Thank you so much for being here today. >> Thank you for

including me. >> I'm so

excited to dig into that career and your thoughts on the Valley.

And I'm going to start us off with one of the things that jumped out at me in my

prep for this interview.

You are an extremely generous tipper. >> Yeah.

>> I love that and

I would like to know why. >> So, I mean,

it's well known and part of why I'm so open about this is that I think

it gives permission for other people just to be honest.

I grew up in a very kind of dysfunctional household on welfare.

And that compounded a bunch of shit in my life that was not great.

We were very focused on money.

It was a huge point of pressure and tension in the family.

It created massive depression in my father, drinking.

Just, it was very dysfunctional.

And there was some point along the way where I was like, okay,

is money like really important or not important?

And I feel very lucky because I don't think if you ask my sisters,

they got to the same place that I did.

But I ended up not coveting it.

And I found it to be something that I could use to really

empower myself to do the things that I wanted to do.

And so, in a situation where you know you go to like a restaurant.

If you really empathize with the people that are working there,

I see people who are like me, brown skinned,

working hard, creating these beautiful experiences.

And then I can celebrate it by, I guess, giving a YELP review.

But you can't buy food for your kids with a fucking YELP review.

>> [LAUGH]

>> So I want a tip.

And, I mean, it gives me so

much joy because it's like you'll have a 3 or $400 bill.

In some cases, you tip 500 bucks or 1,000, and you close it.

And they're expecting $40.

And, I mean, I'll get a little emotional, but

they will come out to you, and it's transformational.

And so it's so great.

It's just like little things like that mean a lot of people.

And just to be anonymously generous like that,

I think it's a great gift that I have the ability to do.

That's why I do it, I love it. >> And

it sounds like the experience of being seen.

And you are seen and the individual is seen, and

you're sharing in that [INAUDIBLE]. >> Well I mean, it's funny.

It's like 99% of the time they don't say anything,

because they do the bill thing afterwards.

And they for sure can't pronounce my name.

And so they for sure have no fucking clue who it was that gave them the tip.

It's fine, it's totally fine.

But I love it, I absolutely love it.

My friends freak out.

Now it's caused tension actually,

because now when I go out with my friends, they know as well.

And I've just made it very easy, which is like, hey, if we're going out,

let me just fucking pay.

Just like, it's fine, and it makes it simpler.

Okay, yeah.

I want to dig into what you were describing about your upbringing and

this unique position that you've gotten to where you don't feel that you covet money.

But you see it's power and

the use that it has in furthering some opportunities for you.

How did you develop that?

How do you distinguish between luck and skill?

How do you end up in that position? >> So I,

My parents craved money, meaning they needed it

because my dad was unemployed for long stretches of time.

My mom was the sole breadwinner.

She was a housekeeper, then she was a nurse's aide.

And I would just see how she grinded.

We didn't have a car for a long time.

She takes the bus, we all take the bus.

When I got my first job, it was at Burger King.

I'd take the money, and I had give it to my parents, and we would buy bus passes.

And I remember telling some of my friends, I went to a very good high school,

kind of like the rich high school.

Not the high school I should've gone to.

I was able to go to this different high school.

And I would tell them, like, I would be so ashamed that I worked at Burger King.

They would sometimes come by, and I would just be like fuck.

And then at some point, it was this release moment where I was,

this is my life.

I can't do anything about it.

This is what it is right now.

And I kind of had a sense that I could figure some stuff out later, but

I didn't really know.

And so I just accepted it.

And then the minute I accepted it, I wasn't ashamed anymore.

And then, when I wasn't ashamed I could start to actually be inside my head, like,

what really matters?

So then what happened was there was these massive racial riots in Los Angeles.

And not as if the fucking American government did anything about it.

But the Canadian government was like, shit, let's get all these black and

brown kids jobs, because we don't want the Rodney King riots in Toronto, and

Ottawa, and parts of Ontario.

And so I was able to take all of my dad's rejection letters, call every single one.

And one of them gave me a job.

And I worked at the well known telecommunication start up in Ottawa.

Ottawa had a really burgeoning tech sense at the time.

And I worked in this organization that was run by this really iconic guy,

Terry Matthews.

And he was a billionaire.

And I was like, what the fuck is that word?

I mean, I didn't even know a fucking thousandaire.

I was like what is a billionaire?

And this guy was risk on.

And he was just so dynamic in the businesses he had started and

how he viewed his place in the world, and I was enthralled.

I was 9 degrees away from him.

But the cult of personality around him in that business, the lore, when it trickles

down to you, was not about his conspicuous consumption or anything else.

It was about okay, we're launching this frame relay switch.

Now we're going to buy this company.

Okay, we're going to pivot the entire business to ATM.

And you were just, it was an amazing time.

And so I took the bus to Newbridge.

Complete luck that the controller of Newbridge would

go from his nice neighborhood through this shitty neighborhood to get on the highway.

And so he would see this guy standing by the bus and

eventually he saw me inside the office.

And one day he stopped.

He said, you want a ride?

Do you work at Newbridge?

I'm like, yeah.

This guy, Sam Legg.

So in the car, he was in the front seat, like beside Terry.

And he was able to tell me how this guy thought about this.

because I would read it in the paper, and I'd be like, why is he doing this?

So it just completely rewired what money was.

For Terry Matthews, money was an instrument of change, right?

He had a market cap, he's like, wow, that's 8 billion dollars of change,

10 billion dollars of change, 15 billion dollars of change.

Versus, there was another guy building a company at the time.

His name was Michael Copeland, who ran a company called Corelle,

also a billionaire.

And he was the exact opposite, had a messy divorce, married some trophy wife.

He took this obscene shiny glass from his building and covered his house in it.

And so you have this dichotomy of two different characters at that time in

the 90sm building really interesting businesses.

Correll, which was a regional business, Newbridge, which was regional business.

They were both very successful, but they manifested money so totally differently.

And I was like, I want to be this guy.

I want to be this mega-compounder,

swashbuckling around, trying to do really cool shit in the world.

How do I do that?

And Sam helped me because you could understand from him what Terry cared about

and then, for me, I just copied.

I mean a lot of my life, quite honestly, is just copying the things that I see.

There's not a lot of original thought here, there truly is not.

We can all pretend we're all fucking geniuses, honestly, be good copiers.

Do you know what I'm saying? >> [LAUGH].

>> It's the best thing in the world.

Be around high functioning, high quality people and

just copy the shit that they do. >> [LAUGH]

>> Observe the shit that's kind of crappy

and then don't do that stuff.

It's not a fucking complicated formula. >> [LAUGH]

>> When did you use that best?

>> No, all the time, now it's funny,

it's like, you have a surface area of ways to spend your time now, or I do.

And I'm in this midst now where we are really scaling up what we're doing as

a business.

And I meet these people that to me are so iconic that they were like

arms length people that are now sitting face to face and

they treat me like a quasi-peer, I wouldn't say peer, but quasi-peer.

But what I see is, I see some amazing stuff and I see some

utter dysfunction in some of the richest, most important people in the world.

And I have to decide how am I going to act?