Vincent Tsang on Dime MTL's early days, his artistic evolution, and Montreal's creative class

Overlooking the St. Lawrence from his Nuns' Island apartment, Vincent Tsang’s place is punctuated by as many books on design as it is by his artwork—flowing, abstract figures that have graced gallery walls and coveted Dime tees. 

A meditative project of the streetwear brand's art and design director's own making, Tsang’s distinctive characters have gone from paintings to sculptures, each new piece exploring how new angles and perspectives could loop back to influence his paintings. It's exactly this kind of creative cross-pollination that's defined his unusual career trajectory.

In a city where ambitious creatives traditionally pack their bags for New York or LA, Tsang has helped build something homegrown that travels in the opposite direction—pulling global attention back to Montreal. What began as skateboarding videos made with childhood friends has evolved into a streetwear phenomenon with collaborations ranging from New Balance to DC Shoe. 

But behind the Dior-style logo and viral skateboarding stunts lies a homegrown Montreal story of ambition, artistic evolution, and a stubborn refusal to abandon the city that shaped him.

Early days in Little Burgundy

Stroll through Little Burgundy today and you’ll probably come out holding a $7 cortado or having dropped a few bills on drinks and dinner. No shade to those businesses, but the neighbourhood Vincent Tsang grew up in during the late '80s and '90s was an entirely different world.

"It was not a nice neighbourhood back then," he says with characteristic understatement. "I would hear gunshots, there was a lot of drug dealing... I was buying weed at trap houses there. It was a scary place."

But Tsang had a front-row seat to the area's dramatic transformation. "I saw the whole thing change—when Joe Beef opened, then Lili and Oli." That very same coffee shop, though, was where Dime's DNA began to crystallize.

"Dime was created in that coffee shop," Tsang explains. "My partner and I would go there, have coffee with Justin Saunders, and we'd be there every day cooking up the brand."

While kids today might dream of becoming full-time YouTube creators or professional sneakerheads, young Tsang faced more practical pressures. "When I was a kid, I wanted to be an artist. That was the first thing," he explains. "But coming from a middle-class family, it seemed far-fetched to become a painter. Design was a compromise—I could still be in a creative field but have a job."

This pragmatic streak led him to Concordia's design program while working his way through Montreal's streetwear institution, Off The Hook. 

"I did pretty much every position at Off The Hook, from the sales floor to management to buying," he says, describing a ground-level education in what would later become his world.

Kickflips, t-shirts, and a streetwear empire

Before the international collaborations, before the Dime Glory Challenge drew skaters from around the world to Montreal, there was just a group of friends with skateboards and a YouTube account.

"It was basically a YouTube page where they were shooting skateboarding. It was like a group of friends. They were just filming skateboard tricks and then putting them up," Tsang recalls of Dime's earliest incarnation. His childhood friends needed a website, and Tsang stepped up.

But YouTube glory doesn't pay the bills. "At one point they were like, 'Hey, like we need to make money somehow—we can't make money just with videos,'" Tsang explains. 

The skateboarding industry was changing, and the DVD era was ending. "Back then in the 80s, the 90s, you could make money with DVDs and tapes... But once YouTube and Instagram started happening, people were just uploading things on YouTube and no one was buying physical media anymore."

"Our angle was: how do we inject fun back into a sport when everyone's trying to quantify it?"

The pivot to merchandise was born of necessity, but executed with that scrappy determination that defines Montreal's creative class. "We made a couple of t-shirt designs, got them printed at in Saint-Henri," Tsang says, which began a slow but steady expansion of flipping and reinvesting.

Meanwhile, the founders—Antoine Asselin and Phil Lavoie, who were joined by Bob Lasalle, Hugo Balek, Charles Rivard, Eric Riedl, and Alexis Lacroix—kept their day jobs.

"We kept reinvesting everything for the first 4-5 years without taking a single dollar out. I was working at a bar, Phil was working at a bar," Tsang recalls of those lean years.

What separated Dime from other skate brands was their natural fluency in what would later be called content creation. "We were really good at making content on Instagram—organic content that people would repost. We were the first brand in skateboarding making viral content," Tsang explains with justified pride.

His position in online fashion communities, writing for Hypebeast and being a prominent personality on forums, created connections that would prove invaluable as the brand grew beyond Montreal's boundaries.

It's the difference between technical perfection and genuine joy—and Tsang bet on joy.

Above the competition

While skate culture was being absorbed into the mainstream sports industrial complex, complete with energy drink sponsorships and ESPN coverage, Dime was brewing something altogether different in Montreal's alleyways and skateparks.

"When at the beginning of the 2000s, skateboarding was in a very strange place where it was becoming very competitive in terms of competitions like X Games and Tampa," Tsang explains. The sport was increasingly focused on "putting a number and a score to a trick, which for them and for us... it didn't make any sense because skateboarding isn't about performance."

This rejection became Dime's north star. "Our angle was: how do we inject fun back into a sport when everyone's trying to quantify it? How can you rate a trick when someone does it differently but it just looks better?"

The answer was simple, if radical at the time: "For us it was like, OK, let's forget all that and make skateboarding fun again."

This philosophy wasn't just good for skateboarding—it made for a brand with staying power in a notoriously fickle industry. "I think that's something that is timeless," Tsang reflects. "The idea of having fun with your friends, whether it be skateboarding or soccer or any sport, is something that just does not go out of style."

He compares it to watching dance: "I'd rather watch someone who's enjoying it more than someone who's not enjoying what they're doing." 

It's the difference between technical perfection and genuine joy—and Tsang bet on joy.

The accidental artist

If you've scrolled through Letter Bet's offerings or seen a Montreal gallery show in recent years, you've likely encountered Tsang's distinctive figures: Flowing, contemplative yet jovial forms that seem both abstract and oddly familiar. 

But this artistic success was never part of the plan: It started, like so many creative careers in Montreal, with t-shirts. "I was drawing these characters for our t-shirts and people really liked them," Tsang recalls. "It brought me joy drawing them and I saw how much joy it brought other people when they saw the art."

The market validated what his instincts were telling him. Commercial success gave him the confidence to make the leap from garments to gallery walls. "I printed this one first print... that sold out instantly and I was like… OK, I can do this."

"It all stems from calligraphy, comes from graffiti, it comes from Picasso, it comes from Matisse. It's all the things that I've liked and got inspired from, put into this one thing," he explains. "Mark Gonzalez... my cultural heritage, the colour choices that I use are from my cultural heritage."

Tsang doesn’t forget that he enjoys the rare luxury of financial independence through Dime, and that emerging artists typically struggle with the brutal economics of the art world. "I'm really lucky that that was the path that I took, because had I gone straight into art and didn't do everything before that led me to it, I think I would be struggling a lot more," he reflects.

This freedom created a virtuous artistic cycle. "Having Dime and having the success of Dime allowed me to make art that didn't need to sell, really. I was just making it for fun and I think that makes the art a lot more authentic." 

"A lot of artists nowadays have this very difficult balance that they need to have in their creation where it's like, 'OK, I want to express myself, but will it sell?' And so their expression is then skewed."

The resulting style draws from a dizzyingly diverse set of influences. "It all stems from calligraphy, comes from graffiti, it comes from Picasso, it comes from Matisse. It's all the things that I've liked and got inspired from, put into this one thing," he explains. "Mark Gonzalez... my cultural heritage, the colour choices that I use are from my cultural heritage."

During COVID, Tsang expanded into sculpture—those same flowing forms rendered in three dimensions. The experiment had unexpected benefits: "Doing the sculptures completely changed how I painted afterward because I was seeing shapes and angles from perspectives that I wasn't able to see in 2D," he says.

"I wanted to prove something good could come from here."

The conventional wisdom for ambitious Montrealers in creative fields has long been brutally simple: leave. Head to New York, Los Angeles, London—anywhere but here. Tsang watched this exodus firsthand.

"For me, I was always thinking like, 'Oh, I'm going to grow up, I'm gonna move to LA or New York, work for Nike or do something like that,'" he recalls. "All my childhood heroes, who were also from Montreal, ended up doing that. They would leave Montreal."

But something made Tsang dig in his heels. "I didn't leave because I wanted to prove that something good could come from here—that a brand could emerge from French Canada and be relevant globally," he explains.

"I saw it as a challenge but also a point of pride. I wanted people to recognize Montreal as a cool city, because it is."

It wasn't just stubborn hometown loyalty that kept him here. Tsang speaks of Montreal with the eloquence of someone who's seen enough of the world to know what makes his city special.

"The food, not gonna lie," he laughs when asked why he stays. "I've traveled to so many places in the world, but I still come back thinking the food's so good here. I miss it whenever I leave." 

"It's the quality of produce, the care and creativity in the kitchen. It's French food, but without the fear of trying shit."

Now settled in Nuns Island ("10 minutes from everywhere I need to go") with his wife, Tsang is entering a new phase. "We're starting to look to have a family," he mentions—a far cry from the skateboarding kid from Little Burgundy or the busboy flipping t-shirt profits into hoodies while dreaming of something bigger.

With Dime now employing about 60 to 70 people at on time and his own artistic practice flourishing, Tsang doesn't just work at the intersection of Montreal's skateboarding, fashion, and art scenes—in many ways, he helped create it. 

From rougher streets of pre-gentrification Little Burgundy to international recognition, Tsang's journey mirrors Montreal's own evolution: authentically local, surprisingly resilient, and (finally) getting some of the global recognition it deserves.