When I reach Montreal professional skateboarder Annie Guglia over the phone, she’s currently recuperating from a training session in advance of the final for the Vans Showdown in Huntington Beach. While billed as a surf event, the skate portion of the contest is not some small affair, with 53 men and nine women entered into the competition. Although those numbers suggest a growing disparity between males and females in professional skateboarding, Guglia isn’t so convinced. In fact, she’s probably one of the best people to be speaking to about the subject given her connection to Canada’s first all-female skate crew (The Skirtboarders), her status as a pro, and her master’s degree in business strategy which centered on a thesis dedicated to exploring the skateboarding industry in North America.

Our call comes at an interesting time for skateboarding. From a strictly athletic POV, 2020’s Tokyo Olympics will see the sport formally added to the Games for the first time. Thomas Bach, President of the IOC, said of the decision to add five different sports, “[they] are an innovative combination of established and emerging youth-focused events that are popular in Japan and will add to the legacy of the Tokyo Games.” According to the press release, this reflects the trend of urbanization of sport. Perhaps this is the same reason why Tokyo will also feature 3×3 basketball, and there’s a strong indication that Paris’ 2024 games will showcase breakdancing.

Furthermore, we’ve seen how brands with skateboarding embedded in their DNA — like Supreme and Palace — continue to thrive, while skaters themselves — like Blondey McCoy, Lucien Clarke, and Tyshawn Jones — maintain the ability to move the cultural needle as both athletes and style icons.

montreals annie guglia breaks career olympic expectations vans
Highsnobiety / Kelly Jacob

Guglia admits she was confused when the Olympic announcement was made. She — like many of her other peers — didn’t know how to react. In her estimation, distilling skateboarding down to an Olympic-style judging standard was problematic.

“There was this really big backlash from the skate community because skateboarders are like that,” Guglia admits. “They don’t want people going outside of skateboarding to have any control of their baby.”

Yet, Guglia slowly came around to the idea because she understood that the immense media platform the Olympics provides is a terrific way to grow the sport.

“My main goal about the Tokyo 2020 Olympics is not even to win a gold medal,” she says. “It’s to have skateboarding showcased positively.”

Every skater has an origin story. Guglia is no different. She grew up in a house where scooters and BMX bikes were scattered throughout the garage. However, when her little brother received a skateboard for Christmas — and he soon was able to ollie curbs — it awakened something in a then 11-year-old Guglia.

“I didn’t understand how to ollie,” she admits. “I kind of got a little bit obsessed with that. Skateboarding is so hard at first. It really got me.”

Once Guglia entered high school, she encountered a group of likeminded skateboarding enthusiasts. Not surprisingly, she was the only woman. Undeterred, she spent an entire year attempting to master the basics. Guglia says this period is usually when the average person allows the frustration — coupled with the purple welts across one’s body from countless falls — to force them to abandon a sport where failure can send you to the emergency room.

“I don’t think everyone has the persistence to become good at skateboarding,” she says. “It’s not like [a] bicycle, when you learn how to [ride] and think that you can do it forever. Skateboarding, if you don’t do it for a week, you’re already going backwards.”

As someone who has felt the trepidation of learning to drop in on a ramp — having taught children to overcome the same sense of impending doom she once felt in the pit of her stomach — it’s reminded Guglia that skateboarding is about commitment. While it doesn’t always work out, she believes her own story reflects the positive outcomes of a “jump and worry later approach.”

montreals annie guglia breaks career olympic expectations vans
Highsnobiety / Kelly Jacob

Of course, no person is immune from considering a plan b. Although Guglia was encouraged when she learned about the Skirtboarders and their mission to grow skateboarding for women throughout Canada, it also exposed her to the grim reality: very few contests with extremely low prize money.

“I didn’t think it was worth it at the time to make a living out of skateboarding,” she says. “So I stayed in school, did a bachelor in marketing, and did a master’s degree in business strategy.”

Although her academic pursuits certainly enriched her life and provided her with unique insights into the skateboarding world, her time away also coincided with a female renaissance in the sport that motivated her to rethink her career path. Guglia specifically points to the success of pros like Leticia Bufoni, Vanessa Torres, and Lacey Baker as individuals who helped female skaters with new and more lucrative opportunities.

“I just realized that now was a really good time for women in skateboarding,” Guglia says. “So, I started doing competitions again.”

At 25 years old, Guglia set a lofty goal to qualify for the X-Games. Within a year, she was competing in Minneapolis where she finished 15th. While a medal would have been nice, Guglia took away something much greater from the experience: that it was possible now to make a career out of skateboarding.

The sport has allowed her to travel the world, and of course, will provide her the opportunity to represent Canada at the 2020 Tokyo Olympics. And yet, I get the sense that Guglia’s most proud of nurturing the next generation of young female skateboarders who are coming of age at a time when people like Lacey Baker are in national Nike campaigns, and prize money is more equally distributed between the sexes.

“This new wave of girl skaters is going to be insane,” Guglia says. “It’s going to be really interesting to watch how far they’re going to push women’s skateboarding. When […] I was 11 and I started skating, people said I was too young. You know what I mean? They’re like, ‘Oh, it’s dangerous. You’re too young.’ Now, kids start skating at four. Basically as soon as they can walk they’re on the skateboard.”

Look no further than prodigies like Sky Brown, a 11-year-old with over 400,000 followers on Instagram, as proof that skills in fact do pay the bills. Brown recently competed at the X Games in Minneapolis where she became the first female skateboarder to land a frontside 540. It’s also expected that Brown will be part of Team Great Britain in Tokyo in 2020.

It isn’t often an Olympic sport will showcase a 28-year-old pro with a master’s degree, and an 11-year-old in 6th grade. Perhaps that’s the real beauty in skateboarding: you never really have to grow up. Only now, Guglia’s youthful pursuit comes with the backing of her entire country.

“I’m honored to represent Canada,” Guglia says. “I get a lot of support from Canadians that I don’t even know that are like, ‘Yay! We’re rooting for you!’ It’s really cool. I love it.”

Words by Alec Banks
Features Editor

Alec Banks is a Los Angeles-based long-form writer with over a decade of experience covering fashion, music, sports, and culture.

What To Read Next