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Among Andy Oliver’s sneaker collection, which totals almost 600 pairs, are custom Nikes that he had made for his wedding day. Unlike other collectors he typically buys his shoes at retail prices – and actually wears them.

"I do a lot of video calls with merchants and brands for work and they always ask, 'Hey, are you calling from a FootLocker?'" Andy Oliver, head of solutions engineering for Canadian e-commerce star Shopify, says with a laugh. It's a fair question since the walls of Oliver's Winnipeg home office are lined floor to ceiling with open shelves of sneakers."I'm not one of the guys who keeps them in a dust bag in a box somewhere."

"I grew up in a single-parent house, and we didn't buy the fancy sneakers. When I was very little I used to draw pictures of them," Oliver, 35, says. Forget teen crush pin-ups: "The black and metallic Jordan 5 was the shoe photo that was literally in my locker as a junior high student. Once I was able to get my feet under me as an adult, I started with buying a lot of the shoes that I had nostalgia for as a teenager. My heartstrings were pulling in that direction."

Oliver's interest exploded once there was a community online he could connect with. "Sneakers are the hub of a lot of different interests. Whenever you meet a sneaker guy he's into sports, music, design art – they're all tenets. And then the technology tie-in. It's been a conduit into meeting like-minded people," he says. "And as silly as the whole sneaker thing is, it's led to a career." Early on, the software engineer combined his skills and interests into developing a platform, KickDeals, which he later sold. "Then I did consulting in the e-commerce space [with Kith New York] because of some of the connections that I made," he says.

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Oliver's collection, over a decade in the making, hovers at just under 600 pairs. "It grows a little every year but I also cull and donate every year to a charitable group in town, to different missions," he says. And he's not overly precious about his footwear: He shares photos of his favourites on Instagram and they aren't pristine because he'd rather wear them than dust them. Most of his shopping is done online – seldom on the secondary market. "Most of what I am purchasing is as a regular consumer, the way anyone else does," Oliver says, adding that even though he has access, and is seeded shoes from brands like Converse, he still spends "much, much less" than other collectors. "I think the number of shoes I've paid over retail at all might be five pairs out of 600. That's probably unique among collectors."

A few pairs with sentimental value are the exception: "Some of the early Kith shoes, when we were just starting the brand up. Or friends that are behind the shoes like Reigning Champ, a Canadian athletic-wear brand coming out with a collaboration with Asics. And the Nike I.D. custom pair I designed for my wedding, that have our wedding date on the heel. I even have a backup pair of those I've never worn. Though I wore dress shoes at the ceremony itself – so that my wife would actually marry me."

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