Skateboarders are a different breed. And I'm talking specifically about the grown-up ones who take it really seriously and who are making a living of it. How is it that full-grown men are putting everything they have - their time, their bodies, their money, their energy - into an activity that doesn't really have any kind of professional sporting association and appears to be completely devoid of structure?

As it turns out, many of them are getting by on that lifestyle, and are finding new ways to sustain themselves on it. They're organizing themselves, getting sponsors involved, building community and solidifying their network, but they've found their own way to establish themselves in the normal, adult world without spoiling their culture of fun.

The latest effort was a skateboard video contest called Connect the Dots that had people from across the country submitting to win a piece of the juicy $10,000 pot (and seeing as this is an article about skateboarding, let me be clear that by pot, I mean award money).

The prizes were handed out at a (very) informal award ceremony at The Baitshop, an expansive 1,500 square foot retail space tucked away in an alley in a corner of Parkdale. The Baitshop is part skateboard shop, part skateboard park (complete with a half-pipe), and also appears to be ground zero for any and all partying for the skate community in Toronto.

It's a calming space that's designed to look like the inside of a cabin, lined with rough wood paneling on the walls and a scattering of Muskoka chairs. On Thursday it was packed to the rim with a couple hundred PBR-drinking skateboard keeners. However, the cops broke it up just after midnight, sending all the happy participants and their friends on their merry way.

Three of the six finalists took home prizes, including $2,500 for Best Skateboarding, $2,500 for Most Creative and the grand prize of $5,000 went to best overall video. Though each winning team put together something quite impressive and is made up of really talented and (though they may cringe to admit it) disciplined men, the community still prides itself on rejecting rules and living outside normal and decent society.

Not taking yourself too seriously is an absolute must for anyone looking to get respect in this crowd. The Baitshop's website describes the store as a place of both "business and leisure" with a "laidback cottage vibe". And the Connect the Dots site takes it even further, saying that the concept of having people submit videos rather than having a contest at a skatepark was born largely of their own laziness: "[We] got together and asked "what the hell kind of contest could we do that's fun ... and doesn't involve us going to some stupid skatepark to judge it?"

Apparently going to a location where they spend all their time anyways, surrounded by friends and like-minded individuals, is a terrible hassle.

They play up their cool indifference, and yet the contest organizers are clearly doing something right. This was the second annual Connect the Dots, and since last year they've raised the stakes, doubling the prize money from $5,000 to $10,000. Plus, the number of people allowed on each team doubled, the amount of time given to create the video went from a week to a month, and there are now three different prizes instead of just one.

Just like anyone else who wants to perfect their craft, these guys are focused, driven, and always searching for new ways to make money doing what they love.

Writing and photo by Emily Burke