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The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More

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The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More

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2432 segments

0:00

Honestly, I would say that

0:01

[clears throat] 90% of the things I do

0:04

happen in the first 5 minutes. 90%. It

0:07

drives me crazy when we get in a room

0:09

and talk about it for 3 months. And I

0:11

respect process, but I think I know what

0:14

I want to do very quickly. We have such

0:17

a small label, so boutique, and we're

0:19

competing with these big companies that

0:21

have been around forever and have all

0:23

these other artists, and we didn't have

0:24

any artists. Mhm.

0:25

>> So when I met an artist and I like them,

0:28

Atlantis Morris said I signed off of one

0:30

song. Muse, I saw them perform one song.

0:34

It shows the artist the passion which is

0:37

very important. This person believes in

0:39

me that much. And also if I left it

0:42

available, maybe someone will offer them

0:44

way more money or make them other

0:46

promises. And I couldn't afford to not

0:49

make fast decisions

0:51

>> or else we would never have gotten to

0:53

where we got to. So, here we are sitting

0:56

in this beautiful home and I wanted you

0:59

to explain this beautiful calligraphy

1:02

behind you that I was admiring. Some of

1:04

the most impeccable handwriting I've

1:06

ever seen. What is it that's sitting

1:08

behind you?

1:09

>> That's purple rain lyrics by Prince.

1:13

>> Just incredible.

1:14

>> I'm a huge fan of Prince. When I was a

1:16

kid, I had Prince posters up on my wall

1:19

and I met him when I was 12.

1:22

>> 12? Yeah.

1:22

>> How did that happen? The place where I

1:25

was living with my dad, an apartment

1:27

building in West Hollywood, was directly

1:29

across the street from a hotel called a

1:31

Park Hotel. And that's when I started

1:33

meeting artists. I started becoming a

1:36

fan. I love music, but I became a fan,

1:41

you know, someone that would actually

1:43

wait to get their album signed or, you

1:45

know, and Prince actually signed

1:46

something for me. He wrote Love God. I

1:48

told him that years years later. We

1:50

became friends and became close. Was it

1:53

love God period or love, God?

1:56

>> It was love God.

1:57

>> Okay.

1:58

>> And it was sign prince.

1:59

>> Wow.

2:00

>> That was a long time ago because he

2:01

later on he he became a Jehovah Witness.

2:04

>> But you could see the posters. I had

2:07

like Billy Idol and Prince on my walls

2:10

and you could see it from the street if

2:12

you looked up. So you can come out if

2:14

you're waiting for your car or whatever

2:15

and you look and you'd see, okay,

2:16

there's someone up there likes music a

2:18

lot. I was on the first floor. There's a

2:20

little balcony there and and I come out

2:23

a lot to meet I met in excess and some

2:27

people I became friends with like Billy

2:28

Idol I became friends with years later

2:29

and Michael Hutchkins I became friends

2:31

with and Morrisy I became friends with

2:32

later but I met them all when I was a

2:34

kid and a really cool thing is other

2:36

kids were around then. They were older

2:38

than me but they were kids and so I

2:40

could hang with them and really get a

2:42

little camaraderie with some of the fans

2:44

out there that were waiting for the

2:45

bands.

2:45

>> I want to talk about addresses and

2:48

Beverly Hills High School. How did you

2:50

end up at Beverly Hills High School and

2:52

why?

2:53

>> Yeah, before Hills High School, I went

2:56

to a school in downtown LA. It was on

2:59

Pico in Arlington. So, it's almost on

3:01

the way to if you're going to go see a

3:02

Laker game, it's on the way to that. And

3:06

I went to that school and it was

3:09

incredible. So many great people,

3:12

different music was a big piece of that

3:14

of my journey there. I took a school bus

3:17

there and the kids would go between two

3:20

radio stations on the bus. So the bus

3:22

driver would play either KDAY, which was

3:24

the first hip-hop station in LA, or they

3:27

would go to K-Rock, which is the

3:29

alternative radio station in LA. And I

3:31

love them both. And so I met a lot of

3:33

really cool kids there who were in these

3:35

groups of people. The there were like

3:37

the punk rockers, the hip hoppers, the

3:39

break dancers, gang members, graffiti

3:42

artists. There just a great eclectic

3:45

group of people during that time period

3:48

where I'm just I'm a sponge. I'm just

3:50

picking up all the energies and really

3:52

falling in love with music. One night I

3:55

was outside the school dance. There was

3:59

the LA Dream Team. That's what they were

4:02

called. This this group that was

4:03

performing that night. And I was waiting

4:05

outside the school. I was very tall. I

4:07

looked a little older than than I was.

4:10

And it was late. My my dad was late to

4:13

pick me up. And while I was out there, I

4:16

saw I saw a guy running past me for his

4:19

life. And then I see a car turn the

4:22

corner. I guess he was chasing the guy

4:24

down. and a guy jumped out of the

4:25

passenger seat and pulled a knife out on

4:28

me and and asked me if I was with that

4:30

guy.

4:31

>> He asked me if I was in a gang and I

4:32

said, "I'm not I'm just a kid waiting

4:35

for my dad. I was school dance and this

4:37

is my school and so he got back in the

4:39

car to chase the guy."

4:41

>> And so, you know, there are no such

4:43

thing as coincidences, but my dad showed

4:46

up. I got in the car and I was like, you

4:50

know, I I almost died and and someone

4:53

pulled out a knife on me and and you

4:55

were late and and I want to go to

4:56

Beverly Hills High School next. And

4:59

again, there's no coincidences that that

5:01

just came to me right then and there

5:03

that I want to go from downtown LA to

5:05

Beverly Hills High and there was a TV

5:08

show 90210 back then. So, I thought I

5:11

want to check that out.

5:12

>> That's a different world from the world

5:13

I'm in now. I want to just see it. And I

5:16

didn't know at the time, but you have to

5:18

live in Beverly Hills to go to Beverly

5:20

Hills High School.

5:21

>> Yeah, it makes sense.

5:22

>> Yeah. I don't know why I didn't put that

5:23

together. [laughter] I just said that to

5:25

my dad and you know, we didn't live in

5:27

Beverly Hills and he knew I that's what

5:30

I wanted and he heard me. He he came

5:33

back to me and said, "There's someone

5:34

who I know who lives in Beverly Hills

5:36

and they will give you their address to

5:41

basically pretend that you live there so

5:43

you can go to that school that you want

5:44

to go to." And the combination of going

5:47

to school in downtown LA and also going

5:50

to Beverly Hills High right after, I

5:52

think that's a big part of of who I am

5:55

today.

5:55

>> Blending the two worlds.

5:56

>> Blending the two worlds. one or the

5:58

other like without the other would would

6:00

not have given me the perspective that I

6:02

needed.

6:02

>> What was the perspective that you got

6:04

once you were transported to this second

6:07

chapter at Beverly Hills High?

6:09

>> Once you walk through those doors, it

6:12

might as well be a TV show from where I

6:15

just came from. people have a lot, you

6:18

know, there's cars and there, you know,

6:20

there's homes [snorts] with pools and

6:24

just the optionality and the potential

6:28

of what they all had was pretty wild.

6:31

And and that actually inspired me to,

6:34

oh, I didn't know you can aim this high.

6:37

I don't have what these people have. I

6:39

don't have the means. I don't have the

6:41

money. I don't have the connections. So,

6:43

I better start working. I think at like

6:45

14 it really started to kick in where I

6:47

go cuz these people are going they go on

6:50

trips and ski trips and I don't know

6:52

anything about skiing. I don't know

6:53

anything about I I just I didn't live

6:55

that world.

6:56

>> So I knew that I needed to do something

6:59

about it. And I started to

7:03

>> I looked what what could I what am I

7:04

good at? What could I be good at? And

7:07

music was my love. It was my passion.

7:08

It's what I I was obsessed over. And so

7:13

I thought something in music

7:15

>> and that's [clears throat] when I

7:16

started to really pay attention to what

7:17

could I do around music. I drew music.

7:18

And then around 15 I really started to

7:21

pick that up and and at 16 I was already

7:23

like really running with it.

7:25

>> So I think this might be a good bridge.

7:28

If I'm missing something in between

7:31

these points, let me know. I'm sure

7:32

there's a lot that we could talk about.

7:34

But Bernie Brilstein, who is that?

7:37

>> So Bernie Brilstein is iconic in

7:39

Hollywood. He's one of the greats. He

7:43

was exceptional. He was one of the

7:45

original managers and he managed all

7:47

these amazing talents. A lot of the

7:50

talents from SNL, he managed all of

7:52

them. He started this idea

7:54

>> John Belalushi, Gary Chandling,

7:57

>> all of them.

7:58

>> And he was beloved. He looked a little

7:59

like Santa Claus. Was a really big guy

8:02

with a white beard. And when I was 15, I

8:05

started to compile artists that I liked

8:08

that were had demos. So, I would go out

8:10

there and try to find artists and try to

8:12

find new artists. And I had like the

8:14

yearbook person come and take photos of

8:16

these. And

8:16

>> this was on your own or were you working

8:18

on your own?

8:19

>> On my own. I didn't know what I was

8:20

doing. I just thought, let me put

8:22

together a portfolio. Let me have

8:24

someone take photos of these artists.

8:25

Let me create get the demos. One day

8:28

I'll get a meeting with somebody

8:30

>> and I'll have something to show when I

8:31

get the meeting.

8:31

>> Yeah. I'll have something to show. I

8:33

think I called it Wise Guy Records. Just

8:36

I didn't know what any of it meant, but

8:37

I had my little logo. So, I did

8:39

everything I could possibly do without

8:40

knowing anything or anyone. And then the

8:43

week I turned 16, I I remember it was

8:46

the week I turned 16 because I didn't

8:47

pass my driver test, [laughter] so I

8:49

needed to be dropped off. So, the week I

8:51

turned 16, I went to meet with Bernie.

8:54

What happened was is I I approached a

8:56

lot of the kids at school at Beverly

8:58

Hills High and I said, "Can I meet your

9:00

dad? Can I meet your dad? Can I meet

9:01

your dad?" Just anyone that was in

9:03

entertainment. And out of all the people

9:05

that I approached, I got two meetings

9:07

that would end up both being really the

9:10

most impactful meetings I could ever

9:12

have. And one of them, the first one I

9:14

got was Bernie Burlstein. And his two

9:17

boys, Nick and Dave, both

9:21

told their dad, you know, you should you

9:23

should meet with Guy. So I go meet with

9:26

Bernie. He was at the 9200 building on

9:28

Sunset. And I played him a song.

9:34

I don't even remember what group or what

9:35

it was at this stage, but I played him a

9:37

song and he just says, he looks at me,

9:39

he goes, "Well, hey kid, how much is it

9:42

going to cost to to put this out?"

9:45

And I knew not to pause cuz then he'd

9:48

know I'm a phony. So I said, " $25,000."

9:54

And he said, "I'll tell you what, kid.

9:56

I'll give you the $25,000.

9:58

If you make it back, pay me back. That's

10:00

all I ask."

10:02

And at the time, I'd never seen $2,500.

10:06

So, I just said, "Bernie, I'd rather you

10:09

make three phone calls for me to music

10:11

people." And I don't want your money. I

10:15

want you. And and he ended up putting

10:16

that in his first book, that story. He's

10:18

passed away, unfortunately. And he

10:21

always felt I said no because I just

10:23

couldn't take the money from him. I said

10:24

no because I didn't know what to do with

10:25

$25,000 and I was a phony. So until his

10:30

last days, he always thought in his

10:31

book, he's like, "The one guy that

10:32

didn't ask that didn't want to take my

10:34

money was Guy Oeri." It's not true. I

10:36

just didn't know what to do with it. So

10:38

he made those three phone calls for me.

10:39

>> Did he pick the people to make the phone

10:41

calls to?

10:42

>> Yeah. I had no idea. I said, "Three

10:43

music business people." He did, and I

10:45

got meetings with with a few of them,

10:48

but they never ended up

10:50

>> going anywhere.

10:51

>> Going anywhere at all. But what ended up

10:52

happening was is I came back home and I

10:56

thought to myself, "Wow, I'm 16 years

10:59

old

11:00

and this guy offered me as much money as

11:04

people make a year in one meeting." If

11:07

people feel they have talent, they don't

11:09

know really. There's no confirmation on

11:10

that talent. You know, people think,

11:12

"Oh, my mom says I'm a good singer or so

11:14

and so says I'm great at this." But you

11:15

don't know until someone confirms it.

11:18

until someone buys your book or goes to

11:20

your show or or whatever until

11:22

>> offers you 25K.

11:24

>> On that day, that was a confirmation I

11:27

needed that I'm on the right path. And I

11:29

went, that's it. From this point on, I'm

11:33

going to turn it up. I'm not looking

11:35

back. This guy offered me 25K in one

11:37

meeting. I just turned 16. I'm going to

11:39

stick to this. I can do this. And many

11:42

years later when I got my first gold

11:44

record, I sent it to Bernie because that

11:46

was so impactful on my life.

11:48

>> You mentioned two meetings.

11:50

>> Yes.

11:50

>> Was the other Freddy?

11:51

>> The other was Freddy De Man.

11:53

>> All right. Who is Freddy De Man?

11:54

>> So Freddy de Man, his daughters Nissa

11:57

and Polar connected me with their dad

11:59

Freddy. And Freddy was iconic as well. I

12:03

mean he worked on Thriller with Michael

12:05

Jackson.

12:06

>> Wow.

12:06

>> He managed Madonna. He managed some of

12:09

the greatest artists of all time and he

12:11

was just a really great human, great

12:14

guy. And he heard me out. It took a few

12:18

meetings to get Freddy to really go for

12:19

it with me. Not that long.

12:21

>> And this meeting was after Bernie.

12:22

>> Meeting was after Bernie. And he just

12:24

learned about me. He heard he heard my

12:26

pitch and I'm trying to do this, I'm

12:27

trying to do that. And he knew I didn't

12:28

really have any money.

12:30

>> Yeah. At that point, what was your

12:31

pitch?

12:32

>> Gosh, I think I just showing him that

12:33

that I I'm in the flow of music. I'm

12:36

around music. I'm around artists

12:38

>> the portfolio.

12:38

>> Yeah. I start but one one of the crews

12:40

that I was working with was Ice Tea. I

12:42

got very lucky got introduced my friend

12:44

Chris Boyd I met when I was working when

12:46

I was 15 at Fred Seagull and Chris Boyd

12:49

another guy was working there and he's

12:50

like oh I know I tea and his producer

12:52

Johnny Rivers and I go would you want to

12:54

come to the studio and check it out and

12:56

I'm like yeah I want to go. So he

12:59

brought me to the studio and actually my

13:01

first day in the studio Iced Tea goes

13:03

come in come into the booth and do a few

13:05

words and I'm actually on the album.

13:07

>> Wow.

13:07

>> Yeah. He had me say like few words on

13:09

the album. But um but I started hanging

13:11

around and I'm like what could I do?

13:13

Could I could I clean up? Could I carry

13:15

someone's bag? Could I you know what?

13:18

How do I be helpful or of service? I'm

13:20

just so happy to be around this energy,

13:22

the music and artists coming in and out.

13:24

And he had a thing called Rhyme

13:25

Syndicate. So, a lot of the artists came

13:28

through there and I was able to be

13:31

around them and help and and then I

13:33

ended up becoming the manager of ICT's

13:36

DJ and his brother who's Henji and

13:40

Eively. Eve Lee is Ice Te's DJ. So, I

13:42

managed them. It's my first group I ever

13:44

managed. And I was 17. We got them a

13:46

record deal.

13:47

>> So, I had that and I always checked in.

13:49

I checked back with Freddy and said,

13:50

"Fred, I just got my first group signed

13:52

to record label." So he knew there was a

13:55

guy named Steve Riiffken who I met who

13:58

knew the record label. He helped me get

14:00

that first record deal.

14:02

>> So when I went to see Steve and I played

14:03

him he's DJ Evelan Brother Henji and I

14:06

said here's the music and said I I know

14:08

a label for you. So he helped me get my

14:10

first record deal. So I always write

14:12

Freddy and go hey Freddy I just got my

14:14

first group signed. I just I'm manager

14:17

you know and he knew I was how is he

14:19

pulling these things off on his own

14:21

without any help or any money. And so I

14:24

met with him and he said, you know,

14:26

Madonna and I are going to start a

14:27

record label one day. So I said to him,

14:30

I'd love to work there. I said, I don't

14:32

need any money. Which I did need money,

14:34

but I wanted to make it really easy for

14:36

him. I said, I don't need money. Just

14:38

give me an office and a desk. That's all

14:41

I ask. And he was like, okay. So he

14:44

brought me in as a, you know, scout cuz

14:48

one day they're going to start a label.

14:49

They didn't even have a name. They were

14:51

just they just knew they were going to

14:52

do it. So I'm scouting

14:54

>> and and then one day I I find Hole,

14:59

which is Courtney Love. I find their

15:01

first song, Teenage [ __ ] and I go, "Oh

15:04

my god, this sounds incredible." I just

15:06

just blown away by the sounds and the

15:08

lyrics and all of it. So I reached out

15:11

to the lawyer, Rosemary Carol,

15:14

and next thing I know, it's in the paper

15:16

the next day. Madonna is trying to sign

15:19

hole. How did that happen?

15:22

>> I mean,

15:22

>> would you ever

15:23

>> I made a I made a phone call. [laughter]

15:25

I was very naive back then, but it was

15:28

like Madonna's trying to sign Hole. So,

15:30

the next day, there was a show that Hull

15:33

was doing at the whiskey. I think Kurt

15:37

was there. Then Madonna was like, "Who's

15:39

this?" Wanted to talk to me about who is

15:43

this whole thing that you're think for a

15:45

second.

15:46

>> Yeah. So I go in a room and I play the

15:48

song for Madonna and for Freddy and it's

15:51

pretty wild. I mean the lyrics are like

15:52

when I was a teenage [ __ ] my mother

15:58

said she said baby what for? I was like

16:01

whoa you got to go back to that like

16:04

>> that time period.

16:05

>> They're like okay all right so go go go

16:09

after it. And so I went after it. I

16:10

didn't get it. It was between us and

16:12

Geffen Records and we didn't get it. It

16:15

went to Geffin Records, but my first

16:17

artist I ever attempted to sign was

16:19

Hole.

16:19

>> So, let me pause you for one second.

16:21

>> Yeah.

16:21

>> All right. So, the meetings

16:23

that you got with Bernie and Freddy. So,

16:26

you got two introductions. How many how

16:30

many kids at school do you think you

16:31

asked in total to end up with those two?

16:34

>> I think I probably asked five.

16:36

>> Okay. All right.

16:37

>> Yeah. I mean, I wasn't social guy. I'm

16:40

not on the football team. I was just

16:42

sort of my own music guy running around

16:44

and I didn't have much. So I did as much

16:47

asking as I can from who I could figure

16:49

out to ask. So I probably asked around

16:50

five. I remember I remember one person

16:52

specific saying my dad doesn't do that.

16:55

Whatever cuz it was rap. I was trying to

16:57

play. Oh, my dad doesn't do that. So but

16:59

I I didn't have any shame. I just I

17:01

needed I needed to figure this out. I

17:03

knew that my time was limited before

17:05

going to college and I better figure

17:06

this out soon. So I was on a hustle.

17:09

This is from an LA Times piece way back

17:11

in the day, 1997. It says something

17:14

along the lines of I gave myself a year,

17:16

which is why I kept pushing people for a

17:18

chance. Maybe that's accurate, maybe it

17:20

isn't. But did you apply pressure to

17:22

yourself in that way, like instead of

17:24

going to college?

17:25

>> No, I went to college. I went for half a

17:27

semester and I got my first group

17:29

signed, which was was just Henjini Vi.

17:31

And then I I remember going to my

17:33

English teacher.

17:34

>> I don't know her name. She was amazing

17:36

because I said, "Hey, I'm thinking of

17:37

dropping out and focusing on this thing

17:39

and she just looked at me and said, "You

17:40

could always come back."

17:42

>> Wow.

17:43

>> Yeah.

17:43

>> It's wild to think about these just

17:44

chance.

17:45

>> That was it. And I go, "Oh,

17:47

>> I could always come back." Okay. So,

17:49

that was it. And by the way, I couldn't

17:51

even afford the $700 per semester, you

17:55

know, and all the things that came with

17:56

that.

17:57

>> So, I I had no choice. Sometimes having

18:00

no options and no choice is really the

18:02

best option. Where did the like hutbah

18:05

come from? Right. I mean, just that

18:07

drive. I mean, was that absorbed from

18:08

the parents? Were you just out of the

18:10

box, very different?

18:11

>> I fell in love with music in a big way.

18:14

>> But I think I realized how lucky I was

18:17

to be at Beverly Hills High and see

18:21

the potential of what was Yeah. of

18:24

what's possible. And I thought, "Wow,

18:26

not everyone is is this lucky. Not

18:28

everyone gets this opportunity." And and

18:31

by the way, I was scared that they would

18:32

kick me out cuz if they found out I

18:34

didn't live there, they kick you out.

18:35

>> So I had to watch how I went to school.

18:37

It was wasn't like an easy thing to do.

18:39

And so I just thought for every day I'm

18:42

here, I'm really lucky and I and I need

18:44

to pay attention to that. And I just

18:47

realized that if I wanted to change my

18:49

destiny, I [clears throat] needed to get

18:51

going.

18:52

>> And at what moment did you realize, oh,

18:54

I think this might just work out. I

18:56

mean, was there a particular

18:59

person or band you signed? Was there any

19:01

flash point or was it really gradual?

19:04

>> The Bernie Burlstein moment where he

19:06

offered me 25 grand the week I turned 16

19:09

was a big game changer for me. And then

19:13

there was a personal moment for me when

19:17

I got a car

19:20

when I finally passed my driving test.

19:21

took a few times when I finally got my

19:24

car. And I remember going to see my old

19:27

friends from my old school cuz I when I

19:29

drove it to Beverly Hills High, it was

19:30

Honda Civic.

19:31

>> When I drove it to Beverly Hills High, I

19:33

got not one person commented or said

19:35

congratulations or nothing. No mention

19:37

of it at all.

19:38

>> Sure. And then I went to my old friends

19:40

from my old school and then they

19:42

couldn't believe they couldn't believe

19:45

that I had a brand new Honda Civic and

19:48

they got in the car and they were

19:51

rolling down the windows and sticking

19:53

their arms and heads out and I was like,

19:54

"Oh, wow. Okay, I got a little

19:56

perspective there to go, oh, these

20:00

people at Beverly, they're not really my

20:01

friends. I'm here for a reason. I I was

20:04

put in in around this community for a

20:06

reason, which is to work and which is to

20:08

build my my name and to build the things

20:10

I want to do. And it wasn't until years

20:12

later I I told that story in that thing

20:13

you're talking about when I was 24 and

20:16

my, you know, my dad mentioned it was

20:18

really hard to even come up with the

20:19

money for that car back then. It was a

20:22

really big deal for us. It was expensive

20:23

back then. And so I think I need a

20:26

perspective a lot of the

20:30

opportunities that were in front of me

20:31

and to really appreciate them.

20:34

>> So it's a combination of those things.

20:38

>> And from the chapters we've discussed so

20:41

far, I mean was then the next phase

20:45

building your relationship with Madonna

20:47

primarily or where did you kind of hop

20:49

off past the things that we've already

20:51

discussed? Madonna and I the first real

20:53

connection was that whole connection

20:55

where I was like well play me this thing

20:57

that you like and then the second one

20:59

second artist I brought was Rage Against

21:01

the Machine and I really wanted to sign

21:03

Rage Against the Machine and so I took

21:05

her to the concert in New York the

21:07

Limelight I think it was called and I

21:09

didn't get them either. I didn't get

21:11

Rage. They ended up going with Michael

21:12

Goldstone at Epic Records. So you know

21:16

God the first two things I competed for

21:18

I didn't get. Well, not only did you not

21:20

get them, but they went on to be

21:21

>> Yeah, it was painful successes, right?

21:23

>> Yeah, it was painful. The third one I

21:25

that I competed for, I did get. It was

21:26

called Candlebox. And at that time,

21:28

actually, I think it outsold both Hole

21:30

and Rage. They ended up doing really,

21:32

really well. But regardless, Hole and

21:34

Rage, even to today, I still listen to

21:37

those. I love them. But I was very lucky

21:39

to get Candlebox. The fact that they

21:41

they bet on me and we didn't have

21:42

anything.

21:43

>> Yeah.

21:43

>> We just had this idea, you know, they

21:46

ended up selling 4 million albums on

21:47

that album. But I'll I'll never forget

21:49

that. I'll never forget that they gave

21:51

me that shot. That was the my first

21:52

success story was

21:54

>> they give you a shot, but just to repeat

21:57

what you just said, like you didn't have

22:00

much, right? Like they were placing a

22:01

bet on you.

22:02

>> What then goes into

22:05

helping make a hit album that sells 4

22:08

million?

22:09

>> Going back to that time period.

22:10

>> Mhm.

22:11

>> First is the music. I saw them. I I was

22:14

so lucky. I walked into almost

22:16

everything that I've been lucky on

22:18

happens within minutes, not within days

22:20

or weeks or months to think about it.

22:22

It's all intuitive and it's very fast. I

22:24

was supposed to be somewhere else that

22:25

night, but I went to I went to this

22:27

party. It was so bad that I thought,

22:28

"Oh, I have time to go see that showcase

22:30

of that band from Seattle." So, I go to

22:33

the lingerie on Sunset and I walk in and

22:38

and these guys start performing. Now,

22:40

there was a screen like a

22:43

[clears throat] like a video screen on

22:45

the side of the stage like and and then

22:48

there's a stage and I was looking at the

22:51

video screen. There were maybe like 30

22:53

people in the audience. It's a showcase

22:56

and I'm looking at that screen and I saw

22:59

thousands of people singing along to

23:02

that band.

23:02

>> In your mind,

23:03

>> I just in my mind. Yeah. But I went to

23:06

the pay phone from that performance,

23:10

called Freddy and said, "Fred, I have

23:11

our band. This is the band. I just saw

23:13

them. This is the one." And so it starts

23:16

with that. It starts with always starts

23:18

with the magic.

23:19

>> I don't care if you're tech company or

23:22

whatever it is, a film, a product, a

23:24

book. Magic. You got to have magic.

23:25

Something something has to pull you in.

23:28

>> And that night, I saw it. I visualized

23:31

it. And the songs were there. The songs

23:32

were so there that when we made the

23:34

album, their first two singles, we could

23:37

not beat the demo. They went into

23:39

re-record them for the album. So,

23:41

whatever they made for a few hundred

23:42

bucks that that I had with a a lot more

23:46

money and a lot more time, we couldn't

23:48

beat. And so, those songs, those first

23:49

two songs on the album are from the

23:52

demo. So, the music was there. They were

23:54

talented. The band was talented. The

23:56

singer Kevin is so great. And they

23:59

really did it the hard way. They chipped

24:00

away. They did show after show after

24:02

show took took few years for every week.

24:06

Every week little by little little by

24:08

little keyword is artist development and

24:10

people don't always develop that much

24:12

but it's something that we all want.

24:14

Every artist wants to have the time to

24:16

build have the time to develop and and

24:18

we really took that time week after week

24:20

after week developing that one. That's

24:23

how we got there. This is maybe jumping

24:26

ahead too far, but what would be an

24:28

example of that in your

24:31

investing later? Could be tech, could be

24:33

outside of tech where you saw something

24:37

or you talked to someone and it was

24:39

within a matter of minutes or one

24:41

conversation. You're like, okay, that is

24:45

that is a horse to bet on. Honestly, I

24:47

would say that 90% of the things I do

24:50

happen in the first 5 minutes. 90%. It

24:53

drives me crazy when we get in a room

24:55

and talk about it for three months. And

24:56

I respect the process. I know there is a

24:58

process to these things, but

25:02

I I think I know what I want to do very

25:06

quickly. It started out I think the

25:08

muscle that got built for fast sort of

25:12

response thinking or intuition was

25:14

really in the music business. We have

25:16

such a small label was so boutique and

25:18

we're competing with these big companies

25:20

that have been around forever and have

25:22

all these other artists and we didn't

25:23

have any artists.

25:24

>> So when I met an artist and I liked

25:26

them, Atlantis Morris said I signed off

25:29

of one song, Muse. I saw them perform

25:32

one song and I stopped them after the

25:35

they flew all the way from London to LA

25:36

to showcase for me and I after the first

25:39

song I stopped them. I said, "You do not

25:40

have to play another song." And they're

25:41

like, "We flew out all the way from

25:43

London. We'd like to play more music." I

25:44

go, but I just want you to know I do not

25:47

need to hear another song that just be

25:49

clear. So it shows the artist the

25:52

passion which is very important. This

25:55

person believes in me that much.

25:56

>> High conviction. Yeah,

25:57

>> high conviction. And also if I left it

26:00

available, maybe someone will offer them

26:03

way more money or make them other

26:05

promises. And I couldn't afford to not

26:08

make fast decisions

26:09

>> or else we would never have gotten to

26:11

where we got to. So, in any of those

26:14

examples, and I know this is possibly

26:17

very hard to verbalize,

26:19

someone said to me recently, and I

26:20

thought it was pretty funny. They're

26:21

like, "Yeah, in Silicon Valley, if you

26:22

say you're using your intuition, nobody

26:24

listens. But if you say pattern

26:25

matching, then they pay attention." But

26:27

if you were trying to explain what you

26:30

intuited or noticed in that one song,

26:33

understanding the music is good, but

26:36

what else are you picking up [snorts]

26:39

from those five minutes?

26:42

because you can't bet on everything,

26:43

right? Especially as a small label. So,

26:45

what were you picking up on that allowed

26:47

you to make a fast decision in that way?

26:49

>> Uh, well, I have to fall in love and you

26:52

know, you can't fall in love every 5

26:53

seconds. I didn't know I was going to

26:55

fall in love with Atlantis when she

26:56

walked in my office with Glenn Ballard.

26:58

They came in to play me. I didn't know

27:00

what that was going on here. I thought

27:01

they were a band. He was the producer

27:03

co-writer. You just have a feeling and

27:06

there is a lot of pattern recognition

27:08

later. Like now with experience,

27:10

>> now I bring other elements into the mix,

27:13

other things I'm looking for

27:15

>> that are different than back then it was

27:17

just I was just gut. It was just like I

27:19

I love it. I'm ready to go. You have I

27:21

feel it and you have to fall in love,

27:23

>> right? And later today, I I would say on

27:25

my tech investing and what I do there,

27:27

it's a it's a combination of gut, a

27:30

combination of pattern recognition. And

27:33

then

27:35

there's a few other things like one of

27:37

the things I look for is can I help it?

27:39

I visualize what I can do for the

27:41

company and that gets me excited too.

27:43

>> So I go, oh wow, okay, I have a feeling

27:45

I can help in a big way or I have a it

27:47

starts the puzzle starts to come

27:48

together for me very quickly. So that's

27:50

important. And then of course there's

27:52

the other aspect of well you got to make

27:54

sure they do what they say. Let's try

27:57

this thing out that you know let's make

27:58

sure the car actually shows up when you

28:00

press the app and it picks you up and it

28:03

well [clears throat] make sure the

28:03

things work. Make sure that you can stay

28:05

at the apartment and it's actually oh I

28:07

press the thing and I can get an

28:08

apartment.

28:09

>> These things have to work.

28:11

>> But for me it all starts with that

28:13

initial pitch.

28:15

>> How does Alanis Moriceet fit into your

28:17

life? Seems like an important piece of

28:19

the puzzle. Yeah, she played a big role

28:22

in my life. She

28:24

was the rocket ship. It just took me to

28:27

the next level. She appeared in my

28:29

office with her with Glenn Ballard.

28:32

>> Mhm.

28:32

>> And they played me one song. They played

28:36

a few songs, but the first song they

28:37

played was a song called Perfect. I

28:40

didn't understand how powerful

28:43

those lyrics were until later when I

28:46

really listened to it. Mhm.

28:48

>> It's really about earning your parents'

28:51

like, do they believe in you? Do they

28:53

love you? I don't know if you know

28:54

lyrics, but sometimes it's never quite

28:56

enough.

28:57

>> When you're flawless, then you'll win my

29:01

love.

29:02

>> Don't forget to win first place. Don't

29:04

forget to keep that smile on your face.

29:08

I didn't even understand. To me, it was

29:10

just, well, how is she putting these

29:12

words together? I just had never heard

29:14

anything like it. Again, later I

29:17

understood how powerful those lyrics

29:19

were. But at that time, I was just in

29:21

love with what I was hearing and I

29:23

hadn't heard anything like it and I

29:25

went, "I'm ready to sign you. I love

29:26

this. I'm all in." I didn't know

29:28

anything. Remember, I didn't know that

29:30

comparisons where people were like, "Oh,

29:31

I thought it was Joanie Mitchell." I

29:34

didn't know Jonie Mitchell. So, to me,

29:35

she was my Jonie Mitchell. I didn't

29:36

never listen to Jonie Mitchell before. I

29:38

listened to it later because of her. I

29:40

wanted to know what people were talking

29:41

about. But to me, she was my she was my

29:44

Jonie Mitchell. And I didn't know any of

29:46

the background. A lot of people

29:47

prejudged her because she had as a teen

29:49

did like a pop album in Canada. And so

29:52

people had all this background. I had no

29:54

background. I literally was asked to

29:56

meet with her and Glenn and I knew

29:59

nothing.

29:59

>> All you had was that meeting.

30:00

>> I knew nothing. They walked in and and I

30:03

thought, "Oh, wow." It felt like a

30:04

hippie group actually. I was like, "Oh,

30:06

maybe there's like some sort of hippie

30:08

vibe kind of what is this going to be

30:10

like kind of thing." But it was again

30:12

another life-changing moment when the

30:14

story is told. It's that everyone

30:15

passed. But I got it. I got I just felt

30:19

it in the first minute. And then we

30:22

ended up working together and working on

30:24

that album and that album ended up

30:26

selling 30 million albums and I think

30:29

top five debut album of all time. That

30:31

really just took me to the, you know,

30:33

cuz not only did I sign it, but everyone

30:36

else didn't want to sign it. So it's not

30:37

like I even competed. So it really

30:41

cemented that, okay, I'm in a good place

30:44

right now that I can do these things and

30:46

I this probably is going to give me more

30:47

opportunity to do more of these things.

30:49

So she's such a big part of my life and

30:51

she's so she's so talented. How lucky

30:56

that

30:58

years later she's right now she's still

31:00

winning awards. She's still out there

31:02

crushing. She's actually doing

31:05

incredibly well right now. And it makes

31:09

me so proud to have played any part of

31:13

that. It would be so sad to have missed

31:16

that one. I'm so happy to have been

31:19

fortunate to have gotten that that

31:21

meeting and to have figured it out. A

31:23

lot of people when they initially heard

31:27

it, I remember Freddy once asking me,

31:30

"What do you think this record could

31:32

sell before it ever came out?" And I go,

31:33

"Millions of albums." I just had a

31:37

feeling that I had not heard anything

31:38

like this and that this was a monumental

31:44

record. The rest is history. Rest is

31:47

history. I'd love to spend a little bit

31:50

of time on what you've learned from

31:54

Madonna. This is an older variety piece,

31:56

but the quote here that's attributed to

31:58

you is she mentored me and by working so

32:00

hard pushed me to work so hard. I didn't

32:02

know [ __ ] until she grabbed me by the

32:04

hand and said, "Let me show it to you."

32:06

And it goes on and it goes on. But what

32:08

did you pick up from Madonna? What are

32:10

the key sort of learnings?

32:12

>> I mean, there's some clear learnings and

32:14

there's stuff that with I'm 36 years

32:16

next to this woman.

32:17

>> Yeah.

32:18

>> And there's things that when you look

32:20

back, you go, "Okay, you know, I got

32:22

that like people who think about things

32:23

that I got that from my brother or my

32:25

mother or my

32:26

>> There are things that I didn't realize I

32:28

was getting the whole time." So, there's

32:29

both. The front part is pretty, I think,

32:32

obvious. You know, her work ethic is

32:35

>> not to be believed. Her commitment to

32:37

her craft not to be believed. her

32:40

passion for

32:43

just the greatest gifts of whether it's

32:48

through the books that she's reading or

32:50

through the art that she's finding or

32:53

the people that inspire her or the

32:55

designers or that she's so surrounded

32:58

herself with a collection of some of the

33:00

most incredible people in the world and

33:02

she identified them. By the way, she is

33:04

the greatest identifier. She found these

33:07

amazing talents early and and was able

33:10

to whether either could they be painters

33:12

or Freda Ko or they could be designers

33:14

or musical people like she's an

33:16

incredible finder of talent. I think the

33:19

thing that has really affected me the

33:22

most is

33:24

that she

33:26

doesn't see any kind of

33:30

there's no walls around her thoughts.

33:33

There's no oh I can't do that.

33:35

>> Right. in terms of constraints, right?

33:36

>> Yeah. Even going back to my first

33:38

experience at Maverick Records,

33:42

if you went to any record label,

33:45

they probably would have they would have

33:46

put me in a compartment. There's the R&B

33:48

department, there's a jazz department,

33:50

the rock department, reggae department,

33:52

pop department, hiphop department, and

33:54

you're oh, what department are you in?

33:57

And they and they sort of bucket you

33:58

into these things. And I think that when

34:01

I look back and I go, how did I not

34:03

really bucket myself? if I went from

34:04

this to this to that to that to that.

34:06

And I think it's it's really just being

34:08

around her has allowed me to never think

34:12

in a limited way

34:14

>> and they all work together. A lot of the

34:16

stuff I do on technology has allowed me

34:19

to bring that into my musical world and

34:22

to understand how these things work

34:23

together or the relationships and

34:25

they're so handinand and of course a few

34:28

decades later now people understand

34:30

that. But at the time it was so

34:33

>> it was it was it was very much like what

34:34

are you doing this tech thing is crazy

34:36

and you're not doing innovation is

34:38

innovation and how we can distribute

34:40

music or how we market and vice versa

34:43

all the stuff from music is you know

34:45

when you when you're launching a new

34:46

company you have you know these founders

34:48

are rock stars in my mind every founder

34:51

I invest in I look at them like they are

34:54

the rockstar I go that person has music

34:56

they want to share with the world they

34:57

have their album and my job is to

35:00

identify that artist, that founder

35:03

before everyone else maybe identifies

35:05

them. And my job is to help you reach

35:06

that audience. How do we tell the story?

35:09

How do we reach the base of your

35:11

audience? How do we grow your audience?

35:13

You know, what's your first single?

35:15

What's your second single? I still work

35:17

in that kind of process, which is very

35:20

musical in my mind. We're going to spend

35:23

a good amount of real estate on on the

35:26

tech. But before we get to it, I want to

35:30

take a moment to explore the the terrain

35:34

of film and how you ended up executive

35:39

producing Twilight and and all the rest

35:42

because as as you mentioned in a

35:44

different environment with a different

35:45

label, you would have been tightly

35:47

siloed and you wouldn't have had that

35:49

ability, right? How did you end up with

35:53

the fora into film?

35:56

>> I'd been signing bands for a long time

35:58

and running the record label and I

36:00

thought, well, why don't we do a film

36:02

company as well? And Madonna and I were

36:04

really in a good groove together and

36:07

thought, let's just let's just start

36:09

this film company. Why did that come to

36:12

mind?

36:12

>> I don't really recall that. I just

36:15

recall thinking about how people do it

36:18

differently. And so again, I didn't have

36:21

context. The best thing sometimes is to

36:23

have zero context. Sometimes fresh is

36:26

okay. Sometimes having a blank canvas.

36:28

And with films, I had a blank canvas. I

36:30

didn't know how it worked,

36:31

>> but I knew I wanted to make some films.

36:33

>> And I So I had this idea of

36:37

bringing in a bunch of producers under

36:39

one roof. And they were all independent

36:43

producers. And the idea was is I'll

36:46

bring them in and you know house them

36:48

and and give them support and pay for a

36:52

lot of the legal things that cost money.

36:53

When you're independent is it's a lot on

36:55

you,

36:55

>> right? All the back office, all of that

36:57

stuff.

36:57

>> We'll take all that on. We'll help you

36:59

and then we'll work on these projects

37:01

together. And we had like a lot of

37:03

producers that I if I was to to pay for

37:06

them, I couldn't have afforded it. But

37:08

we did it that way. and and out of that

37:11

came a lot of films and a lot of

37:13

Twilight and and Percy Jackson and a few

37:15

others that I was very lucky to be part

37:16

of. The guy who ran at Mark Morgan was

37:19

really good at it, but there were a lot

37:22

of complications.

37:24

And I was at that same moment that we

37:27

were that it started to take off, I

37:29

picked up Madonna as manager with my

37:34

partner at the time, Angela, and I took

37:36

on Confessions, which was the pretty

37:39

massive tour that year and I think the

37:41

biggest selling record of that year. So

37:43

as a I don't know how old I was back

37:44

then, but that was a major

37:46

responsibility for me.

37:48

>> Hard to ride both of those horses at the

37:50

same time.

37:50

>> Just that alone, just Madonna at that

37:52

moment in time for someone I had not

37:54

been a music manager for, you know, and

37:57

anything near that level. And so to take

37:59

that on and to, you know, work on all

38:02

things the tour and the album and all

38:04

that. And for people who have no context

38:07

on music at all, what does a music

38:11

manager do in that type of situation?

38:14

>> It's a tricky question because no one

38:16

manager is the same. Everyone's

38:18

different,

38:18

>> I guess. What was your umbrella of

38:19

responsibilities?

38:21

>> When Madonna started working on Ray of

38:24

Light, I found the producer, William

38:27

Orbit, but I was not managing her. I was

38:30

her partner at the record label Maverick

38:32

Records and not her own not Warner

38:33

Brothers which is where she was she was

38:35

on War Brothers but I was just we were

38:36

just friends and working together but I

38:39

fed ideas I found the director Yonas

38:42

Aland and so I was creatively really

38:45

working on this project called Ray of

38:47

Light. So we're already building a

38:48

creative rapport and on music Stefan

38:51

Sidenway the director introduced me to a

38:54

producer named Her Ways. He gave me a

38:55

demo. I loved it and I gave it to

38:57

Madonna and I ended up becoming music.

38:59

So I found on those two albums I really

39:01

even though I wasn't managing her I was

39:03

creatively helping here and there bring

39:05

in some ideas.

39:06

>> Mhm.

39:07

>> So we already had a rhythm on the

39:11

creative side. Now, there are some

39:13

managers that don't do any creative and

39:14

there are some that are very creative,

39:16

but I was coming from the creative point

39:17

of view on ideas, ideulating. Here's

39:20

here's things we could do. Here's things

39:22

we could build. So, I think I think for

39:23

me as that's the management that I am. I

39:27

I'm more creative. When I'm working with

39:29

someone, I I'm I'm sort of in it. And

39:33

there are other managers [clears throat]

39:34

I've worked with who they really just

39:37

they don't do the creative but they do

39:38

an incredible job managing everything

39:40

keeping you know putting together the

39:42

tour but they're not in there going what

39:44

if we did this of you know what if we

39:46

there's different kinds of managers I'm

39:48

creative for example when I showed her

39:52

Jonas Arland did a video for Prodigy

39:54

which is a band I signed and it was

39:56

really provocative and I just showed it

39:57

to her this guy this is crazy and she

39:59

goes he's doing my first video or or

40:01

he's doing that like you I showed her

40:03

there's a a guy named Chris Cunningham.

40:05

He made a song called Come to Daddy by

40:07

AEX Twin, which is really insane. It's a

40:09

$30,000 video. I just showed it to her

40:12

just to show her this. Look at this

40:13

crazy thing. And she's like, "That guy's

40:15

doing that video." So, she had Chris

40:17

Cunningham do Frozen, which is an

40:20

incredible video. And she had Jonas

40:22

Aland do Ray of Light. So, it was just a

40:25

really great back and forth. We had

40:27

really great energy together that I she

40:29

she was open to my craziness and and

40:32

then she would take it to the next

40:33

level. What and and this is this is my

40:38

even when I was very very young and

40:40

everybody knew Madonna. I was constantly

40:43

impressed by her longevity and ability

40:46

to seemingly reinvent herself. And I'm

40:50

just wondering why you think she has

40:53

been so consistently good at that over

40:56

decades. I mean, it was the first

40:58

example that I remember even as a young

41:00

pretty young kid be marveling over and

41:04

I'm just wondering if you could add any

41:07

any color to that. She doesn't sit

41:12

well on her past.

41:15

She's not high-fiving herself.

41:19

>> [laughter]

41:19

>> She's not really a Oh my god, I've done

41:22

all these. She's just keeps it moving

41:24

forward. Yeah, I think that that's a

41:27

that is, you know, part of the

41:29

inspiration for continually

41:32

trying to move forward myself is I'm

41:35

have a front row seat or shotgun to this

41:39

incredible

41:40

journey of this woman who just

41:43

continually

41:45

defies all the odds and

41:48

fights the fight. It is not easy. It

41:51

it's not just like it's not that she's

41:53

maintained or stayed around. It's

41:55

actually that she's had to fight her way

41:58

through it a lot. She's breaking ground

42:00

for a lot of other people who are coming

42:02

behind her who can say, "Oh, Madonna's

42:05

done it. I can do it." But it is no easy

42:07

feat. There is a lot of a lot of

42:10

[ __ ] to deal with.

42:12

>> And I think it comes from she just

42:14

doesn't celebrate her accomplishments.

42:17

She just starts like it's a brand new a

42:20

brand new day.

42:22

>> How did you end up and I don't know if

42:24

this is a good starting point but I'll

42:27

throw it out there as an example. Your

42:29

first consumer investment vitoo well

42:32

done.

42:33

>> Thank you. Uh, I don't know if that was

42:36

your 10th investment overall or your

42:39

first, but how did you end up edging

42:42

into the world of investing, whether it

42:45

was CPG and consumer stuff or tech? How

42:48

did that even come to be? Wow. Well, the

42:51

original

42:53

original original was

42:56

I was on a plane to Milan for an MTV

43:01

Awards

43:03

and I don't remember how old I was. was

43:05

in my 20s and I was reading in a

43:09

magazine about Sky Dayton and it said he

43:12

started Earthlink and he was worth $100

43:15

million and he was really I'm like wait

43:17

what you can wait what is he doing and

43:20

how old is he? And so I go when I get

43:22

back home I want to meet this guy. So, I

43:26

came back and I took me a while, but I

43:28

finally tracked him down and we went to

43:29

have lunch at Four Seasons Hotel and and

43:32

he was like, "Wow, if you're impressed

43:33

by me, have you ever heard of Bill

43:35

Gross?"

43:36

>> And I go, "No, who's that?" He goes,

43:38

"Well, he started a incubator."

43:40

>> Mhm.

43:41

>> And he's launched three billion dollar

43:43

companies in one year. And I go, "Sky, I

43:45

like you, but can you just [laughter]

43:46

can you get out of the way? I want

43:48

>> This time has been great."

43:48

>> Yeah. It's time to move on. I need to

43:51

talk to this Bill Gross guy. So, he sets

43:53

me up with Bill Gross. Bill Gross ran an

43:54

incubator called Ideal Lab in Pasadena

43:57

and I just loved it. I love the idea of

44:01

a lot of ideas. Reminded me of the

44:02

record label where you had all these

44:04

artists and you had all these project

44:06

managers

44:06

>> or the independent producers

44:08

>> a version of that and you can walk in

44:09

and out of different rooms and you can

44:10

say, "Oh, okay. What are we doing here?

44:12

What are we doing here?" And so he was

44:13

building all these different companies

44:15

and I would go in and out of ones that I

44:16

could be helpful to

44:18

>> and I would learn about it. So that was

44:20

like a oh, okay, an incubator. I really

44:22

fell in love with that idea. And there's

44:24

bad news to the story, but as like all

44:27

things, it worked out in the end.

44:28

>> Well, wait a second.

44:30

>> My listeners gonna kill me if I don't

44:31

follow. What's the bad news?

44:33

>> Well, I mean, the bad news is is that I

44:35

worked there for a year helping and then

44:38

one day someone I really trust that

44:44

they don't know it to this day, but

44:45

they're they're an incredible human. And

44:48

I was lucky to sit with them at dinner

44:49

one night and they were telling me how

44:51

Bill Gross is one of the greatest

44:53

investments they've ever made.

44:55

>> So I I called up Bill and and I go,

44:58

"Bill, I want to put money in into Ideal

45:01

Lab." And he goes, "Well, you know, I

45:02

was going to surprise you and I was

45:04

going to put, you know, X dollars in for

45:06

you from bottom of my heart for all the

45:09

work you've done here." And I go, "Oh,

45:10

what is that worth?" And he's like, you

45:12

know, he told me what he thinks it's

45:14

going to be worth when it comes out. And

45:16

I was, by the way, it's worth a lot. And

45:18

I go, that's not enough. I'm thinking,

45:20

right, I'm thinking to myself, that's

45:21

not enough. So I go, Bill, I want to put

45:22

more in, a lot more in. And he's like,

45:24

hey, for you, I'll let you do whatever

45:26

you want. And he did. He's he's really

45:28

really sweet guy. And that's the bad

45:30

news. I he let me do whatever I wanted.

45:32

>> What year was this?

45:34

>> It was before the crash. Right. It, by

45:36

the way, it wasn't a year before the

45:37

crash.

45:38

>> I think it was like an hour before the

45:40

crash. [laughter]

45:41

>> Okay. So, I put every dollar I have plus

45:46

dollars I didn't have.

45:48

>> I picked out three investments at that

45:50

time. Ideal Lab because of Bill Gross.

45:53

Bill was the first guy in I think in in

45:56

LA to have the Blackberries. So, I was

45:59

the first guy from Hollywood to even

46:02

know what the hell Blackberries were. So

46:04

I ended up buying 400 of them and I gave

46:07

them to all the people in Hollywood so I

46:08

could connect and when I needed to and

46:10

talk to them and and so I made a deal

46:12

with Jim Bowsley to be an adviser

46:14

because I was I was the guy that put it

46:16

in everyone's hands. This is smartphones

46:18

before anyone else was doing it. And

46:20

then I also my friend Seth Rossky

46:22

brought me vitamin water.

46:23

>> Yeah.

46:24

>> So those were going to be my first three

46:26

investments.

46:27

What happened was is the ideal lab thing

46:31

once I put that money in and I don't

46:33

know the the timeline cuz I tried it's

46:35

almost like something you want to wash

46:36

away from your mind,

46:37

>> right?

46:38

>> It collapsed.

46:39

>> Fever dream you're trying to forget.

46:40

>> The bubble burst so fast on all of that

46:43

that I didn't have the heart to invest

46:47

into. I never signed my deal with Jim

46:50

Bowsley and Research in Motion. And I

46:52

never and I never did my deal with

46:54

Vitamin Water, which both ended up, this

46:56

is almost like the the hole and rage

46:59

analogy. They both ended up being

47:01

massive.

47:02

>> Yeah.

47:02

>> And then I and I lost all my money with

47:04

the first one. So I learned about a lot.

47:06

I learned about diversification.

47:08

>> I didn't diversify. I put

47:10

>> the majority of my money in one thing

47:13

>> and I paid the price for it. I really

47:16

for the next two years I only thought

47:19

about that about 15 times a day.

47:21

[laughter]

47:22

It didn't matter if I was sitting here

47:23

with you right now. Back then I'd be

47:24

thinking about it. I' I'd have

47:26

conversation with you, but I wasn't

47:27

thinking about you. I was thinking about

47:28

how did I lose all my money on that one

47:30

investment. Everything I saved my whole

47:32

life. I was mad that Sky Dayton

47:34

introduced me. Like I was like mad at

47:36

all the wrong reasons, you know?

47:37

>> Everyone was just trying to help me. But

47:39

now I'm like, why did I even read that

47:41

magazine? I should just stayed in my

47:42

music lane. Yeah.

47:44

>> So, but what happened was years later

47:45

after my first Madonna tour, I started

47:47

to think about it again and I go,

47:51

>> I wasn't so off.

47:53

>> I was off. The timing was wrong on the

47:56

ideal lab part. The other two worked.

47:58

Had I diversified

48:01

incredibly well.

48:02

>> Yeah. You would have been great.

48:03

>> And so, I got two out of the three. And

48:05

the truth is is, you know, it's not fair

48:08

to Bill because he really built an

48:10

incredible company. and some of the

48:12

stuff that he had built ended up

48:13

becoming search for Google and a bunch

48:15

of amazing things but it just didn't

48:17

work out and that's life sometimes they

48:19

don't work out these deals

48:21

>> a lot of the time

48:22

>> I think I had done three Madonna tours

48:24

in a row so I came back at my you know

48:28

all the money I'd lost I made that back

48:30

to survive

48:31

>> and then I had a window where I knew we

48:34

were three tours in a row we're going to

48:36

take some time off and I thought to

48:38

myself I didn't get it so punk.

48:41

So, I'm going to try this one more time.

48:42

I'm good at identifying the ideas. I'm

48:45

good at identifying the talent. I'm

48:47

going to do it one more time. And that's

48:49

when I So, I started and the same guy

48:53

that brought me Vitamin Water, Seth

48:55

Rossky.

48:55

>> Did he later work with Reese

48:57

Witherspoon?

48:58

>> Exactly.

48:59

>> Huge.

48:59

>> Yeah. He's done well for himself. And

49:01

then he called me one day and goes,

49:03

"Hey, have you heard of this coconut

49:04

water thing?" So, of course, I'd heard

49:08

about coconut water. One, my wife is

49:10

Brazilian, and you know, my son, my

49:12

first son, his first words were like,

49:14

"Awa to cocoa." So, we drink coconut

49:17

water at the house. But the whole

49:18

coconut water sector

49:20

>> in America, if you added all the

49:22

companies together was maybe a five or

49:24

seven million business. It was nothing.

49:26

Nothing. But Madonna on tour, on the

49:29

previous tour, she would have the

49:31

trainer would go in different markets to

49:34

find fresh coconut for her for the

49:38

coconut water.

49:39

>> And I like, wow, every location we went

49:41

to, we had to find fresh coconuts. And

49:42

so I started to hear that other people

49:44

were doing that as well. Other people

49:46

who cared about their health were

49:47

drinking coconut water. I started to

49:48

see, again, back to pattern recognition,

49:51

I started to see this thing. And then

49:53

one day the New York Post ran an article

49:55

about coconut water. There's a photo of

49:58

Jazelle drinking from a coconut and

49:59

they're talking about coconut water and

50:01

I had cut that out. I put that article

50:04

on my desk and when Seth called me and

50:07

said, "Have you heard about coconut

50:08

water?" I go, "You have to be kidding

50:10

me. I have

50:12

>> sitting on my desk.

50:12

>> I have the only thing that I've torn out

50:15

that's sitting on my desk is an article

50:17

about coconut water. It's on my desk and

50:19

it's like my todo like I need to figure

50:21

this thing out and here you are calling

50:22

me." He goes, "Well, there's a company

50:23

called Vita Coco and out of New York."

50:25

And I go, "Uh, count me in." I got on a

50:28

plane. I went to meet with the founder,

50:29

Mike Kurban. The company was a I think

50:32

it was a $35 million valuation at the

50:34

time. And I literally just here we go.

50:38

I'm jumping back in. And I went in

50:40

really big. And I brought Madonna into

50:42

that. I brought Demi Moore. I brought

50:44

Matthew McConnA, Anthony Key. I brought

50:46

a bunch of people into this thing

50:48

because they were all healthy people who

50:49

drank coconut water. I'm like, "Let's

50:50

blow this thing up." And that was that

50:53

was the first time back after the the

50:57

crazy run.

50:58

>> For people who don't know, how did that

50:59

turn out?

51:00

>> It's a public company today. I think

51:02

it's $4 billion market cap.

51:05

>> So you were back in the game.

51:06

>> Yes. It takes time.

51:08

>> It takes time. Yeah. Didn't happen

51:09

overnight.

51:11

>> What were you

51:13

looking for?

51:15

How would you replay that meeting with

51:16

the founder in your mind? You fly out,

51:18

you meet with the founder.

51:20

How did you approach that meeting?

51:22

>> I think I approached it the way I

51:24

approached everything. It was it wasn't

51:26

let's think about it. It was like I'm

51:27

all in. Let's go. I want to do this.

51:29

Here's what I can do. And and I think

51:32

they were probably overwhelmed by whoa.

51:36

Okay, let's and we just ran. He's

51:40

awesome what he's done with the company.

51:41

We went public I think at like two

51:43

billion and now it's at five. Like he's

51:44

done an incredible job. So, we're going

51:46

to hop to some more recent examples

51:48

which may or may not include this chair

51:50

in a moment, but I want to focus on a

51:53

term or phrase that I've seen applied to

51:55

you a lot, which is great curator of

51:57

people. Chris Rock has said this.

52:00

Matthew, you just mentioned said this.

52:01

Woody Harlson have have all described

52:03

you in this way. And you seem very

52:07

intentional with

52:10

the people you surround yourself with.

52:11

Not only that, but you have these very

52:13

long-term relationships with a lot of

52:15

people. And I'm wondering how you think

52:19

about building relationships. I'm not

52:22

saying you have to come up with the

52:23

guy's ten commandments of long-term

52:25

relationships, but how would you think

52:27

about that? Right? If you're in front of

52:29

a class of students and you're like,

52:31

"Look, a lot of people get this wrong."

52:33

Or at least let me tell you how I

52:34

approach relationships. like any any

52:37

particular rules that you use for

52:39

yourself or just approaches, things you

52:41

keep in mind because that's certainly

52:42

not true for everybody, right? You just

52:44

have this long-term

52:46

cohesion of these people around you. And

52:49

I'm just I'm wondering if you can

52:52

perhaps just speak to that in any way.

52:54

Well, I think it started early in my

52:58

teens. There was a a group of us that

53:02

were running around and all we found

53:05

each other.

53:07

>> So you find the other people who are

53:09

also on the hustle who are also

53:11

creative. I wasn't a comedian or

53:14

musician or an actor or a director. I

53:19

was like an executive.

53:20

>> Mhm.

53:21

>> And there's a little responsibility.

53:23

He's a responsible one. I don't drink. I

53:25

don't do drugs. So I I found my position

53:29

was to really

53:31

be a safe zone for people and they knew

53:33

I worked with Madonna which pretty much

53:35

gave a lot of credibility to okay this

53:37

guy is she trusts him maybe we should

53:40

trust him maybe back in the day but I

53:42

think over a period of time my house

53:44

became the place that people would come

53:47

to or people would congregate and feel

53:50

safe you know even when I do events here

53:53

or anything there's not a lot of photos

53:54

there's no cameras like I I think safety

53:56

and support has always been in my DNA

54:00

from an early age of just making sure

54:03

that people are protected and again I

54:05

think I identifying really incredible

54:08

people to be around same way identify

54:11

the greatest companies to invest in like

54:12

I think I identified really amazing

54:14

incredibly talented friends who inspire

54:17

me and who've been who you know early

54:19

days may not you may not have known them

54:21

30 years ago but you identify them you

54:24

they identify you and so there's

54:26

camaraderie and there's this trust and I

54:30

do try to bring them all together a lot.

54:32

I I think it's important.

54:34

>> That was going to be actually my next

54:35

question which is along those lines

54:38

which is how often do you gather people

54:41

whether it's at this house or at events

54:44

that you put together just to facilitate

54:46

that long-term cohesion. How how often

54:50

do you organize or host things like

54:52

that?

54:53

>> A lot. I think I even if I'm landing in

54:55

New York this week, I'll probably do a

54:58

dinner and I'll invite the 15 or 20

55:00

friends and we sit down and we talk and

55:01

we So, I'm always staying connected and

55:04

in touch.

55:05

>> It's not like, oh, I haven't talked to

55:06

you in a year. No, I'm checking in on my

55:07

friends a lot.

55:09

>> I'm finding out how they are and always

55:11

we're I'm always checking in on

55:13

everybody.

55:13

>> Mhm.

55:14

>> I grew up just with my dad. My two

55:17

sisters were older. They weren't they

55:19

weren't around. So, my friends are

55:23

really like they're my they're

55:25

everything I had. I didn't before I had

55:27

a family. My friends were

55:29

>> everything to me. I'm lucky I get to

55:31

work with some of my family. You know,

55:33

Madonna's I've been beside her for 36

55:35

years.

55:36

>> The Chili Peppers, my best friend in the

55:39

world's godfather of my first son is

55:41

Anthony. The whole band, all of them,

55:43

Flee, Chad, John, they're family. So,

55:46

it's a dynamic that I've chosen for

55:49

myself is to really support and be

55:51

around my friends a lot. It's a big part

55:54

of my life, which is to keep that close.

55:56

And again, if someone's in need, you

55:58

know, this is the number. Call me. I

56:00

want to hop back to the investing. I

56:02

mean, you've you've had a lot of hits.

56:03

Airbnb, Uber, Spotify, it goes on and on

56:06

and on. I mean, I don't know how many

56:09

IPOs and so on that you've had. I mean,

56:11

gazillion. Let's talk about one. So, you

56:14

put in, tell me if I'm getting this

56:15

right, 35 million at a 5 billion

56:18

valuation into Anthropic. This is a

56:20

company that's been in the news a lot. I

56:22

think the last round was what, 965

56:25

billion, something like that. Are those

56:26

numbers roughly accurate?

56:28

>> Yes.

56:28

>> Okay. So, that's pretty nice multiple so

56:31

far. You know, we'll see how things go.

56:33

How did that anthropic deal happen?

56:38

Well, it starts a little before the

56:41

day that OpenAI came out was on my dad's

56:46

birthday, Chat Chippy PT.

56:50

It was life-changing. And I you remember

56:54

those moments. And again, I go back to

56:55

music. I remember when I heard Smells

56:57

Like Teen Spirit by Nirvana. I pulled

56:59

over the car and I went, "What is this?"

57:03

And when Chhat GPT came out, that was a

57:06

what is this moment for me. And if you

57:08

saw me any time after Chat GPT came out,

57:12

I would have harassed you to show you

57:14

Chat GPT. There's no one, every artist,

57:17

every actor, everyone I walked around

57:19

and met. I'm like, check this out. Check

57:21

this out. Check this out. And I was

57:24

obsessed. And I called Ashton and I

57:26

said, Ashton, this is it. Open AI. We're

57:29

doing OpenAI. This is the greatest thing

57:31

I've ever seen. We have to do it. I have

57:32

to do it. I have to do it. And so that

57:35

was our first this is the one we're

57:37

going to go after. But then when we

57:40

first started investing, Ashton and I,

57:42

it was when the iPhone and the app store

57:46

were happening. And so for the first

57:49

time ever,

57:50

you can scale companies like never

57:53

before. And I think anyone would have

57:56

done well at that time. We were like

57:59

lucky people that came in at the right

58:01

time and were looking at the right time

58:04

and started our fund at that very

58:06

moment, which is crazy. And so we had

58:09

this incredible success because of that.

58:11

I saw it again back to pattern

58:14

recognition.

58:16

If you fast forward, we're we're still

58:17

using Uber and Airbnb and Spotify. We're

58:19

still using those things from that time

58:21

period. And we felt that this is it.

58:24

these foundational AI models in 10 or 15

58:27

years will be how we plug into all these

58:30

things. So,

58:34

we really felt like we had a 3-month

58:36

window. We told people we have a

58:37

three-month window. Now, it came out

58:39

November 30th of 2022.

58:44

So, there's not much you can do. This

58:46

people are going away. There's this

58:48

Christmas time break, blah blah. But as

58:50

soon as January came, we went out there

58:52

and told people, "This is the vision.

58:55

We're going to do a foundational AI

58:56

model fund."

58:57

>> I got it. LPS mean.

58:59

>> Yeah. Raise money. Raise money and

59:00

create this fund, which is which was a

59:02

crazy idea at the time.

59:03

>> Now, had you already confirmed that

59:04

you'd be able to get allocations or you

59:06

just had complete confidence?

59:07

>> Ashton spoke to Sam, we were able to get

59:10

OpenAI. What happened was is I'm very

59:12

close to Mark Beni off and Salesforce

59:16

ventures. People don't really understand

59:19

how smart they are. They don't get

59:22

>> They're really smart.

59:23

>> They don't get all the press on. They

59:24

are one of the best investors in the

59:26

world. There's two guys there, John

59:28

Simari and Paul Drews, who were when I

59:32

was doing my research cuz now I'm on the

59:34

I'm on the lookout. What should I know

59:36

about an AI? Once I find out about

59:38

something, I just lock in. So, and and I

59:41

want to know everything about it. And I

59:42

I was as I was doing my research, I was

59:45

finding out that they were going to do

59:47

anthropic and they were very bullish

59:51

about it. And I found out from a friend

59:53

that works with like a job hunter kind

59:56

of people who help find jobs for people.

59:59

>> Oh, like head hunters.

60:00

>> Head hunters that everyone's going to

60:03

this company called Enthropic, you know,

60:05

like people are really going to this

60:06

anthropic place and they're not going

60:08

anywhere else. I'm like, whoa, okay, I I

60:11

need to pay attention. So I I asked Paul

60:13

and John connect me with with this

60:16

founder Dario. So they connect me with

60:19

Dario and Nero. They come here in this

60:22

room and that's where we made the deal

60:24

to invest in in Anthropic. So we did a

60:28

bunch of other companies in that

60:29

foundational AI fund. It was a

60:31

three-month window.

60:32

>> So it was before a bunch of other things

60:34

have come out since.

60:36

>> But we we set ourselves up for exactly

60:39

what we did. this is going to be within

60:41

3 months. We're going to deploy 80% of

60:43

the money within the next 3 months. And

60:45

that's what that's what we did and

60:46

that's over 3 years ago.

60:48

>> How did you know the window was going to

60:49

be so narrow? Right. I imagine did you

60:52

get any push back from LPs when you said

60:53

we're going to deploy 80% of this in 3

60:55

months?

60:56

>> Well, we didn't have there was no LPs,

60:58

meaning we just it was that was the

61:00

pitch.

61:01

>> Yeah. Yeah.

61:01

>> So, it wasn't like we it wasn't like we

61:03

raised money.

61:04

>> They either bought in or they

61:05

>> Yeah. It wasn't like we raised money and

61:06

then told them the pitch. It was like

61:08

here's the pitch.

61:08

>> Here's what we're going to do. There's a

61:10

window of opportunity here. We think

61:11

this is the future and that was it.

61:14

>> They had opted in.

61:15

>> Yeah. Opt in or opt out. We didn't know

61:16

what we were going to raise. It just

61:18

whatever came up is what it was going to

61:20

be.

61:20

>> So I was trying to pull from memory, but

61:23

looks like sound at this point is that

61:27

86 exits and 26 IPOs. That's insane. I

61:31

mean that is

61:32

>> it's been fun. [laughter]

61:34

>> You have seemingly different batteries

61:38

certainly. I mean, you've got good

61:39

batteries. What is the next

61:43

5 years, do you think, look like for

61:45

you? I mean, is it is it more of this

61:47

type of investing? What do you see? Is

61:50

it switching gears entirely and looking

61:52

at the prison through a totally

61:53

different way? I mean, what is what is

61:55

next for Guy? I feel like

61:58

going back to the core, really honing in

62:02

that antenna for the greatest talent in

62:06

the world, the greatest ideas in the

62:08

world. This is an incredible time where

62:12

people can scale up a company

62:15

in in the quickest ways. And I'm excited

62:18

about the potential of what's to come.

62:21

I've already identified three things I

62:24

want to do today. So, I can only imagine

62:28

what's to come. But it's just really

62:30

just I don't I'm okay doing a version of

62:33

what I've been doing, which is identify

62:36

great talent and help them help them in

62:38

every which way that I can and pick the

62:40

teams that you want to back.

62:43

>> So, I I I'm I'm feeling pretty good

62:45

about that. They're just continuing on

62:47

this best-in-class talent idea. The hard

62:51

part is for a lot of people is the

62:54

access. So we're very lucky we have

62:57

access and we also do the job. We we

63:03

have more than enough proof of

63:07

people that come through when you work

63:09

with them.

63:10

>> And we're a different kind of investor

63:12

on the cap table.

63:14

>> We're not in the valley. We're here in

63:15

Hollywood. And we bring a different

63:17

dynamic, a different, you know,

63:19

obviously narrative is something that I

63:20

that I'm very focused on. Marketing is

63:22

something I've been doing since I was a

63:24

teen. And so, you know, marketing,

63:27

strategy, media, partnerships,

63:29

narrative, storytelling, hey, if you

63:32

want someone like that on your cap

63:34

table, I might be interesting to you and

63:36

hopefully I can be helpful. And that's

63:38

what I need to find that dynamic of a

63:40

company that I'm in love with. And

63:41

hopefully the founder believes that

63:44

having me would be a great advantage to

63:47

them.

63:48

>> Mhm. A lot of founders listen to this

63:50

podcast. Is there any uh are there any

63:52

particular things that

63:55

have your interest right now or types of

63:57

companies, types of founders? Anything

63:59

that you'd like to sort of make clear to

64:02

people who are listening or otherwise?

64:04

Also, where can people learn

64:06

[clears throat] more about what you're

64:08

up to? like is is there anywhere that

64:10

you would point them in particular?

64:11

>> I'm a generalist.

64:13

>> Mhm.

64:13

>> I don't I don't care. That particular AI

64:16

fund was very specific and we may have

64:18

thematic funds from time to time. If an

64:20

idea comes and you go, you know what,

64:22

I've got an idea. It's going to be built

64:24

around this one idea. But usually I'm a

64:26

generalist. I really like

64:27

>> I just like talented people. And in

64:30

regards to sharing, you know, where can

64:32

they find out what I'm up to?

64:34

>> I'm not really This is it.

64:35

>> Yeah, this is it. You know, as you know,

64:37

this is my first podcast.

64:38

>> Yeah.

64:40

>> And depending how this goes, could be my

64:42

last. And if it goes well, maybe one

64:44

more. But I I'm I'm not out there.

64:47

>> Everything is is is has been fine

64:49

without doing that. Yeah. You know,

64:52

people either find us word of mouth

64:54

through friends or I find them. It's

64:56

okay. It all works out. I'm not out

64:58

there, you know, yelling, "Hey, find me

65:00

1800 whatever." Or it's like it'll it'll

65:03

work itself out. the right people will

65:05

find each other.

65:07

>> Well, Guy, I mean, we've covered a lot

65:08

of ground. Is there anything else that

65:10

you would like to say before we start

65:13

landing the plane?

65:14

>> I'd say that

65:16

AI and music content. It's on one level

65:21

exciting that so many people are

65:24

experimenting,

65:25

writing songs for the first time,

65:28

>> writing beats, creating sounds for the

65:30

first time. That's pretty exciting. At

65:32

the same time, the idea that there's

65:36

companies out there

65:38

valued at billions of dollars

65:42

that are built on the top of

65:47

other people's music

65:50

where not one artist has ever gotten

65:52

paid a dollar is not okay.

65:55

>> Yeah. So, I don't want to bundle it all

65:58

up where people get it all becomes one

66:00

thing. It's not all one thing. Mikey, he

66:03

runs. He's a great guy.

66:05

>> I mean, great guy, like I really like

66:06

him as a person, but every time I read

66:08

about the company and it's now at a $5

66:10

billion valuation and next thing you

66:12

know, it's at a $10 billion valuation

66:14

and it's all built off of the world's

66:18

music.

66:21

But yet, not one music artist has gotten

66:22

a dollar.

66:24

>> So, that's not okay. That has to be

66:27

fixed. I'm hoping Mikey does the right

66:29

thing and fixes that. Comes up with a

66:32

system

66:33

>> that allows artists if they want to opt

66:36

in. Either let them opt out, do not use

66:39

my music to build your business. Okay,

66:43

I'm opting out. But if I opt in, find a

66:46

way to pay us. Mhm.

66:48

>> And I'm really concerned for that

66:51

because the other part which is

66:55

right now currently

66:58

every two weeks

67:01

more music is made on AI than all of the

67:04

music that's on Spotify today.

67:08

That's every two weeks.

67:10

And all of that is going somewhere and

67:13

people are inspired and they're creating

67:14

songs. Awesome. But don't build a

67:17

business

67:20

using our music without getting those

67:23

rights. And that's something I'm that

67:25

I'm been trying to work on for a long

67:27

time. I've met with Mikey many times.

67:30

I've met with lots of people many times.

67:32

I I hope that this gets solved. You

67:34

know, when Napster first started, I met

67:36

with Sean and Sean when they started

67:37

because it was so exciting to see people

67:40

were all, you know, downloading music,

67:42

but it was illegal. So, you were hoping

67:44

they'd crack the code on, okay, how do

67:46

you turn this into how artists get paid

67:49

and before they I don't know if they

67:51

were going to or not going to, but

67:53

before that could even happen, it got

67:54

shut down. So, and out of nowhere,

67:58

Daniel Ek in Stockholm

68:02

built Spotify and figured out that

68:05

people would pay for music if you give

68:07

it to them in this way where they had

68:10

all the music in the world without

68:12

having to try to piece it together or

68:15

try to illegally download songs that

68:18

were not even clean or clear and they it

68:21

could be corrupt.

68:22

to get it clean, to hold on to it,

68:26

they'll pay for it. And he was right.

68:28

They have paid for it. Now, are all the

68:30

payment plans there picture perfect? No.

68:33

But it is the core of where money is

68:36

coming in today to music artists is

68:38

through streaming. And I'm hoping that

68:41

people figure out how if you're going to

68:46

be using people's music, how you pay for

68:48

it.

68:49

>> Yeah.

68:50

>> Fair use is not fair.

68:51

>> Yeah. I'm curious to see where it goes

68:53

because if you say create a song that

68:56

sounds like Metallica, it'll say we

68:58

cannot serve up any copyrighted music.

69:01

If you say, "Serve me up some music that

69:02

sounds like Moralica." And you just

69:05

misspell it, then lo and behold, it

69:07

looks like it was trained.

69:08

>> Yeah, that's the problem.

69:09

>> This corpus, there's a lot of

69:11

workarounds and they'll, you know, you

69:14

they'll look you in the eye and tell

69:15

you, "No, no, you can't. You cannot type

69:16

in Madonna."

69:17

>> But you can sort of describe Madonna.

69:20

The problem is is when in in Discovery

69:22

we're going to find out a lot.

69:23

>> Sure.

69:24

>> And Discovery is going to say all of

69:28

this music is in there and they know

69:30

that.

69:30

>> Yeah.

69:31

>> And that's not okay. It's just like

69:34

literally not okay. I don't understand

69:35

it. And by the way, what's wrong with

69:37

paying artists?

69:38

>> Yeah.

69:39

>> Why not figure out a way to do it? Sit

69:41

down with a team, figure out how to pay

69:43

music artists if you're going to train

69:45

on their music.

69:46

>> Where do you think it goes? Because I

69:47

could see one future. for instance, even

69:49

if

69:51

legally they aren't required or for

69:53

whatever reason that's not compatible

69:56

with the vision they've pitched to

69:57

investors and and I'm not singling out.

70:01

I mean, there are lots of lots of

70:02

different options here.

70:03

>> They're the main ones.

70:04

>> They're the big they're the 800 pound,

70:06

>> but I could see a point at which

70:09

possibly

70:12

>> Claude Chat GPT become the interfaces to

70:15

everything, right? It's almost like the

70:17

app store but somewhat like WeChat in

70:20

China. Like if you want to do anything,

70:22

you want to book a restaurant, you want

70:24

to make a song,

70:26

>> okay,

70:26

>> there are few interfaces to everything.

70:28

At which point then

70:30

>> those companies, right? OpenAI,

70:32

Anthropic

70:34

>> can gatekeep in some way and maybe they

70:38

end up being the entities that

70:40

incentivize these other companies like

70:43

the Sunnas of the world to to reimburse

70:47

artists. I guess I'm just wondering if

70:48

you have any thoughts on this

70:51

>> because if if Claude or Chat is the

70:54

distribution,

70:55

>> they probably won't carry it because

70:57

it's it's got so many lawsuits involved

71:00

>> and it's just not worth

71:02

>> taking on that responsibility.

71:04

>> And

71:05

>> again, the guy who runs I find to be a

71:07

really good guy and I'm hoping that he

71:09

does the right thing, but it's really

71:11

their responsibility. They're they're

71:13

sitting at the the top of this

71:15

opportunity. Take off the artists that

71:17

don't want to be on there

71:19

>> and find a way to pay the ones that are

71:21

okay being on there. It's that simple.

71:22

It's not complicated. I think go in a

71:25

room, lock yourself in a room for 3 days

71:27

and come out and figure out how to pay

71:28

people and take people off

71:30

>> that don't want to be on there. Madonna

71:32

does not want her music trained on.

71:35

>> Don't care what you want to pay her.

71:36

>> Yeah.

71:37

>> She's very clear. I do not want my music

71:39

to be trained on. I want my music to be

71:41

its own thing.

71:42

>> Mhm.

71:43

>> So, take her off.

71:44

>> Yeah.

71:44

>> It's okay. you you'll still do fine.

71:46

Take her off. You don't have to have her

71:49

music.

71:50

>> So, we'll see where this goes. But this

71:53

is I've been the last few years I've

71:54

really tried to figure this out. And

71:56

even, you know, Sam at one point, he's

71:58

really wanted to figure this out, too.

72:00

Like Sam was a lot of people give my

72:02

hard time on this stuff, but he really

72:04

did dedicate time to trying to figure

72:08

out if there was a music thing to do,

72:10

how to do it in a way that supported

72:13

artists.

72:14

>> Yeah. Yeah, I mean there may be someone

72:15

who comes along also if it's not Sununo.

72:17

Someone who comes from behind like a

72:19

next generation Spotify

72:20

>> and figures out how to do it.

72:22

>> Spotify can do it.

72:22

>> Yes, more Spotify can do it.

72:24

>> Yeah.

72:24

>> You mentioned there were three things

72:26

that you'd like to do today. I'm not

72:28

going to ask you to name those things,

72:30

>> but how did you find those things or how

72:34

did those things find you?

72:35

>> Right. one of them. Well, I'm working on

72:38

this platform that I'm going to announce

72:40

in a few months that you're part of is

72:42

how we connected you and I. And I'm able

72:44

to ask investors what companies

72:47

>> that they're looking at and and so

72:49

>> two of those came from that

72:51

>> conversation. Good good information.

72:53

>> Yeah. They're like, "What are you

72:54

looking at? What are you liking?" And

72:55

then they tell me and then I go, "Oh,

72:56

let me look into it." And some things I

72:58

just read about. I read every single

73:00

day. I I'm checking things out every

73:02

single day and I'm making sure I'm not

73:04

missing an idea or I'm hearing about

73:06

things.

73:06

>> Well, I'm on X a lot. I see a lot of the

73:09

stuff, a lot of information on on X

73:12

that's flying by. So, it's sort of my my

73:15

start of information.

73:18

>> You mentioned missing

73:21

Blackberry and Vitamin Water. Do you

73:24

have And this could go way back in the

73:27

catalog. Could go back to being 10 years

73:29

old. There's there's no limitation here.

73:31

Any favorite failures or parent

73:34

failures, meaning failures that taught

73:36

you a lot or that set you up somehow for

73:38

later success?

73:40

>> There's

73:42

it's endless endless. You know, uh, one

73:44

of the things that Ashton is really was

73:46

really good about

73:48

not looking back like that. He sort of

73:50

just keeps it moving forward and I'm

73:52

always like, I can't believe we're not

73:53

in that and I had it and my I had it and

73:55

we had it and we and he's like, come on,

73:57

just move. Let's go. Let's go. He's

73:59

like, he always gives me like, oh gosh,

74:01

he's going to complain about not being

74:02

in a

74:04

but you know what motivates him is he

74:06

just keeps it moving forward and it's

74:07

awesome and what motivates me is like

74:09

I'm not going to let that happen again.

74:10

>> Yeah. I mean looking back right it seems

74:12

like

74:14

>> in [snorts] some ways like missing hole

74:17

missing fill in the blank was almost a

74:20

prerequisite source of fuel.

74:23

>> Yeah.

74:23

>> For the things.

74:24

>> Yeah. It's scary though. It drove you

74:26

towards the

74:27

>> It's scary though when you miss it. I,

74:29

you know, when Ash and I invested in

74:31

Bitcoin on our own, you know, when it

74:33

was at $22 [laughter]

74:35

>> and then it when it hit $250, I thought

74:38

I just made 10 times my money.

74:40

>> Yeah. Yeah.

74:40

>> I'm a genius. So, I sold then and

74:44

clearly not a genius. So, that hurts.

74:47

And I remember um Anthony, gentleman on

74:50

that wall.

74:51

>> Mhm.

74:51

>> Elon invited Anthony from the Chili

74:54

Peppers to see SpaceX. Early days.

74:58

>> Yeah.

74:59

>> Very early days.

75:00

>> And I went with Anthony. I tagged along.

75:02

It's the first time I met Elon. When we

75:04

went to SpaceX,

75:06

>> I was so wowed by the concept that I

75:09

didn't even pay attention to the

75:11

business model or what could be the

75:12

business model. I was just like, "Wow,

75:14

this guy's building rockets." that

75:16

moment in time Anthony and I had the

75:18

wherewithal to go what business model I

75:21

didn't even ask those words. I was just,

75:23

you know, sometimes I go to shows like

75:25

I've seen shows where people are so

75:27

wowed that they're just like they're

75:29

like this from a show and they they

75:32

didn't even take in all the songs or

75:33

just like oh my god what I mean if you

75:35

ever look back at the Sex Pistols shows

75:37

people are just like what and they're

75:39

like was I actually there? I think I was

75:41

more blown away by the concept of what

75:44

Elon was building that I did not

75:46

understand

75:48

that there was a business model and I

75:50

really wish I just would have asked one

75:52

more question like

75:54

>> hey how do you monetize this? How does

75:56

this work? Can we invest?

75:58

>> So I have hundreds of those stories but

76:01

those are two that stand out today.

76:03

>> I want to talk about the longevity for a

76:05

second. you mentioned, and fact check me

76:08

if I'm getting this wrong, but like the

76:10

three was it back-toback tours with

76:12

Madonna.

76:14

>> I mean, that sounds impossible just from

76:15

a the demands of the the physicality of

76:18

that and she's kind of legendary, of

76:20

course, for her

76:21

>> training and [snorts] endurance and

76:22

everything else, but for you personally,

76:26

what were the keys to end enduring that

76:29

and being able to function at a high

76:31

level for that?

76:32

>> I think it's different as the years go

76:34

by. There was a point around 10 years

76:37

ago, 11, 12 years ago where I was, it

76:40

was a lot for me. I was also changing

76:42

and growing and having kids and I was

76:45

just sort of losing myself cuz you're

76:47

really in a you're going to a different

76:50

city every other day.

76:52

>> And the amount of things you're missing

76:53

back home, you sort of you sort of, you

76:56

know, forget you have a family. You

76:58

forget that you can go do other things.

77:01

or you forget to call back Stripe or you

77:03

forget to right all the things you just

77:05

you just forget everything and then one

77:07

day your dad calls you and goes oh hey

77:09

I'm at your house with your kids and oh

77:11

I have kids I have a house so if you

77:13

look at the first three tours those

77:15

three tours that I did those are 240

77:17

shows 80 average I [snorts] missed three

77:20

of those shows

77:22

three out of the 240 one I was sick and

77:26

then I missed two because it was my 40th

77:28

birthday and I really didn't feel like

77:29

being in Seattle that

77:31

I wanted to be home with my friends. So,

77:33

my 40th birthday spent here in this

77:34

house. So, I missed three shows out of

77:36

240. But we're talking about a different

77:39

city, a different hotel, a different and

77:42

you in order to like move along, you

77:44

sort of have to block everything else

77:46

out. You have to forget and it's a very

77:48

selfish, very

77:51

for me is otherwise if you think about

77:54

back home or your family or other

77:55

things, it hurts. So, I just go, "Okay,

77:58

I'm off and I'll see you. I bet I bet

78:00

it's what actors do when they go away

78:01

and make a movie for 3 months and then

78:02

they come back.

78:03

>> They probably just compartmentalize a

78:06

little bit, but you know, in the last

78:08

few years, I've I've stopped doing as

78:10

much. I still go, but not as much. I've

78:12

I've went it down. There's a moment

78:13

there where I managed the Red Hot Shield

78:15

Peppers, you two and Madonna. They're

78:17

all going on tour. It was a lot to

78:20

>> process. How do you even make decisions

78:23

about where to be in a case like that?

78:25

You can't be in three places at once.

78:26

It's hard, but it sort of tells its own

78:29

story. You, you know, you're not going

78:31

to miss New York. You're not going to

78:33

miss London. You're not going to miss

78:34

some of the major moments. And then you

78:37

look at the calendar and go, "Oh, we

78:39

have this time off. Let's go to New

78:41

Zealand with Madonna or let's go to so-

78:43

and so with you two or let's go to so

78:45

and so with the peppers." And you find

78:46

your way around it. You just you just

78:48

make it work.

78:49

>> So, if you look at let's just say the

78:50

last 10 years.

78:51

>> Yeah.

78:52

And

78:54

presumably a lot of your focus is on the

78:57

investing. How do you mind the different

79:00

responsibilities

79:01

if that makes sense?

79:02

>> I think when I when I think of

79:03

responsibilities I always think of

79:06

management. That's a really big

79:07

responsibility and I don't take it

79:09

lightly.

79:10

>> Mhm.

79:10

>> This is just there's no way around it.

79:12

That's that's something's going on there

79:14

that's a focus. It is cyclical.

79:17

>> Mhm.

79:17

>> So like the Peppers are not touring this

79:21

year. They don't have an album this

79:22

year. They aren't touring next year.

79:24

They don't have an album next year. So,

79:26

you know, there's there's a lot of time

79:28

in between and they're going to where

79:29

they're coming up with the creative.

79:31

They're going to make an album. They're

79:32

going to do all the things. They're

79:33

going to write songs, right? So, that

79:35

takes time. So, you get these windows of

79:37

opportunity where you go all in and you

79:39

get windows opportunity where you have a

79:41

moment to breathe just like they do.

79:42

They all need it too. Madonna after the

79:44

cycle will probably need a minute to

79:46

just sort of catch her breath and figure

79:47

out what she does next. So, these are

79:49

cyclical things.

79:51

What I don't do is I'm not out there

79:52

trying to sign 10 more bands or 10 more

79:54

artists. So that's where the balance

79:56

comes in and which is continually be

79:58

creative through other ways.

80:00

>> And so when the cycle starts, my

80:03

creativity has never stopped.

80:04

>> Mhm.

80:05

>> So that I still have those things. I'm

80:07

I'm not starting from scratch. I'm I'm

80:09

always looking and meeting with people

80:11

and understanding what's going on in

80:13

technology. And so when when Madonna

80:16

comes back into cycle, I can bring some

80:18

of those ideas or some of those new

80:20

relationships I met while she was off.

80:22

>> And so I just I found a way to to to

80:25

make it work. Maybe I'm sure misquoting,

80:29

but roughly paraphrasing

80:32

much earlier in the conversation. And I

80:34

feel like you said part of Madonna's

80:36

ability to reinvent was not resting on

80:38

her laurels obviously, but not patting

80:41

herself on the back for what she's done

80:43

and sort of marching forward.

80:46

>> And I'm wondering how you've thought

80:48

about for yourself

80:50

the drive and velocity of

80:53

forward-looking achievement versus

80:57

sort of appreciating what has been done

80:59

or savoring the time that you have. I

81:02

mean, I imagine you get a lot of that

81:03

with

81:04

congregating friends and so on, but I'm

81:07

wondering if you have any thoughts.

81:09

>> You know, my friends and I don't spend a

81:12

lot of time talking about what I do.

81:15

>> A little bit. I share with them so

81:17

they're in the know, but we don't spend

81:18

a lot of time on it.

81:20

>> We don't work together on these deals.

81:25

>> My wife and I don't talk about work

81:27

much. Like, I think I just keep it

81:29

moving, too. And again, I when you look

81:31

back 36 years, it's probably Madonna

81:35

that is responsible for how I also think

81:38

of just keep it moving forward. Keep it

81:40

moving forward. And and you know, maybe

81:43

one day sometimes when I'm telling my

81:45

kids a story about the past or someone

81:48

asks me a question and I tell them about

81:49

the past, I go, "Oh my god, I forgot I

81:51

even did all those things." Or I see

81:53

something pop up and I go, "Oh, I was I

81:55

I you know, I was there for that." And

81:56

but I really don't think about it that

81:58

much. Things pop up every now and then.

82:00

When I wake up tomorrow, I'm like, I

82:01

haven't done anything today. I better

82:02

figure it out. [snorts] I need to step

82:04

my game up. That's how I feel. I don't

82:06

feel

82:08

accomplished

82:09

at all. I feel like I still have so much

82:11

to prove and so much to do. Well, at the

82:15

same time, I do know if I if I really

82:18

took a minute, I would go, "Oh, wow.

82:20

Okay. Oh, that's Oh, I didn't I should

82:22

probably

82:23

>> take a moment and take that in." But I

82:26

really don't.

82:27

>> Is that okay? Is that a problem? Is it

82:29

fine?

82:30

>> I just keep it moving. I I don't know.

82:32

You know, at some point, you know, there

82:34

I I can visualize being on the beach and

82:37

and, you know, high-fiving with my

82:40

friends and having fun.

82:42

>> But I I again, I don't they don't do it

82:44

either. A lot of my friends were we

82:46

don't talk about it like that either. I

82:47

mean,

82:48

>> I think we just sort of

82:50

>> how cool that we're survive this period

82:52

of time. How cool is it that we're even

82:54

able to do what we love? Mhm.

82:56

>> Waking up and being able to do what you

82:57

love. There's a Josh Kushner quote that

83:00

that I love that he says about success.

83:04

He says, Tim, success is being excited

83:07

to go to work and also being excited to

83:10

go home.

83:10

>> Yeah.

83:11

>> And I got that. I'm excited to go to

83:13

work and I'm excited to go home. That's

83:15

pretty cool.

83:16

>> Yeah.

83:16

>> And you know, not a lot of people get to

83:18

do that and I don't take that for

83:19

granted. And I work hard because of that

83:21

cuz I go this is not a given. you know,

83:24

the potential and the opportunities. And

83:26

I'm trying to bring in other friends and

83:27

other people into my world to say, plug

83:30

into this. Let's help you figure this

83:32

out. I'm not just doing it for myself.

83:34

Like, you should use what I have. You

83:36

should meet some of these people. You

83:37

should come to this event. You should go

83:39

to this. So, I like sharing that.

83:42

So after 20 years, you and Ashton are

83:46

going to be doing different things, it

83:48

sounds like, and I was wondering if you

83:49

could just share a bit of the background

83:52

and what that looks like.

83:54

>> We've had an incredible run

83:57

>> and

83:58

this AI fund is I don't know what to

84:01

compare it to other than like winning

84:03

the Super Bowl

84:04

>> for what we do,

84:05

>> right?

84:05

>> And you know, between the investments in

84:07

Open Eye, anthropic and we also did SPVS

84:09

the whole way up a lot. So,

84:13

we're really fortunate and blessed. And

84:15

after 20 years, Ash and I asked the

84:17

question of now that we've done that and

84:19

we've hit it out of the park, what do we

84:22

want to do for the next 10 years? What

84:24

makes us happy? What what are we going

84:26

to get enjoyment out of doing? And it's

84:28

a really strong question and we all gave

84:32

it some thought. This is a few months

84:34

ago. We we we looked at each other's

84:38

visions of what he wanted to do that

84:40

make him happy and what he wanted to

84:42

build and what I wanted to do and and

84:44

then we have a third partner her name's

84:45

Effie and what she wanted to do and it

84:47

turned out that we had different visions

84:49

and when you look at his vision which he

84:52

will share at some point so I'm not

84:53

going to share any of it pretty awesome

84:55

vision

84:56

>> it's an incredible vision and the guy is

84:59

mind-blowingly smart and talented

85:03

And

85:05

I support that vision for him.

85:07

>> Mhm.

85:08

>> It isn't my vision.

85:09

>> And I will support it financially and I

85:11

will support it with energy. I want him

85:14

to win. And then I have mine which is

85:18

the things that we're talking about

85:20

today and the things that I want to

85:21

build. And I have a version of the

85:24

things I want to do that I haven't

85:25

shared with everyone in full. But it's a

85:29

new chapter and I've had many new

85:31

chapters my whole life. I went with the

85:33

record label for a certain time and then

85:34

I moved on. I went to music management.

85:36

I went to crypto and I went to film. I

85:39

mean, I have so many different chapters

85:41

in my life that this is a beautiful

85:42

chapter that is we're in a celebratory

85:46

mode.

85:47

>> Mhm.

85:47

>> So, we're sort of hoping to be on the

85:49

beach high-fiving each other at some

85:50

point on the work that we've done and

85:53

have worked hard to get here and taken a

85:55

lot of risks and a lot of chances and

85:57

put in our own money. And so this

85:59

decision was made out of joy and and to

86:03

support each other's visions. There are

86:06

going to be times where we'll cross over

86:08

and we'll work on things together

86:12

because we do have some crossover of

86:13

things that are part of things we both

86:15

like.

86:16

>> But he's very specific on he wants to do

86:18

it. I'm very specific I want to do.

86:19

Effie and I are going to continue on

86:21

with sound and what we've built the last

86:24

10 years with sound. So we'll continue

86:25

to build that. And then we've got some

86:27

surprises of how we want to build that

86:29

out too. It's all really good. It's all

86:31

very supportive. It's just another

86:33

chapter.

86:34

>> Guy, this has been a wide-ranging

86:37

conversation. What a life. What a

86:40

journey. And it's not over. Obviously,

86:42

you got lots of battery left for what's

86:45

ahead.

86:47

Thank you for the time.

86:48

>> Thank you.

86:48

>> Thanks for inviting me here.

86:49

>> My first podcast.

86:50

>> I know. I know. Mine, too. [laughter]

86:54

Your first podcast with me. Yes,

86:56

>> exactly. And people can find you on

86:59

Instagram XGO

87:02

Siri, no apostrophe. Guy O S E A R Y.

87:07

And we will link to everything in the

87:10

show notes as per usual at

87:12

tim.blog/mpodcast.

87:14

And until next time everybody, thanks

87:17

for tuning in. Be just a bit kinder than

87:19

is necessary to others, but also to

87:21

yourself. Compassion is not complete if

87:23

it doesn't include you. Thank you, Jack

87:25

Cornfield. And as always, thanks for

87:27

tuning in. Thanks, Guy.

87:28

>> Thank you.

Interactive Summary

The speaker, a prominent figure in the music and tech industries, details his journey from a fast-decision-making record label executive to a successful investor. He shares how early life experiences, including a traumatic event and attending two vastly different high schools, shaped his drive and perspective. Key career moments include his pivotal encounters with music industry legends Bernie Brilstein and Freddy De Man, leading to his first artist signings like Candlebox, and his significant role in Madonna's career, from creative contributions to management. He recounts a major early investment failure that taught him the importance of diversification, followed by a triumphant return to investing with companies like Vita Coco and Anthropic. Throughout his narrative, he emphasizes intuition, pattern recognition, and fostering strong, long-term relationships, drawing parallels between identifying music talent and backing successful founders. He also voices strong concerns about the current state of AI's use of artists' music without compensation.

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