On the Line (18 page)

Coming up on the tour, I always wanted what Venus had. I repeat myself, I know, but it’s one of the great themes of my life
and career: Venus cut the path I meant to follow, so when she signed a big sponsorship deal with Reebok I came away thinking
I wanted a sponsor of my own. I was still a long way from having any kind of real business sense, so my desire wasn’t about
money or financial security or any of those pragmatic things. No, it was about matching V and getting my own. Only trouble
with this was that I didn’t have the profile Venus had when I first joined the tour. This was back when V was the Next Big
Thing and I was still just the Next Big Thing’s Kid Sister, so it’s not like all these sportswear companies were lining up
to give me a deal. Plus, it was a time in the sport when there weren’t a whole lot of sponsorship deals to be had beyond the
very top-ranked players. About the best you could hope for as a middle-of-the-pack pro or an up-and-coming rookie was to get
your gear for free, from companies like Wilson or Nike or Head or Reebok. You’d wear their stuff, they’d slap their logo on
the sleeve, and it was a good deal all around.

Somehow, Daddy was able to negotiate this tremendous Reebok deal for V, but after that it seemed nobody was really interested
in me. I guess there wasn’t enough hype to lift two sisters to such heights, so I was grounded. I
got
that, but at the same time I resented it, and yet the harsh reality of big-time tennis was that there wasn’t much of a market
for a teenage player who hadn’t really done much on the tour just yet. I understand that now, but I was really upset about
it back then. There was a brief period in there when Nike expressed an interest, but it never went anywhere. I wore their
clothes for a while, but then just after I had a great, deep run at a tournament in Chicago in 1997, that interest fell away.
I’d just played my sixth-ever tournament and reached all the way to the semifinals. Along the way, I’d beaten Mary Pierce,
the number seven player in the world, and Monica Seles, the number four player, before losing to the number five player, Lindsay
Davenport, in the semis. For the first time, it felt to me like I was on my way, bound for some tennis glory of my own, but
then I was left hanging—with only a couple complimentary Nike outfits to show for it.

I was only sixteen years old, and still I was left thinking,
What does a girl have to do to get a sponsorship deal around here?

It was around this time that Daddy hooked up with a man named Arnon Milchon—a real mover-and-shaker out in Los Angeles. Over
the years, Arnon has become a great friend and mentor. When I met him, he was a successful Hollywood producer and a real risk
taker. He also owned a stake in Puma, which was how we got together. He was a huge tennis fan and one of the few people outside
my family who saw my potential—at least in endorsement terms. He thought I had a big future in tennis, and that while I was
at it I could help lift the Puma brand, so it looked like there’d be a good fit all around.

Arnon came along at just the right time. In my head, I was back to thinking no one believed in me, just like that newspaper
reporter, or anyone else in tennis. This wasn’t about tennis, not really, but at the same time it was. No one could see past
the fact that I was Venus’s sister. No one thought I’d be a force in my own right, even after Chicago. That is, no one until
Arnon. He’s been an unbelievable person in my life from the day we met. One of my dreams, outside of tennis, was to be an
actress, so he was helpful to me in that arena as well. He set me up on a bunch of screen tests and auditions, and introduced
me to casting people and acting coaches. Whenever people ask me what I would have done if I couldn’t play tennis, I tell them
I would have been an actress. Okay, so I probably would have been a struggling actress, but I would have given it a shot—and
Arnon helped me reach for that as well. I used to tease him that he was like my adopted stepfather.

Arnon had faith in me, and he convinced his team at Puma to have faith as well. Daddy and I flew out to Los Angeles to meet
with them. Arnon’s daughter Alexandra was involved in the business, so she was there, too. It was the longest meeting. We
got started around lunchtime and we were still going at midnight. It was one of those negotiations where everyone was getting
along, and we were all determined to get a deal done, no matter how long it took. At some point, I put my head down on this
big conference table where we were sitting and fell asleep. The holdup seemed to be between Arnon and his partner, Jochen
Zeitz. Arnon was a bit more of a risk taker than Jochen, and at first it was kind of funny to watch them go back and forth
about whether they should do a deal, and at what level, but after a while it wasn’t so funny. I didn’t care so much about
the deal terms. All I cared about, really, was the deal itself. I wanted a sponsor. I wanted someone to believe in me. That
was my bottom line. I wanted to be able to shake hands with these people, deposit the good faith they had in me, and then
step out on a court and show the world that there was this great company behind me, Puma. It would be like a seal of approval,
at a time in my life when I desperately needed a seal of approval.

Alexandra Milchon was so nice, so attentive. When I fell asleep, she came over, gently shook me awake, and asked me if I’d
be more comfortable lying down. Daddy told her I was fine just where I was. He wanted me to be at the table, even if I couldn’t
keep my eyes open. I was just a kid, but he thought it was important that I be in on this. And it was—as long as I could stay
awake!

The key message here was that it wasn’t just Puma taking a chance on an upstart like me. It was me taking a chance on Puma.
It cut both ways. Daddy helped me recognize that. Usually, in a successful partnership, both sides have as much at stake.
That’s how it shook out here. Puma hadn’t really sponsored anyone in tennis before. They were big in soccer and other sports
like track and field, but not tennis. In fact, they didn’t even have a line of tennis shoes, like Reebok or Nike, so it was
a big risk for me, too, throwing in with them. The idea was they were going to create a whole new tennis line with me in mind,
which was kind of exciting, but at the same time it was kind of uncertain, so each side was taking a leap. At sixteen, I didn’t
have the most sophisticated business sense, but even I could see that with great risk comes great reward, and happily that’s
just how it turned out.

When we finally shook hands on a deal, all I wanted was a bed. I was still operating on Florida time, so I was wiped. But
at the same time, underneath this allover exhaustion, I had this tremendous feeling of validation. Again, I didn’t care about
the money. I cared about the handshake. I cared about the vote of confidence, that these Puma people believed in me enough
to cut a deal and get behind me in this big-time way. That was everything.

Well, not quite everything. There was also the matter of the clothes! Fast-forward another week or so. I was home in Florida,
back to my routine of school and practice and school and practice, when this huge box arrived from Puma. I couldn’t wait to
see what was inside. They still didn’t have a tennis line, but they were a European company, and they had all this great gear.
Extremely cool stuff. Out-there stuff. Exciting stuff. Sportswear, mostly. I tried it all on, and it was such a thrilling
moment, because I knew at the other end someone or some group of someones had collected all this stuff hoping I would like
it. They put this box together with me in mind. Me! Forget all the little tastes of success I was having on the court. Forget
that thrilling run to the semis in Chicago, past all those top-ranked players. It was this moment, going through this giant
box of Puma gear that all fit perfectly, where I felt I’d finally arrived as a player.

Before I hit another tennis ball, I knew I’d grown my game.

For the first couple tournaments after I’d signed my deal, Puma still didn’t have a pure tennis line, so they threw together
something appropriate for me to wear. One of the first things I got to wear for them was this adorable neon blue shirt, with
the Puma cat in the middle. It was my very favorite shirt, then we highlighted it with a cute white skirt—and I felt like
such a princess when I took to the court in my thrown-together outfit—a powerful, purposeful princess. I had my own hopes
and dreams on my racquet, along with the hopes and dreams of this great company.

From the very beginning, Puma wanted me to work with them on their designs. By that point, I guess I’d developed a kind of
trademark look on the court, so they sought my input. That made me so happy! We used to sit together with a design pad and
work out these different ideas, like the one we came up with for the famous catsuit I wore at the 2002 U.S. Open. Man, that
outfit turned a lot of heads and caused a lot of controversy, but what most people didn’t realize was it was so comfortable!
Of course, that catsuit was so hot I would have worn it even if it was the most uncomfortable thing in the world, but it was
designed with performance in mind.

They had me wearing all kinds of outrageous outfits. It got to where people started to wonder what I’d wear at the start of
each tournament. I became known for my outfits as much as for my aggressive, relentless style of play. Spandex. Polyester.
Lycra. Denim—later on, when I signed with Nike. Best I could tell, no one had ever worn denim on the tour, other than Andre
Agassi on the men’s side, so that was our inspiration, to try something a little different, and here it was a sport denim
so there was some give to it. Whatever the designers could put together in an exciting, cutting-edge sort of way, I’d try
it on or maybe give it my own spin or flourish. And then we’d accessorize, with big hoop earrings, or a bold new hairstyle.

Sometimes, if I was uncertain about a particular look or outfit, I’d run it by V, who also had a flair for what she wore on
the court. Her advice was always the same. “Looks like fun, Serena,” she’d say. “If you don’t wear it, I will.”

And that was usually that.

T
he second development on the fashion front came with a gentle push from Venus. Actually, it was more like a shove. I was sitting
at home at the house we now shared in Florida, twiddling my thumbs, not doing much of anything beyond tennis. I’d graduated
a year early from high school and never really saw the need to continue with my education. I thought I knew what I needed
to know—and what I didn’t know, I could learn soon enough.

But Venus had taken a different approach. After high school, she signed up for college. It wasn’t a full-time deal because
of the demands of the tour, but once our season began to wind down in late fall she’d sign up for a couple courses at the
Art Institute and use her time productively until the season started again in January. The way she worked it out, it was just
enough time to complete the winter semester.

V was on me all the time to join her at school, but I couldn’t be bothered. She insisted it would be fun, but I was too busy
doing nothing. I was back into
Golden Girls
mode, the way I’d been during that stretch when I was home-schooled in seventh and eighth grade. I was watching television,
hanging out, playing tennis, watching television, hanging out, playing tennis… I’d sit down on the couch in front of the set,
and I couldn’t get up if I tried. V would burst in after another one of her busy days and say, “You’re wasting your life,
Serena.”

Oh my goodness, she was on me. And she had a point. I was such a slug! One day, she got so fed up with me she just signed
me up for classes, without even discussing it. She came home that afternoon and said, “That’s it. I’m tired of watching you
waste your time like this. You’re going to college.”

So that’s what I did, all on the back of V’s gentle shove, and it was a good thing, too, because I really was just wasting
away in front of the television. Leave it to my big sister to know what was best for me. School was a blast. It was so much
work, but at the same time it was so much fun. Most nights, we were there until eight or nine o’clock, working on some project
or other. I studied design and fashion, so most of my courses had me sewing and drawing, learning the construction of a garment,
considering which fabrics might work on which designs. I also took a sampling of liberal arts courses—math, science, and history—but
most of my efforts were in the fashion curriculum, and I developed a real appreciation for design. In one class, we had to
learn about more than one hundred different fabrics, so I came away with a great understanding of the manufacturing end of
the business, and at the other end I really knew my stuff when I sat down with those Puma designers to develop a new line.

The school year was broken into quarters, and because of our wall-to-wall tennis schedules we could only attend during the
fall-winter quarter. Normally, it’s a two-and-a-half-year haul for an associate’s degree, so on our slow-track schedule it
would have taken just short of forever for us to complete the degree, but we stuck with it. In the end, Venus stuck with it
a whole lot longer than me. But it was a great experience and a fantastic introduction into the fashion industry. Without
those courses as a foundation, I don’t think I ever would have been confident enough to start designing my own clothes, my
own jewelry, or my own handbag collection—all of which came soon enough.

Somewhere along the way, I developed this obsession with Vera Wang. I started to think if things didn’t work out for me in
tennis, I could always design wedding dresses for a living. I have piles and piles of sketch pads at home, with pages and
pages of designs. That’s how I passed the time on those long plane rides back and forth to tournaments, or those long, lazy
afternoons stuck in my hotel rooms, with nothing to do between matches but hit and work out and watch what I ate. I sketched
and sketched, and dreamed of the day when I could finally launch my own line.