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, Vita Coco.

Well well done.

>> Thank you.

>> 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. It

was in my 20s. And I

was reading in a magazine about Sky

Dayton.

And it said he started EarthLink, and he

was worth a hundred million dollars, and

he was with I'm like, wait, what? You

can [laughter] 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 Four Seasons Hotel,

and

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

impressed by me, have you ever heard of

Bill Gross?"

>> Uh Idealab.

>> 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

Can Can you get out of the way? I want

to

>> time has been great.

>> [laughter]

>> 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 Idealab in Pasadena.

And I just loved it. I loved 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, and

>> 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.

>> So, well, wait a second.

>> But

>> But but my listeners are going to kill

me if I don't follow up. 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 they don't know it to this day.

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.

>> Mhm.

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

"Bill, I want to put

money in into Idealab." 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 a 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

Now, what By the way, it wasn't a year

before the crash.

>> Yeah.

>> I think it was like an hour before the

crash.

Okay? [laughter]

So, I put every dollar I have plus

dollars I didn't have.

>> Yeah.

>> I picked out three investments at that

time.

Idealab, 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 them when I needed to and talk

to them. And And so, I made a deal with

Jim Balsillie to be an advisor 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 Rogan brought

me Vitamin Water.

>> Yeah.

>> So, those were all going to be my first

three investments.

What happened was

that the Ideal app 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

>> dream you're trying to forget.

>> burst so fast on all of that that I

didn't have the heart

to invest into I never signed my deal

with Jim Balsillie and Research In

Motion and I never and I never did my

deal with Vitamin Water, which both

ended up So, it's almost like the the

hole in 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.

>> Mhm.

>> I didn't diversify. I put

>> everything

>> of my money in one thing.

>> Mhm.

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

For the next 2 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 I'd have a

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?

>> [laughter]

>> I should have 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, really.

>> Mhm.

>> I was off the the timing was wrong on

the Ideal app part. The other two

worked. Had I diversified, I would have

done 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 it's not fair to to Bill cuz he

built an incredible company and let's

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. It sometimes they don't work out

these deals.

>> A lot of the time.

>> I think I'd 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 wrong.

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 Goldman.

>> 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 agua de coco.

>> [laughter]

>> 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 dollar business.

It was nothing.

>> Tiny.

>> 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.

>> Mhm.

>> And I like, "Wow, every location went to

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 was a photo of Gisele 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

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 to-do, 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 Kirban.

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. I brought Madonna

into that. I brought Demi Moore. I

brought Matthew McConaughey, Anthony

Kiedis. We brought a bunch of people

into this thing cuz they were all

healthy people who drink 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're back in the game.

>> Yes. It takes time. It takes time. It

takes time. It 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

approach 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 a

like 2 billion and now it's at 5. Like

he's done an incredible job.