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Using a U.S. Open underdog to refresh a classic tennis brand

2015 U.S. Open - Day 62015 U.S. Open - Day 6
Donald Young returns a shot to Viktor Troicki of Serbia during Day Six of the 2015 US Open at the USTA Billie Jean King National Tennis Center on September 5, 2015 in New YorkPhotograph by Matthew Stockman — Getty Images

It’s not a marijuana leaf.

That’s the most common misunderstanding about tennis apparel brand Boast. The logo is a Japanese maple leaf, and it’s been the brand’s symbol since its founding in 1973 by a group of former Ivy League squash and tennis players. But that doesn’t keep people from thinking it’s a pot leaf. And that’s okay with owner/president John Dowling, who bought the dormant brand in 2010 with his own capital. “It’s a wink,” he says of the logo.

Dowling has been running Boast like a startup, and won’t share revenue figures, but says the brand was once losing money and is now profitable. He’s working to get Boast back on the tennis court—and the beach, and the country club, and in bars—by sticking to the company’s roots but adding a modern look and tone that you might place somewhere between preppy and hipster. (See throughout this story for photos from Boast on Instagram.) It helps that he has Donald Young, a 26-year-old from Chicago ranked No. 68 in the world, sporting Boast from head to toe on the court at this year’s U.S. Open, where he is unseeded. Young finished a stunning comeback in his match on Day Six to make it to the Round of 16. (Boast also sponsors American player Andrew Carter.)

Dowling stopped by the Fortune offices in August, just before the start of the U.S. Open, to talk about his efforts to revitalize the brand. What follows is an edited transcript.

Fortune: What did you do to acquire Boast in 2010?

John Dowling: We had to track down the founder of the company, negotiate with him a little, acquire the intellectual property. And I think he liked the thought that we’d preserve the character.

Was it defunct?

Yes and no. In the 90s, the founder started doing only custom-label embroidery for private clubs. Which he had been doing all along, but he basically said he wasn’t going to deal with Macy’s and other big retailers anymore. That way you’re not sticking your neck out on seasonal styles. It’s not the stupidest way to go.

I saw Boast when I was 11 years old at tennis camps in Vermont. I had a bunch of Lacoste shirts, but I saw the older counselors wearing Boast, and they were usually the cooler dudes—the guys who played tennis really well but didn’t take it that seriously, maybe wore a bandana… I admired them, and I wanted a Boast shirt.

A lot of people, when they’re playing tennis, may want high-performing stuff, and care less about fashion. They want the wicking, tight shirt…

I think the quintessential Boast moment is the dude pulling his socks off in front of a teak locker, and then he showers, and then what does he wear off the court? It’s an on- and off-the-court look for that dude, or that girl, for that matter. When we developed the fabric for our active polo, I wanted it to have that traditional look, and also performance. But I wasn’t trying to look like Under Armour or Nike. I wanted it to mimic the perforated look of a Lacoste shirt. A guy on Wall Street wants to buy a polo and have it feel worn in the next day. A Boast polo is more like a Levi’s jean jacket—you want to wash it on low heat, treat it nicely. And our stuff isn’t cheap, because we use really nice materials. I don’t think I’m going to be able to go into a big-box sporting goods stores right now and compete with Nike or Adidas. They make tens of thousands of units, and there are a lot of people out there who don’t want to spend more than $50 for an active polo. [Boast polos are priced at around $70.] But we have seen the most growth in our active polos and t-shirts. People are starting to get that we make some stylish activewear that performs well.

It’s not meant to be just a tennis brand anymore. Right?

Yeah, that’s the way I’m thinking of it. I mean, I want to reference our tennis roots, but people look at our shorts, which are really lightweight with a little bit of stretch, and they’re swimming in them or playing basketball in them. Our shorts are our most popular item.

Tennis endorsements are so funny nowadays—Federer is Nike, Nadal is Nike, but then Djokovic wears head-to-toe Uniqlo.

Right, it’s weird because it’s not a tennis brand. Frankly, Nike doesn’t make sense either, if you look at it. I mean, to me, Nike is running shoes, not tennis. But they just dominate everything. On the other hand, if I see a player wearing Lacoste, I think that’s sweet, I love it. [Note: Andy Roddick was sponsored by Lacoste, in his day; now you can see the crocodile on John Isner.]

So if you want to be tied to tennis, are endorsement deals the way to go?

A big endorsement deal is out of my budget. But we sponsored the Connecticut Open at Yale. We sponsor the Atlanta Open. I was down there and I saw Patrick McEnroe, and I said, “Hey man, remember Boast? Boast is back, here’s what we’re doing…” and he said, “Do I remember Boast? Oh man, of course.” He was aware, which was great. But when I find guys in their 40s or 50s that come up to me and say, “Oh my god, I didn’t know Boast was back,” then I’m not doing my job, because they should know. And then my job is to focus on getting the 20-somethings.

So who is the target customer?

Well, we’re a little expensive for college students. Although we have a great campus ambassador program. The target is probably that athletic, clubby, young guy in the suburbs. But we’re not the guy that wears the whale pants. I think of Boast as saying “F you” to the obnoxious preppy guy.

We do well in places like Atlanta, the Southeast, Dallas, Brooklyn. We’re in hip sneaker shops, we’ve been in hoodie-and-hat shops, we’re in pro shops. The best place for us is like a Paragon Sports, the store everyone goes to in New York to get their racket strung.

Do you find that there’s any stigma from the logo looking like a pot leaf?

I just don’t want people to think it’s a gimmick, like a joke brand. Because it’s not. And when they learn the history and learn it’s a Japanese maple leaf, they think it’s cool. Or they’re just going to laugh. It’s a wink. It’s a mystery. It’s like, “could that possibly be…?” I mean, I met a tennis coach at West Point who had his players wear Boast.

Where do you want the brand to be five years from now? Is a player like Nadal wearing it on the court, are people wearing it in The Hamptons, is GQ featuring it? All those things?

Well, it kills me when we’re not listed as one of the best polos. We often are. I’m still trying to catch on with women, off-the-court. We have awesome women’s stuff—it’s about 30% of sales and it’s mostly the active stuff. It’s hard because our main outlet is online, and women want to try the stuff on.

I want to show guys that you can play in our stuff. And you’re going to look a little more stylish. We have these two twins out in Arizona, Nic and Tristan Puehse, who used to be skaters and now play tennis, and they wear our stuff. We just have a loose agreement that they wear Boast, not any official deal—and I’ll do things like that all day. I was bumping into young players in Atlanta and they said, “I’d love to wear your stuff!” And you know, tennis players used to pick out their clothes in the morning, themselves. So maybe something will happen serendipitously.

Something did happen serendipitously: after this interview, just days before the U.S. Open, Dowling got connected with Donald Young, who decided to wear Boast—for free, not under an official endorsement contract. Young made a big comeback on Day Six, clad in a Boast hat, polo shirt, and shorts, and will play again on Labor Day in the Round of 16. He will also wear Boast when he represents the U.S. in the Davis Cup later in September. That means additional eyeballs for the leaf.