Video summary
Guy Oseary recounts his accidental entry into venture investing, which began not through strategic planning but via a magazine article about entrepreneur Sky Dayton during a flight to Milan in the MTV Awards era. Intrigued by Dayton's success with EarthLink and subsequently introduced to Bill Gross of Idealab, an incubator that operated like a record label for startups, Oseary became deeply fascinated by the concept of investing in multiple ideas simultaneously. He initially poured all his savings into this venture based on trust and enthusiasm, only to face devastating losses when the company collapsed shortly before the dot-com crash. This failure left him financially ruined and emotionally devastated for two years, a period during which he obsessively replayed the mistake of lacking diversification while feeling betrayed by the very people who had tried to help him enter the field.
Despite the heartbreak caused by losing his life savings on Idealab, Oseary eventually realized that the timing was merely off rather than the strategy entirely wrong, as two other potential investments he considered—Vitamin Water and a deal with Research In Motion—would have succeeded if pursued at different times. After successfully recouping his losses through three consecutive Madonna tours, he decided to attempt investing one more time by leveraging his unique ability to identify talent and ideas within the entertainment industry. His next opportunity arose when Seth Goldman, who had previously introduced him to Vitamin Water, called regarding coconut water; Oseary recognized an emerging trend after noticing that tour trainers were traveling globally just to find fresh coconuts for Madonna's hydration needs, a pattern he connected with growing health consciousness among celebrities like Demi Moore and Matthew McConaughey.
Seizing this opportunity, Oseary immediately flew out to meet the founder of Vita Coco and decided to go "all in," bringing his vast network of Hollywood stars into the business to accelerate its growth from a tiny niche market into a major industry player. He recalls feeling overwhelmed by the founders' reaction to such immediate support but remained committed to blowing up the concept, transforming what was once a small five-million-dollar sector into a public company with a massive valuation today. This comeback story highlights his resilience and pattern recognition skills, proving that even after losing everything due to poor diversification in one specific deal, he could rebuild wealth by applying similar instincts to new opportunities while learning from past mistakes over time.
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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.