The Legendary Hollywood Power Broker — Guy Oseary on 36 Years of Managing Madonna, 26 IPOs, and More
2432 segments
Honestly, I would say that
[clears throat] 90% of the things I do
happen in the first 5 minutes. 90%. It
drives me crazy when we get in a room
and talk about it for 3 months. And I
respect process, but I think I know what
I want to do very quickly. We have such
a small label, so boutique, and we're
competing with these big companies that
have been around forever and have all
these other artists, and we didn't have
any artists. Mhm.
>> So when I met an artist and I like them,
Atlantis Morris said I signed off of one
song. Muse, I saw them perform one song.
It shows the artist the passion which is
very important. This person believes in
me that much. And also if I left it
available, maybe someone will offer them
way more money or make them other
promises. And I couldn't afford to not
make fast decisions
>> or else we would never have gotten to
where we got to. So, here we are sitting
in this beautiful home and I wanted you
to explain this beautiful calligraphy
behind you that I was admiring. Some of
the most impeccable handwriting I've
ever seen. What is it that's sitting
behind you?
>> That's purple rain lyrics by Prince.
>> Just incredible.
>> I'm a huge fan of Prince. When I was a
kid, I had Prince posters up on my wall
and I met him when I was 12.
>> 12? Yeah.
>> How did that happen? The place where I
was living with my dad, an apartment
building in West Hollywood, was directly
across the street from a hotel called a
Park Hotel. And that's when I started
meeting artists. I started becoming a
fan. I love music, but I became a fan,
you know, someone that would actually
wait to get their album signed or, you
know, and Prince actually signed
something for me. He wrote Love God. I
told him that years years later. We
became friends and became close. Was it
love God period or love, God?
>> It was love God.
>> Okay.
>> And it was sign prince.
>> Wow.
>> That was a long time ago because he
later on he he became a Jehovah Witness.
>> But you could see the posters. I had
like Billy Idol and Prince on my walls
and you could see it from the street if
you looked up. So you can come out if
you're waiting for your car or whatever
and you look and you'd see, okay,
there's someone up there likes music a
lot. I was on the first floor. There's a
little balcony there and and I come out
a lot to meet I met in excess and some
people I became friends with like Billy
Idol I became friends with years later
and Michael Hutchkins I became friends
with and Morrisy I became friends with
later but I met them all when I was a
kid and a really cool thing is other
kids were around then. They were older
than me but they were kids and so I
could hang with them and really get a
little camaraderie with some of the fans
out there that were waiting for the
bands.
>> I want to talk about addresses and
Beverly Hills High School. How did you
end up at Beverly Hills High School and
why?
>> Yeah, before Hills High School, I went
to a school in downtown LA. It was on
Pico in Arlington. So, it's almost on
the way to if you're going to go see a
Laker game, it's on the way to that. And
I went to that school and it was
incredible. So many great people,
different music was a big piece of that
of my journey there. I took a school bus
there and the kids would go between two
radio stations on the bus. So the bus
driver would play either KDAY, which was
the first hip-hop station in LA, or they
would go to K-Rock, which is the
alternative radio station in LA. And I
love them both. And so I met a lot of
really cool kids there who were in these
groups of people. The there were like
the punk rockers, the hip hoppers, the
break dancers, gang members, graffiti
artists. There just a great eclectic
group of people during that time period
where I'm just I'm a sponge. I'm just
picking up all the energies and really
falling in love with music. One night I
was outside the school dance. There was
the LA Dream Team. That's what they were
called. This this group that was
performing that night. And I was waiting
outside the school. I was very tall. I
looked a little older than than I was.
And it was late. My my dad was late to
pick me up. And while I was out there, I
saw I saw a guy running past me for his
life. And then I see a car turn the
corner. I guess he was chasing the guy
down. and a guy jumped out of the
passenger seat and pulled a knife out on
me and and asked me if I was with that
guy.
>> He asked me if I was in a gang and I
said, "I'm not I'm just a kid waiting
for my dad. I was school dance and this
is my school and so he got back in the
car to chase the guy."
>> And so, you know, there are no such
thing as coincidences, but my dad showed
up. I got in the car and I was like, you
know, I I almost died and and someone
pulled out a knife on me and and you
were late and and I want to go to
Beverly Hills High School next. And
again, there's no coincidences that that
just came to me right then and there
that I want to go from downtown LA to
Beverly Hills High and there was a TV
show 90210 back then. So, I thought I
want to check that out.
>> That's a different world from the world
I'm in now. I want to just see it. And I
didn't know at the time, but you have to
live in Beverly Hills to go to Beverly
Hills High School.
>> Yeah, it makes sense.
>> Yeah. I don't know why I didn't put that
together. [laughter] I just said that to
my dad and you know, we didn't live in
Beverly Hills and he knew I that's what
I wanted and he heard me. He he came
back to me and said, "There's someone
who I know who lives in Beverly Hills
and they will give you their address to
basically pretend that you live there so
you can go to that school that you want
to go to." And the combination of going
to school in downtown LA and also going
to Beverly Hills High right after, I
think that's a big part of of who I am
today.
>> Blending the two worlds.
>> Blending the two worlds. one or the
other like without the other would would
not have given me the perspective that I
needed.
>> What was the perspective that you got
once you were transported to this second
chapter at Beverly Hills High?
>> Once you walk through those doors, it
might as well be a TV show from where I
just came from. people have a lot, you
know, there's cars and there, you know,
there's homes [snorts] with pools and
just the optionality and the potential
of what they all had was pretty wild.
And and that actually inspired me to,
oh, I didn't know you can aim this high.
I don't have what these people have. I
don't have the means. I don't have the
money. I don't have the connections. So,
I better start working. I think at like
14 it really started to kick in where I
go cuz these people are going they go on
trips and ski trips and I don't know
anything about skiing. I don't know
anything about I I just I didn't live
that world.
>> So I knew that I needed to do something
about it. And I started to
>> I looked what what could I what am I
good at? What could I be good at? And
music was my love. It was my passion.
It's what I I was obsessed over. And so
I thought something in music
>> and that's [clears throat] when I
started to really pay attention to what
could I do around music. I drew music.
And then around 15 I really started to
pick that up and and at 16 I was already
like really running with it.
>> So I think this might be a good bridge.
If I'm missing something in between
these points, let me know. I'm sure
there's a lot that we could talk about.
But Bernie Brilstein, who is that?
>> So Bernie Brilstein is iconic in
Hollywood. He's one of the greats. He
was exceptional. He was one of the
original managers and he managed all
these amazing talents. A lot of the
talents from SNL, he managed all of
them. He started this idea
>> John Belalushi, Gary Chandling,
>> all of them.
>> And he was beloved. He looked a little
like Santa Claus. Was a really big guy
with a white beard. And when I was 15, I
started to compile artists that I liked
that were had demos. So, I would go out
there and try to find artists and try to
find new artists. And I had like the
yearbook person come and take photos of
these. And
>> this was on your own or were you working
on your own?
>> On my own. I didn't know what I was
doing. I just thought, let me put
together a portfolio. Let me have
someone take photos of these artists.
Let me create get the demos. One day
I'll get a meeting with somebody
>> and I'll have something to show when I
get the meeting.
>> Yeah. I'll have something to show. I
think I called it Wise Guy Records. Just
I didn't know what any of it meant, but
I had my little logo. So, I did
everything I could possibly do without
knowing anything or anyone. And then the
week I turned 16, I I remember it was
the week I turned 16 because I didn't
pass my driver test, [laughter] so I
needed to be dropped off. So, the week I
turned 16, I went to meet with Bernie.
What happened was is I I approached a
lot of the kids at school at Beverly
Hills High and I said, "Can I meet your
dad? Can I meet your dad? Can I meet
your dad?" Just anyone that was in
entertainment. And out of all the people
that I approached, I got two meetings
that would end up both being really the
most impactful meetings I could ever
have. And one of them, the first one I
got was Bernie Burlstein. And his two
boys, Nick and Dave, both
told their dad, you know, you should you
should meet with Guy. So I go meet with
Bernie. He was at the 9200 building on
Sunset. And I played him a song.
I don't even remember what group or what
it was at this stage, but I played him a
song and he just says, he looks at me,
he goes, "Well, hey kid, how much is it
going to cost to to put this out?"
And I knew not to pause cuz then he'd
know I'm a phony. So I said, " $25,000."
And he said, "I'll tell you what, kid.
I'll give you the $25,000.
If you make it back, pay me back. That's
all I ask."
And at the time, I'd never seen $2,500.
So, I just said, "Bernie, I'd rather you
make three phone calls for me to music
people." And I don't want your money. I
want you. And and he ended up putting
that in his first book, that story. He's
passed away, unfortunately. And he
always felt I said no because I just
couldn't take the money from him. I said
no because I didn't know what to do with
$25,000 and I was a phony. So until his
last days, he always thought in his
book, he's like, "The one guy that
didn't ask that didn't want to take my
money was Guy Oeri." It's not true. I
just didn't know what to do with it. So
he made those three phone calls for me.
>> Did he pick the people to make the phone
calls to?
>> Yeah. I had no idea. I said, "Three
music business people." He did, and I
got meetings with with a few of them,
but they never ended up
>> going anywhere.
>> Going anywhere at all. But what ended up
happening was is I came back home and I
thought to myself, "Wow, I'm 16 years
old
and this guy offered me as much money as
people make a year in one meeting." If
people feel they have talent, they don't
know really. There's no confirmation on
that talent. You know, people think,
"Oh, my mom says I'm a good singer or so
and so says I'm great at this." But you
don't know until someone confirms it.
until someone buys your book or goes to
your show or or whatever until
>> offers you 25K.
>> On that day, that was a confirmation I
needed that I'm on the right path. And I
went, that's it. From this point on, I'm
going to turn it up. I'm not looking
back. This guy offered me 25K in one
meeting. I just turned 16. I'm going to
stick to this. I can do this. And many
years later when I got my first gold
record, I sent it to Bernie because that
was so impactful on my life.
>> You mentioned two meetings.
>> Yes.
>> Was the other Freddy?
>> The other was Freddy De Man.
>> All right. Who is Freddy De Man?
>> So Freddy de Man, his daughters Nissa
and Polar connected me with their dad
Freddy. And Freddy was iconic as well. I
mean he worked on Thriller with Michael
Jackson.
>> Wow.
>> He managed Madonna. He managed some of
the greatest artists of all time and he
was just a really great human, great
guy. And he heard me out. It took a few
meetings to get Freddy to really go for
it with me. Not that long.
>> And this meeting was after Bernie.
>> Meeting was after Bernie. And he just
learned about me. He heard he heard my
pitch and I'm trying to do this, I'm
trying to do that. And he knew I didn't
really have any money.
>> Yeah. At that point, what was your
pitch?
>> Gosh, I think I just showing him that
that I I'm in the flow of music. I'm
around music. I'm around artists
>> the portfolio.
>> Yeah. I start but one one of the crews
that I was working with was Ice Tea. I
got very lucky got introduced my friend
Chris Boyd I met when I was working when
I was 15 at Fred Seagull and Chris Boyd
another guy was working there and he's
like oh I know I tea and his producer
Johnny Rivers and I go would you want to
come to the studio and check it out and
I'm like yeah I want to go. So he
brought me to the studio and actually my
first day in the studio Iced Tea goes
come in come into the booth and do a few
words and I'm actually on the album.
>> Wow.
>> Yeah. He had me say like few words on
the album. But um but I started hanging
around and I'm like what could I do?
Could I could I clean up? Could I carry
someone's bag? Could I you know what?
How do I be helpful or of service? I'm
just so happy to be around this energy,
the music and artists coming in and out.
And he had a thing called Rhyme
Syndicate. So, a lot of the artists came
through there and I was able to be
around them and help and and then I
ended up becoming the manager of ICT's
DJ and his brother who's Henji and
Eively. Eve Lee is Ice Te's DJ. So, I
managed them. It's my first group I ever
managed. And I was 17. We got them a
record deal.
>> So, I had that and I always checked in.
I checked back with Freddy and said,
"Fred, I just got my first group signed
to record label." So he knew there was a
guy named Steve Riiffken who I met who
knew the record label. He helped me get
that first record deal.
>> So when I went to see Steve and I played
him he's DJ Evelan Brother Henji and I
said here's the music and said I I know
a label for you. So he helped me get my
first record deal. So I always write
Freddy and go hey Freddy I just got my
first group signed. I just I'm manager
you know and he knew I was how is he
pulling these things off on his own
without any help or any money. And so I
met with him and he said, you know,
Madonna and I are going to start a
record label one day. So I said to him,
I'd love to work there. I said, I don't
need any money. Which I did need money,
but I wanted to make it really easy for
him. I said, I don't need money. Just
give me an office and a desk. That's all
I ask. And he was like, okay. So he
brought me in as a, you know, scout cuz
one day they're going to start a label.
They didn't even have a name. They were
just they just knew they were going to
do it. So I'm scouting
>> and and then one day I I find Hole,
which is Courtney Love. I find their
first song, Teenage [ __ ] and I go, "Oh
my god, this sounds incredible." I just
just blown away by the sounds and the
lyrics and all of it. So I reached out
to the lawyer, Rosemary Carol,
and next thing I know, it's in the paper
the next day. Madonna is trying to sign
hole. How did that happen?
>> I mean,
>> would you ever
>> I made a I made a phone call. [laughter]
I was very naive back then, but it was
like Madonna's trying to sign Hole. So,
the next day, there was a show that Hull
was doing at the whiskey. I think Kurt
was there. Then Madonna was like, "Who's
this?" Wanted to talk to me about who is
this whole thing that you're think for a
second.
>> Yeah. So I go in a room and I play the
song for Madonna and for Freddy and it's
pretty wild. I mean the lyrics are like
when I was a teenage [ __ ] my mother
said she said baby what for? I was like
whoa you got to go back to that like
>> that time period.
>> They're like okay all right so go go go
after it. And so I went after it. I
didn't get it. It was between us and
Geffen Records and we didn't get it. It
went to Geffin Records, but my first
artist I ever attempted to sign was
Hole.
>> So, let me pause you for one second.
>> Yeah.
>> All right. So, the meetings
that you got with Bernie and Freddy. So,
you got two introductions. How many how
many kids at school do you think you
asked in total to end up with those two?
>> I think I probably asked five.
>> Okay. All right.
>> Yeah. I mean, I wasn't social guy. I'm
not on the football team. I was just
sort of my own music guy running around
and I didn't have much. So I did as much
asking as I can from who I could figure
out to ask. So I probably asked around
five. I remember I remember one person
specific saying my dad doesn't do that.
Whatever cuz it was rap. I was trying to
play. Oh, my dad doesn't do that. So but
I I didn't have any shame. I just I
needed I needed to figure this out. I
knew that my time was limited before
going to college and I better figure
this out soon. So I was on a hustle.
This is from an LA Times piece way back
in the day, 1997. It says something
along the lines of I gave myself a year,
which is why I kept pushing people for a
chance. Maybe that's accurate, maybe it
isn't. But did you apply pressure to
yourself in that way, like instead of
going to college?
>> No, I went to college. I went for half a
semester and I got my first group
signed, which was was just Henjini Vi.
And then I I remember going to my
English teacher.
>> I don't know her name. She was amazing
because I said, "Hey, I'm thinking of
dropping out and focusing on this thing
and she just looked at me and said, "You
could always come back."
>> Wow.
>> Yeah.
>> It's wild to think about these just
chance.
>> That was it. And I go, "Oh,
>> I could always come back." Okay. So,
that was it. And by the way, I couldn't
even afford the $700 per semester, you
know, and all the things that came with
that.
>> So, I I had no choice. Sometimes having
no options and no choice is really the
best option. Where did the like hutbah
come from? Right. I mean, just that
drive. I mean, was that absorbed from
the parents? Were you just out of the
box, very different?
>> I fell in love with music in a big way.
>> But I think I realized how lucky I was
to be at Beverly Hills High and see
the potential of what was Yeah. of
what's possible. And I thought, "Wow,
not everyone is is this lucky. Not
everyone gets this opportunity." And and
by the way, I was scared that they would
kick me out cuz if they found out I
didn't live there, they kick you out.
>> So I had to watch how I went to school.
It was wasn't like an easy thing to do.
And so I just thought for every day I'm
here, I'm really lucky and I and I need
to pay attention to that. And I just
realized that if I wanted to change my
destiny, I [clears throat] needed to get
going.
>> And at what moment did you realize, oh,
I think this might just work out. I
mean, was there a particular
person or band you signed? Was there any
flash point or was it really gradual?
>> The Bernie Burlstein moment where he
offered me 25 grand the week I turned 16
was a big game changer for me. And then
there was a personal moment for me when
I got a car
when I finally passed my driving test.
took a few times when I finally got my
car. And I remember going to see my old
friends from my old school cuz I when I
drove it to Beverly Hills High, it was
Honda Civic.
>> When I drove it to Beverly Hills High, I
got not one person commented or said
congratulations or nothing. No mention
of it at all.
>> Sure. And then I went to my old friends
from my old school and then they
couldn't believe they couldn't believe
that I had a brand new Honda Civic and
they got in the car and they were
rolling down the windows and sticking
their arms and heads out and I was like,
"Oh, wow. Okay, I got a little
perspective there to go, oh, these
people at Beverly, they're not really my
friends. I'm here for a reason. I I was
put in in around this community for a
reason, which is to work and which is to
build my my name and to build the things
I want to do. And it wasn't until years
later I I told that story in that thing
you're talking about when I was 24 and
my, you know, my dad mentioned it was
really hard to even come up with the
money for that car back then. It was a
really big deal for us. It was expensive
back then. And so I think I need a
perspective a lot of the
opportunities that were in front of me
and to really appreciate them.
>> So it's a combination of those things.
>> And from the chapters we've discussed so
far, I mean was then the next phase
building your relationship with Madonna
primarily or where did you kind of hop
off past the things that we've already
discussed? Madonna and I the first real
connection was that whole connection
where I was like well play me this thing
that you like and then the second one
second artist I brought was Rage Against
the Machine and I really wanted to sign
Rage Against the Machine and so I took
her to the concert in New York the
Limelight I think it was called and I
didn't get them either. I didn't get
Rage. They ended up going with Michael
Goldstone at Epic Records. So you know
God the first two things I competed for
I didn't get. Well, not only did you not
get them, but they went on to be
>> Yeah, it was painful successes, right?
>> Yeah, it was painful. The third one I
that I competed for, I did get. It was
called Candlebox. And at that time,
actually, I think it outsold both Hole
and Rage. They ended up doing really,
really well. But regardless, Hole and
Rage, even to today, I still listen to
those. I love them. But I was very lucky
to get Candlebox. The fact that they
they bet on me and we didn't have
anything.
>> Yeah.
>> We just had this idea, you know, they
ended up selling 4 million albums on
that album. But I'll I'll never forget
that. I'll never forget that they gave
me that shot. That was the my first
success story was
>> they give you a shot, but just to repeat
what you just said, like you didn't have
much, right? Like they were placing a
bet on you.
>> What then goes into
helping make a hit album that sells 4
million?
>> Going back to that time period.
>> Mhm.
>> First is the music. I saw them. I I was
so lucky. I walked into almost
everything that I've been lucky on
happens within minutes, not within days
or weeks or months to think about it.
It's all intuitive and it's very fast. I
was supposed to be somewhere else that
night, but I went to I went to this
party. It was so bad that I thought,
"Oh, I have time to go see that showcase
of that band from Seattle." So, I go to
the lingerie on Sunset and I walk in and
and these guys start performing. Now,
there was a screen like a
[clears throat] like a video screen on
the side of the stage like and and then
there's a stage and I was looking at the
video screen. There were maybe like 30
people in the audience. It's a showcase
and I'm looking at that screen and I saw
thousands of people singing along to
that band.
>> In your mind,
>> I just in my mind. Yeah. But I went to
the pay phone from that performance,
called Freddy and said, "Fred, I have
our band. This is the band. I just saw
them. This is the one." And so it starts
with that. It starts with always starts
with the magic.
>> I don't care if you're tech company or
whatever it is, a film, a product, a
book. Magic. You got to have magic.
Something something has to pull you in.
>> And that night, I saw it. I visualized
it. And the songs were there. The songs
were so there that when we made the
album, their first two singles, we could
not beat the demo. They went into
re-record them for the album. So,
whatever they made for a few hundred
bucks that that I had with a a lot more
money and a lot more time, we couldn't
beat. And so, those songs, those first
two songs on the album are from the
demo. So, the music was there. They were
talented. The band was talented. The
singer Kevin is so great. And they
really did it the hard way. They chipped
away. They did show after show after
show took took few years for every week.
Every week little by little little by
little keyword is artist development and
people don't always develop that much
but it's something that we all want.
Every artist wants to have the time to
build have the time to develop and and
we really took that time week after week
after week developing that one. That's
how we got there. This is maybe jumping
ahead too far, but what would be an
example of that in your
investing later? Could be tech, could be
outside of tech where you saw something
or you talked to someone and it was
within a matter of minutes or one
conversation. You're like, okay, that is
that is a horse to bet on. Honestly, I
would say that 90% of the things I do
happen in the first 5 minutes. 90%. It
drives me crazy when we get in a room
and talk about it for three months. And
I respect the process. I know there is a
process to these things, but
I I think I know what I want to do very
quickly. It started out I think the
muscle that got built for fast sort of
response thinking or intuition was
really in the music business. We have
such a small label was so boutique and
we're competing with these big companies
that have been around forever and have
all these other artists and we didn't
have any artists.
>> So when I met an artist and I liked
them, Atlantis Morris said I signed off
of one song, Muse. I saw them perform
one song and I stopped them after the
they flew all the way from London to LA
to showcase for me and I after the first
song I stopped them. I said, "You do not
have to play another song." And they're
like, "We flew out all the way from
London. We'd like to play more music." I
go, but I just want you to know I do not
need to hear another song that just be
clear. So it shows the artist the
passion which is very important. This
person believes in me that much.
>> High conviction. Yeah,
>> high conviction. And also if I left it
available, maybe someone will offer them
way more money or make them other
promises. And I couldn't afford to not
make fast decisions
>> or else we would never have gotten to
where we got to. So, in any of those
examples, and I know this is possibly
very hard to verbalize,
someone said to me recently, and I
thought it was pretty funny. They're
like, "Yeah, in Silicon Valley, if you
say you're using your intuition, nobody
listens. But if you say pattern
matching, then they pay attention." But
if you were trying to explain what you
intuited or noticed in that one song,
understanding the music is good, but
what else are you picking up [snorts]
from those five minutes?
because you can't bet on everything,
right? Especially as a small label. So,
what were you picking up on that allowed
you to make a fast decision in that way?
>> Uh, well, I have to fall in love and you
know, you can't fall in love every 5
seconds. I didn't know I was going to
fall in love with Atlantis when she
walked in my office with Glenn Ballard.
They came in to play me. I didn't know
what that was going on here. I thought
they were a band. He was the producer
co-writer. You just have a feeling and
there is a lot of pattern recognition
later. Like now with experience,
>> now I bring other elements into the mix,
other things I'm looking for
>> that are different than back then it was
just I was just gut. It was just like I
I love it. I'm ready to go. You have I
feel it and you have to fall in love,
>> right? And later today, I I would say on
my tech investing and what I do there,
it's a it's a combination of gut, a
combination of pattern recognition. And
then
there's a few other things like one of
the things I look for is can I help it?
I visualize what I can do for the
company and that gets me excited too.
>> So I go, oh wow, okay, I have a feeling
I can help in a big way or I have a it
starts the puzzle starts to come
together for me very quickly. So that's
important. And then of course there's
the other aspect of well you got to make
sure they do what they say. Let's try
this thing out that you know let's make
sure the car actually shows up when you
press the app and it picks you up and it
well [clears throat] make sure the
things work. Make sure that you can stay
at the apartment and it's actually oh I
press the thing and I can get an
apartment.
>> These things have to work.
>> But for me it all starts with that
initial pitch.
>> How does Alanis Moriceet fit into your
life? Seems like an important piece of
the puzzle. Yeah, she played a big role
in my life. She
was the rocket ship. It just took me to
the next level. She appeared in my
office with her with Glenn Ballard.
>> Mhm.
>> And they played me one song. They played
a few songs, but the first song they
played was a song called Perfect. I
didn't understand how powerful
those lyrics were until later when I
really listened to it. Mhm.
>> It's really about earning your parents'
like, do they believe in you? Do they
love you? I don't know if you know
lyrics, but sometimes it's never quite
enough.
>> When you're flawless, then you'll win my
love.
>> Don't forget to win first place. Don't
forget to keep that smile on your face.
I didn't even understand. To me, it was
just, well, how is she putting these
words together? I just had never heard
anything like it. Again, later I
understood how powerful those lyrics
were. But at that time, I was just in
love with what I was hearing and I
hadn't heard anything like it and I
went, "I'm ready to sign you. I love
this. I'm all in." I didn't know
anything. Remember, I didn't know that
comparisons where people were like, "Oh,
I thought it was Joanie Mitchell." I
didn't know Jonie Mitchell. So, to me,
she was my Jonie Mitchell. I didn't
never listen to Jonie Mitchell before. I
listened to it later because of her. I
wanted to know what people were talking
about. But to me, she was my she was my
Jonie Mitchell. And I didn't know any of
the background. A lot of people
prejudged her because she had as a teen
did like a pop album in Canada. And so
people had all this background. I had no
background. I literally was asked to
meet with her and Glenn and I knew
nothing.
>> All you had was that meeting.
>> I knew nothing. They walked in and and I
thought, "Oh, wow." It felt like a
hippie group actually. I was like, "Oh,
maybe there's like some sort of hippie
vibe kind of what is this going to be
like kind of thing." But it was again
another life-changing moment when the
story is told. It's that everyone
passed. But I got it. I got I just felt
it in the first minute. And then we
ended up working together and working on
that album and that album ended up
selling 30 million albums and I think
top five debut album of all time. That
really just took me to the, you know,
cuz not only did I sign it, but everyone
else didn't want to sign it. So it's not
like I even competed. So it really
cemented that, okay, I'm in a good place
right now that I can do these things and
I this probably is going to give me more
opportunity to do more of these things.
So she's such a big part of my life and
she's so she's so talented. How lucky
that
years later she's right now she's still
winning awards. She's still out there
crushing. She's actually doing
incredibly well right now. And it makes
me so proud to have played any part of
that. It would be so sad to have missed
that one. I'm so happy to have been
fortunate to have gotten that that
meeting and to have figured it out. A
lot of people when they initially heard
it, I remember Freddy once asking me,
"What do you think this record could
sell before it ever came out?" And I go,
"Millions of albums." I just had a
feeling that I had not heard anything
like this and that this was a monumental
record. The rest is history. Rest is
history. I'd love to spend a little bit
of time on what you've learned from
Madonna. This is an older variety piece,
but the quote here that's attributed to
you is she mentored me and by working so
hard pushed me to work so hard. I didn't
know [ __ ] until she grabbed me by the
hand and said, "Let me show it to you."
And it goes on and it goes on. But what
did you pick up from Madonna? What are
the key sort of learnings?
>> I mean, there's some clear learnings and
there's stuff that with I'm 36 years
next to this woman.
>> Yeah.
>> And there's things that when you look
back, you go, "Okay, you know, I got
that like people who think about things
that I got that from my brother or my
mother or my
>> There are things that I didn't realize I
was getting the whole time." So, there's
both. The front part is pretty, I think,
obvious. You know, her work ethic is
>> not to be believed. Her commitment to
her craft not to be believed. her
passion for
just the greatest gifts of whether it's
through the books that she's reading or
through the art that she's finding or
the people that inspire her or the
designers or that she's so surrounded
herself with a collection of some of the
most incredible people in the world and
she identified them. By the way, she is
the greatest identifier. She found these
amazing talents early and and was able
to whether either could they be painters
or Freda Ko or they could be designers
or musical people like she's an
incredible finder of talent. I think the
thing that has really affected me the
most is
that she
doesn't see any kind of
there's no walls around her thoughts.
There's no oh I can't do that.
>> Right. in terms of constraints, right?
>> Yeah. Even going back to my first
experience at Maverick Records,
if you went to any record label,
they probably would have they would have
put me in a compartment. There's the R&B
department, there's a jazz department,
the rock department, reggae department,
pop department, hiphop department, and
you're oh, what department are you in?
And they and they sort of bucket you
into these things. And I think that when
I look back and I go, how did I not
really bucket myself? if I went from
this to this to that to that to that.
And I think it's it's really just being
around her has allowed me to never think
in a limited way
>> and they all work together. A lot of the
stuff I do on technology has allowed me
to bring that into my musical world and
to understand how these things work
together or the relationships and
they're so handinand and of course a few
decades later now people understand
that. But at the time it was so
>> it was it was it was very much like what
are you doing this tech thing is crazy
and you're not doing innovation is
innovation and how we can distribute
music or how we market and vice versa
all the stuff from music is you know
when you when you're launching a new
company you have you know these founders
are rock stars in my mind every founder
I invest in I look at them like they are
the rockstar I go that person has music
they want to share with the world they
have their album and my job is to
identify that artist, that founder
before everyone else maybe identifies
them. And my job is to help you reach
that audience. How do we tell the story?
How do we reach the base of your
audience? How do we grow your audience?
You know, what's your first single?
What's your second single? I still work
in that kind of process, which is very
musical in my mind. We're going to spend
a good amount of real estate on on the
tech. But before we get to it, I want to
take a moment to explore the the terrain
of film and how you ended up executive
producing Twilight and and all the rest
because as as you mentioned in a
different environment with a different
label, you would have been tightly
siloed and you wouldn't have had that
ability, right? How did you end up with
the fora into film?
>> I'd been signing bands for a long time
and running the record label and I
thought, well, why don't we do a film
company as well? And Madonna and I were
really in a good groove together and
thought, let's just let's just start
this film company. Why did that come to
mind?
>> I don't really recall that. I just
recall thinking about how people do it
differently. And so again, I didn't have
context. The best thing sometimes is to
have zero context. Sometimes fresh is
okay. Sometimes having a blank canvas.
And with films, I had a blank canvas. I
didn't know how it worked,
>> but I knew I wanted to make some films.
>> And I So I had this idea of
bringing in a bunch of producers under
one roof. And they were all independent
producers. And the idea was is I'll
bring them in and you know house them
and and give them support and pay for a
lot of the legal things that cost money.
When you're independent is it's a lot on
you,
>> right? All the back office, all of that
stuff.
>> We'll take all that on. We'll help you
and then we'll work on these projects
together. And we had like a lot of
producers that I if I was to to pay for
them, I couldn't have afforded it. But
we did it that way. and and out of that
came a lot of films and a lot of
Twilight and and Percy Jackson and a few
others that I was very lucky to be part
of. The guy who ran at Mark Morgan was
really good at it, but there were a lot
of complications.
And I was at that same moment that we
were that it started to take off, I
picked up Madonna as manager with my
partner at the time, Angela, and I took
on Confessions, which was the pretty
massive tour that year and I think the
biggest selling record of that year. So
as a I don't know how old I was back
then, but that was a major
responsibility for me.
>> Hard to ride both of those horses at the
same time.
>> Just that alone, just Madonna at that
moment in time for someone I had not
been a music manager for, you know, and
anything near that level. And so to take
that on and to, you know, work on all
things the tour and the album and all
that. And for people who have no context
on music at all, what does a music
manager do in that type of situation?
>> It's a tricky question because no one
manager is the same. Everyone's
different,
>> I guess. What was your umbrella of
responsibilities?
>> When Madonna started working on Ray of
Light, I found the producer, William
Orbit, but I was not managing her. I was
her partner at the record label Maverick
Records and not her own not Warner
Brothers which is where she was she was
on War Brothers but I was just we were
just friends and working together but I
fed ideas I found the director Yonas
Aland and so I was creatively really
working on this project called Ray of
Light. So we're already building a
creative rapport and on music Stefan
Sidenway the director introduced me to a
producer named Her Ways. He gave me a
demo. I loved it and I gave it to
Madonna and I ended up becoming music.
So I found on those two albums I really
even though I wasn't managing her I was
creatively helping here and there bring
in some ideas.
>> Mhm.
>> So we already had a rhythm on the
creative side. Now, there are some
managers that don't do any creative and
there are some that are very creative,
but I was coming from the creative point
of view on ideas, ideulating. Here's
here's things we could do. Here's things
we could build. So, I think I think for
me as that's the management that I am. I
I'm more creative. When I'm working with
someone, I I'm I'm sort of in it. And
there are other managers [clears throat]
I've worked with who they really just
they don't do the creative but they do
an incredible job managing everything
keeping you know putting together the
tour but they're not in there going what
if we did this of you know what if we
there's different kinds of managers I'm
creative for example when I showed her
Jonas Arland did a video for Prodigy
which is a band I signed and it was
really provocative and I just showed it
to her this guy this is crazy and she
goes he's doing my first video or or
he's doing that like you I showed her
there's a a guy named Chris Cunningham.
He made a song called Come to Daddy by
AEX Twin, which is really insane. It's a
$30,000 video. I just showed it to her
just to show her this. Look at this
crazy thing. And she's like, "That guy's
doing that video." So, she had Chris
Cunningham do Frozen, which is an
incredible video. And she had Jonas
Aland do Ray of Light. So, it was just a
really great back and forth. We had
really great energy together that I she
she was open to my craziness and and
then she would take it to the next
level. What and and this is this is my
even when I was very very young and
everybody knew Madonna. I was constantly
impressed by her longevity and ability
to seemingly reinvent herself. And I'm
just wondering why you think she has
been so consistently good at that over
decades. I mean, it was the first
example that I remember even as a young
pretty young kid be marveling over and
I'm just wondering if you could add any
any color to that. She doesn't sit
well on her past.
She's not high-fiving herself.
>> [laughter]
>> She's not really a Oh my god, I've done
all these. She's just keeps it moving
forward. Yeah, I think that that's a
that is, you know, part of the
inspiration for continually
trying to move forward myself is I'm
have a front row seat or shotgun to this
incredible
journey of this woman who just
continually
defies all the odds and
fights the fight. It is not easy. It
it's not just like it's not that she's
maintained or stayed around. It's
actually that she's had to fight her way
through it a lot. She's breaking ground
for a lot of other people who are coming
behind her who can say, "Oh, Madonna's
done it. I can do it." But it is no easy
feat. There is a lot of a lot of
[ __ ] to deal with.
>> And I think it comes from she just
doesn't celebrate her accomplishments.
She just starts like it's a brand new a
brand new day.
>> How did you end up and I don't know if
this is a good starting point but I'll
throw it out there as an example. Your
first consumer investment vitoo well
done.
>> Thank you. Uh, I don't know if that was
your 10th investment overall or your
first, but how did you end up edging
into the world of investing, whether it
was CPG and consumer stuff or tech? How
did that even come to be? Wow. Well, the
original
original original was
I was on a plane to Milan for an MTV
Awards
and I don't remember how old I was. was
in my 20s and I was reading in a
magazine about Sky Dayton and it said he
started Earthlink and he was worth $100
million and he was really I'm like wait
what you can wait what is he doing and
how old is he? And so I go when I get
back home I want to meet this guy. So, I
came back and I took me a while, but I
finally tracked him down and we went to
have lunch at Four Seasons Hotel and and
he was like, "Wow, if you're impressed
by me, have you ever heard of Bill
Gross?"
>> And I go, "No, who's that?" He goes,
"Well, he started a incubator."
>> Mhm.
>> And he's launched three billion dollar
companies in one year. And I go, "Sky, I
like you, but can you just [laughter]
can you get out of the way? I want
>> This time has been great."
>> Yeah. It's time to move on. I need to
talk to this Bill Gross guy. So, he sets
me up with Bill Gross. Bill Gross ran an
incubator called Ideal Lab in Pasadena
and I just loved it. I love the idea of
a lot of ideas. Reminded me of the
record label where you had all these
artists and you had all these project
managers
>> or the independent producers
>> a version of that and you can walk in
and out of different rooms and you can
say, "Oh, okay. What are we doing here?
What are we doing here?" And so he was
building all these different companies
and I would go in and out of ones that I
could be helpful to
>> and I would learn about it. So that was
like a oh, okay, an incubator. I really
fell in love with that idea. And there's
bad news to the story, but as like all
things, it worked out in the end.
>> Well, wait a second.
>> My listeners gonna kill me if I don't
follow. What's the bad news?
>> Well, I mean, the bad news is is that I
worked there for a year helping and then
one day someone I really trust that
they don't know it to this day, but
they're they're an incredible human. And
I was lucky to sit with them at dinner
one night and they were telling me how
Bill Gross is one of the greatest
investments they've ever made.
>> So I I called up Bill and and I go,
"Bill, I want to put money in into Ideal
Lab." And he goes, "Well, you know, I
was going to surprise you and I was
going to put, you know, X dollars in for
you from bottom of my heart for all the
work you've done here." And I go, "Oh,
what is that worth?" And he's like, you
know, he told me what he thinks it's
going to be worth when it comes out. And
I was, by the way, it's worth a lot. And
I go, that's not enough. I'm thinking,
right, I'm thinking to myself, that's
not enough. So I go, Bill, I want to put
more in, a lot more in. And he's like,
hey, for you, I'll let you do whatever
you want. And he did. He's he's really
really sweet guy. And that's the bad
news. I he let me do whatever I wanted.
>> What year was this?
>> It was before the crash. Right. It, by
the way, it wasn't a year before the
crash.
>> I think it was like an hour before the
crash. [laughter]
>> Okay. So, I put every dollar I have plus
dollars I didn't have.
>> I picked out three investments at that
time. Ideal Lab because of Bill Gross.
Bill was the first guy in I think in in
LA to have the Blackberries. So, I was
the first guy from Hollywood to even
know what the hell Blackberries were. So
I ended up buying 400 of them and I gave
them to all the people in Hollywood so I
could connect and when I needed to and
talk to them and and so I made a deal
with Jim Bowsley to be an adviser
because I was I was the guy that put it
in everyone's hands. This is smartphones
before anyone else was doing it. And
then I also my friend Seth Rossky
brought me vitamin water.
>> Yeah.
>> So those were going to be my first three
investments.
What happened was is the ideal lab thing
once I put that money in and I don't
know the the timeline cuz I tried it's
almost like something you want to wash
away from your mind,
>> right?
>> It collapsed.
>> Fever dream you're trying to forget.
>> The bubble burst so fast on all of that
that I didn't have the heart to invest
into. I never signed my deal with Jim
Bowsley and Research in Motion. And I
never and I never did my deal with
Vitamin Water, which both ended up, this
is almost like the the hole and rage
analogy. They both ended up being
massive.
>> Yeah.
>> And then I and I lost all my money with
the first one. So I learned about a lot.
I learned about diversification.
>> I didn't diversify. I put
>> the majority of my money in one thing
>> and I paid the price for it. I really
for the next two years I only thought
about that about 15 times a day.
[laughter]
It didn't matter if I was sitting here
with you right now. Back then I'd be
thinking about it. I' I'd have
conversation with you, but I wasn't
thinking about you. I was thinking about
how did I lose all my money on that one
investment. Everything I saved my whole
life. I was mad that Sky Dayton
introduced me. Like I was like mad at
all the wrong reasons, you know?
>> Everyone was just trying to help me. But
now I'm like, why did I even read that
magazine? I should just stayed in my
music lane. Yeah.
>> So, but what happened was years later
after my first Madonna tour, I started
to think about it again and I go,
>> I wasn't so off.
>> I was off. The timing was wrong on the
ideal lab part. The other two worked.
Had I diversified
incredibly well.
>> Yeah. You would have been great.
>> And so, I got two out of the three. And
the truth is is, you know, it's not fair
to Bill because he really built an
incredible company. and some of the
stuff that he had built ended up
becoming search for Google and a bunch
of amazing things but it just didn't
work out and that's life sometimes they
don't work out these deals
>> a lot of the time
>> I think I had done three Madonna tours
in a row so I came back at my you know
all the money I'd lost I made that back
to survive
>> and then I had a window where I knew we
were three tours in a row we're going to
take some time off and I thought to
myself I didn't get it so punk.
So, I'm going to try this one more time.
I'm good at identifying the ideas. I'm
good at identifying the talent. I'm
going to do it one more time. And that's
when I So, I started and the same guy
that brought me Vitamin Water, Seth
Rossky.
>> Did he later work with Reese
Witherspoon?
>> Exactly.
>> Huge.
>> Yeah. He's done well for himself. And
then he called me one day and goes,
"Hey, have you heard of this coconut
water thing?" So, of course, I'd heard
about coconut water. One, my wife is
Brazilian, and you know, my son, my
first son, his first words were like,
"Awa to cocoa." So, we drink coconut
water at the house. But the whole
coconut water sector
>> in America, if you added all the
companies together was maybe a five or
seven million business. It was nothing.
Nothing. But Madonna on tour, on the
previous tour, she would have the
trainer would go in different markets to
find fresh coconut for her for the
coconut water.
>> And I like, wow, every location we went
to, we had to find fresh coconuts. And
so I started to hear that other people
were doing that as well. Other people
who cared about their health were
drinking coconut water. I started to
see, again, back to pattern recognition,
I started to see this thing. And then
one day the New York Post ran an article
about coconut water. There's a photo of
Jazelle drinking from a coconut and
they're talking about coconut water and
I had cut that out. I put that article
on my desk and when Seth called me and
said, "Have you heard about coconut
water?" I go, "You have to be kidding
me. I have
>> sitting on my desk.
>> I have the only thing that I've torn out
that's sitting on my desk is an article
about coconut water. It's on my desk and
it's like my todo like I need to figure
this thing out and here you are calling
me." He goes, "Well, there's a company
called Vita Coco and out of New York."
And I go, "Uh, count me in." I got on a
plane. I went to meet with the founder,
Mike Kurban. The company was a I think
it was a $35 million valuation at the
time. And I literally just here we go.
I'm jumping back in. And I went in
really big. And I brought Madonna into
that. I brought Demi Moore. I brought
Matthew McConnA, Anthony Key. I brought
a bunch of people into this thing
because they were all healthy people who
drank coconut water. I'm like, "Let's
blow this thing up." And that was that
was the first time back after the the
crazy run.
>> For people who don't know, how did that
turn out?
>> It's a public company today. I think
it's $4 billion market cap.
>> So you were back in the game.
>> Yes. It takes time.
>> It takes time. Yeah. Didn't happen
overnight.
>> What were you
looking for?
How would you replay that meeting with
the founder in your mind? You fly out,
you meet with the founder.
How did you approach that meeting?
>> I think I approached it the way I
approached everything. It was it wasn't
let's think about it. It was like I'm
all in. Let's go. I want to do this.
Here's what I can do. And and I think
they were probably overwhelmed by whoa.
Okay, let's and we just ran. He's
awesome what he's done with the company.
We went public I think at like two
billion and now it's at five. Like he's
done an incredible job. So, we're going
to hop to some more recent examples
which may or may not include this chair
in a moment, but I want to focus on a
term or phrase that I've seen applied to
you a lot, which is great curator of
people. Chris Rock has said this.
Matthew, you just mentioned said this.
Woody Harlson have have all described
you in this way. And you seem very
intentional with
the people you surround yourself with.
Not only that, but you have these very
long-term relationships with a lot of
people. And I'm wondering how you think
about building relationships. I'm not
saying you have to come up with the
guy's ten commandments of long-term
relationships, but how would you think
about that? Right? If you're in front of
a class of students and you're like,
"Look, a lot of people get this wrong."
Or at least let me tell you how I
approach relationships. like any any
particular rules that you use for
yourself or just approaches, things you
keep in mind because that's certainly
not true for everybody, right? You just
have this long-term
cohesion of these people around you. And
I'm just I'm wondering if you can
perhaps just speak to that in any way.
Well, I think it started early in my
teens. There was a a group of us that
were running around and all we found
each other.
>> So you find the other people who are
also on the hustle who are also
creative. I wasn't a comedian or
musician or an actor or a director. I
was like an executive.
>> Mhm.
>> And there's a little responsibility.
He's a responsible one. I don't drink. I
don't do drugs. So I I found my position
was to really
be a safe zone for people and they knew
I worked with Madonna which pretty much
gave a lot of credibility to okay this
guy is she trusts him maybe we should
trust him maybe back in the day but I
think over a period of time my house
became the place that people would come
to or people would congregate and feel
safe you know even when I do events here
or anything there's not a lot of photos
there's no cameras like I I think safety
and support has always been in my DNA
from an early age of just making sure
that people are protected and again I
think I identifying really incredible
people to be around same way identify
the greatest companies to invest in like
I think I identified really amazing
incredibly talented friends who inspire
me and who've been who you know early
days may not you may not have known them
30 years ago but you identify them you
they identify you and so there's
camaraderie and there's this trust and I
do try to bring them all together a lot.
I I think it's important.
>> That was going to be actually my next
question which is along those lines
which is how often do you gather people
whether it's at this house or at events
that you put together just to facilitate
that long-term cohesion. How how often
do you organize or host things like
that?
>> A lot. I think I even if I'm landing in
New York this week, I'll probably do a
dinner and I'll invite the 15 or 20
friends and we sit down and we talk and
we So, I'm always staying connected and
in touch.
>> It's not like, oh, I haven't talked to
you in a year. No, I'm checking in on my
friends a lot.
>> I'm finding out how they are and always
we're I'm always checking in on
everybody.
>> Mhm.
>> I grew up just with my dad. My two
sisters were older. They weren't they
weren't around. So, my friends are
really like they're my they're
everything I had. I didn't before I had
a family. My friends were
>> everything to me. I'm lucky I get to
work with some of my family. You know,
Madonna's I've been beside her for 36
years.
>> The Chili Peppers, my best friend in the
world's godfather of my first son is
Anthony. The whole band, all of them,
Flee, Chad, John, they're family. So,
it's a dynamic that I've chosen for
myself is to really support and be
around my friends a lot. It's a big part
of my life, which is to keep that close.
And again, if someone's in need, you
know, this is the number. Call me. I
want to hop back to the investing. I
mean, you've you've had a lot of hits.
Airbnb, Uber, Spotify, it goes on and on
and on. I mean, I don't know how many
IPOs and so on that you've had. I mean,
gazillion. Let's talk about one. So, you
put in, tell me if I'm getting this
right, 35 million at a 5 billion
valuation into Anthropic. This is a
company that's been in the news a lot. I
think the last round was what, 965
billion, something like that. Are those
numbers roughly accurate?
>> Yes.
>> Okay. So, that's pretty nice multiple so
far. You know, we'll see how things go.
How did that anthropic deal happen?
Well, it starts a little before the
day that OpenAI came out was on my dad's
birthday, Chat Chippy PT.
It was life-changing. And I you remember
those moments. And again, I go back to
music. I remember when I heard Smells
Like Teen Spirit by Nirvana. I pulled
over the car and I went, "What is this?"
And when Chhat GPT came out, that was a
what is this moment for me. And if you
saw me any time after Chat GPT came out,
I would have harassed you to show you
Chat GPT. There's no one, every artist,
every actor, everyone I walked around
and met. I'm like, check this out. Check
this out. Check this out. And I was
obsessed. And I called Ashton and I
said, Ashton, this is it. Open AI. We're
doing OpenAI. This is the greatest thing
I've ever seen. We have to do it. I have
to do it. I have to do it. And so that
was our first this is the one we're
going to go after. But then when we
first started investing, Ashton and I,
it was when the iPhone and the app store
were happening. And so for the first
time ever,
you can scale companies like never
before. And I think anyone would have
done well at that time. We were like
lucky people that came in at the right
time and were looking at the right time
and started our fund at that very
moment, which is crazy. And so we had
this incredible success because of that.
I saw it again back to pattern
recognition.
If you fast forward, we're we're still
using Uber and Airbnb and Spotify. We're
still using those things from that time
period. And we felt that this is it.
these foundational AI models in 10 or 15
years will be how we plug into all these
things. So,
we really felt like we had a 3-month
window. We told people we have a
three-month window. Now, it came out
November 30th of 2022.
So, there's not much you can do. This
people are going away. There's this
Christmas time break, blah blah. But as
soon as January came, we went out there
and told people, "This is the vision.
We're going to do a foundational AI
model fund."
>> I got it. LPS mean.
>> Yeah. Raise money. Raise money and
create this fund, which is which was a
crazy idea at the time.
>> Now, had you already confirmed that
you'd be able to get allocations or you
just had complete confidence?
>> Ashton spoke to Sam, we were able to get
OpenAI. What happened was is I'm very
close to Mark Beni off and Salesforce
ventures. People don't really understand
how smart they are. They don't get
>> They're really smart.
>> They don't get all the press on. They
are one of the best investors in the
world. There's two guys there, John
Simari and Paul Drews, who were when I
was doing my research cuz now I'm on the
I'm on the lookout. What should I know
about an AI? Once I find out about
something, I just lock in. So, and and I
want to know everything about it. And I
I was as I was doing my research, I was
finding out that they were going to do
anthropic and they were very bullish
about it. And I found out from a friend
that works with like a job hunter kind
of people who help find jobs for people.
>> Oh, like head hunters.
>> Head hunters that everyone's going to
this company called Enthropic, you know,
like people are really going to this
anthropic place and they're not going
anywhere else. I'm like, whoa, okay, I I
need to pay attention. So I I asked Paul
and John connect me with with this
founder Dario. So they connect me with
Dario and Nero. They come here in this
room and that's where we made the deal
to invest in in Anthropic. So we did a
bunch of other companies in that
foundational AI fund. It was a
three-month window.
>> So it was before a bunch of other things
have come out since.
>> But we we set ourselves up for exactly
what we did. this is going to be within
3 months. We're going to deploy 80% of
the money within the next 3 months. And
that's what that's what we did and
that's over 3 years ago.
>> How did you know the window was going to
be so narrow? Right. I imagine did you
get any push back from LPs when you said
we're going to deploy 80% of this in 3
months?
>> Well, we didn't have there was no LPs,
meaning we just it was that was the
pitch.
>> Yeah. Yeah.
>> So, it wasn't like we it wasn't like we
raised money.
>> They either bought in or they
>> Yeah. It wasn't like we raised money and
then told them the pitch. It was like
here's the pitch.
>> Here's what we're going to do. There's a
window of opportunity here. We think
this is the future and that was it.
>> They had opted in.
>> Yeah. Opt in or opt out. We didn't know
what we were going to raise. It just
whatever came up is what it was going to
be.
>> So I was trying to pull from memory, but
looks like sound at this point is that
86 exits and 26 IPOs. That's insane. I
mean that is
>> it's been fun. [laughter]
>> You have seemingly different batteries
certainly. I mean, you've got good
batteries. What is the next
5 years, do you think, look like for
you? I mean, is it is it more of this
type of investing? What do you see? Is
it switching gears entirely and looking
at the prison through a totally
different way? I mean, what is what is
next for Guy? I feel like
going back to the core, really honing in
that antenna for the greatest talent in
the world, the greatest ideas in the
world. This is an incredible time where
people can scale up a company
in in the quickest ways. And I'm excited
about the potential of what's to come.
I've already identified three things I
want to do today. So, I can only imagine
what's to come. But it's just really
just I don't I'm okay doing a version of
what I've been doing, which is identify
great talent and help them help them in
every which way that I can and pick the
teams that you want to back.
>> So, I I I'm I'm feeling pretty good
about that. They're just continuing on
this best-in-class talent idea. The hard
part is for a lot of people is the
access. So we're very lucky we have
access and we also do the job. We we
have more than enough proof of
people that come through when you work
with them.
>> And we're a different kind of investor
on the cap table.
>> We're not in the valley. We're here in
Hollywood. And we bring a different
dynamic, a different, you know,
obviously narrative is something that I
that I'm very focused on. Marketing is
something I've been doing since I was a
teen. And so, you know, marketing,
strategy, media, partnerships,
narrative, storytelling, hey, if you
want someone like that on your cap
table, I might be interesting to you and
hopefully I can be helpful. And that's
what I need to find that dynamic of a
company that I'm in love with. And
hopefully the founder believes that
having me would be a great advantage to
them.
>> Mhm. A lot of founders listen to this
podcast. Is there any uh are there any
particular things that
have your interest right now or types of
companies, types of founders? Anything
that you'd like to sort of make clear to
people who are listening or otherwise?
Also, where can people learn
[clears throat] more about what you're
up to? like is is there anywhere that
you would point them in particular?
>> I'm a generalist.
>> Mhm.
>> I don't I don't care. That particular AI
fund was very specific and we may have
thematic funds from time to time. If an
idea comes and you go, you know what,
I've got an idea. It's going to be built
around this one idea. But usually I'm a
generalist. I really like
>> I just like talented people. And in
regards to sharing, you know, where can
they find out what I'm up to?
>> I'm not really This is it.
>> Yeah, this is it. You know, as you know,
this is my first podcast.
>> Yeah.
>> And depending how this goes, could be my
last. And if it goes well, maybe one
more. But I I'm I'm not out there.
>> Everything is is is has been fine
without doing that. Yeah. You know,
people either find us word of mouth
through friends or I find them. It's
okay. It all works out. I'm not out
there, you know, yelling, "Hey, find me
1800 whatever." Or it's like it'll it'll
work itself out. the right people will
find each other.
>> Well, Guy, I mean, we've covered a lot
of ground. Is there anything else that
you would like to say before we start
landing the plane?
>> I'd say that
AI and music content. It's on one level
exciting that so many people are
experimenting,
writing songs for the first time,
>> writing beats, creating sounds for the
first time. That's pretty exciting. At
the same time, the idea that there's
companies out there
valued at billions of dollars
that are built on the top of
other people's music
where not one artist has ever gotten
paid a dollar is not okay.
>> Yeah. So, I don't want to bundle it all
up where people get it all becomes one
thing. It's not all one thing. Mikey, he
runs. He's a great guy.
>> I mean, great guy, like I really like
him as a person, but every time I read
about the company and it's now at a $5
billion valuation and next thing you
know, it's at a $10 billion valuation
and it's all built off of the world's
music.
But yet, not one music artist has gotten
a dollar.
>> So, that's not okay. That has to be
fixed. I'm hoping Mikey does the right
thing and fixes that. Comes up with a
system
>> that allows artists if they want to opt
in. Either let them opt out, do not use
my music to build your business. Okay,
I'm opting out. But if I opt in, find a
way to pay us. Mhm.
>> And I'm really concerned for that
because the other part which is
right now currently
every two weeks
more music is made on AI than all of the
music that's on Spotify today.
That's every two weeks.
And all of that is going somewhere and
people are inspired and they're creating
songs. Awesome. But don't build a
business
using our music without getting those
rights. And that's something I'm that
I'm been trying to work on for a long
time. I've met with Mikey many times.
I've met with lots of people many times.
I I hope that this gets solved. You
know, when Napster first started, I met
with Sean and Sean when they started
because it was so exciting to see people
were all, you know, downloading music,
but it was illegal. So, you were hoping
they'd crack the code on, okay, how do
you turn this into how artists get paid
and before they I don't know if they
were going to or not going to, but
before that could even happen, it got
shut down. So, and out of nowhere,
Daniel Ek in Stockholm
built Spotify and figured out that
people would pay for music if you give
it to them in this way where they had
all the music in the world without
having to try to piece it together or
try to illegally download songs that
were not even clean or clear and they it
could be corrupt.
to get it clean, to hold on to it,
they'll pay for it. And he was right.
They have paid for it. Now, are all the
payment plans there picture perfect? No.
But it is the core of where money is
coming in today to music artists is
through streaming. And I'm hoping that
people figure out how if you're going to
be using people's music, how you pay for
it.
>> Yeah.
>> Fair use is not fair.
>> Yeah. I'm curious to see where it goes
because if you say create a song that
sounds like Metallica, it'll say we
cannot serve up any copyrighted music.
If you say, "Serve me up some music that
sounds like Moralica." And you just
misspell it, then lo and behold, it
looks like it was trained.
>> Yeah, that's the problem.
>> This corpus, there's a lot of
workarounds and they'll, you know, you
they'll look you in the eye and tell
you, "No, no, you can't. You cannot type
in Madonna."
>> But you can sort of describe Madonna.
The problem is is when in in Discovery
we're going to find out a lot.
>> Sure.
>> And Discovery is going to say all of
this music is in there and they know
that.
>> Yeah.
>> And that's not okay. It's just like
literally not okay. I don't understand
it. And by the way, what's wrong with
paying artists?
>> Yeah.
>> Why not figure out a way to do it? Sit
down with a team, figure out how to pay
music artists if you're going to train
on their music.
>> Where do you think it goes? Because I
could see one future. for instance, even
if
legally they aren't required or for
whatever reason that's not compatible
with the vision they've pitched to
investors and and I'm not singling out.
I mean, there are lots of lots of
different options here.
>> They're the main ones.
>> They're the big they're the 800 pound,
>> but I could see a point at which
possibly
>> Claude Chat GPT become the interfaces to
everything, right? It's almost like the
app store but somewhat like WeChat in
China. Like if you want to do anything,
you want to book a restaurant, you want
to make a song,
>> okay,
>> there are few interfaces to everything.
At which point then
>> those companies, right? OpenAI,
Anthropic
>> can gatekeep in some way and maybe they
end up being the entities that
incentivize these other companies like
the Sunnas of the world to to reimburse
artists. I guess I'm just wondering if
you have any thoughts on this
>> because if if Claude or Chat is the
distribution,
>> they probably won't carry it because
it's it's got so many lawsuits involved
>> and it's just not worth
>> taking on that responsibility.
>> And
>> again, the guy who runs I find to be a
really good guy and I'm hoping that he
does the right thing, but it's really
their responsibility. They're they're
sitting at the the top of this
opportunity. Take off the artists that
don't want to be on there
>> and find a way to pay the ones that are
okay being on there. It's that simple.
It's not complicated. I think go in a
room, lock yourself in a room for 3 days
and come out and figure out how to pay
people and take people off
>> that don't want to be on there. Madonna
does not want her music trained on.
>> Don't care what you want to pay her.
>> Yeah.
>> She's very clear. I do not want my music
to be trained on. I want my music to be
its own thing.
>> Mhm.
>> So, take her off.
>> Yeah.
>> It's okay. you you'll still do fine.
Take her off. You don't have to have her
music.
>> So, we'll see where this goes. But this
is I've been the last few years I've
really tried to figure this out. And
even, you know, Sam at one point, he's
really wanted to figure this out, too.
Like Sam was a lot of people give my
hard time on this stuff, but he really
did dedicate time to trying to figure
out if there was a music thing to do,
how to do it in a way that supported
artists.
>> Yeah. Yeah, I mean there may be someone
who comes along also if it's not Sununo.
Someone who comes from behind like a
next generation Spotify
>> and figures out how to do it.
>> Spotify can do it.
>> Yes, more Spotify can do it.
>> Yeah.
>> You mentioned there were three things
that you'd like to do today. I'm not
going to ask you to name those things,
>> but how did you find those things or how
did those things find you?
>> Right. one of them. Well, I'm working on
this platform that I'm going to announce
in a few months that you're part of is
how we connected you and I. And I'm able
to ask investors what companies
>> that they're looking at and and so
>> two of those came from that
>> conversation. Good good information.
>> Yeah. They're like, "What are you
looking at? What are you liking?" And
then they tell me and then I go, "Oh,
let me look into it." And some things I
just read about. I read every single
day. I I'm checking things out every
single day and I'm making sure I'm not
missing an idea or I'm hearing about
things.
>> Well, I'm on X a lot. I see a lot of the
stuff, a lot of information on on X
that's flying by. So, it's sort of my my
start of information.
>> You mentioned missing
Blackberry and Vitamin Water. Do you
have And this could go way back in the
catalog. Could go back to being 10 years
old. There's there's no limitation here.
Any favorite failures or parent
failures, meaning failures that taught
you a lot or that set you up somehow for
later success?
>> There's
it's endless endless. You know, uh, one
of the things that Ashton is really was
really good about
not looking back like that. He sort of
just keeps it moving forward and I'm
always like, I can't believe we're not
in that and I had it and my I had it and
we had it and we and he's like, come on,
just move. Let's go. Let's go. He's
like, he always gives me like, oh gosh,
he's going to complain about not being
in a
but you know what motivates him is he
just keeps it moving forward and it's
awesome and what motivates me is like
I'm not going to let that happen again.
>> Yeah. I mean looking back right it seems
like
>> in [snorts] some ways like missing hole
missing fill in the blank was almost a
prerequisite source of fuel.
>> Yeah.
>> For the things.
>> Yeah. It's scary though. It drove you
towards the
>> It's scary though when you miss it. I,
you know, when Ash and I invested in
Bitcoin on our own, you know, when it
was at $22 [laughter]
>> and then it when it hit $250, I thought
I just made 10 times my money.
>> Yeah. Yeah.
>> I'm a genius. So, I sold then and
clearly not a genius. So, that hurts.
And I remember um Anthony, gentleman on
that wall.
>> Mhm.
>> Elon invited Anthony from the Chili
Peppers to see SpaceX. Early days.
>> Yeah.
>> Very early days.
>> And I went with Anthony. I tagged along.
It's the first time I met Elon. When we
went to SpaceX,
>> I was so wowed by the concept that I
didn't even pay attention to the
business model or what could be the
business model. I was just like, "Wow,
this guy's building rockets." that
moment in time Anthony and I had the
wherewithal to go what business model I
didn't even ask those words. I was just,
you know, sometimes I go to shows like
I've seen shows where people are so
wowed that they're just like they're
like this from a show and they they
didn't even take in all the songs or
just like oh my god what I mean if you
ever look back at the Sex Pistols shows
people are just like what and they're
like was I actually there? I think I was
more blown away by the concept of what
Elon was building that I did not
understand
that there was a business model and I
really wish I just would have asked one
more question like
>> hey how do you monetize this? How does
this work? Can we invest?
>> So I have hundreds of those stories but
those are two that stand out today.
>> I want to talk about the longevity for a
second. you mentioned, and fact check me
if I'm getting this wrong, but like the
three was it back-toback tours with
Madonna.
>> I mean, that sounds impossible just from
a the demands of the the physicality of
that and she's kind of legendary, of
course, for her
>> training and [snorts] endurance and
everything else, but for you personally,
what were the keys to end enduring that
and being able to function at a high
level for that?
>> I think it's different as the years go
by. There was a point around 10 years
ago, 11, 12 years ago where I was, it
was a lot for me. I was also changing
and growing and having kids and I was
just sort of losing myself cuz you're
really in a you're going to a different
city every other day.
>> And the amount of things you're missing
back home, you sort of you sort of, you
know, forget you have a family. You
forget that you can go do other things.
or you forget to call back Stripe or you
forget to right all the things you just
you just forget everything and then one
day your dad calls you and goes oh hey
I'm at your house with your kids and oh
I have kids I have a house so if you
look at the first three tours those
three tours that I did those are 240
shows 80 average I [snorts] missed three
of those shows
three out of the 240 one I was sick and
then I missed two because it was my 40th
birthday and I really didn't feel like
being in Seattle that
I wanted to be home with my friends. So,
my 40th birthday spent here in this
house. So, I missed three shows out of
240. But we're talking about a different
city, a different hotel, a different and
you in order to like move along, you
sort of have to block everything else
out. You have to forget and it's a very
selfish, very
for me is otherwise if you think about
back home or your family or other
things, it hurts. So, I just go, "Okay,
I'm off and I'll see you. I bet I bet
it's what actors do when they go away
and make a movie for 3 months and then
they come back.
>> They probably just compartmentalize a
little bit, but you know, in the last
few years, I've I've stopped doing as
much. I still go, but not as much. I've
I've went it down. There's a moment
there where I managed the Red Hot Shield
Peppers, you two and Madonna. They're
all going on tour. It was a lot to
>> process. How do you even make decisions
about where to be in a case like that?
You can't be in three places at once.
It's hard, but it sort of tells its own
story. You, you know, you're not going
to miss New York. You're not going to
miss London. You're not going to miss
some of the major moments. And then you
look at the calendar and go, "Oh, we
have this time off. Let's go to New
Zealand with Madonna or let's go to so-
and so with you two or let's go to so
and so with the peppers." And you find
your way around it. You just you just
make it work.
>> So, if you look at let's just say the
last 10 years.
>> Yeah.
And
presumably a lot of your focus is on the
investing. How do you mind the different
responsibilities
if that makes sense?
>> I think when I when I think of
responsibilities I always think of
management. That's a really big
responsibility and I don't take it
lightly.
>> Mhm.
>> This is just there's no way around it.
That's that's something's going on there
that's a focus. It is cyclical.
>> Mhm.
>> So like the Peppers are not touring this
year. They don't have an album this
year. They aren't touring next year.
They don't have an album next year. So,
you know, there's there's a lot of time
in between and they're going to where
they're coming up with the creative.
They're going to make an album. They're
going to do all the things. They're
going to write songs, right? So, that
takes time. So, you get these windows of
opportunity where you go all in and you
get windows opportunity where you have a
moment to breathe just like they do.
They all need it too. Madonna after the
cycle will probably need a minute to
just sort of catch her breath and figure
out what she does next. So, these are
cyclical things.
What I don't do is I'm not out there
trying to sign 10 more bands or 10 more
artists. So that's where the balance
comes in and which is continually be
creative through other ways.
>> And so when the cycle starts, my
creativity has never stopped.
>> Mhm.
>> So that I still have those things. I'm
I'm not starting from scratch. I'm I'm
always looking and meeting with people
and understanding what's going on in
technology. And so when when Madonna
comes back into cycle, I can bring some
of those ideas or some of those new
relationships I met while she was off.
>> And so I just I found a way to to to
make it work. Maybe I'm sure misquoting,
but roughly paraphrasing
much earlier in the conversation. And I
feel like you said part of Madonna's
ability to reinvent was not resting on
her laurels obviously, but not patting
herself on the back for what she's done
and sort of marching forward.
>> And I'm wondering how you've thought
about for yourself
the drive and velocity of
forward-looking achievement versus
sort of appreciating what has been done
or savoring the time that you have. I
mean, I imagine you get a lot of that
with
congregating friends and so on, but I'm
wondering if you have any thoughts.
>> You know, my friends and I don't spend a
lot of time talking about what I do.
>> A little bit. I share with them so
they're in the know, but we don't spend
a lot of time on it.
>> We don't work together on these deals.
>> My wife and I don't talk about work
much. Like, I think I just keep it
moving, too. And again, I when you look
back 36 years, it's probably Madonna
that is responsible for how I also think
of just keep it moving forward. Keep it
moving forward. And and you know, maybe
one day sometimes when I'm telling my
kids a story about the past or someone
asks me a question and I tell them about
the past, I go, "Oh my god, I forgot I
even did all those things." Or I see
something pop up and I go, "Oh, I was I
I you know, I was there for that." And
but I really don't think about it that
much. Things pop up every now and then.
When I wake up tomorrow, I'm like, I
haven't done anything today. I better
figure it out. [snorts] I need to step
my game up. That's how I feel. I don't
feel
accomplished
at all. I feel like I still have so much
to prove and so much to do. Well, at the
same time, I do know if I if I really
took a minute, I would go, "Oh, wow.
Okay. Oh, that's Oh, I didn't I should
probably
>> take a moment and take that in." But I
really don't.
>> Is that okay? Is that a problem? Is it
fine?
>> I just keep it moving. I I don't know.
You know, at some point, you know, there
I I can visualize being on the beach and
and, you know, high-fiving with my
friends and having fun.
>> But I I again, I don't they don't do it
either. A lot of my friends were we
don't talk about it like that either. I
mean,
>> I think we just sort of
>> how cool that we're survive this period
of time. How cool is it that we're even
able to do what we love? Mhm.
>> Waking up and being able to do what you
love. There's a Josh Kushner quote that
that I love that he says about success.
He says, Tim, success is being excited
to go to work and also being excited to
go home.
>> Yeah.
>> And I got that. I'm excited to go to
work and I'm excited to go home. That's
pretty cool.
>> Yeah.
>> And you know, not a lot of people get to
do that and I don't take that for
granted. And I work hard because of that
cuz I go this is not a given. you know,
the potential and the opportunities. And
I'm trying to bring in other friends and
other people into my world to say, plug
into this. Let's help you figure this
out. I'm not just doing it for myself.
Like, you should use what I have. You
should meet some of these people. You
should come to this event. You should go
to this. So, I like sharing that.
So after 20 years, you and Ashton are
going to be doing different things, it
sounds like, and I was wondering if you
could just share a bit of the background
and what that looks like.
>> We've had an incredible run
>> and
this AI fund is I don't know what to
compare it to other than like winning
the Super Bowl
>> for what we do,
>> right?
>> And you know, between the investments in
Open Eye, anthropic and we also did SPVS
the whole way up a lot. So,
we're really fortunate and blessed. And
after 20 years, Ash and I asked the
question of now that we've done that and
we've hit it out of the park, what do we
want to do for the next 10 years? What
makes us happy? What what are we going
to get enjoyment out of doing? And it's
a really strong question and we all gave
it some thought. This is a few months
ago. We we we looked at each other's
visions of what he wanted to do that
make him happy and what he wanted to
build and what I wanted to do and and
then we have a third partner her name's
Effie and what she wanted to do and it
turned out that we had different visions
and when you look at his vision which he
will share at some point so I'm not
going to share any of it pretty awesome
vision
>> it's an incredible vision and the guy is
mind-blowingly smart and talented
And
I support that vision for him.
>> Mhm.
>> It isn't my vision.
>> And I will support it financially and I
will support it with energy. I want him
to win. And then I have mine which is
the things that we're talking about
today and the things that I want to
build. And I have a version of the
things I want to do that I haven't
shared with everyone in full. But it's a
new chapter and I've had many new
chapters my whole life. I went with the
record label for a certain time and then
I moved on. I went to music management.
I went to crypto and I went to film. I
mean, I have so many different chapters
in my life that this is a beautiful
chapter that is we're in a celebratory
mode.
>> Mhm.
>> So, we're sort of hoping to be on the
beach high-fiving each other at some
point on the work that we've done and
have worked hard to get here and taken a
lot of risks and a lot of chances and
put in our own money. And so this
decision was made out of joy and and to
support each other's visions. There are
going to be times where we'll cross over
and we'll work on things together
because we do have some crossover of
things that are part of things we both
like.
>> But he's very specific on he wants to do
it. I'm very specific I want to do.
Effie and I are going to continue on
with sound and what we've built the last
10 years with sound. So we'll continue
to build that. And then we've got some
surprises of how we want to build that
out too. It's all really good. It's all
very supportive. It's just another
chapter.
>> Guy, this has been a wide-ranging
conversation. What a life. What a
journey. And it's not over. Obviously,
you got lots of battery left for what's
ahead.
Thank you for the time.
>> Thank you.
>> Thanks for inviting me here.
>> My first podcast.
>> I know. I know. Mine, too. [laughter]
Your first podcast with me. Yes,
>> exactly. And people can find you on
Instagram XGO
Siri, no apostrophe. Guy O S E A R Y.
And we will link to everything in the
show notes as per usual at
tim.blog/mpodcast.
And until next time everybody, thanks
for tuning in. Be just a bit kinder than
is necessary to others, but also to
yourself. Compassion is not complete if
it doesn't include you. Thank you, Jack
Cornfield. And as always, thanks for
tuning in. Thanks, Guy.
>> Thank you.
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