“Dead Presidents III”]♪ ♪– ♪ High-school graduates ♪♪ Straight to the league ♪♪ I ain’t waiting
for my knee to blow ♪♪ Yesterday
I was needin’ this dough ♪♪ Get it?
I was kneadin’ this dough ♪♪ ♪– So, glad to be here with you. What are
the determining factors for you as you look at
businesses to invest in that you start to think through
for investing in things? – Well, for me, investments
are really important in terms of, who are
the other investors? Like, what does their portfolio
look like? What does their past
look like? Have they been successful,
or are they a brand-new company? Is it a good product?
Is it something you believe in? I never do anything if I don’t
really believe in the product. – Is there one that sticks out
in your head that was your favorite or the best investment
that you made? – As a competitor,
I just keep thinking about the ones that I missed on
that I had an opportunity to do. But you know what? You can’t miss what you
don’t have, first of all. – Exactly.
– And what I’ve done now is I’ve developed a team that’s specifically only
for investment, and they just work
strictly on that. They work strictly on meeting
with companies, meeting with different
portfolios, meeting with different
VC firms and then deciding
from there, like, “Is this good for Serena?” Of course,
I’m maybe too hands-on. – [laughs]
– So… I’m super, super involved. So we’ve built a team now
that does strictly that. And my fiancé’s in finance, so kind of had
a cheat sheet, which is a little bit
of unfair advantage. So he always be like,
“Okay, this company– you want to invest
in this. – Look at this.
Take a look at this. – So it’s been like
I’ve been cheating a little bit the past couple years,
but it’s been great. – What part of it
do you love the most? Some people like the process.
– I like building. – You like building.
You like the process. – I do. I feel like if I believe
in something, I really like
to build on it. And I really love believing
in some of these companies, you know, so that, for me,
is my favorite part. – No matter
how many accomplishments, no matter
how much money you get, what is it that keeps you
the best tennis player that you can be, which is the
best tennis player in the world? What is it that keeps you
wanting to kick people’s ass on the tennis court? – I love what I do. I’ve always loved what I do, and I think it goes back
from my first year on tour, where I just never picked up
my checks, ’cause I did it because I wanted
to be the best, I loved what I did, and I never
wanted to do anything else. And also, I hate to lose,
and so, for me, those elements
create who I am. And that’s why I’m Serena,
and that’s just who I am. – Is there, like,
a guilty-pleasure purchase that you just
can’t stop buying? It could be purses.
It could be some kind of food. Is there a thing or things
that you’re like, “Damn, I want to
stop buying that”? – I have the weirdest one.
[chuckles] It’s property. [both laughing] Yeah, that’s really random. So how many homes, properties
do you have, and where? – I don’t know.
A lot. – A lot?
– Yeah. It’s… – And you never sell? Some people do get that thing,
and they just sell. – I know.
They, like, go and sell. I don’t sell a lot,
and when I do, I regret it. Oh, I’m still regretting
that one sell. – There was one you sold? – I did.
I should’ve never sold it. – Where was it at?
– It was on the water. – In L.A. or here?
– In Florida. – Oh.
– I know, see? I know. What was I thinking? – There’s a rule–you should
never sell beachfront, ’cause they’re not making
any more. – Right. – As you think
about your tennis career– Now you’re gonna have a child Like, have you thought about how
that affects your tennis career as far as time commitments? – Yeah, I haven’t thought about
it a lot in my career at all. – Mm-hmm.
– I’ve always been really– [both laughing] – Really one direction
kind of individual. But I feel
like having a child is really opening
new doors, ’cause I feel like I can
understand parents and especially mothers. I feel like I can understand,
you know, even more companies. Juts–I honestly feel
like it opens a whole nother… – It does.
You’re right. – Aspect of business
opportunities. And even, like, looking
from child food– Like, I’m really
a health nut, so I’m like, “I want to make
sure my baby eats really healthy.” And so it’s just, like–
that just– all new other opportunities
for investments… – That you never paid
attention to. – That I would’ve never paid
attention to. So it’s really interesting,
and, you know, I never– But most of all, I just want
to give the baby lost of love.[electronic music]♪ ♪