0:00

I find myself in my early 20s waiting

0:02

tables and I'm looking around and obviously no

0:04

disrespect to anybody that works in the restaurant

0:06

industry, but you could see two

0:08

decades could pass by a blink of

0:10

the eye and I'd still be waiting tables. It's

0:12

the misnomer that entrepreneurs are mistaken with. We're risk

0:15

mitigators. You mitigate the risk so much

0:17

until then you have to take the leap. And

0:19

that's what I think the creativity in entrepreneurship comes

0:22

from risk mitigation. And I always think intuitively

0:24

I always had a good sense of arbitrage as

0:26

an optionality. This is why I can't stand this

0:28

industry we're in, these podcasts we're in. It's like

0:30

it's this gel man amnesia, this Dun & Kruger

0:32

effect where we think that like just because somebody

0:34

has money that they know about everything. Everybody

0:37

has these religions when it comes to investing,

0:39

right? Like the value religion, you know, the

0:41

momentum religion. Everybody's got

0:43

these religions and they never cross over. But

0:45

if you're trying to truly build a diversified

0:48

portfolio of different asset classes

0:50

that you know, Zig, Win the other Zag, et

0:52

cetera, it's like you have to be able to

0:54

put those religions aside and combine things that can

0:57

work at different times and different time horizons in

1:00

ways that people will normally never do. Welcome

1:03

to the intentional investor with Matt

1:05

Ziegler, where he and his guests

1:08

explore the intersection of investing and

1:10

life, portfolio and purpose. Nothing

1:13

in this podcast is investment advice. Nothing

1:15

in this podcast is advising you to buy

1:18

or sell any security or to do anything

1:20

with your money. Seriously. We

1:23

should only act on investment advice from

1:25

someone you know and who knows your

1:27

unique situation. We are not

1:29

that person. Matt Ziegler

1:31

is a managing director at Sunpoint Investments

1:33

and the opinions expressed on this

1:35

show do not necessarily reflect the

1:38

opinions of Sunpoint Investments or

1:40

of Second Foundation Partners. Security

1:42

is discussed in the podcast, maybe

1:44

holdings of Sunpoint Investments. You're

1:47

watching the intentional investor right here on

1:49

Epsilon Theory YouTube. I'm your host Matt

1:51

Ziegler and my guest this week straight

1:54

from the precursor to the lyricist

1:56

lounge. Now, is that some salt and

1:58

pepper in your hair? just the appearance

2:00

of a permanent portfolio of in

2:03

equal parts, salt, pepper, spinderella,

2:05

aka the only artist to be the first

2:08

on the first and last episode of Yo

2:10

MTV Raps. I want to know if you

2:12

got them on your mixtapes. I know we're

2:14

going to get there because I have so

2:17

many questions about those tapes and outside of

2:19

Cassette culture, I can't decide if he's the

2:21

Kobe Jones or the Claudia Reyna or the

2:23

Tab Ramos of finance. Now I know I've

2:26

determined he's not the Alexi Lalas of finance

2:28

because he's definitely going to box the box

2:30

on these vol curve options with the ability

2:32

to play Route 1 on a counter, of

2:34

course, or maybe he's some modern Aladdin

2:37

on a magic Persian carpet ride, stealing mystical

2:39

lamps, Robin Williams's genie, not Homer, of course,

2:41

and not for the in-movie versions of the

2:43

songs because he's playing for the big hits.

2:45

So if I'm keeping it a buck and

2:47

I know he's keeping it a buck, he

2:50

respects Pivo Bryson and Regina

2:52

Bell as much as the next 90s

2:55

slow jam man could. Without further ado,

2:57

ladies and gentlemen, the Teenage Mutant mutiny

2:59

ninja himself, the Captain Hook of the

3:01

Pirates of Pineance. Oh, Captain, my captain,

3:03

the only cockroach you'd ever want to

3:05

see in Napa, but that totally explains

3:08

his move to greater Philadelphia. Mr. Jason

3:10

Buck, welcome to the show. Let's

3:16

go. Let's go. Let's go. I've been so looking forward

3:18

to- Drop the bomb on them. Drop the bomb on

3:20

them. So looking forward to this and you exceeded. I

3:22

didn't even want to tell you how much I was

3:24

looking forward to the intro because I didn't want to

3:26

put pressure on you, but you absolutely crushed

3:28

it. I'm crying. I got to wipe my eyes. That

3:31

is just it is so good. It's ridiculous. But I

3:33

have two things for you. Oh, yeah. Here's

3:35

my guess. All right. I

3:37

think I know who the inspiration is for those

3:39

intros. And I'm pretty sure none of your other

3:41

guests have clocked it. All

3:43

right. You know, we've got there's been a couple

3:46

of comments of people pinching at the edges, but

3:48

let's hear them. Let's hear it. I really hope

3:50

I got this. I believe it's Roger Bennett for

3:52

Men in Blazers. big

4:01

more than anything. Yes. And

4:04

a mix of some other stuff, radio, personalities

4:06

and other things too. But without question, years

4:08

and years of consuming men and blazers and the Raj

4:10

Bennett stuff, I was just like, where, you know, what's

4:13

happening? The greatest thing. I can put my spin on

4:15

this. And you're crushing it. Yeah. It's, it's, it's, it's

4:17

got a little, maybe Pat McAfee sprinkled in there. You

4:19

know, a little showmanship. Oh,

4:21

man. Showmanship. It's just, it's a little sway in the

4:23

morning show. It helped. Yeah. Yeah.

4:26

We're going to, we're going to go deep. Unfortunately,

4:28

there's going to be zero finance in this conversation at

4:30

all. It's just going to be all nineties hip hop

4:33

references. But like, I want to compliment you for two

4:35

things. One is obviously the intros are absolute bangers and

4:37

nobody's doing them quite like you're doing. But then the

4:39

other thing, like when I would listen to these episodes,

4:41

what I don't know how in real time too, you're

4:43

taking such great notes and you recap so

4:46

well, like your skillset is a little bit of a, a little bit of a,

4:48

a little bit of a, a little bit

4:50

of a, a little bit of a, a little bit

4:52

of a, a little bit of a note and you

4:55

recap so well, like your skillset is unparalleled in this

4:57

space as in finance podcasting. And then I'm

4:59

also kind of pissed off though, honestly, because my thesis

5:01

always was like, I always wanted to do a podcast

5:03

with people in finance, and we talked about anything but

5:05

finance, right? Cause I, my thesis was that like, you're

5:07

getting some of the most intellectually curious,

5:10

fascinating people in the world. And let's talk about

5:12

anything but finance. But when I found, when I

5:14

tried to do it is, uh,

5:16

they didn't want to do that. They didn't want

5:18

to expose themselves to not talking about finance. And

5:20

so I applaud and commend you for getting people

5:22

to not talk about finance and expose their, their

5:24

soft underbellities of their childhoods and kind of sit

5:27

back on the, uh, on the therapist

5:29

couch with you. Thank

5:31

you. I'll let that all go to my head

5:33

immediately after we press stop afterwards. But I think

5:35

this is really important because you actually, you hit

5:37

on something right off the top here. Why

5:40

do you think so many people, you've

5:44

got a background in all sorts of stuff. We're going to

5:46

get into this, but there's so many people in finance. They're

5:48

just so much more interesting. Like the

5:50

day to day portfolio management or the tax planning or

5:52

whatever else you start to talk to them and it's

5:54

just, I, I

5:57

never would have dreamt like as a,

5:59

as a. 90s kid who

6:01

wanted nothing to do with anything like

6:03

career path like this. How

6:05

many cool people are gonna get sucked into it? People

6:07

from all stretches of the humanities that would end up

6:09

in this business. Why do you think that

6:11

happens? This is all gonna

6:13

be, I just patted you on the back now, pat myself on

6:15

the back, this is just gonna be for you here to solipsism.

6:18

But a part of it is I think there's two

6:20

kind of things that work. One is a lot

6:23

of, at least on the hedge fund side and

6:26

everything, it's usually people that couldn't really work for

6:28

anybody else. I actually

6:30

say entrepreneurship is a bug, not a feature.

6:33

It's only in the last decade or so that

6:35

we've exalted entrepreneurships, but I've been an entrepreneur my

6:37

whole life and you're just a loser before to

6:39

be an entrepreneur and it's quite frankly, to me,

6:41

you have poor brain chemistry. Like if you had

6:43

good brain chemistry, you'd take a bi-monthly paycheck, right?

6:46

So one, you're gonna have some weirdos there in

6:48

that space. Then I

6:50

just traffic in the deepest

6:53

darkest corners of the esoterica and so I'm

6:55

filled with weirdos in the long ball and

6:57

commodity space cuz nobody's really there, so that's

6:59

kind of self selects. But

7:01

then more importantly, I think when we talk about, like you said,

7:03

how did we end up here? Is like,

7:06

I think in a way portfolio construction is

7:08

like the apogee of a liberal arts education,

7:10

right? Because you have, it's a bit

7:12

of a centaur too, you have this art and science

7:14

to it, right? You have to be able to crunch

7:16

all the data and have all the numbers, but then

7:19

use your imagination to realize what's not in that data

7:21

set. And so those kind of things combine, I think,

7:23

to make that insatiable curiosity that maybe

7:25

you have from a liberal arts education of like, how

7:27

do you apply that to the real world? And

7:30

solve a practical problem of like, what do I do if

7:32

I have savings left over? So

7:34

maybe that's, like I said, that's

7:37

all just patting both of us on the backs, I think, I'm gonna

7:39

break my arm here. Well, there's

7:42

something too about it, the whole, the

7:45

entrepreneur as somebody who's fundamentally unemployable in

7:47

some way. And then

7:49

there's this sick thing about the people

7:51

who are fundamentally unemployable who aren't just

7:53

looking for people to necessarily

7:55

like employ to amass their own operations

7:58

through their own things. like

8:00

we want to go out and invest in other people

8:02

or partner with people. And this was, spoil

8:05

this if you want to at all, like the whole Pirates

8:07

of Finance thing, like that's a whole thing. Like a bunch

8:09

of entrepreneurs on a ship together who are out on the

8:11

high seas like trying to like get the bounty. There's

8:14

a real spirit of that in the corners of this

8:16

industry. I think it's a beautiful thing. Yeah,

8:18

I think there's, you know, we have these

8:21

unconventional names, right? Like media funds or a cockroach

8:23

fund, you know, strategy is like, you

8:25

know, why do I do that? Well, one, I'm

8:27

always fascinated by naming conventions, right? But the hard part

8:29

is every name is taken. You think you have a

8:32

great name that you Google it's already taken. And then

8:34

in finance, people have all of these, you

8:36

know, Greek mythology names and

8:38

or like three letter acronyms. One, I can't remember the

8:40

three letter acronyms. So there's no way I was doing

8:42

that. And then yes, I can do the Greek

8:44

mythology and philosophy with the best of them. But I just felt

8:47

it was a little maybe too pretentious for us. And

8:49

you know, we come from outside the industry. So

8:51

I was like, you know, I had this idea

8:53

for a mutiny for a long time. And I

8:55

was like, you know, it's probably you know, actually,

8:57

our original working title is ataraxia, which is inter-Greek

8:59

philosophy for unperturbed by external events. And luckily, like,

9:01

what are you doing? And then for like the

9:06

idea of mutiny, though, there's many reasons behind it. But

9:08

one of them is like, yeah, we're the the

9:11

mutinous, you know, entrepreneurs, where are the people that are

9:13

really going for it? Where are the people are doing

9:15

something different, where there's just so much like kind of

9:18

CYA sameness, like kind of across finance and investing these

9:20

days, that we just played up that, you know, we

9:22

come from outside the space. And so we're not going

9:24

to hide from that. And we're gonna have a little

9:26

fun with it. And to me, like, you know,

9:28

you can do that stuff at the end of the day, you

9:31

got to be so good, they can't ignore you, right? Like, it's a little

9:33

bit of a, you put a target on your

9:35

back at the same time. So I don't know, I'm willing to

9:37

take that pressure, I guess. And you

9:39

know, here's the targets on our backs. We can

9:41

pat those targets all the way to all the

9:43

way home. All right, take me take me all

9:45

the way back. I mean, you can tell me whatever

9:47

you want about childhood. One of the big things I

9:49

need to know about your childhood specifically is

9:52

the attitude towards sports in your household

9:54

as a kid. Because my understanding

9:56

is pre soccer, like you

9:58

guys like I guess we

10:00

grew up in the round the same

10:02

generation. Like even watching soccer was not

10:04

normal. No, no, I'm so jealous

10:06

now that with the amount of soccer you can watch and basically

10:08

you can watch any league in the world, right? Like so exciting.

10:11

So I'm glad we have it now, but we didn't have it

10:13

then. I mean, I remember I had all

10:15

these like VHS tapes of

10:17

like premiership, like highlights that I would just. The best

10:19

goals, the best goals. The ear tapes. The best because

10:22

they'll have some. The hard men too, like Vinny Gascoigne

10:24

and stuff like that. Like, do you remember those ones?

10:26

Those were the ones we were hearing. Oh my God,

10:28

yeah. Take it way back on

10:30

those. Those beautiful baggy Umbro uniforms. Those are

10:32

the good old days. So

10:35

yeah, I just grew up in a fairly unconventional

10:37

household in many respects. One of which

10:39

is a lot of people joke we were raised

10:41

by like the Royal Tenenbaums. And so Mavia, my mother,

10:43

we had to, you had to be like number one

10:46

in your class in schoolwork. And then you had to

10:48

be like number one on the athletic field no matter

10:50

what your domain was. And then

10:52

through my father, my father

10:54

was really into unconventional sports. So he was a

10:56

triathlete, a mountain climber, a sailboat

10:59

racer, a scuba

11:01

diving instructor. So it was like we, you know, in

11:03

our house, we grew up watching, you know,

11:05

they had triathlons, the Tour de France and,

11:08

you know, America's Cup. So we didn't really

11:10

watch conventional sports. So it

11:12

just turned out over time, you know, we played pretty much every

11:14

sport growing up, all of us did. But

11:16

then my brother and sister are twins. They're only a year and

11:18

a half younger than me. So we're all basically the same age

11:20

and same household. And so I ended

11:22

up going on to play like division one soccer.

11:25

My sister was an all American gymnast at Brown.

11:28

My brother played on the number one hockey team

11:30

in North America. He decided to not go play

11:32

juniors, but he could probably went that route and

11:34

played at Boston College eventually. But so yeah, that

11:36

was the chaos we were raised in is like

11:39

you, you know, you had to be number one

11:41

in school and you had to be number one on the field. Was

11:45

dad just showing you like by example, like,

11:47

hey, I'm into these weird other things or

11:49

was he like taking out scuba diving and

11:51

sailboating and all the other things? Yeah,

11:54

he'd take you out, of course you do everything.

11:56

But I mean, it was, there's so many, I've

11:58

tried to think of so many stories. Like you

12:00

would, even, he was windsurfing in like the 80s

12:02

on our lake in rural Michigan. And

12:04

so he would put me on the front as a toddler

12:06

on the front of the windsurfing board. So I would go

12:08

out windsurfing with him in the mornings. With him. Yeah,

12:11

with him. And then before school, in

12:14

high school, him and I would go, we'd go water

12:16

skiing on the lake. You know,

12:18

at school, you know, when September, October, the lake

12:20

got too cold, we'd water ski before class every

12:23

day. You know, he

12:25

was always just, and then triathlon training, he was

12:27

just always out running, biking, and so it was

12:29

just part of it. We had actually a dog

12:31

that would go running with him. The dog would

12:33

do 12 to 15 miles a day with him.

12:35

So it was just like, we were raised in

12:37

a very odd household. And so my dad was

12:39

one of his side hustles was basically he became

12:42

a, he had assistant scuba diving instructor for a

12:44

scuba diving shop in rural Michigan. But

12:46

then these guys would take their clients out to

12:48

like Micronesia and all over the world on the

12:50

scuba diving trip. So my dad would get the

12:52

trip paid for because he was an assistant scuba

12:54

diving instructor. And so when we were all

12:56

like 13 years old, we were all PADI certified, like as soon

12:58

as you could be and everything like that. And

13:00

so the way you know, now that I've gotten older, I

13:03

can reflect the hard part about this is like, I kind

13:05

of hate narratives is because, you know, narratives, we just tell

13:07

the highlights, you know, we forget all the other parts, and

13:09

we make it sound like it was some sort of linear

13:11

progression. But the way I kind of

13:13

think about it is we were raised in this kind of

13:16

very bipolar childhood, in the sense that like

13:18

my father was like, this weird Buddhist,

13:20

you know, Zen Buddhist in rural

13:22

Michigan into alternative sports and was

13:24

like a dirty hippie. And

13:26

then my mom was like this hardcore entrepreneurial,

13:28

you know, Catholic capitalist, and you know, really

13:30

into these other things. So it's like, we

13:32

got pulled so hard in both directions that

13:34

like we kind of figured out our own

13:37

path down the middle, hopefully. So

13:39

talk more about your mom then for a second.

13:41

Like what do you mean she was the Catholic

13:43

capitalist? So if

13:46

you want me to make a state joke now,

13:48

I can make that here comes the Dapopa. Yeah,

13:51

exactly. So her family

13:53

like grew up, you know, when those big Irish Catholic

13:55

like kind of rural families were like, you know, they

13:57

had, you know, chickens and vegetables in

13:59

their yard. You know, they were they were organic

14:01

farmers before organic became cool. It was organic because

14:03

you were poor, right? And the second day, right?

14:07

And so they grew

14:09

up, you know, like nine kids, like that

14:11

typical kind of rural Michigan Irish Catholic household.

14:14

And you know, she was just always, you know, trying

14:16

to make a buck. And so she was always an

14:18

entrepreneur. She was a realtor for most

14:20

of my life. Now she owns a movie theater

14:22

at Napa Valley. And, you know, she was always

14:25

hustling. We grew up, I think I lived in

14:27

12 different houses

14:29

by the time I was 18, because she was like

14:31

she was flipping houses before that came a thing. And

14:33

so we were always living in construction zones and everything

14:35

like that. And so my

14:38

dad came from a more well off family where my

14:40

great grandfather was an inventor that invented a lot like

14:42

machine tool stuff and had some companies. And it just

14:44

so happened they went to the same high school. And

14:47

and so that's where they got together. Where'd

14:50

they like where where'd they meet? Where'd that relationship start?

14:52

What school or what high school did that happen? What

14:54

part of the country? So this is

14:56

great. It's called Gullick High School. It's

14:58

in rural Michigan, outside of Kalamazoo, Michigan.

15:01

And the funny part, like my mom

15:03

was like top 10 in her class. And my dad

15:05

actually got kicked out of high school. And so they

15:08

were they were pulled, they've always been polar opposites. And

15:10

so my parents were very young when

15:12

they had me, I think my dad was only like 19 when they

15:14

had me. And so when I went to high school, I would end

15:16

up going to the same high school. And the

15:18

first day of class, they'd always go like Jason Buck. And

15:20

I'd be like, yes. And I'd be like, wait,

15:22

you're not related to Tracy Buck, are you? And I'd be like,

15:25

yeah, so I had a lot of the same teachers that had

15:27

kicked my dad out of school. And so

15:29

it was just like, starting off on like a

15:31

bad foot, like every time, but it's just one

15:33

thing to have a bad older sibling. Nothing to

15:35

have a bad dad. Yeah, it's like, that's my

15:37

father. I got all those genes in me. So

15:39

yeah, but my mom was top 10. Like I

15:41

think she was like number three in her class

15:43

or something. So it's just it that's something they're

15:45

both just kind of polar opposites. And

15:48

I mean, we're gonna keep on filling in

15:50

the nuance around your details here. Just curious.

15:52

So the the twin brother and

15:54

sister just behind you. So she

15:57

goes gymnast, he goes hockey.

16:00

But I'm assuming she's not a professional gymnast anymore

16:02

and we know he's not a professional hockey

16:04

player. Where did they end up or are

16:07

they like running hedge funds somewhere too? No,

16:09

when my brother, when he

16:11

ever stopped playing hockey, I think he had like five of his

16:13

teammates played in the NHL and everything like that. One

16:17

of his best friends was Ryan Miller, the goalie that won like

16:19

the Hobie Baker award play for the Sabres. So he probably might

16:21

have heard of him. And then he

16:23

decided when he wanted to go to college, he didn't want to... Typically

16:26

in hockey, you go play juniors in Ontario for a few

16:28

years and then you go to college. And he

16:30

just wanted to go right away. So he ended up

16:32

going to Boston College, got a degree in like biopsychology,

16:35

which prepared him well to now own

16:38

restaurants. So he owns a restaurant in

16:40

Charleston, South Carolina, shout out to Coterie.

16:43

But he eventually he kind of worked his way

16:45

through the death and colonnage in New York for

16:47

a craft cocktail bartending. And he ended up opening

16:49

bars in New York for them and even moved

16:51

to Mumbai for two years and opened up like

16:54

the best bar in Mumbai. And

16:56

so he went down that path. My sister has

16:58

always been the the Golden Child, the high achiever.

17:00

So she she's pretty much stopped at every Ivy

17:02

League school on her way to becoming a gynecological

17:05

surgeon, actually a Eurogynecological surgeon. And yeah,

17:07

she lives with her surgeon husband in

17:09

Miami and they met at University of

17:12

Chicago. So so she's

17:14

definitely the Golden Child. And they add that that

17:16

that gymnast gymnastics career is always cut short. And

17:18

I was shocked. She's actually like five seven. So

17:20

she's always been very tall for a gymnast. But

17:23

it was always one of the best gymnasts in

17:25

the country. Like growing up was, you know, an

17:27

all American or freshman year at Brown and just

17:29

always crushed it. Were all of

17:31

you like at least at the young age because

17:33

of probably especially because of dad's influence. You're also

17:35

the generation where everybody plays 18 different

17:37

sports to start. And then you slowly narrow

17:40

in. Yeah. How many sports did young

17:42

Jason play? Man, that's

17:44

right. I think I've said I played I played ice

17:46

hockey, soccer, basketball,

17:48

tennis. I did water

17:50

ski, snow ski, snowboard. It

17:54

just basically everything but like football and

17:56

baseball. Like everything like your traditional sport.

17:59

Yeah. and you hate steak and

18:01

potatoes. And yeah. So

18:04

you skip out on all those. Does that like, do

18:07

you find yourself in an, are you in an

18:09

out group like from growing up because you're not

18:11

in those main core things, especially that part of

18:13

the country, not playing baseball and football. Are you

18:15

aware of the city young age or are you

18:17

just totally integrated because you're who

18:19

you are? Yeah, just, I wonder if

18:21

like, I assume like, it

18:23

maybe took me till I was a lot older in life where I realized

18:25

maybe I am slightly different, but I don't want to assume I'm different from

18:27

everybody, but I always felt like I was an out group. Like I always

18:29

just felt I was very different. The one

18:32

good thing is like where I grew up, it was

18:34

a very like soccer centric community. So like the football

18:36

team sucked, but the soccer team was great. And a

18:38

lot of these guys went on to like national careers

18:40

and everything. So at least that was fairly normal. It

18:42

was just like a lot of the other little things

18:44

too, is like I said, with a Zen Buddhist father

18:47

and a Catholic mother, they let us choose our own

18:49

adventure with religion. And so that's one of the deep

18:51

explorations I started at like 12, 13 years old. And

18:54

so I was always kind of out of step there. Yeah,

18:57

I've always, I mean, a lot

19:00

of people think I'm just blatantly contrarian, but I

19:02

think for the most part, I go along to

19:04

get along, but maybe because of that weird upbringing,

19:06

I have some contrarian streaks to me. Church

19:10

as a kid, like was mom taking me to mass?

19:12

Were you doing communion and all that stuff? Or was

19:14

dad intervening and saying, you can do this much so

19:17

long as we do whatever else? They

19:19

let us do what they wanted. So my dad taught us meditation

19:22

in, I mean, as far

19:24

back as I can remember. And this

19:27

is like I said, as you know, it's very popular now, but

19:29

in the early eighties in rural

19:32

Michigan, not popular. And then

19:34

we would go to church with my mom's

19:36

family. And this was even at a time

19:38

when they would do mass in Latin. So

19:41

we were mass in Latin at the Catholic church with

19:43

my grandparents, doing Buddhist meditation with my

19:45

dad. But then when I started around 13, I

19:48

would ask my parents, I'd go with friends to other

19:50

churches, synagogues, everything. I just wanted to

19:53

explore all of it. And we'll get

19:55

into that, I'm sure. So that's what

19:57

led me down the path of exploring

19:59

kind of comparative religions and. just the

20:01

global sense of either traditional churches or

20:04

mysticism, etc. So

20:06

is, we're definitely getting into all that. We'll probably

20:08

get to you at age 19 by

20:10

the end of this conversation. It's where I'm assuming. This

20:16

piece, do you get good at, what's the first

20:18

thing you get really good at? Is soccer the

20:20

emergent skill that all of a sudden you're like,

20:23

this is an area of focus or does something

20:25

else happen first? That you get really good at,

20:27

that adults are like, whoa, Jason's good at this

20:29

thing. I was really good at hockey first. And

20:31

so that was the one that really blew my

20:33

mind. That was the one where I was really

20:35

winning all the awards and everything was in hockey.

20:39

And then my brother's playing the same sport. So around 13,

20:41

for whatever reason, if I can recall correctly, I

20:44

switched to soccer and my brother stayed with hockey.

20:47

But that was where I first started

20:49

getting those accolades in hockey. And then

20:51

we were all in these gifted education

20:54

programs. I would go to a separate classroom with

20:56

me and two other kids, and we had special

20:58

teachers and all that stuff. So that was part

21:00

of it all. But I say

21:02

all that with, smiley because then

21:04

once puberty hit, I just went totally downhill.

21:07

Everything changed in my life. I went

21:09

from probably straight A's to D's immediately.

21:11

Once I discovered girls and all this

21:13

other stuff, everything changed from

21:15

that aspect. But it was originally more

21:17

like academics and athletics with hockey first.

21:19

And then I started, I guess, selling

21:22

stuff as an entrepreneur school at 12, 13. So

21:25

I was always trying to make a little

21:27

hustle here. So that's the other part of

21:29

that bipolar upbringing or tripartite upbringing. It was

21:31

like, we just, yeah, I always was selling

21:33

stuff, trying to get some freedom, make a

21:36

little money, buy some candy. So

21:38

let's talk about finding a little scratch

21:41

as a middle schooler and getting this

21:43

together. We have this

21:45

in common too, where there's just, what

21:47

do you think? What was the, was

21:50

it just mom and dad saying, I'm not giving you

21:52

money for that, but if you have your own money,

21:54

it's okay. Was it just the sense of independence that

21:56

came with it? And then what

21:58

was the first magic trick where you're like, oh, somebody

22:00

give me money for this stupid thing that cost me

22:02

nothing. Yeah, unfortunately we learned too early that their money

22:04

makes the world go round. But it's also

22:06

one of the things I think about when I talk about

22:08

entrepreneurship being a bug, not a feature. And it's very rare

22:11

that I find anybody, even in our age just now, is

22:13

like, tell me what you sold at 12 or 13, right?

22:16

And then I'll tell you if you're an entrepreneur

22:18

or not. Rarely does somebody come to entrepreneurship late

22:20

in life. It's usually these kids that were hustling

22:22

something and then, what's that Yvon

22:25

Chouinard quote or something? Show

22:28

me an entrepreneur and I'll show you, like a juvenile delinquent.

22:31

If somebody says, this sucks, I'll do my own thing. And

22:33

so it was like that freedom,

22:36

that juice it gave you. And

22:38

then it's just honestly, I think more than anything,

22:41

it's like solving complex problems or just figuring out

22:43

a solution. And so one of the first ones I

22:45

think was just making bracelets, right? Like braiding

22:47

bracelets and selling those in school at 10, 11. The

22:51

one where you and I are gonna get along all

22:53

too well on is setting my alarm in

22:56

rural Michigan to get up at two o'clock in the morning

22:58

for YomTV raps to, I had a

23:00

dual cassette tape player that I plugged into

23:02

my TV. And I would wait for

23:04

the commercial brace to come off and then when they jump into a

23:07

video and hit record. And so from like

23:09

one to two AM, I would record YomTV raps. Then

23:11

after putting all those together, then I'd burn them on

23:13

the dual cassette. And then I would take cassettes

23:15

to school and I'd flip them for like five bucks at cassette

23:17

when I was like 13, 14 years old. And

23:20

so I was like the purveyor of

23:22

rap in like southwest Michigan, growing

23:24

up because I don't think anybody else had heard of it at

23:27

that point. We'll be able to

23:29

trace all these weird things back to, were

23:31

there any downstream effects that you're aware of? Did you inspire

23:34

anybody to go off and do anything cool? God, that would

23:36

be amazing if I had a story. I was like, yeah,

23:38

you know this guy named Mike Posner or Big Sean? Right,

23:40

right, right. No, I don't have any. I don't have any.

23:43

My tapes. They would. They

23:45

would. Fill up the mixtape like

23:47

you owe me royalties now or something. No,

23:50

not that I know of, but it's

23:52

amazing. Have you heard the theory, The Browning

23:55

of America? You're

23:57

talking about Steven Stout, like the whole tanning of America,

23:59

that whole thing? Yeah, I think of Steve

24:01

it's out but like I think you got it from somebody

24:03

else originally but it was about like basically our generation grew

24:05

up with like MTV and then more importantly Yum TV raps

24:07

and BT and then like, you know other generation

24:09

like kind of copy black music but it was like for

24:11

ours was like front and center but then even more so

24:14

than like our heroes our TV shows are

24:16

entrepreneurial like people we looked up to were all

24:18

black and so it's like this was the first

24:20

generation that they think almost led to like Obama's

24:22

election because it was like the browning or tanning

24:25

of America because it just became part

24:27

of our daily lives to like aspire to

24:29

be like you know like like black culture

24:31

in general yeah it's really

24:34

interesting to start to unpack the whole aspirational shift that's

24:36

probably a rabbit hole that was to put down on

24:38

and all the routes on the time for this but

24:40

the hard part is to is like you know unfortunately

24:42

we're going up one of the biggest ones is far

24:44

from they both rap to entrepreneurial to a producer scene

24:46

was P Diddy so now I'm not sure how much

24:48

you want to say you know you looked up to

24:51

P Diddy as a teenager right but you know yeah

24:54

but there's I don't know it's the cross currents of

24:56

all these things like you have to unpack from like

24:58

what we know now versus what we know then and

25:00

what parts of the culture of all sorts of cultures

25:02

that we are a part of it and

25:05

touched on because even that stuff's weird I mean

25:07

I'm still at some point

25:09

I get around to it I need to do a

25:11

review of the Rick Rubin book that I I

25:14

love the Rick Rubin book but I've noticed I've

25:16

had a completely different experience from that book than

25:18

most people who talk about that book because

25:21

they're like I feel like all

25:23

these people think he's like this like Zen philosopher yeah

25:25

and I'm like Rick Roman toll tagline

25:28

was like I like the worst shit so

25:33

it is the ultimate highbrow lowbrow yeah well so

25:35

it's your general takeaway well I that's

25:37

different a quick aside only because you'll appreciate

25:40

this like do you know who we co-wrote that book

25:42

with the the creative act I do you know who

25:44

the co-writer is basically the ghostwriter on the book it's

25:46

the guy who wrote the pickup artist like

25:48

it's like nothing as

25:52

Neil Strauss or the crew he's built or anything else but

25:55

like a key to understanding like how this book came

25:57

to be is understanding that this is a guy who

25:59

loves the worst shit. Like

26:01

he wants extreme highbrow and lowbrow mixed together.

26:04

And that's what makes it interesting. If we

26:06

focus it just on the Zen philosopher side,

26:08

we miss out on all that beautiful nuance.

26:10

And that to me is the

26:12

interesting thing here. So other related question

26:15

to that, do you have the audiobook version? I

26:18

actually ended up doing both because I was really curious

26:20

about it. I love the audiobook. Did you? Yeah. Because

26:22

I just throw it on every once in a while,

26:24

right? When I'm like, I need to kind of zone

26:26

out Zen out and be a little meditative is like

26:28

just listening to Rick's voice is like the one thing

26:30

I won't listen to on 2X speed, which by the

26:32

way, I wish like it's so weird listening like hearing

26:35

your voice on 1X speed. But

26:37

yeah, that's I know I'm the same with all that

26:39

stuff. Yeah, I highly recommend the audiobook for anybody because

26:41

you can just dip in and dip out. Right. And

26:43

then just Rick's voice is so good on the audiobook.

26:45

And then and then his podcast is so aspirational to

26:48

me in the sense that like you can just say

26:50

five words and have a three hour podcast. That's awesome.

26:52

I want to do that. Him

26:55

and the Rory Sutherland one. That's one that

26:57

I've gone back to multiple times because that

26:59

one is just like that's yeah,

27:01

it's basically the walk where I can't stop taking my

27:03

phone out to take notes even on re-listens, which I

27:05

can't understand. Rory Sutherland is

27:08

human catnip for entrepreneurs. What

27:11

do you make of that? Like why like that? That's

27:13

also one where I mean since what 2000 basically

27:16

since the financial crisis sometime around there was when the

27:18

first one of his like YouTube speeches went viral and

27:20

I was just like to your point

27:23

human catnip. Like I can't do this.

27:25

This is I've read Alchemy like Seth

27:27

Godin with a British accent giving me

27:29

twice the provocations. I love it. Crack.

27:32

Everything you said it like it must be

27:34

right. He's got that British accent. So I

27:36

think it's going to that entrepreneurial sake of

27:38

like you need a contrarian idea,

27:40

right? You need to solve a blue ocean problem.

27:42

And that's what Rory Sutherland is so good at

27:44

thinking about. And then it maybe starts shifting your

27:46

brain to see things like or like it's an

27:49

inversion in a way too of like just looking

27:51

at, you know, things from a different point of

27:53

view. Last

27:56

Rick Rubin thing and then we're going back to, you know,

27:58

middle school mixtapes. hear this

28:00

Alfred Hitchcock interview thing that they posted on

28:02

the Tetra Gramit, whatever that is. I don't

28:04

know how they did it. It's just it's

28:06

been working me for the last like week

28:08

or two since it came out. It's really

28:10

cool. I think they assembled like

28:12

snippets of this Hitchcock interview with like

28:14

him. So it's like he's asking questions.

28:17

But it's, are you a Hitchcock person at all?

28:19

Any fast news with that or? Somewhat. Like I

28:21

do like Hitchcock. Like I wonder if they stitched

28:23

together like a notebook, like LM styles, that kind

28:26

of. That's what they did. I'm very curious if

28:28

they used AI in some way, which almost would

28:30

make it even more interesting to me. But it

28:33

was really good. It's really worth your time.

28:35

You want more catnip in your life. Yeah,

28:37

I tend to dip in a different type

28:39

of Tetra-Gymaton and then likewise in Hitchcock. I

28:41

saw you like a pre-war German cinema. I'm

28:44

a huge. I love movies. And

28:46

I always liked Hitchcock. Never necessarily been my

28:48

favorite. Okay, interesting.

28:51

So old movies, you're a big movie nerd.

28:53

Yeah, I mean, over my

28:55

lifetime, I probably watched thousands of movies and read

28:58

thousands of books. And to me, they're pretty much

29:00

equal in entertainment value. And one of my one

29:02

of my life goals one of these days is

29:04

just to like somehow take two years off and

29:06

just watch the Criterion Collection over like a two

29:09

year period. Oh my god, yeah, absolutely. Just get

29:11

like a nice seaside, like, you know, hotel room

29:13

or something and just just two or

29:15

three movies a day. Every day. Absolutely.

29:17

A man can dream. Like, isn't it great? Like, the

29:20

quote the other day is like, I was like, you

29:22

know, getting older is just saying, you know, if I can just

29:24

get through the next two weeks, things will slow down. And

29:27

that's just like that forever. And I just feel

29:29

like that's it's all my life is anymore. Yes.

29:33

And then there's also those weird glimpses of

29:35

where you see stuff. So now take me

29:37

back in middle school and be another

29:40

segue before we get back to music. So

29:42

movies at that age, were you a consumer

29:44

of movies from that era? Yeah,

29:46

I'm trying to. And I'm not asking about movies from that

29:49

era. I'm more curious in the question. My wife always asked

29:51

me, how the hell did you see this when you were

29:53

like in middle school? Like, who was giving you the blockbuster

29:55

card to go out and get this? Oh, my God, that's

29:57

so good. That's such a good thing. Well, one, I generally

30:00

I hate the. for like movies, fashion, everything. Like I just

30:02

think it's one of the worst variations of all time. So

30:05

you got a Rick Rubin, like, high-low, bro, right? And

30:08

I hate to do a broad paintbrush like that, but.

30:11

I'm pissed. I was laughing because

30:13

you ever seen the Brothers Bloom? So we get a

30:15

movie, like. Yeah, yeah, yeah. With

30:17

Mark Ruffalo and Adrian Brody. And

30:19

he's just like, he's like, I hate

30:21

to paint an entire country with a paintbrush, but

30:23

Mexico's a horrible place. It

30:25

was a thing we laughed just generally. I'm trying to feel

30:27

like. So the movies was

30:30

hard, right? Because like back then, right?

30:32

Like, how did you get that content? And so

30:34

I would go to all the local ones, but

30:36

like where we live, we had to drive like

30:38

30 minutes even to get to a blockbuster. And

30:40

yeah, I was prime blockbuster days and everything. But

30:42

then I remember from like the Kalamazoo, Michigan area,

30:44

you can take the train to Chicago or Detroit.

30:46

And so I would go to Chicago a

30:48

lot as a kid or when we were younger, and I

30:50

would just, the art house films there, like art house theaters

30:53

just blew my mind. Like that was one of the most

30:55

exciting times in my life. You know, we go to cities

30:57

to see art house films. The other thing our mom would

30:59

take us into Chicago a lot to see like plays

31:02

and musical theater. Like that was one of our other things

31:04

is like, we also had to be educated in the arts.

31:06

Like, you know, so I'm saying we would have raised by

31:08

like by wolves and savages trying to like, I don't know

31:10

what they're trying to do with us, but try

31:13

to create, I don't know, Uber mentions or something,

31:15

I don't know. And they, but we would go

31:17

in to see plays and live theater all the

31:19

time and stuff like that. So that's, I guess

31:21

like the art house film scene, I don't know

31:23

when exactly what age or what film. I don't

31:25

have like a real epiphany moment in that that

31:27

I can recall, but it's been

31:29

something I've just been obsessed with. And I just, I

31:31

watch films every day. I just obsess over films and

31:34

like every genre of film, it's separate like four or

31:36

stuff like that. I don't really watch, but like, I

31:38

just, nothing. I get totally lost

31:40

in films. And all the time people get mad at

31:42

me. Cause I'm like, hey, have you seen this? And

31:44

they're like, I watched it with you. And I'm like,

31:46

yeah, I, I co-lead, I zone out. Like willing suspension

31:48

of disbelief. I'm fully immersed. I have no idea who's

31:50

with me, what's going on. You know, I'm just in

31:52

the, in the film. Are you

31:54

the same way with music or theater or

31:57

anything else? Or is film a unique experience for

31:59

you? I think films generally

32:01

meet that way, but I think it happens. Yeah,

32:03

I can get really lost in music. Theater,

32:07

somewhat, not as much. Maybe

32:09

it's not as immersive or I get distracted by other people in

32:11

the audience. That's the other thing. I don't, even

32:13

though my mom owns a single screen theater, one of the

32:15

oldest ones in the country, like I hate watching movies with

32:17

other people. I just want them to shut up, you know,

32:19

especially. Like, so I just like, I like to focus in.

32:21

So maybe that's why theater maybe is a little more difficult.

32:23

And then books, I just get fully just

32:25

zoned in and immersed in books. But I think like

32:28

all of those things have a meditative

32:30

quality to them. Right. Like, I

32:32

think meditation is generally overrated. But

32:35

I think the other ways in life through

32:37

exercise, through reading books, et cetera, or taking

32:39

naps or other ways that we can relax

32:42

and meditate that we don't need to be

32:44

so pretentious with our morning routines and our

32:46

meditation practices. I

32:48

love that idea. And I think. I

32:52

can't remember if I'm sourcing this from like a

32:55

comedian or somewhere else, but it's just this idea

32:57

of meditation as like there's lots of

32:59

ways to meditate that don't include you paying

33:01

your subscription fee to call them on your phone or

33:03

something. Yeah. Like you can go for

33:05

a walk. You can jump. You can jump at a

33:07

pool. I just did this interview with like two guys

33:09

who are coaches, Shawn Delaney and Mark McCarty. And they're

33:11

both like, like Shawn, like I jump in the pool.

33:13

Mark's like, I walk my dog and like more

33:16

or less has a conversation with this dog while he walks.

33:18

And like these guys are trained professional coaches and

33:20

they're like, this is meditation. Well,

33:23

there's why don't more people know this? Did you ever

33:25

read the prize of Superman? Kotler's

33:27

book. Basically the book. The

33:30

premise is like basically that the

33:33

extreme sports athletes are pushing the forefront of

33:35

like that mind body connection more than anything

33:37

else in that meditative. The

33:40

six Saint Mahali like flow state is

33:42

like the people that are hella skiing

33:44

or, you know, wing

33:46

suiting or whatever. They're the ones pushing flow

33:49

state more than anybody else. And

33:51

that's the most meditative hardcore thing you can have is

33:53

when you have that element of danger and death on

33:55

your side. And so maybe that's part of it too is like,

33:57

like you said in the pool or other places you

34:00

can get absorbed, we're like, it's really hard. Our

34:02

lives are all consuming, especially as entrepreneurs, and it's

34:04

24 seven. So it's like, yeah, how do you

34:06

find these ways where you need something pretty extreme,

34:08

maybe to have that pattern interrupt, to maybe get

34:11

you out of that state? And then you're saying

34:13

the other one though, and I think it makes

34:15

me funny to me, is the idea of meditation,

34:17

like you said, walking the dog or whatever is

34:19

not as cool as something that started in India,

34:22

and has this whole yodick, Vedic kind of pathway to

34:25

it. The other one, the way I always said, my

34:27

sister went to Brown, and all those kids that

34:30

Brown understandably wanted to save the world, yet

34:32

they'd like kicked the bum on the corner

34:34

as they walked by because it wasn't cool,

34:36

right? It was a local charity, not a

34:38

global charity. And it's like, it didn't

34:41

have some nice patina to it, that

34:43

looked more international. I

34:45

made a lot of enemies in college when

34:47

they wanted to protest something for employee

34:50

rights, and the way they were gonna protest was they

34:52

were gonna block all these roads. I

34:54

was like, but if you block those roads at eight o'clock

34:56

in the morning, you're gonna get all the people you're fighting

34:58

for fired. None of them want this.

35:00

I have to get to work. Those

35:02

people, please don't block this. I'm late

35:05

for work, get out of my way.

35:07

Yeah, you're not helping the cause, people. All

35:10

right, so take me back to, you're hustling,

35:12

you're making some money, you're figuring out, are

35:14

you trying to figure out how to not

35:17

work a crappy teenager job? Do you have

35:19

a crappy teenager job? I had so many.

35:21

So many. So one of my

35:23

mom's other terrible philosophies was that if we

35:25

worked hard physical labor, then we wanted to

35:27

get an education. So

35:29

I was going to be the first person,

35:33

my family had graduated from college, but I never graduated.

35:36

So that gives me that my parents didn't really go

35:38

to college. And so my mom's

35:40

philosophy, yeah, it was hard labor. So she

35:42

was also a realtor at the time. So when she was trying

35:44

to close a house, people would be like, well, I love this

35:47

house, but I'd really like a koi pond. And she'd be like,

35:49

oh, no problem, my sons will come build it for you

35:51

for free. And so we would

35:53

start- She'd promise you her time. So

35:55

we were digging koi ponds, trenches, their high

35:58

paid work when we were growing up. was

36:00

like building houses. So like I work for

36:02

electricians, crawling up in attics

36:04

in the middle of summer to feed wires

36:06

through, like in asbestos ridden, like insulation

36:09

was always felt great at the end of the

36:11

day. And then like I had at 13,

36:14

I worked at a place called Echo Park that was

36:16

a toboggan run. So it was just like iced sled

36:19

trails and the toboggan would go up and down. And

36:21

from when I got off for freshman basketball, my buddy's

36:23

dad owned it, that was in freshman. He'd pick us

36:25

up and we'd go work until like two in the

36:27

morning, get up at like five in the morning, like

36:31

every weekend for like 375 an hour. So

36:34

I'm really dating myself. And then like after that,

36:36

I worked like tons of fast food jobs, circling

36:38

back to blockbuster. I eventually worked at blockbuster as

36:41

well. Like, so I was a fry cook at

36:43

KFC. You talk about like all of these things

36:45

weren't long stints. By the way, this is part

36:47

of my juvenile delinquent is like, yeah, yeah. Six

36:50

weeks at a clip, two phase cycles are here

36:52

out. Exactly. Exactly, I can't

36:54

do this anymore. All

36:56

right, so in the midst of doing like all

36:58

this stuff, where's

37:01

the religion and the philosophy interest? Like when's that

37:03

kick into high gear where you're like, this is

37:05

a viable path to college or was soccer just

37:08

a path to college? Soccer was the path actually,

37:11

unfortunately, like you're saying, like, you know, we grew

37:13

up watching these VHS tapes, right? Like I'm so

37:15

jealous of the kids now as like one,

37:17

not only do you get to watch soccer

37:20

at the highest level anytime you want, right? On your phone,

37:22

if you want. It was like, you

37:24

also had these paths of like, you can see

37:26

how like Christian Polisic like went to Dortmund as

37:28

a 13 year old, right? You know that like

37:30

La Masilla is where the Barcelona youth grow up.

37:33

Like, you know, there's these paths, right? Like I

37:35

didn't know any of that existed, right? Like I

37:37

just know. Nobody heard about that. I was in

37:39

Pennsylvania, Christian Polisic in Hershey, Pennsylvania. No, we knew

37:41

Sesame Place was near him in Hershey Park. How

37:44

the hell did he find that out? Well,

37:46

it helps that his dad's a professional indoor soccer player

37:48

too, right? Like it all comes out of there. So

37:52

speaking of movies, I love Dead Poets

37:54

Society. So I thought, I thought I

37:56

got to know Captain Mike Captain, right?

37:58

You did. I had no idea. This

38:01

is great. Okay. And so

38:03

I thought college university was gonna be

38:05

like dead poet society. Boy, was I

38:07

disciplined. Oh man. And so I

38:09

was- Should've gone to a preparatory boys high school.

38:11

Exactly. You could've had that experience, yeah. So I

38:13

always thought that soccer was

38:15

a pathway to college. I would play

38:18

soccer, I could get a scholarship, and then

38:20

I'd go to college and I would have

38:22

this unbelievably rigorous academic environment that I would

38:24

be fully consumed by. All these

38:26

sort of romantic notions I had at the

38:29

time. So I use soccer to go to

38:31

school. I was living

38:33

at, I went to the IMG Academy in between.

38:35

So I lived at the sports academy in Florida

38:37

with all the professional tennis players, but now it's

38:39

totally different. I get so much credit for it

38:41

now because that place is like a college campus

38:43

and it's state of the art, but back then

38:46

it was a piece of shit. It was like-

38:48

Piggy's got the- It was Florida. Yeah, like she

38:50

was like eight 16 year old boys living at

38:52

a two room apartment, like going to school from

38:54

seven to 11 in the morning, training professionally for

38:56

the rest of the day, and then just wrestling

38:58

in the dorms at night, and just seeing who's

39:00

king of the hill, right? And so it was

39:03

an, and you just smelled like burnt oranges from

39:05

the Tropicana factory. It was a nightmare. Like if

39:07

you've ever read Andre Agassi's open biography, he

39:09

describes it perfectly, and he was just a few

39:12

years before me. And then now it's like this

39:14

fancy place. Okay. So

39:16

yeah, all the kids in my class were like professional tennis

39:19

players. So I was like valedictorian in my class because I

39:21

knew how to read. I mean, it wasn't really impressive. Then

39:24

after that I was supposed to go to, I was going

39:26

to go to UNC Charlotte because they

39:28

had like the number two soccer team in the country. One

39:31

of my teammates at IMG and buddies was

39:33

going there. So I was going

39:35

to go there. And then my other

39:37

friend from IMG was going to a college at

39:39

Charleston. And he's like, don't go to UNC Charlotte,

39:41

like come to college at Charleston. And I was

39:43

like, how's the coach? She's like, just, I mean,

39:45

it's a six girl to guy ratio. I was

39:47

like, how's the coach? He's like, the architecture is

39:49

amazing. I was like, how's, okay. So

39:52

needless to say, I ended up going to college at

39:54

Charleston, loved it there. I absolutely

39:56

love architecture, loved everything about the city, but

39:58

the coach. was like an ex-Marine that never

40:00

played soccer. So him and I did not

40:02

get along well. Well,

40:06

to the ex-Marines who, yeah. Right. And they

40:08

all know on the. I

40:10

was just going to say, on your question though, I originally,

40:12

when I went to school, I actually started as

40:15

an international business major. And I

40:17

found that to be unbelievably boring and easy,

40:19

just given like background of a family of

40:21

entrepreneurs, you know, always having entrepreneurial

40:23

stuff myself. And then so I switched

40:25

to always what I really wanted to do, and I switched to

40:27

comparative religions. So it was in college

40:30

where I really switched. But I started, I said from 13 to

40:32

18, I was

40:34

just going to churches, synagogues, every denomination,

40:36

Christianity, just reading and learning everything I

40:39

could about religion in general. So

40:43

I have a weird, I don't want to say

40:45

it's definitely not even a theory. It's more half-baked

40:47

than even that. But there was something also going

40:49

on, I think, culturally, especially like in the 90s.

40:51

And I don't know if it was just our

40:53

willingness to skip genres in music or

40:56

in the blockbuster line. Oh, we were going

40:58

to watch that night. But that

41:01

whole willingness to just be like, oh, I slept over this

41:03

kid's house, so I guess I'm going to the synagogue this

41:05

weekend or I'm hanging out over here. So I guess I'm

41:07

going to a Baptist church. Like

41:09

there was, I also had a

41:11

lot of exposure to a lot of different groups

41:14

like this. It was really curious about them. Just

41:16

like, oh, this is so weird that your family

41:18

thinks this, but like I'm so curious about it.

41:21

So that was kind of like wrapped into your upbringing? Yeah,

41:23

like you said, it was like you should stay over and then

41:25

you go to these places. You're trying

41:27

to date this girl and she goes to church on

41:29

Sundays, so you're like, yeah, I'll go, whatever. You just

41:32

fall into these things, right? Because you're trying to get

41:34

rides everywhere. And it also goes back to what you're

41:36

saying. When we were growing up, we were all

41:38

playing all these sports. And then my brother and sister and I,

41:40

as we advanced to those ranks, we're playing international. We're playing all

41:42

over the place. My poor parents is like, we're just

41:44

going with friends, like teammates. So you're always in

41:46

the car with somebody else or hanging

41:49

out at somebody else's house. So yeah, you eat what

41:51

they eat. You go to the church

41:53

or synagogue they go to and you get the experience

41:55

that way. But it's always fascinating to me. I

41:58

just, I always understood. I'm

42:01

just fascinated by why people think the way

42:03

they do or what they believe. And

42:05

it goes back to entrepreneurship and sexual curiosity

42:08

is like to me why I really love

42:10

studying comparative religions. Is it because it encompasses

42:12

everything, right? It was history, philosophy, art, religion,

42:15

wars, politics. All

42:18

of that in the history of humanity

42:20

is enraptured or under the umbrella of

42:22

religion. And so you could kind

42:24

of study anything under religion and try to learn

42:27

about history and society. So it's probably more from

42:29

a historical psychological perspective that I wanted to learn

42:31

more of, I was just fascinated by the way

42:34

people believed in things and then there's competing beliefs and

42:36

how do you reconcile that in your own mind? When

42:40

do you first, and this is a timeline

42:42

agnostic question. When do you first

42:45

in the same way see religion

42:48

is the common thread that ties all things together

42:50

as is money, like as

42:52

is finance. When does that first

42:55

happen where you're like money is connected to everything

42:57

too? It's probably had

42:59

been before that, right? Like I'm still trying to- That's

43:01

what it sounds like, that's what I'm curious. Yeah, I'm

43:03

still trying to reconcile in my mind if money

43:06

doesn't mean anything or if it's the only thing that

43:08

has meaning, right? And then as you're referencing is like

43:10

we think about it as a religion. My

43:14

friends I would talk about a lot often it's

43:16

like, yeah, it's a way to just harness resources,

43:18

right? It's a tool, like for harnessing

43:20

resources when you need them. But it

43:22

has become the secular religion of our day,

43:24

right? And maybe that's part of the Nietzschean

43:27

ideal of God is dead or maybe when we landed

43:31

on the moon, allegedly, allegedly

43:33

for that. Thank you. The

43:36

conspiracy theorists in the comments, they

43:38

want me to say thank you. Thank you.

43:41

Okay. Like how much I remember

43:43

reading about an Irish priest that

43:45

all the village people came

43:48

up to him after we allegedly landed on the moon. And

43:50

they're like, what does this mean about heaven? And he had

43:52

to answer a lot of questions like then. And so it's

43:56

interesting how we've shifted that way and then you

43:58

brought even the word agnostic. I even always

44:00

hated that agnostic or atheist because

44:02

like you're defining yourself by God, but you're trying

44:04

to say you're anti-God. So it doesn't make a

44:07

lot of sense to me. But like there was

44:09

this Austrian movement called the logical positivists that got

44:11

a lot of things wrong. But one of the

44:13

things they talked about was called agnostic, I G.

44:16

And they said, until you can put forth a

44:18

logical argument about God, I won't

44:20

even entertain the sentence or question. So they

44:23

weren't like anti-God. They were like, you have to

44:25

say something that makes sense to me before I'll

44:27

even respond. And so the

44:30

burden of proof was like on the

44:32

interlocutor. And that's the way they always

44:34

looked at it. But I think you're

44:36

still putting gnosis or Gnosticism in there,

44:39

which is God-centric. Yeah,

44:41

that's so interesting. And it's funny. I don't

44:43

know if I know that word or just the

44:47

no pun intended spirit of the word. I'm

44:49

thinking about like, you're

44:52

of the age, we're both of the age where

44:54

like we had enough exposure to Carl Sagan, but

44:56

not necessarily directly. Did you become a Carl Sagan

44:59

person at any point in life? No, my dad

45:01

was a huge Sagan as a mom of all

45:03

that stuff. I just I don't get into any

45:05

of like the fantasy stuff at all, which to

45:07

me, like reality has just a surprising amount of

45:09

fantasy to it. Like, I mean, this whole thing

45:11

is magical to me. So I don't need an

45:13

extra layer of magic on top. It drives.

45:15

I know this drives people nuts. Like even like Game of

45:17

Thrones, I'm like, are there dragons in it? And they're like,

45:19

no, but like, I'm like, but are there? I

45:22

don't like any fantasy. Well, that's but that's

45:24

so you know, and this is the

45:27

plea for when I say Sagan, I mean,

45:29

like the science communicator Sagan, like this is one of

45:31

the great thing. He had this great story about the

45:33

dragon in the garage. And it's basically

45:35

like Gnosticism as you define it. He's like, if somebody tells

45:37

me they have a dragon in the garage, like the burden

45:39

of proof is on the person telling me they have a

45:41

great because he's like, there's lots of things they can say

45:44

where they're like, oh, smoke comes out when I crack the

45:46

door a little bit. Like there's lots of things you can

45:48

say that point to that. But if you would drag them

45:50

in the garage, I really just need you to prove me

45:52

that first before we can talk about anything else. Exactly. Then

45:55

you're you're really just waiting for the hate comments on

45:57

this one, aren't you? Like we're just going down there.

46:00

How many people could we offend on this show

46:02

today? Oh, trust me. I've seen some

46:05

real gems of comments on some of the other

46:07

ones, where I'm just like, people are just out

46:09

there wanting to be angry about stuff. But that's

46:11

okay. I'm having a good time. So take me

46:13

back now. So college, and you're

46:15

playing soccer. Now you're playing for

46:17

the marine. Hey, on the bright side, he didn't

46:19

read extreme ownership. You got there before that happens.

46:22

Congratulations. Does

46:25

that... Is that what fizzles the ambitions on

46:27

what else with soccer? Or were you already

46:29

of the mindset that like, I'm not going

46:31

pro, so... I

46:34

got part of it. Yeah,

46:36

I wasn't even thinking about pro. I really wish I would

46:38

have, because like I played with some professional teams in Bolivia

46:40

and I got invited to play with professional teams in Scotland

46:42

and stuff like that. So I really wish I went down

46:44

the route. Like, and let me qualify this of like, I

46:46

would have never been in like the premiership or anything, but

46:49

I probably could have played like Division two

46:51

or three and in some, you know, I don't know,

46:53

in Belgium or something, you know, sort of church or

46:55

something like that. And it was

46:57

weird because like I was as a youth in America, I

46:59

was probably one of the top like 100 players in the

47:01

country, but never broke into the national team. And I had

47:03

like most of my teammates played in the national team. I

47:06

mean, my roommate when I was younger

47:08

was Tim Howard, the goalkeeper for the national team.

47:11

And so like I know all these guys like really well

47:13

and like it, but it's frustrating. And I always ask my

47:15

sister that too. She was probably one of the top 20

47:17

to 50 gymnasts in the world but never made the Olympic

47:19

team. And it's like it's unbelievably frustrating when

47:21

you get to that level and know you're never going to

47:24

crack through that top. And like that

47:26

can be incredibly frustrating is like to

47:28

know you're there, but you're never

47:30

going to be there. And like you just so you know

47:32

exactly what that ceiling is, where most people never get to

47:34

point to know exactly what that ceiling is. And

47:37

so I mean, I would say playing at College of Charleston, I think

47:39

in our first year, we kind of got in and out of the

47:41

top 25, even as freshmen,

47:43

you know, I played maybe a few games

47:45

a freshman sophomore year, but like I got

47:47

disillusioned by the coach, was not enjoying playing

47:50

anymore. Also got disillusioned by university. Like I

47:52

said, it wasn't like dead poet society. And

47:54

unfortunately, what I did is I took all

47:56

of the I don't even know school still

47:58

work this way, all the. 400

48:00

level and 300 level like religion courses first,

48:02

in my first for two years. And

48:05

then they just like cleared the shelf on like

48:07

the hardest classes. They're like, I can't, guys. Yeah,

48:09

so I went back to do like the remedial,

48:11

like the 100 level like ones. And I was

48:13

just like, I was arguing with the teachers and

48:15

they're like, yeah, you're right. But I had to

48:17

teach the lowest common denominator. And I was like,

48:20

I'm out. And so I ended

48:22

up at quit school, quit playing soccer.

48:26

I went in, I was

48:28

working in restaurants. So I met a

48:31

Turkish gentleman owned the restaurant I was working in.

48:33

So he was telling me all about Istanbul. So

48:35

I eventually I went and sold

48:37

Turkish rugs to American tourists in Istanbul for a

48:39

while after I took off time from school. I

48:41

eventually went back to school and I tried going

48:43

back home in Michigan. We have a place called

48:45

Kalamazoo College. That's one of the best like small

48:47

liberal arts schools in the country. And

48:49

so I thought I could test myself. That was much more like

48:51

dead poet society. But I

48:54

felt like I was still bored. It still wasn't for

48:56

me. Like I should have gone to like St. John's

48:58

College and done like

49:00

their reading program or something that would probably have

49:02

been better for me. But I just find I'm

49:04

much better auto-diadact. I'm much more self driven, self

49:06

taught. I just like to learn on my own

49:09

pace and speed. So.

49:13

Focus just on the Turkish rug selling for

49:15

a second. And then we're gonna get back

49:17

to you as a frustrated board, you know,

49:19

20 something at this point, figuring out the

49:21

world. Not

49:24

a lot of people go, I met this guy in

49:27

a restaurant and now I'm

49:29

gonna go hanging on Turkey for a while. I mean, I

49:32

have the they might be giants tape. I know

49:34

that Istanbul is not Constantinople. Like I have got

49:36

this nailed down. Also know that, you know, a

49:38

bag of groceries left upon a shelf and whatever

49:40

other. A particle man trying to remember

49:42

what else was on that tape. So

49:44

as you piece this together, like what

49:47

made this a good idea for you to go over there?

49:50

How did he talk to you into this? How did you get on

49:52

the plane? Well, this is the hard

49:54

part about narratives and like I have

49:56

a hard time leaving in free will either. So it's like,

49:59

this is like, okay. the curious past in life is like,

50:01

I think it goes back to like, one, I can't believe

50:03

my parents, right? Like when I was 15, I went and

50:05

lived in Bolivia for summer, like with a host family in

50:07

like a third world country. And then I'm

50:09

like 19 going to live in Istanbul. And like,

50:11

this is at a time just to get, contextually

50:13

is like, it was either the first or second

50:15

time I was living in Istanbul, I think it might have been

50:17

the first. I signed up for a Hotmail account at a, at

50:19

a computer bar, right? Like it was

50:22

like, you know, internet cafe. Internet bar. Yeah. Yeah. And

50:24

this is at a time like where you signed up

50:26

for Hotmail, maybe only a few hundred, like you're trying

50:28

to get the network effects. Like this is how early

50:30

on it was. So like, I would buy

50:32

a calling card that was enormously expensive, be able to

50:34

call my parents like once a month and

50:36

for like 90 seconds be like, I'm

50:38

okay. Like it's just unreal. I'm alive.

50:40

Yeah. This is not a terrorist. Luckily

50:42

taken has not come out next. I'll

50:45

talk to you in a month. Probably. So I can't

50:47

believe they won. Let me do it. But

50:49

too, I think it's because I come from a family that has

50:51

pretty much wanderlust. Like that was the other part of my dad

50:54

too is like, he was like, he said, did

50:56

he take you to do these things? One of the things like

50:58

even when we went camping as kids, we used to ask, beg

51:00

my dad to bring a tent because he thought like

51:02

tents were for pussies. So like we had to go with like,

51:04

dig a hole and like a sleeping, like, I mean,

51:06

it was just wild stuff. And so he had kind

51:08

of traveled the world hitchhiked across America, like done all

51:11

this stuff like, and then and his, my dad's side

51:13

of the family, my grandfather, my great grandfather at all,

51:15

like travel the world like my great grandfather

51:17

worked on like merchant ships and he didn't even know

51:19

how to swim. And so I come from this long

51:21

line of like lunatics. So the idea

51:23

of traveling to these countries was not,

51:26

you know, this is why one, why they let me go because they were

51:28

kind of used to it. But then two, it was like, I've

51:30

always heard those stories growing up. And then that romanticism

51:32

of movies and books, right? Like we didn't really, we

51:34

didn't have the internet. So I wanted to

51:37

go see for myself. And thankfully, for all the things

51:39

that have changed for our generation and our time growing

51:41

up is like, well, that's one of the things I'm

51:43

so glad we got to experience was like traveling

51:45

the world pre internet was a totally different place.

51:47

Where now you have like the California vacation or

51:50

the Airbnb vacation of the world like right, like

51:52

now we could go to Bangkok and

51:54

watch the premiership on a 70 inch flat screen

51:56

TV, right? And yeah, it has a little bit

51:58

slightly different background. you're probably getting an

52:00

acai bowl in the morning, you know, and a matcha latte.

52:03

It's all kind of unfortunately the same. So I'm

52:05

so glad I got to experience it then, but

52:07

it was just more of like growing up in

52:09

rural Michigan, I really wanted to get out. But

52:11

luckily when we would go on vacations, my

52:14

dad was doing business in China in the 80s and

52:16

stuff like that. So it was like, our family was

52:18

kind of accustomed to travel and his

52:20

best friend lived in Columbia and stuff like that. So

52:23

we got associated with travel a lot. And so the

52:25

other part of it was after that, I was working

52:27

in restaurants. And so I would just save up as

52:29

much money as I could work in restaurants, then go

52:31

travel in Europe until six months a year until I

52:33

ran out of money, come back to Charleston, work in

52:36

restaurants, and yeah, just kind of like lived a lot

52:38

of that life. So

52:40

talk to me about like the restaurant jobs and

52:42

stuff like that. Do you get

52:44

fully just indoctrinated because you

52:46

were the line, the fry

52:48

cook at KSC and whatever else, that you're

52:51

just like, this is another viable couple of

52:53

paychecks I can pick up? No, it's a

52:55

simple money and freedom is like, I've

52:57

done everything in restaurants from dishwasher to owner

52:59

at this point, but back then

53:01

in, let's see, it would have

53:04

been late 90s early 2000s, like

53:06

I was making anywhere from

53:08

a hundred to $300 a night, working

53:11

in restaurants, like waiting tables. And

53:13

going back, my buddies were building houses in

53:15

Michigan in the freezing cold of winter for

53:17

like, I don't know, six, seven,

53:19

eight bucks an hour. Like this was just magic

53:21

to me. Like I started probably making more than

53:23

my parents as like a 20 year old waiting

53:26

tables in Charleston. It was just

53:28

totally magical at that time. Now the problem is everybody

53:30

knows that if you get deep in the restaurant business,

53:32

is at the end of the shift, all the servers

53:34

are then so burnt out from like the pressure of

53:36

waiting on tables all night that they all go to

53:39

the bar after and then drink away half their tips.

53:41

And so it's really hard to save money that way.

53:44

But the bar industry stays afloat. It's a

53:46

stimulus package for the bar industry. I'm

53:49

like, why are we doing, like I tried for a while,

53:51

like I would go on runs at like midnight when I

53:53

got off shifts, because you just have all this pent up

53:55

energy from like the palpable nature

53:57

of like waiting tables and the risk of

53:59

it all. trying to provide good service. But

54:01

yeah, you can, it's really easy to kind

54:03

of fall into alcoholism and Charleston

54:05

is one of those cities that's just a heavy

54:08

drinking town. So it's very, very, very normalized. Like

54:10

it wasn't anywhere different than

54:12

that. But like the, yeah, so it

54:14

was more about the love of the

54:16

cash and the freedom of that and

54:18

being able to kind of dip in and dip out and

54:20

go and travel and do things. But

54:23

otherwise I'm extremely introverted. People

54:25

are always surprised by this, but like that was one

54:27

of the reasons I kind of forced myself to sell rugs

54:30

on the street at Istanbul's because like it forced me

54:32

to be more extroverted. Waiting tables forced

54:34

me or extroverted, but I hated like every

54:36

second of it. I'd rather, that's why I

54:38

actually liked working, behind

54:41

the scenes, I much prefer being a cook or a

54:43

dishwasher or a back waiter where I really don't have

54:45

to talk to the tables. What

54:48

do you think about it? Like, how do you reconcile this? So you're

54:50

not, in a setting

54:52

like this, you're not going to come across

54:54

as an introvert to somebody. Right. And I

54:57

think this is important, like extra, and

54:59

all the praise to like Susan Cain, and I don't know

55:01

how much of her stuff you've read or whatever, but like

55:03

the, there's actual valuable nuance

55:06

to this. How do you understand your

55:09

flavor of introversion? How do you think of it

55:11

and explain it? Well, what Susan popularized is the

55:13

idea is like, how do you get, how do

55:15

you restore your energy? Do you do it around

55:17

other people or alone? And for me, it's 100%

55:19

alone. Like it's just, I prefer

55:21

to be alone almost all the time. And

55:24

like you said, it's really weird being in this business where like, luckily

55:27

when I started doing a lot of interviews

55:29

and everything, it was right after the pandemic.

55:31

And so like in this scenario, right? It's just like you and

55:33

I talking to each other and we forget

55:35

there's an audience out there. Or when I'm speaking on

55:38

stage, it's actually really easy too, because it's just one

55:40

to many. It's the one-on-one conversations

55:42

where especially you have to come up with

55:44

a small talk about like the weather or

55:47

like whatever, I just couldn't care less. And

55:49

I'm just like, let's talk about something real. Like,

55:51

you know, like, so those are the hard parts

55:54

for me, but like generally, I have a really

55:56

small circle. I spend most of my time alone.

55:59

I try to spend deep. amount of times just by

56:01

myself, like talking to the no one. Do

56:05

you feel like and how aware of you that are

56:07

you with this because of this is how you are

56:09

with like the other people you work with? So that's

56:11

current day just for a second. When you think about

56:13

the other people you work with, are you gauging or

56:15

measuring how introverted or extroverted, where that energy, where that

56:17

recharge comes from, what the people you surround yourself with?

56:20

Yeah, I try to do a lot. But we also we've

56:22

always been a distributed company, too. And so that's that comes

56:24

with a whole other set of challenges where you almost have

56:27

to like over communicate in a way, especially

56:29

if like all your meetings are over Zoom, like our

56:31

employees are all over the world. And so, you know,

56:34

you had to over communicate that way. You

56:36

try to really learn people's different styles, communications,

56:38

you know, in not just extroversion, introversion, written

56:40

forms, you know, emojis. Like you just it

56:42

takes a long time to kind of figure

56:44

that out, to try to, you know, get

56:46

those right buttons. And then what's shocking, like

56:48

you're saying is like, I'm technically like the

56:50

face of our firm. And so but I'm

56:52

extremely introverted. And so

56:54

that that presents its own dilemmas.

56:58

But I think it's like every entrepreneur,

57:00

it's like it's punctuated extroversion because like

57:02

to bring your ideas from your head

57:04

into reality takes a tremendous amount of

57:06

energy, right? To me, like you're animating

57:08

this 3D hologram. And to

57:10

do that, though, you have to get other people to buy

57:12

in. So you're going to have to talk to people. But

57:14

the other book that I think helped me a long time

57:16

ago when I was in my early 20s was called The

57:18

Hypomaniacs Edge. And the idea in that

57:21

book is that every entrepreneur, explorer, anybody that

57:23

does anything interesting has a mild form of

57:25

bipolar, right? To do anything that requires that

57:27

tremendous amount of energy to push these ideas

57:29

from your head out into the real world

57:31

and instantiate them requires a tremendous

57:33

amount of energy that's going to have a commensurate downside. So

57:36

that's why I know like if I'm out there at like all

57:38

these events I have to go to and everything, I know

57:40

I'm going to have to bifurcate that with a lot of downtime

57:43

afterwards, right? I had to block off my schedule.

57:45

Like so it's like I wish I could figure

57:47

out how to run at a more marathon pace,

57:49

but it's more sprint walk for me in general

57:51

or sprint lay down. Maybe like, you know, sprint

57:54

nap, sprint nap. That's the way to do this. Yeah.

57:59

And I see this as And maybe I'm trying

58:01

to put a grand theory of everything on this.

58:03

But I see this as related. This ties back

58:05

to becoming an

58:08

athlete up to a certain level and

58:10

understanding the recharge and then working in

58:12

a restaurant and understanding maybe a run

58:14

after the shift because all the

58:16

things that happen in the rest on industry night are

58:19

not the thing that I need at midnight in my

58:21

life. I'm going to do things the next day. Understanding

58:23

that if I go on stage or I

58:25

go travel, I'm actually going to need some

58:27

serious downtime afterwards because I just need to

58:29

be in a dark room away from anyone

58:31

with my Criterion Collection. That's

58:34

a lot of variations on that theme

58:36

that you're actually dancing through pretty

58:38

well. Are you aware of that? Hopefully,

58:41

I mean, I

58:43

wish I could find secular versions of a lot of

58:45

these things, but I was going to say from your

58:47

lips to God's ears. But it sounds great. That's what

58:49

I'm saying about this narrative in hindsight. I need to

58:51

do such a good way of syncretizing this and tying

58:53

it up in a nice bow. I

58:55

remember even my brother-in-law that lives in Miami,

58:57

he's like Ivy the Educated Surgeon. He's like,

59:00

there's not a lot of smart people that hang out and have

59:02

conversations with the Miami and everything. I go, what are you talking

59:04

about? I was like, that's what books are for. I

59:06

don't expect real life. Like this thing.

59:10

Have you met humanity? Yeah. Did you grow

59:12

up in the house I grew up in?

59:14

Yeah. Yeah, you just- Like have you not

59:16

met these friends? You could talk to the

59:18

eminent dead and the great philosophers throughout

59:21

human history. The other way, I think to me

59:23

what it ties in, I was trying to, I was

59:25

starting to really work on this idea with our mutual

59:29

friends' by-laws on value after hours. And

59:31

I had this idea, I was like, you studied comparative

59:33

religions. What you're studying is like, I studied all the

59:35

world's like classical Abrahamic kind of

59:37

traditions that kind of all stem out of there.

59:39

But then I specialize in like Eastern mysticism. And

59:42

so you could kind of break it down as

59:44

like, you have more of the physical,

59:47

instantiated place religions through the Abrahamic tradition.

59:49

Or you have one person

59:51

going their own way in more of the shamanic tradition. But

59:54

they all kind of come out of the similar lineages as

59:56

well. And they both have like similarities. But what

59:58

I found is like we use this word. agnostic or

1:00:00

agnostic or atheist is like this is why

1:00:02

I think that religion hopefully helps me or it's

1:00:04

the way I lie to myself and tell me

1:00:07

it helps me by studying this stuff, compared

1:00:09

to the kind of cross religions, is when

1:00:11

you're constructing portfolios of different asset classes, right? I

1:00:13

find myself to be, I say it's agnosticism,

1:00:15

right? There's like, even though I don't like

1:00:17

that word, is like everybody has

1:00:19

these religions when it comes to investing, right?

1:00:21

Like the value religion, you know, the momentum

1:00:23

religion, everybody's got these religions

1:00:25

and they never cross over. But if

1:00:28

you're trying to truly build a diversified

1:00:30

portfolio of different asset classes

1:00:32

that is, you know, Zig, when the others ag,

1:00:34

et cetera, it's like you have to be able

1:00:36

to put those religions aside and combine things that

1:00:38

can work at different times and different time horizons

1:00:42

in ways that people will normally never do.

1:00:46

It's amazing because it's like the tide, the

1:00:48

other skill of being like, I really want

1:00:50

to date that girl, but I guess her

1:00:53

dad's the local pastor or

1:00:55

whatever. So I'm going to find a new

1:00:57

denomination this week and we'll see what happens.

1:01:00

Oh, these lawyer skills. All right. So take me

1:01:02

back to your working in kitchens, you're doing that

1:01:04

stuff. How's the real estate stuff start to happen

1:01:07

for you? Well, first of all, like, so

1:01:09

one thing I hate about when people tell like their narratives,

1:01:11

like we were saying about we skip over, we always hit

1:01:13

the highlights, right? Is that after

1:01:16

quitting school several

1:01:19

times, quitting the soccer team, you know, to kind of travel

1:01:21

in the other world, I find myself in

1:01:23

like my early twenties waiting tables and I'm looking

1:01:25

around and obviously no disrespect to anybody that works

1:01:27

in the restaurant industry, but you can

1:01:29

see like a lot, two decades could pass by like

1:01:31

a blink of the eye and I'd still be waiting

1:01:33

tables and I was just like, and then now I

1:01:36

don't have an education. I don't have any skill sets

1:01:38

like and those are some saying people skip over all

1:01:40

these tough times and I would I just want to

1:01:42

highlight for anybody that's going through it. It's really tough.

1:01:44

Like you're those those early to mid twenties when you

1:01:46

realize, oh, I'm not I don't really have an education.

1:01:48

I don't have a skill set. Like what am I

1:01:50

going to do with my life? And I have no

1:01:52

clue what I'm going to do. Like that is what

1:01:54

those are extremely painful years and you don't know

1:01:56

what you're going to do. And so eventually I

1:01:58

kind of got off my ass. and realized, like I

1:02:00

said, my mom was in a realtor at the time,

1:02:03

growing up, she flipped houses and everything. So I started,

1:02:05

I was always fascinated

1:02:07

more by design and architecture. So living

1:02:09

in Charleston was amazing because on that

1:02:11

peninsula, they have over 800 antebellum homes,

1:02:13

pre-Civil War homes. And I was fascinated

1:02:15

by that architecture and design work. And

1:02:17

so I just started, luckily

1:02:21

I was born with a good memory, I just started kind

1:02:23

of memorizing the MLS and every kind

1:02:25

of house on the peninsula and like

1:02:27

the price points and everything. I'd just start going through

1:02:29

the list and over time, because I

1:02:31

love walking, that's my favorite path times, just walking. So I just

1:02:33

walked the city endlessly and I'd look at the houses and I'd

1:02:35

look up how much they cost eventually. And that just kind of

1:02:38

created my own kind of memory palace of what the

1:02:40

city and the price point should be. So

1:02:43

I started off originally just kind of

1:02:45

doing some residential kind of realtor work,

1:02:47

which I absolutely hated. Like

1:02:49

I remember her showing, like it was like the third

1:02:52

time showing somebody a house and

1:02:54

the wife was like, I don't like that

1:02:56

couch. And I was like, it's

1:02:58

not your fucking couch. You're

1:03:00

not buying the couch, you're buying the

1:03:02

house. What are you failing to

1:03:04

connect to? The couch religion is a

1:03:06

strong, it's really hard to break people. But

1:03:09

I mean, and now I understand what she's really saying. It's like, she

1:03:11

does a guys view a good vibe from that house. It really doesn't

1:03:13

have anything to do with the couch. But at the time that blew

1:03:15

my mind. I was like, this is not for me. And

1:03:17

then so I got to know

1:03:19

this couple that was developing some of the best condos

1:03:21

in Charleston at the time. And so he was a

1:03:24

commercial real estate developer. And I just told

1:03:26

him, I was like, look, you were having mobility issues. What if

1:03:28

I drive you to work every morning and drive you home? And

1:03:31

so it just started getting in with him there. And so in the car,

1:03:33

I could pick his brain about how do you do this? How do you

1:03:35

finance this? How do you do it? And

1:03:37

so it just came through osmosis and

1:03:39

just asked me a lot of questions.

1:03:41

And unfortunately, anybody's learned, you do

1:03:43

not want me to go, hey, can I pick your brain? Because

1:03:46

I will just excavate your brain with

1:03:48

a bulldozer. I will just

1:03:50

go deep and just keep asking you questions

1:03:52

so you're exhausted. And so I

1:03:54

just learned kind of through asking those questions and then

1:03:57

doing it myself, just started to buy properties, fix

1:03:59

them up. I just got really lucky at the time. Charleston,

1:04:02

when I first moved to Charleston, it didn't have

1:04:05

a single national chain store on King Street, which

1:04:07

now King Street is one of the best commercial

1:04:09

districts in the world, like has Apple stores, everything.

1:04:12

It was like since one

1:04:15

of the last hurricanes, the buildings,

1:04:17

those beautiful historic buildings on King Street, the

1:04:19

retail would be occupied, but second, third, and

1:04:21

fourth floors were empty. They're

1:04:23

selling on cap rates just based on that retail floor.

1:04:26

I could get ideas from New York, San Francisco,

1:04:28

London and go, hey, I wonder if we did

1:04:30

this in Charleston because we're just 10 years behind.

1:04:32

It's a way to catch up. I would just

1:04:35

work on really developing those second, third, and fourth

1:04:37

floors into either hotels, condos, apartments,

1:04:39

that sort of thing. Then at one point,

1:04:41

like I said, I owned restaurants. Sometimes

1:04:44

that'd give me a free call option on putting the

1:04:46

restaurant in the ground floor. Then if the restaurant fails,

1:04:48

which they eventually do, now I can

1:04:50

release that for maybe triple the price. It was part

1:04:52

of my outfit costs. So you could get a free

1:04:54

call option on restaurants if you own the building. That's

1:04:57

what I recommend for everybody because that was I

1:05:00

say mentors, I never really had any mentors in my life, but

1:05:02

I knew a guy that had over time owned 16

1:05:04

restaurants in Charleston, all of which

1:05:06

were subsequently no longer in business, but he had

1:05:09

bought every building that his restaurant was in, and

1:05:11

now he was worth like 60 million bucks back

1:05:13

in the early 2000s. So

1:05:16

I learned from him, you want to own the building.

1:05:18

Know whatever it takes, own that building. It's

1:05:21

one of those funny things in the, whatever

1:05:25

the first real Anthony Bourdain book

1:05:27

is, that's one

1:05:29

of the recurring things. I reread that earlier this

1:05:31

year and it's just every restaurant and like

1:05:34

lesson ends with like, oh, but they didn't own the

1:05:36

building or like they should have owned the building or

1:05:38

this guy's only here because he owns the building and

1:05:40

it's always just like a sentence, but

1:05:42

it's that most important business sense sentence in

1:05:44

any of these insane stories that he's telling

1:05:46

comes back to do they own the real

1:05:48

estate? Yeah, it's a sure

1:05:50

answer to explain to my brother. Like I

1:05:53

think Taleb talked about it as like, we should have like national

1:05:55

restaurant tours day, right? Like, because like, if you go to like

1:05:57

a New York City, you have 10,000 as a restaurant, 10,000. are

1:06:00

going to be out of business this year, but we all

1:06:02

reap the benefits of having all this diverse cuisine and things

1:06:04

to try at all times and get our fingers on any

1:06:06

chance we get. So it's a

1:06:08

terrible business to be in. And like I was telling my

1:06:10

brother about it, I was like, yeah, you can raise,

1:06:12

you know, half a million bucks, two million bucks to

1:06:15

build out a restaurant, but it's most you have to

1:06:17

be realistic, it's most likely to fail. But

1:06:20

if you own the building, now you have an asset,

1:06:22

right? And it may you may have to raise a

1:06:24

couple million dollars to buy the building. But now you

1:06:26

have a physical asset with a, you know, with a

1:06:28

title and a deed. And so investors are much more

1:06:30

likely to invest in that. And it's just having a

1:06:32

fiduciary responsibility to your investors is like, look, my restaurant

1:06:34

got out of business when it does, hopefully the city's

1:06:36

increased in value over the last five years. And now

1:06:38

I can release that for two to three times the

1:06:40

rent and now that building is that much more valuable.

1:06:42

So it's just a way of hedging

1:06:44

that risk of being a restaurateur.

1:06:48

Do you feel like you intuitively grasped that?

1:06:50

Or did you build this intuitive understanding of

1:06:52

this of this basically like this call option

1:06:54

of having this asset that you're doing this?

1:06:56

I think it's

1:06:58

a very it's a very optional framework that you're

1:07:00

imposing on this. And I want to know how

1:07:02

much you knew it then. I

1:07:05

think about most of my life, I think entrepreneurs,

1:07:07

right, this the misnomer that entrepreneurs are mistaken, right?

1:07:09

We're risk mitigators. We mitigate the risk so much

1:07:11

and to you, then you have to take the

1:07:14

leap, right? And that's what I think the creativity

1:07:16

and entrepreneurship comes from risk mitigation. And I

1:07:18

always think intuitively, I always had

1:07:20

a good sense of arbitrage is an optionality. And

1:07:23

it was getting a better sense of that. But I

1:07:25

also want to reiterate, though, this this is this is

1:07:27

me telling my own narrative. But let's be honest, like,

1:07:29

as a commercial real estate developer, I blew up in

1:07:31

the great financial crisis. So there's a lot of things

1:07:34

I did wrong to like as taking on too much

1:07:36

leverage and not think, you know, cash flow time horizons,

1:07:38

there's a lot of things I did wrong. But I

1:07:40

think intuitively, entrepreneurs that mitigate risk, we're essentially always trying

1:07:43

to find an arbitrage or some sort of, you know,

1:07:45

call option on anything we're doing. And

1:07:47

that's the beautiful creativity you get from entrepreneurship. Like I

1:07:49

even think about like, I used to even

1:07:51

you know, middle middle

1:07:54

soccer bats using, you know, UK bookies and everything

1:07:56

like because you could guarantee an arbitrage, right? Like

1:07:58

if you could find those those different or

1:08:00

I used to count cards in bakarat,

1:08:02

right? That's an arbitrage. I like risk-free

1:08:04

money. I don't really like taking risks.

1:08:07

It makes me feel bad. It hurts. I don't

1:08:09

like being up at night. But unfortunately,

1:08:11

lack of free will, this is the unfortunate roller

1:08:13

coaster I'm on that I just beat myself in

1:08:15

the head every day through entrepreneurship and trying to

1:08:18

suck less. Talk

1:08:22

about the failure. Talk

1:08:24

about, and this is funny too, I've heard you

1:08:26

say this before. People in real estate

1:08:28

say the market is being topped at a different point than

1:08:30

people in stock markets. Say

1:08:32

what that is and just say

1:08:34

this. Yeah, for

1:08:37

the GFC, for the great financial crisis, everybody

1:08:39

goes, 2008, that's for the financial

1:08:41

markets. It was 2007 for real estate. So all

1:08:43

the signs were there. But I remember in 2006,

1:08:48

I kind of saw the running on the wall, right?

1:08:50

I noticed it was getting harder for the people that

1:08:52

buying the condos of buildings I was renovating to get

1:08:54

mortgages. And so I kind of saw, and I saw

1:08:56

who were like, back

1:08:58

then it was your countrywide, your Washmu,

1:09:01

all those people that were writing those ridiculous

1:09:03

loans. So I saw who the worst on

1:09:05

the actors were. But I remember I got

1:09:07

together with six of the other real

1:09:10

estate developers in the Charleston area, all of them over the age of

1:09:12

50 or 60 at the time. And I was only in my mid

1:09:14

20s. And I said, guys, I'm seeing

1:09:16

cracks here, it's making me nervous, but I don't have contacts.

1:09:19

And to a man, they said, no, this time's different, you're fine.

1:09:21

So in hindsight, I had to

1:09:24

learn that commercial real estate guys, are

1:09:26

pretty naturally optimists, right? And all they do is declare

1:09:28

bankruptcy and start over, right? I didn't understand that at the

1:09:30

time. But once again, any of

1:09:32

it's all my fault, right? And the thing is that

1:09:34

I had to learn the hard way, is

1:09:36

everybody thinks it was about leverage or real estate, which

1:09:38

is why everybody loves real estate, because you can leverage

1:09:40

it more than most other things individuals can invest in.

1:09:43

But to me, it's more time horizons, right? And

1:09:45

so it's more about time horizons

1:09:47

and volatility. And what

1:09:50

I mean by that is like, whenever you're projecting a

1:09:52

project out one, two, five years in the future, you

1:09:54

need the future to look like the present, or you

1:09:56

need to be as low volatile as possible, right? If

1:09:58

you're creating your projections. your P&L, your pro forma, you

1:10:00

know, you need the future to look like the present

1:10:02

or you need the volatility to be lower over time.

1:10:05

And if during that time volatility picks up

1:10:08

or credit dries up globally, well, you're absolutely

1:10:10

screwed. It didn't matter what your projections were.

1:10:13

So that's part of the leverage time horizon

1:10:15

combo that you need with a lot of

1:10:17

these more granular private assets, whether

1:10:19

it's PE, private credit, venture capital, you know,

1:10:22

real estate. Those are the things

1:10:24

you got to worry about more is more is your

1:10:26

time horizon and what's the global macro volatility or liquidity

1:10:28

cycle look like? And so

1:10:30

the pain of losing that money,

1:10:32

that's one of the things I don't want to gloss over is

1:10:35

it probably I was for not knowing because

1:10:37

I don't go to like psychologists, I was probably

1:10:39

depressed for deeply depressed for years after that. And

1:10:42

because it's one thing to like lose your money and your

1:10:45

own money and everything, but when you lose family and friends money,

1:10:47

it's not their money, it's the belief in you. And

1:10:50

so the things I've had to learn throughout

1:10:52

life too was like, so I go to

1:10:54

college, right? And I'm playing on a D1

1:10:56

soccer team. I'm an international business major. All

1:10:59

the family and friends like, oh, you're crushing it. You're

1:11:01

doing great, right? I switched my

1:11:03

major to comparative religions. They're like, what kind

1:11:05

of loser are you? Right? I quit the

1:11:07

soccer team. They're like, loser, quit school, loser,

1:11:09

you know, like move to Istanbul, like all

1:11:11

this stuff, just loser, right? Then

1:11:13

real estate comes along. I'm starting to develop

1:11:15

those properties. You know, I build up to

1:11:18

a multi-million dollar network statement in my early

1:11:20

to mid 20s, which net worth is meaningless

1:11:22

kids, is

1:11:25

now I'm a genius again. Right. And then the

1:11:27

crash comes. I lose everything. Now I'm a moron

1:11:29

again. Like I'm the devil incarnate. So it's just

1:11:31

like you learn through these cycles too, it's like

1:11:34

people's perceptions of you versus who you really are.

1:11:36

Or even if you could find out who you

1:11:38

really are, it's just like they fluctuate based on

1:11:40

like this religion that you brought up before of

1:11:42

money. You know, like this is

1:11:44

why I can't stand this industry we're in,

1:11:46

these podcasts we're in. It's like, it's this

1:11:48

gel man amnesia, this Dunning-Kruber effect where we

1:11:50

think that like just because somebody has money

1:11:52

that they know about everything and then their

1:11:55

omniscient. No, these people got lucky. They were

1:11:57

very domain specific and now they

1:11:59

don't know anything. about anything else. Yet

1:12:01

we give this imprint

1:12:03

on them that they're cross-sectional genius and

1:12:05

everything they say is gold. No, they're

1:12:07

saying moronic things, but yet because they

1:12:09

have a billion dollars, you believe anything

1:12:11

they say. Funny,

1:12:15

funny, the amount of perceived wisdom a bunch

1:12:17

of comments after your name grants

1:12:19

to you. Never ceases

1:12:21

to amaze me. Yeah, you take away that billionaire status

1:12:23

all of a sudden, you'd be like, what the hell

1:12:26

is this person talking about? But no, you just, you

1:12:28

swallow everything they say. And that's why you're saying it's

1:12:30

the religion of our secular society has got to be

1:12:32

money. Those

1:12:34

are our priests, our potents

1:12:36

that they hand down the

1:12:39

clay tablets from above and tell us how to live

1:12:41

our lives. And then in

1:12:43

a more interesting way, to me at least, is nature,

1:12:47

as we know, doesn't create any copies when

1:12:49

it creates humans. Yet all of human society

1:12:51

is about creating copies. Be like

1:12:53

these other people. Be like Jesus. Be

1:12:55

like the trucking miller. Be like these people.

1:12:58

We're just trying to create all these copies.

1:13:00

And to me, man's at war with himself

1:13:02

in a sense that we're total wild animals,

1:13:05

yet this society is trying to comport us

1:13:07

into this polite culture and to be like

1:13:09

everybody else. And so we're always fighting that

1:13:11

battle internally. And it's interesting to

1:13:14

me that you should be like Ray Dalio.

1:13:16

Why? Why would I want to

1:13:18

be, or Warren Buffett, why? I don't see the point. There's

1:13:22

that weird thing. I actually think about this maybe

1:13:24

way too much where it's the, kind

1:13:27

of goes back to like, be acceptable and

1:13:29

be aware of the worst shit. Be aware

1:13:31

of this idea. It's like being like Jesus,

1:13:34

whatever your religious beliefs may be, is like

1:13:36

being a good guy. It's like, okay, we're doing

1:13:39

some stuff. Have your occasional glass of

1:13:41

wine if you want it, whatever. But

1:13:43

that's a lot more noble path in

1:13:45

many cases than be something that's impossible

1:13:47

or unreachable. I was talking with

1:13:49

another person who's like a first-generation,

1:13:52

I think she's first-generation American and a

1:13:55

financial planner. And she was like, stop with the Buffett

1:13:57

narratives. Not starting an insurance company. company,

1:14:01

don't talk about investing your float or

1:14:03

whatever. Like, nope, it's not the

1:14:05

way it works. Like, you're running the

1:14:07

Asian grocery in town. Like, I'm going to help you out

1:14:09

figuring out what this thing is. Those

1:14:12

stories are harder to tell. If it is, it's

1:14:15

always fascinating because I love it. I have so many

1:14:17

friends that are like Buffett Acolytes, you know, or Munger.

1:14:19

And so, yeah, I don't get it. Great religion. It's

1:14:21

a great religion. I guess it's a great religion. It's

1:14:23

just like you want like and then somebody else said,

1:14:25

like, if you want to admire this person and be

1:14:28

like this person, you have to take their own terrible

1:14:30

life. And so that means like Buffett, are you

1:14:32

stepping over your kids when they have a broken

1:14:34

arm? You know, how's that polyamory situation? Like, people

1:14:36

forget all these other things like, oh, no, he's

1:14:38

just got this nice old house in Omaha. I'm

1:14:40

like, did you forget about his house in Laguna

1:14:42

Beach that we started selling for 14 million? Like,

1:14:44

there's a lot of little things that don't quite

1:14:46

add up to this cuddly grandpa. But I tend

1:14:48

to get in trouble whenever I talk about Buffett

1:14:50

and Munger. But it's just like I never

1:14:52

understood as a grown man to like to agilate. It

1:14:54

has so much adulation for another grown man. It's just

1:14:56

like like sports, like traditional sports. Like, am I going

1:14:58

to look up to a 20 year old that can

1:15:00

throw football? It doesn't make sense to me. Yeah,

1:15:04

it's a very dangerous thing. And you have

1:15:06

to and I wonder if

1:15:08

that comes back to some of the other stuff, too. Like you

1:15:10

have to you have to brush with that. You have to stumble

1:15:12

into it to be like, oh, it's it's just

1:15:14

a regular guy, like just a regular

1:15:16

lady, like just a regular human. There's

1:15:18

nothing special about them. They've

1:15:21

achieved something special. That specialness

1:15:23

is not. It

1:15:25

shouldn't change the way I go about the rest of

1:15:27

my life or think it's repeatable in many cases. And

1:15:29

unfortunately, for me, if I'm honest, it's also probably extreme

1:15:31

arrogance because I do because we're talking about childhood. I

1:15:33

do remember as kids, like meeting like professional hockey players

1:15:35

and everything. And I was like, I don't care

1:15:37

about them. I'm trying to be the first Jason Buck.

1:15:39

You know, like those like this things to be very

1:15:41

good. And so like, that's what we're going to feel

1:15:43

like Wayne Gretzky. I'm trying to be the first Jason

1:15:45

Buck. And then the other one is making me think

1:15:47

about that. You do remind me a lot of is

1:15:49

like Stephen Colbert. I know that's the highest

1:15:51

form of compliment for you. But like, you know, I'll

1:15:53

take it. He's a huge fan of the Colbert report.

1:15:55

I have I am American. So can you back there

1:15:58

on the shelf? Fantastic. He's the best. about

1:16:00

two things of that. One is like, I

1:16:02

had friends that have been on the show and they tell

1:16:04

them like, when you're going, don't try to bar- like don't

1:16:06

try to like to play with him. Like don't try to

1:16:08

be as funny as him. Like everybody tries and you're not

1:16:11

even close. You're not as quick-witted like, that's not gonna happen.

1:16:13

Like and I know on this like, I'm not gonna spar

1:16:15

with you. So like, that's part of it. And then the

1:16:17

other one was like, I remember this one he had this

1:16:19

skit called, he wrote a children's book and the children's book

1:16:21

was called, Fuck It We're All Gonna Die. And

1:16:24

like, that's kind of the way I view life. What are

1:16:26

we talking about? I don't know, it's a great thing. I

1:16:29

don't know, it's a great thing. He has a thing, I'm pretty

1:16:31

sure it's, I cite this way too much in casual conversation. I

1:16:33

need to actually pull that book off the shelf and find it.

1:16:35

But it was basically like, if you want

1:16:38

to raise your kids to be like good adults, you

1:16:40

have to raise them religious and you have

1:16:42

to raise them in like the Abraham money.

1:16:45

Like you want that religion type

1:16:47

specifically, because you want them to be

1:16:49

raised with a God character that's even

1:16:51

bigger than the parents, who

1:16:54

is totally arbitrary and the rebels. Like

1:16:58

you need to beat that into their heads

1:17:00

that no matter what arbitrary forces abound and

1:17:02

that's all you're gonna have to go on.

1:17:04

So just like find your North, keep walking,

1:17:06

it's gonna be a mess. Well, that's what's

1:17:09

beautiful about the, or interesting

1:17:11

about the Abrahamic traditions is like they would, they

1:17:13

call like the full pleroma of how they get

1:17:16

you, right? If you think about you have a

1:17:18

developing mind and you're walking into like these Catholic

1:17:20

churches, right? And they have like stained glass windows,

1:17:22

they have incense, they have music, they have reading,

1:17:24

like they're hitting you from every sense you can.

1:17:26

Supportive. And it's just like indoctrinating

1:17:29

you. So it's almost like, especially Catholics, I feel like

1:17:31

they can, even though they try to go agnostic or

1:17:33

atheist, they never works out, like they can never do

1:17:35

it. They're just fully indoctrinated, like they're never, they're always

1:17:37

gonna have that seed of doubt that always gets them.

1:17:39

But also like you're saying, how do you raise good

1:17:41

kids? Like I was just having this conversation in the

1:17:43

car, they did in that fiance, we talk about all

1:17:45

the times, like I have a bunch of friends that

1:17:47

are like stand up comedians and everything. And it's like,

1:17:49

they're very cognizant of it in the stand

1:17:51

up comedian world that like, their messed up

1:17:53

childhoods are what creates great comedians. And like, you know,

1:17:55

their kids, if they make it as comedians and they're

1:17:58

wealthy, like their kids are gonna have a plush childhoods,

1:18:00

they're not gonna be comedians, right? And that's what I

1:18:02

was saying, entrepreneurship's a bug, not a feature. The

1:18:04

arrogance of thinking I could be the first Jason

1:18:07

Bug. All of that is a broken brain, that

1:18:09

comes from a broken childhood that you desire so

1:18:11

badly to achieve such great things in the world.

1:18:13

So you were saying, not only do we look

1:18:15

at these heroes that made money and go, that's

1:18:17

just a regular person, I look at

1:18:20

all of those rooms and go, these are broken people. Especially

1:18:22

when I'm at hedge fund conferences and everything, I just

1:18:24

look out across the room, all I

1:18:26

see is just people riddled with insecurities and

1:18:29

childhood trauma. Yeah.

1:18:31

How broken were you to fill whatever gap that you're

1:18:33

filling in your life? Be it financial or be it

1:18:35

just like, please everyone just get

1:18:38

along in this room, the ancient

1:18:40

comedian story of like, just no

1:18:42

one hit me. What do I need to

1:18:44

do to control this? Attack first. Yeah,

1:18:48

attack first. Yeah,

1:18:51

we won't get into the, he had the

1:18:54

metaphysiology of 106 and Park and

1:18:57

the freestyle rap competition. That's all that

1:18:59

God says for another day. Yeah, Jin

1:19:01

had the great, I

1:19:04

will do personal attack at a level

1:19:06

of things you can't even say. Things

1:19:09

you can't even say, I will insult

1:19:11

myself to just take every card off

1:19:14

the table and I

1:19:16

will win by savagely destroying myself first. So

1:19:20

the business then, and we're gonna go

1:19:22

to notes after this. This is a perfect, I feel

1:19:24

like, endpoint for us to recap after this. But all

1:19:27

this experience is to say the financial crisis happens,

1:19:29

all this devastation for you to go, I

1:19:32

am not exactly gonna do that again. You didn't

1:19:35

wanna lose the entrepreneurial itch. Like that was the

1:19:37

thing that made you, you. You

1:19:39

said, I am actually gonna start a business to

1:19:41

try to say, how can I do this, but not

1:19:44

below the assets that I save along the way? Is that

1:19:46

a fair way to say it or how do you tell

1:19:48

this story? Yeah, the pain was so great of it that

1:19:51

it never went to experience that again. And so I

1:19:53

looked at it from two perspectives. One,

1:19:56

I had that generational experience with my father's side of

1:19:59

the family of Rob Sh shirt sleeves and shirt sleeves.

1:20:01

My father was the third generation. And

1:20:03

so I was obsessed from a young age with

1:20:05

like multi-generational wealth or, you know, how do you

1:20:07

maintain, how do you get wealthy? How do you

1:20:09

stay wealthy? Like I was obsessed with even like

1:20:11

Worth Magazine when I was like 17 years old,

1:20:13

like all those kinds of things like- That's healthy.

1:20:16

Just a weird kick. Yeah, it was just a weird kick.

1:20:18

Yeah, yeah. So I was obsessed with that as like, how

1:20:20

do you stay wealthy? And so part of that is now

1:20:22

we work with a lot of entrepreneurs and I say, look,

1:20:25

you got, you had to take unbelievably concentrated risk

1:20:27

to get wealthy and you got very lucky. And

1:20:30

that's hard for them to handle that. But like now to keep it, you have to

1:20:32

do a 180 and you have to diversify

1:20:34

broadly to be able to keep that wealth. And

1:20:36

for a lot of people that mental shift, that

1:20:38

true 180 is very hard to handle. So that

1:20:40

was one perspective I had is like, how do

1:20:42

you maintain wealth and or build wealth over the

1:20:44

long run? But then how do I

1:20:46

know if as an entrepreneur, I'm gonna be mitigate

1:20:48

risk, but then take risk, right? And it's very offensive

1:20:50

when you want to take that risk. So

1:20:52

what I was saying earlier is about the

1:20:55

time horizons is like, how do you hedge

1:20:57

that global macro liquidity risk, right? Like, we

1:20:59

can't be global macro traders, right? We have

1:21:01

to be very deep in our idiosyncratic risk

1:21:03

in our business and not really pay attention

1:21:05

to the global macro scenario. So coming

1:21:07

out of the great financial crisis, obviously

1:21:09

was a huge fan of Tlaib and like black swans and

1:21:12

everything made a lot of sense to me. And

1:21:14

so I had taught myself over the years or

1:21:17

decades how to like trade futures, options, all those

1:21:19

sorts of things. And so

1:21:22

for me, it was like, okay, how do I hedge my entrepreneurial

1:21:24

risk? And so I can hedge that

1:21:26

entrepreneurial risk with tail risk liquidity, because when global

1:21:28

critic dries up and manifest in the SP 500,

1:21:31

so I can have that put option like insurance. And

1:21:33

then things like inflation or protracted recessions, it's like commodity

1:21:36

trend followers tend to do well. And I've been studying

1:21:38

them since I was like a teenager too, going back

1:21:40

to like a market wizard books. So I was like,

1:21:42

okay, how do I put this kind of stuff together?

1:21:45

And the idea there is like, you know, most people

1:21:47

when they look at their portfolio, they get a pie

1:21:49

chart from their financial advisor and they go, look, you're

1:21:51

broadly diversified. And I go, look, you're 100% in offensive

1:21:53

assets. When correlations

1:21:55

go to one, those are all going down together.

1:21:57

Doesn't matter what diversification you think you have, it's

1:21:59

conditional. And so we try to focus

1:22:01

on the defensive side. So we always say offense

1:22:04

plus defense wins investing championships. And so

1:22:06

we kind of put that together in a total portfolio

1:22:08

solution with our cockroach strategy. But that's the idea is

1:22:10

it kind of muddles along kind of whatever global macro

1:22:12

quadrant we're in and you can sleep at night. And

1:22:15

I built that as more of a portfolio to stay

1:22:18

wealthy. But the way I view it as maybe a

1:22:20

bit different is I view it

1:22:22

as like whenever I want to embark on

1:22:24

an entrepreneurial venture, like it's high

1:22:26

risk no matter what, no matter how much you

1:22:28

mitigate that risk. So I'm like, maybe if I

1:22:30

can have this liquid portfolio that kind of hedges

1:22:32

out my risks and I can use some of

1:22:34

this portable alpha of this cash I'm setting on,

1:22:37

well, maybe I use 10, 20% to take this entrepreneurial adventure.

1:22:41

If it completely crashes out, well, I have

1:22:43

this portfolio that's kind of chugging along and

1:22:45

mitigating those risks. So to me, it

1:22:47

was a way to like, knowing I can't help

1:22:50

myself, I'm going to want to build businesses, but

1:22:52

knowing the risk that's entailed with that is how

1:22:54

can I mitigate that risk? Or it's almost like

1:22:56

going back to like, if a restaurant's that risky,

1:22:58

how do I de-risk it by buying the building,

1:23:00

right? So if a business is risky, how do

1:23:03

I de-risk it with maybe having this overarching liquid

1:23:05

portfolio that can handle kind of anything that goes

1:23:07

on in the global macro environment or in markets

1:23:09

in general? It's

1:23:12

so interesting and we're going to

1:23:15

go through notes here. We got notes to talk about. Oh man,

1:23:17

I don't know how you do this in real time. I'm so

1:23:19

impressed by the way. I know it sounds like I'm patting you

1:23:21

on the back. After doing hundreds of podcasts myself and being on

1:23:24

hundreds, like I'm in awe of how you

1:23:26

do this in real time. We're doing this

1:23:28

in real time. And I think like this, and

1:23:31

you hit it upon it towards the end, so all my paper

1:23:33

fumbling, I was like, where the hell did I just write

1:23:35

this down? And it was almost at the

1:23:37

end of what we were just talking about right

1:23:39

before that, because you were talking about being

1:23:41

risk mitigators and not risk takers.

1:23:44

And the way that, or one of the ways

1:23:46

that I'll often try to explain this to people

1:23:49

is it's like, you want upside to thrive in

1:23:51

whatever you're doing, but like

1:23:53

downside's all about survival. Like

1:23:56

downside all the way to zero is

1:23:58

not good. And

1:24:00

if you've never experienced that before, like

1:24:03

we want to intervene and try to help you

1:24:05

understand like there's a lot

1:24:07

of shades of gray between here and

1:24:10

when you're actually like in the red and when it's

1:24:12

over. And that kind of that punctuates all

1:24:14

these levels of the story. So all

1:24:16

the way at the back of the beginning

1:24:19

and the ultimate hedge my entrepreneurial risk is

1:24:21

is a liberal arts education like the ultimate.

1:24:24

Is it the ultimate hedge or is it the

1:24:26

ultimate like all offense approach to life like

1:24:28

a true liberal arts education? I mean,

1:24:30

I have my knee jerk is is that it's

1:24:32

the it's the all natural naval gazing way of

1:24:34

life. It's a way to overthink

1:24:37

everything and enthralling and never do anything

1:24:39

ultimate analysis paralysis. Yeah, maybe that's

1:24:41

it. But no, I think I think it

1:24:43

does help because you have to be highly

1:24:45

creative in business to figure out what risks

1:24:48

because like it's a it's a Kierkegaardian problem, right?

1:24:50

Like we were looking and trying to understand life

1:24:52

through the rearview mirror, but we had to live

1:24:54

moving forward through the windshield. And

1:24:56

so to live moving forward through the windshield, you can't

1:24:59

fight the last battle of risk. You

1:25:01

have to think of what are the risks I'm not thinking of. And

1:25:03

so the more broadly to me, the

1:25:06

more broadly you read, watch movies, interact

1:25:08

with people, everything like the more broad

1:25:10

data set you have to putting together

1:25:12

unique ideas like I don't think anybody

1:25:14

has original ideas. I think we

1:25:16

can put together ideas from disparate elements in

1:25:18

unique ways. And so to me, it

1:25:20

goes back to maybe Timothy Wilson

1:25:22

wrote a book called like understanding

1:25:25

adaptive unconscious. And the idea was like, you know, we

1:25:27

have lack of free will or maybe the only free

1:25:29

will we have is to put things

1:25:31

into our conscious that then our subconscious can work

1:25:33

on. So and once again, solipsism

1:25:35

for me, you know, there's a confirmation bias.

1:25:38

I'm just trying to put as much content

1:25:40

as I can kind of in my conscious

1:25:42

so that my subconscious has more data to

1:25:44

kind of work through to work those connections

1:25:46

and break a lot of those things together.

1:25:50

That's beautiful. And basically, this is my

1:25:52

Paul's boutique theory of like where there isn't nothing new,

1:25:54

but you can do really ridiculous things if you're willing

1:25:56

to put the work into how you're going to assemble

1:25:59

this. We talked about naming

1:26:01

conventions. You know, if Cockroach

1:26:03

portfolios and mutiny didn't work out, if you

1:26:05

wanted an acronym like CYA Capital, I mean,

1:26:07

come on, you could have been with CYA

1:26:09

Cap. It would have been awesome. I

1:26:12

have to tell you too, from those wonderful

1:26:15

VHS tapes, so

1:26:17

I had this pair of shorts and they were like somewhere

1:26:20

between a neon green and like a forest green. One

1:26:22

of those only could have happened in like the early

1:26:24

90s covers, colors. And so

1:26:26

they looked like umbros. And

1:26:29

you know, you had the UM on the front and

1:26:31

the BO on the back, but this was the thing

1:26:33

about like the generic shorts of the era. They were

1:26:35

just, they were just umbos. So

1:26:39

it perfectly captured as

1:26:41

you turned, like where the R should be

1:26:43

was like on the side of the thigh.

1:26:46

And so from the front or the back, they look

1:26:48

just like umbra, but on the side.

1:26:50

I remember realizing this like after wearing them

1:26:52

for multiple years or seasons or something, and

1:26:55

just being like, oh my God, my parents

1:26:57

got me umbos. That's

1:26:59

a good mom there. Like I've always

1:27:02

been in the, unfortunately I've always been in like fashion my

1:27:04

whole life, but we were shopping at TJ Maxx, right? But

1:27:06

I could put things together at TJ Maxx. And

1:27:08

there you get these off brands, like your mom's like,

1:27:10

well, it looked like the ones you wanted, like it's

1:27:12

just missing the R there. Like what do you- It's

1:27:14

not the ones involved. You know what's gonna shock me

1:27:16

the other day is my fiance

1:27:19

got some new running shoes. They were Diodorus.

1:27:22

I remember like, I remember Diodorus. I haven't seen

1:27:24

a Diodorus in the- They're making a comeback apparently

1:27:26

in the running space. I

1:27:28

know who's getting a trap sheet for Christmas. That's

1:27:33

amazing. I

1:27:35

love this idea of your dad as the

1:27:37

assistant to the regional manager scuba diver. All

1:27:40

this stuff about like you and your siblings getting

1:27:42

exposed to this stuff is fantastic. Dad

1:27:45

is the Buddhist hippie, mom as the

1:27:47

capitalist Catholic. There's just so much inside

1:27:50

of this that I think is so,

1:27:52

is just so fascinating to me that

1:27:54

inside of the house, there was a non-conflict

1:27:56

way that they were playing with these ideas

1:27:59

demonstrating that you co-exists. this stuff and demonstrating

1:28:01

that it wasn't... like

1:28:04

it wasn't the one true way. Non-conflict is

1:28:06

not my household at all. So

1:28:09

was it just like high conflict but nobody dies

1:28:11

and that's the lesson? Drive

1:28:14

on the upside, survive on the downside? Well, nobody

1:28:17

died so I guess it was okay. It was

1:28:19

definitely a high conflict, high touch household. I

1:28:22

was like, okay.

1:28:25

That's a fair way to say it. No, there were not recent

1:28:28

arguments at dinner of Catholicism

1:28:30

versus Buddhism. And unfortunately,

1:28:32

like we said, the Joshua

1:28:35

Wolk chips on, shoulders put chips in pockets. I think

1:28:38

and going back to that religion is money thing is

1:28:40

like my parents yelling

1:28:42

at each other more my mom yelling at my

1:28:44

dad at night, like late into the

1:28:46

night was never about like who loved each other more.

1:28:49

It was always about money issues. And so I think

1:28:51

that left an indelible oppression on me of

1:28:54

like how much this one weird coinage

1:28:56

thing could affect our lives in

1:28:58

so many different ways. Was

1:29:01

that part of the impetus when you started like doing

1:29:03

the bracelets, doing the mix

1:29:05

tapes, doing the stuff like that? Was that part of

1:29:08

the impetus to like control your own money so it

1:29:10

was separate from the family finances? Yeah, because I just

1:29:12

don't want anybody to control me too. I just... it's

1:29:15

just one of that freedom, right? That you can't tell me what to

1:29:17

do. Like I got my own shackles

1:29:19

over here. Because I could imagine like I would

1:29:21

have been so unbearable. Like if I was able

1:29:23

to grow up now with the internet and like

1:29:25

I would have had an Amazon FBA business at

1:29:27

like 13 years old, I would have been one

1:29:29

of those kids making like 10k a month and

1:29:32

just telling my parents, you know, just horrific things.

1:29:34

And you know, like basically leaving home probably at

1:29:36

like 13, 14. I'd be dead by

1:29:38

19, but like, I mean, it would have been

1:29:40

a good time. Jason

1:29:43

Buck died after his e-bike sales

1:29:45

business took a wrong turn somewhere

1:29:47

in Istanbul. He almost made it

1:29:49

to watch his criterion collection. I want to just

1:29:51

shout out you and the friendship bracelets business. I

1:29:53

want to point out you were the original Taylor

1:29:55

Swift. Take that straight to Reading, Pennsylvania next time

1:29:57

you're in the area. Let them know. The

1:30:02

meditative quality of activities, that's something that I

1:30:04

just, I think is fantastic that you brought

1:30:06

up. Hard labor with

1:30:08

your mom. Extra shout out to

1:30:10

just the hard labor approach, going to Florida, being a

1:30:12

part of the IMG Academy and

1:30:14

doing that stuff. Bonus

1:30:16

shout out for the Piggy's Got the Conch

1:30:18

reference that you dropped inside of that. That was

1:30:21

incredible. Made me really happy. This

1:30:24

belief in curiosity and asking why

1:30:26

that really stems from you when

1:30:28

you make that switch and extra,

1:30:31

extra highlighter on this. Running

1:30:34

in to the 1% of the 1% of the

1:30:36

1%, like experiencing the ceiling of greatness in

1:30:40

a tangible way. Like

1:30:42

you said, Tim Howard was your roommate. Like

1:30:44

that thing where you're like, I'm not messing with this guy.

1:30:48

I'm not messing with this guy at all. Like,

1:30:52

what does that mean to like run into that?

1:30:54

Again, like the 1% of the 1% of greatness

1:30:56

where you're like, that's a ceiling and I respect

1:30:58

it and I understand why I can't cross it.

1:31:00

In sport, it's such a profoundly relatable

1:31:02

thing. Well I put this way, you

1:31:04

may know this, like Tim could also 360 dunk. Like

1:31:08

I'm 5'9 and slow. Like

1:31:10

I'm not, I maximize my

1:31:12

physical guess. And what you find

1:31:14

at that highest level, it's not even your ability

1:31:17

creatively. It's your ability

1:31:19

to work at high speed and mitigate

1:31:21

mistakes. And that's what it was.

1:31:24

Those guys just didn't make mistakes and they could play. And

1:31:26

each level of the speed got higher and higher. So

1:31:28

I might have had some more creativity gifts, but

1:31:30

I would make more mistakes. And that was unacceptable

1:31:33

at the highest level. And

1:31:35

I didn't even think about it, so you said it. Yeah, like I

1:31:37

got to live with some of the best in the world, like from

1:31:39

a young age, like and be a part of that. And then like

1:31:41

now, you know, it was related to the

1:31:43

thing you said before is like asking why is like, I

1:31:45

get it. Fortunately or unfortunately, getting these

1:31:47

rooms with some of the best hedge fund managers in the world. But

1:31:51

for kids out there, they're just people. Ask

1:31:53

them why three times like a four year old and

1:31:55

they usually crumble. And so

1:31:57

that's the deep dark secret of our industry is

1:31:59

maybe why these guys don't want about non-finance things or

1:32:01

whatever, or all the macro pontification.

1:32:04

If you ask him why three times,

1:32:06

it tends to fall apart. It tends to

1:32:08

fall apart. Much like my theory of making the Aladdin

1:32:11

reference in the beginning probably falls apart, so I don't

1:32:13

think that took place in Turkey, but weren't there a

1:32:15

lot of Disney coming to the comments on that? They'll

1:32:17

all take credit. He

1:32:21

came from every country over there. It's crazy.

1:32:24

Everybody claim it. It's fine. Everybody claim it.

1:32:27

Private curiosities, the

1:32:29

punctuated extroversion. This

1:32:31

is another thing that people just spend some

1:32:33

time understanding this about yourself and then with

1:32:35

others. I think about a lot. I made

1:32:38

this note to myself. I think it was when we were talking about

1:32:41

you've been everything from a dishwasher to owner and

1:32:43

all the stories of the restaurant along the way.

1:32:46

Understanding leverage in the entrepreneurial sense is

1:32:48

not just financial leverage. A lot of

1:32:50

it's understanding operational leverage, the

1:32:52

actual jobs or the things you

1:32:54

do, and organizational

1:32:57

leverage, the people that are involved. The

1:32:59

combinations of those two things, all of

1:33:01

them give leverage. They give you upside

1:33:04

optionality. They give you downside exposure, but

1:33:06

that's just the combination of people. How do you

1:33:08

think about the combination of people and organizations and

1:33:11

just the way different combinatorial things can

1:33:14

be explosively disastrous or surging to the

1:33:16

upside? I think

1:33:18

it's one of the hardest things. I'm not a great

1:33:20

operator. I'm good at bringing

1:33:22

an idea into reality and getting it from zero

1:33:24

to one. I'm not a great operator necessarily one

1:33:26

to ten. Luckily, I have

1:33:28

people in my life that are very helpful with that

1:33:31

in our business sense. But the other thing that really

1:33:33

bothers me about our business actually maybe goes, you just

1:33:35

made me think about it for the first time, that

1:33:37

goes back to front of the house, back of the

1:33:40

house for restaurants. I feel the same way about the

1:33:42

hedge fund space is everybody in the front of the

1:33:44

house, the portfolio manager, the CIO gets all the accolades.

1:33:46

But it's the people in the back of the house

1:33:48

working on the onboarding, on the compliance, everything. They get

1:33:51

paid the lease, but the business does not function without

1:33:53

it. It's actually very similar to

1:33:55

restaurants where people are a good home cook or

1:33:57

they throw a good party. Everybody's like, you should

1:33:59

own a restaurant. And it's like, no, you shouldn't. It's

1:34:01

the business of owning restaurants, the hard part. And I

1:34:03

find it's exactly the same in hedge fund space as

1:34:05

like, everybody goes, you're a great trader or whatever. You

1:34:07

should start a hedge fund. No, the business of running

1:34:10

an investment, banning your business is a true business. And

1:34:12

that's very hard to do. And like you said, you

1:34:14

need to get together these different personalities and you need

1:34:16

that front of the back of the house to work

1:34:18

in synergies together. And the back of the house doesn't

1:34:20

get the love that the front of the house does

1:34:22

even from remuneration or just accolades. And it's shocking to

1:34:24

me. And like we tried to have a very maybe

1:34:26

I'm too egalitarian. And this is my dirty hippie nature

1:34:28

is like all of that stuff. We try to try

1:34:30

to do that in that sense. And we even have

1:34:32

like all of our clients pay the same fees no

1:34:34

matter if you're the smallest client or the biggest client.

1:34:37

Like we do all that and we lose business because

1:34:39

of that. But and then I try to pay my

1:34:41

back of house almost the same as the front of

1:34:43

the house. Because I just think

1:34:45

it creates a more synergistic work environment. And you have

1:34:47

to realize like without that function and this is the

1:34:49

hard part I had to learn in life, without

1:34:52

the people to do those detailed things on that

1:34:54

daily basis, that's not in my personality type, there

1:34:57

is no business without them. Like it doesn't matter what

1:34:59

you do, what money you raise, how ever you get

1:35:02

out there on podcasts, none of that stuff matters. It's

1:35:06

so interesting. And there's the any

1:35:08

Kim Scott's work like radical candor or

1:35:10

any of those like yes, there's like

1:35:13

cultural organizational cultural stuff. She's

1:35:15

got this great metaphor that's been with me for since

1:35:18

whenever that book came out of just like you have

1:35:20

your rock of Gibraltar people and then your rock star

1:35:22

people and you have to give

1:35:24

them the same attention and the same types of things and

1:35:26

like helping them with their career path and whatever else and

1:35:28

she did this at Google or Apple or wherever it was

1:35:30

at the time years and years ago. But it was like

1:35:34

you got to put as much effort into the person who

1:35:36

needs the career path and is going to run away unless

1:35:38

you keep them on the career path that you need them

1:35:40

to progress through to help you out or

1:35:42

the people who just need to like process the paperwork.

1:35:45

We just have to be the physical body who answers

1:35:47

the phone. It has an empathetic relationship on the other

1:35:49

on the other side. And if you put yourself with

1:35:52

all rock stars, you're going to fall apart as soon

1:35:54

as that rock suit takes off. And likewise, if you

1:35:56

have all rocks at Gibraltar is like you're never going

1:35:58

to have. the business that

1:36:00

takes off either. That's the combination

1:36:02

of both and it's so hard. And the

1:36:04

other way I think about it that I think has

1:36:07

helped me cross that chasm a little bit is like

1:36:09