Olympic skateboarder Annie Guglia is on a mission to grow the sport, especially among girls

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Olympic skateboarder Annie Guglia is on an epic month-long summer road trip spanning Montreal to Vancouver, travelling in a Dodge Ram van with her girlfriend and their two dogs.

They are camping along the way, vacationing a little, and skateboarding with many. Their visits will include a Canada Skateboard Open tour stop in Calgary, a Mohawk community skatepark in Akwesasne and a Queer Skate Jam during Pride Toronto.

Guglia was the first female skateboarder to represent Canada at an Olympics as the event debuted at the Tokyo Summer Games in 2021. Some call the national street skating champion the queen of Canadian skateboarding. Now the 32 year old is the president of Canada Skateboard, recently elected to lead the small-but-mighty national federation for a sport whose global popularity has widened beyond its earliest outsider origins on the street.

On a skateboard for more than two decades, Guglia has become as adept about the business of skateboarding as she has executing ollies and kickflips. The Montrealer wrote her master’s thesis in business school on the skateboarding industry and she has a full-time job in community marketing for Vans, the iconic skateboard shoe and apparel brand.

Her unique mix of experiences has Guglia well suited as volunteer president of a national sport body trying to qualify athletes for the 2024 Paris Olympics, while also promoting and growing skateboarding in Canada. The openly gay Olympian is passionate about making skateboarding more inclusive, from getting more Canadians on boards, to encouraging more females to participate in competitions.

“It wasn’t always seen as a good thing – making skateboarding more accessible to everybody – because some people liked that it was a closed environment and an outsider culture,” Guglia said. “But I think the mindset is changing towards diversity, equity, inclusion. I love seeing skateboarding go everywhere. Skateboarding is for everybody.”

When previous president Ben Stoddard prepared to step down, he asked Guglia to consider taking the job next. Initially an athlete rep, Guglia has volunteered on Canada Skateboard’s board of directors since the organization formed in 2016 when the International Olympic Committee first announced plans to add skateboarding. Across the world, some skateboarders welcomed the visibility the Olympics would provide; others considered it an unholy alliance.

Canada Skateboard is one of more than 60 national sport organizations recognized by Sport Canada, most of whom get some federal funding.

Back in April, Guglia was in Toronto to attend her first Canadian Olympic Committee session in the job, with leaders from all the sports, many of which are much bigger and have decades of experience competing at Olympic Games and creating pathways for high-performance athletes. She took away some learnings, finding similarities especially with Canada Snowboard.

“As skateboarders we’ve always wanted to make sure our national organization is done the right way, and [that] the essence of skateboarding stays and that the skateboarders felt represented,” Guglia told The Globe and Mail in an interview during that trip to Toronto, at an indoor park called Skate Loft.

Guglia looked on at an organized skateboarding lesson taking place at Skate Loft for kids during the interview, with parents watching from an observation area.

“These parents are now my age, and they grew up with skateboarding and they’re not afraid to introduce their kids to it and put them in programs,” she added. “It’s growing very fast. When I was growing up, we didn’t really have skate parks, and if we did, they weren’t that good.”

Fast-forward to June, and Guglia is busy, juggling her roles for Vans and Canada Skateboard. It’s high season. She’s retired from the national team, but she’ll be a lifelong rider, both for fun and work, especially at community events where she delights in putting someone on a board for the first time, or teaching tricks.

This past Wednesday was both Go Skateboarding Day and National Indigenous Peoples Day, so Guglia spent it at a sprawling new skatepark in the Mohawk Nation of Akwesasne, south of Cornwall, Ont., showing skills to kids and handing out white Vans skateboarding shoes for them to paint. This weekend, she will host free trick clinics at Dufferin Grove Skatepark during Pride celebrations with Queer Skate Toronto, a collective of queer and allied skateboarders.

She will stop at events in Thunder Bay, Winnipeg, Saskatoon and onto Calgary for one of the tour stops of the Slurpee Canada Skateboard Open, a series of national street and park competitions for all ages and skill levels, where riders can compete for cash, exposure and to build national rankings. Each of the six stops on the Canada Open series also has a community day with activities for all, which Guglia considers equally as important.

“Growing the sport is part of our mission and we’re also trying to build people’s confidence for competitions,” Guglia said. “Competition is cool for some people, but for others it’s scary. So we want to get people comfortable so they’ll think about it, especially girls and women, because there are still less competitors on the female side.”

Guglia has been a leader in growing women’s skateboarding. She first tried it after her brother got a board for Christmas in 2000, and she watched him learn to ollie, the most basic skateboard trick. She grinded at it also, but for two years, she never saw another girl on a skateboard. Some girls told her they wanted to try but didn’t feel comfortable hitting a busy skatepark full of boys, and had no idea where to start. Guglia eventually met a group of female skaters in Montreal called the Skirtboarders. She also organized monthly skateboard meetups for girls.

As a teen, she never believed she could make a living in skateboarding. When she started competing in 2006, the prize money for females was paltry compared to that for males. She recalls one contest where the men had a $25,000 prize purse, and the women $900.

The Tokyo Olympics spotlighted males and females, each having 20 skateboarders in the park and street competitions for a total of 80. Young female medallists such as Sky Brown, Momiji Nishiya and Rayssa Leal were among the stars of the competition. The Olympics, and the popularity of skateboarders around the world on social media have been factors in its growth.

“An Olympic gold medal is the same for men and women,” said Guglia, who finished 19th after flying to Japan last minute having originally narrowly failed to qualify but being added as an alternate when another athlete got injured. “There’s been lots of new opportunities in skateboarding, new jobs, new skate parks.”

Guglia got her own skateboard in 2021, with Meow Skateboards, an independent company founded by skateboarder Lisa Whitaker that focuses on products for girls and women. Guglia is also one of the skateboarders in the street skating video game Session: Skate Sim.

While pursuing a master’s degree in business strategy at HEC Montreal, which she finished in 2017, Guglia wrote a thesis exploring businesses in the skateboarding industry and probing the possible contradiction between commercialization and the sport’s subculture, identifying that there are three types of managers: nostalgics, pragmatics and promoters.

Her varied experience gave her a solid résumé for her role as president of the national organization for her sport. “Canada Skateboard is in great hands with Ms. Guglia at the helm. Long live the queen of Canadian skateboarding!” read Stoddard’s comments from the news release. Guglia was buoyed in knowing other board members saw her as an ideal leader too.

“That boosted my confidence, knowing that I had unanimous support from the board,” Guglia said. “I’ve never been president of a national sport organization and there’s a lot I don’t know, but I have great people helping me and I am very keen to learn.”