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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.

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