Chris Evert Talks Business

The tennis superstar discusses her journey as an entrepreneur.
Freelance Writer and editor, Self-employed
September 29, 2016

If tennis had a royal family, Chris Evert would be the matriarch. Now in her 60s, Evert dominated the court in the 1970s and 1980s, ultimately becoming the No. 1 player in the world during her career, winning 18 grand slams and 154 singles titles.

 She retired in 1989 and didn't slow down.

Since then, Evert has been known more as a businesswoman and philanthropist. She runs the annual Chris Evert Raymond James Pro-Celebrity Tennis Classic, a tournament in Boca Raton, Florida, and has raised millions for the local community. In addition, she and her brother John operate the Evert Tennis Academy where pro-hopefuls come to train; she is part-owner and columnist at Tennis magazine; is the muse and brains behind Chrissie by Tail, a women's athletic wear collection; and commentates on tennis matches for ESPN.

Even so, she quips and laughs, “My life is pretty quiet and boring." Most of us, of course, would disagree. I caught up with her to find out more about her day-to-day and how she handles being an entrepreneur.

Did you always want to be an entrepreneur?

I don't think I ever thought about it that way. Nearing the end of my tennis career, I thought about the fact that I still needed to earn money and find a passion. I had kids right after I retired and for about 10 years I was a stay-at-home mom. I kept relationships going with my endorsement deals, but that was it. About 20 years ago, my brother John approached me about doing a tennis academy. He told me he'd manage it, that I could come in when I wanted, but that I would have to put up the money. [laughs]

I loved the idea and we decided to join forces. Evert Tennis Academy is very successful and has gotten a great response.

What about the Chris Evert tennis tournament? That was started early on, correct?

Yes, that is true. The year I retired, I decided to have a celebrity tennis event because I had the network of people in the tennis world and wanted to do something to prevent drug abuse and child neglect in Florida. I started the tournament and it has been incredibly successful. We've raised more than $22 million so far.

How did your commentating gig come about?

About five years after I retired, I did some commentating for NBC and didn't think I was any good, so I shied away from that line of work for a while. But then, about five years ago, ESPN approached me and asked me to do Wimbledon. I decided to give it a try and ended up loving it so much that I signed a long-term contract with them. I'm on the road maybe eight to 12 weeks with them—it is during those weeks I have to be “Chrissie Evert." Otherwise, I'm just a normal person, at home in Boca.

Could you tell me about this "normal" life of yours? It sounds so glamorous to me. What does your average day look like?

Honestly, I think my life right now is what I've always wanted it to be. Even though it may seem like I'm super busy, I'm really not. I don't want things to be intense because between the ages of 6 and 32, I was really working. I was training and serious and grinding it out every day. After I retired and had kids, I just wanted to relax. Now I'm focused on taking time for me.

So, a normal day? Well, I usually get up around 8 a.m., go to the tennis academy from 9 a.m. to 12 p.m. and train with the kids, I'll go see my mom two or three times a week. In the afternoons I will work on Chrissie by Tail and sometimes I'll take in a yoga class.

That sounds fabulous.

It is. I'm lucky. I don't think a lot of people realize that I really didn't have a normal childhood. I was playing tournaments at 10 years old and had to give up a lot. It was worth it and I'm glad I did it, but I'm also happy that it has paid off in the second half of my life.

Tell me about Chrissie by Tail. How did that come about?

Back when I was playing in the ’70s, I was a trendsetter. When everyone else was wearing skirts and blouses, I was wearing sundresses and halter dresses with cutouts on the sides. I've always liked fashion. In the ’70s, tennis was a man's sport and I was the girl on the court that wore pretty dresses with ribbons in my hair.

Later, after I retired, I would bring my boys to school and literally have women pop their heads in my car asking me to design a line of tennis clothes for them. They were sick of wearing the tight clothes that 20-somethings wear. I didn't have time back then, but my time has opened up in the last five years, so I thought I'd give it a try.

How do you come up with the designs?

When I first started working with Tail Activewear, they actually came to my house and went into my closet. They took back a ton of my clothes because they loved the designs and colors. We worked together and came up with a line. Now we collaborate four times a year for the seasons. It's been a lot of fun.

Do you have any other entrepreneurial aspirations?

I think I'm OK right now. I've always been very competitive on the court, but as for life in general, I'm not super ambitious. I don't feel like I need to make $100 million or follow anyone's rules. Right now my passion is mentoring and teaching kids, designing clothes and commentating—writing and talking about the sport I love. I'm really very happy in the place where I am right now.

What kind of advice can you offer people who want to launch a business but aren't sure how to start?

Get good advice from other business people and don't go in over your head. Be conservative from the beginning. Find a passion you love and believe in what you are doing. But, really, it is most important to surround yourself with the right people and keep at it. Soon, you will see things start to happen.

Photo: Fred and Susan Mullane