Valley. It just perpetuates.

And to be honest with you, I think it’s better that we don’t know anything about these spaces. We learn with them, which means that we’re more inclined to take the kind of disproportionate risk that traditional folks won’t take.

https://www.youtube.com/watch?v=59uTUpO8Dzw (10:40)

https://www.youtube.com/watch?v=6H37iyvEZJ8 (1:17:50)

Like as an example, so Punit [Singh Soni] and I work together right now. He’s an EIR. It’s so funny, he doesn’t want to talk to me because it’s just too bursty. You can’t deal with it all. He has an amazing team that he’s working with, so it’s like, “I’m just gonna come to a point of view, I’ll give you like 30 minutes to give me some feedback,” and literally we sit in the room and he just goes, “I just need yes, no’s, yes – no – yes – no – yes – no – yes – no. [Laughs]

And we try to react and interchange and then he goes off. He makes different decisions, hopefully some better. I make a different set of conclusions because of his feedback so… Yeah, I’m not going to claim like I’m a know-it-all or like a company whisperer, that’s not what I do.

I have a very precise sense of what is possible in the future, and I’m not afraid to lose money. That’s the best two things you can have as a VC. I think. Because I just don’t care about the money. And so it’s wonderful. All we’re ever going to do is learn, or be right.

In no context are we ever wrong. We’re learning or we’re right, that’s it.

https://www.youtube.com/watch?v=D82_ppT2iic (31:54)

An interesting question would be, well what would happen if companies were forced to pay more towards the theoretical ceiling of what an individual generated for that company? 50% of the value. 80% of the value. You can’t do that in the absence of transparency.

When you’re hiring me, it’s not like every other person who’s trying to hire me also knows.

So to me, it’s a really disruptive idea that the very, very, good can basically become like free agents in sports. You can’t hide Lebron’s value. Lebron gets max value. Dwight Howard gets max value. Brent Seabrook gets paid what Brent Seabrook gets paid. It’s beautiful. If you bring that sort of clarifying logic into the business world, it could be really transformational, and it lifts up all these amazing people from all the four corners of the world.

https://www.youtube.com/watch?v=pDVDWNguPs4 (41:36)

I wanted Facebook to build a phone. I think that was well-known. I think it was also well-known that I was building a version of a phone. Whatever.

At the time, it didn’t make sense because it just needed capital and focus and the kind of separation… almost like a Google X kind of an approach, that I think was kind of antithetical to the culture, at the time, of that company. And, in fairness, I think that was absolutely the right decision, and it’s a failure of me, because I also exacerbated that tension.

I had a tremendous amount of political and social capital at that company because of what I was doing. I like lost myself for a little bit and fed my own ego and was on this mission to build a phone, in a not really great collaborative way, using a bunch of decisions that I made myself. That stuff just never ends well.

This was an insight also into what I’m good at. I’m not good at bringing people along. I mean, I’m good at building products and bringing small teams along, and then building things. But I’m not good at leading thousands of people in like an organized way. I’m good at telling 1,000 people what to do, but I’m not good at leading 1,000 people in a collaborative, “Let me get you over the line.” That’s not how I roll. It’s like, “This is what we’re fucking doing, and we’re gonna do it.”

That dog doesn’t hunt at a multi-thousand person company.

https://www.youtube.com/watch?v=pDVDWNguPs4 (21:55)

We would say, “aggressive” and “competitive.” People didn’t like that. We would say, “High quality bar bordering on perfectionism.” But what you realize is, unless you believe that, then you just believe in nothing.

But if you believe in that, you end up self-selecting to those folks that really believe that. When you go and attack a problem, you’re able to work together in a way that just isn’t possible. And that’s what made that place special. And so the next great company that gets built will find a way to thread that magic together. But it’s a people magic. Product market fit exists in a lot of companies.

https://www.youtube.com/watch?v=1dUbrL8b9l8 (25:10)

https://www.youtube.com/watch?v=6H37iyvEZJ8 (1:14:15)

And what that really means is, at least with consumer software, do you understand the psychology of what you’re building to enough of a degree where you can isolate these key points where an average person has this dopamine rush around a reaction to something you’re doing. And then, can you capture it? And, can you make it mechanistic?

And that sounds like a bunch of gobbledygook, and what it meant to Facebook was, I would see how literally people would emotionally react when they saw somebody from 10 or 15 years in their past, as an example. And then we saw that when women would post seven photos men would actually post three more photos, and it’s like all these things and so we just started to document, characterize, measure, analyze. We built it into a massive system that allowed us to amplify what was naturally happening.

So the takeaway when I left and I started Social Capital was, “Wow, we can probably do that.” And the question was, can we do that for any kind of company? Can we do it for an enterprise company? A healthcare company? A rocket company?

And it turns out you can. Because they’re all struggling with the same thing. It’s how do you get a group of people to understand the context of what you’re doing? How do you make it analytical enough so that it’s measureable, so that you can scrub out all the anecdote and the lore. Everybody loves the bullshitter at the water cooler who has their version of history, but we all know they’re a bullshitter, but when nobody else says anything we take it as fact.

You have to basically invalidate that guy. And then you can actually start to have a systematic way of understanding how to make a company successful, and it applies to anything. You know, my wife and I have started a bunch of local businesses in the Palo Alto area to make the culture and… they’re food businesses. Artisanal ice cream in a restaurant. And it applies to there, too.

You create context, you create some measurability, you create some analytical framework, and that’s succeeding. I just think it’s a universal principle: a collection of people against a mission, embodying a similar set of values, understanding context, and then not being able to bullshit. It’s amazing, that last part, how important that is.

https://www.youtube.com/watch?v=D82_ppT2iic (18:33)

So, it’s not a checkbox, you can’t have a person with the rule, it’s just how you have to live. You know, in Waterloo the biggest thing that I lacked the most was any of that. I had maybe two or three electives. My entire time here. It’s limiting, because there’s just so much of the world that I just didn’t understand. I would not have said that I was an open-minded as I am today. And by having gone to San Francisco, which probably is the most extreme form of open-mindedness possible, I was forced to confront a lot of the biases that I’ve had. And what I realize is now, the people that I surround myself with today are so different than the people that I surrounded myself with earlier on and I’m so much better for it.

So there has to be mechanisms where, at a very young age, you push yourself out of your comfort zone. I remember in Waterloo, there were all these Indian people and all they would do is hang out with each other.

I just found it so stupid. If I wanted that, my parents should never have left Sri Lanka. I could have been as happy as — what was the point? I remember when Brigette and I first started dating it was just so uncommon because you have this Asian, and a South Asian. And now it’s much more common. You just have to force yourself into states of discomfort so you can expose these boundary conditions. Otherwise you are just emotionally and intellectually stunted. And I think you’re never going to achieve your potential that way.

https://www.youtube.com/watch?v=TlIyhYALSLA (9:20)