Meeting up with Gillian Andrewshenko, it was mildly amusing to see how jazzed she was to fly back home to Winnipeg and party with a bunch of old fogies. Why? Because her dad had just won $350,000 in one of those hospital lotteries - just weeks after retiring from firefighting. Minutes later she mentioned her grandma had once won a house the same way. "Wha-wait a minute," I asked. "If a season of contest wins doesn't prove that luck runs in the you're bloodline, then why the hell are you not on a quick flight to Vegas? Suddenly I stopped my jabber, realizing that it takes more than being somewhat talented at fist-pumping dollar bills into slot machines to cleanup like this grinning ball of energy did over this past winter. Not only did she finish first overall in the You Look Good series, she doubled down, flipped the idea of Vegas upside down, and earned herself a trip to El Salvador instead.

Start off with some throwback memories of growing up with the Gypsy Mob in Winnipeg.
I started boarding with Kevin (Griffin) and Andrew (Geeves) at Stony Mountain. Everyone would attend contests/events together, and that is how I met Jody (Wachniak), Jake (Kuzyk), (Chris) Saniuk and the other ‘Springers' (Springhill riders). When our hill started to shit the bed, we all switched over and that's when The Gypsy Mob, as it is today, was born. They took Darrah and I to hit our first handrail; I almost crashed my car and killed us all on the way. We would journey from the city to their small town of Oakbank for boarder parties every weekend, where we would watch videos they had made. The best being the "Girls Just Wanna Have Fun" music video, where Jesse and Anthony dressed up in drag and performed the song.

More dirt please...
One evening during high school I was at a musical practice and I had let Kevin use my 1986 Ford Tempo to go hang out with Andrew. The next day I noticed that the back bumper was a little out of shape and there was a crack in it. I wasn't too worried as it was such a beater; a few days later my stepdad (it was insured under his name) received a ticket in the mail for like $300 for mischief, as the guys were towing one another on GT's and snowboards throughout the city streets. I wasn't supposed to lend out my car, ultimate bust.

What about that other ballsy Winnipeg chick, Darrah Reid-McLean?
I've always thought that Darrah is the coolest girl. I was a pretty normal Roxy wearing teenager that liked Blue Crush and was in the school musicals, but Darrah was this new-age vegan, hipster chick who wore dresses over jeans, had a stretched ear lobe, facial piercings, and listened to Frou Frou. When we starting riding together, we got along pretty naturally because of our differences - things were never competitive between us because we've always had different trick choices and different goals. She is the best person to ride with on a pow day because if I fall off a cliff, she'd fall off right behind me. Consequently, we'd laugh about it in the landing and continue on our merry way.

Best shred trip?
I really enjoyed traveling to Australia and New Zealand with the Endeavor Team last summer (video), but the best would have to be my trip to Helsinki, Finland, this past February. Helsinki is such a mecca of urban snowboarding: I saw spots that Eddie Wall, JP Walker and various other pro shreds had hit throughout the years in the videos that made snowboarding seem so magical to me.

Tell us about winning the overall You Look Good Riders Cup this year.
I have done a lot of these contests over the years, and I always enjoyed their element. The EventSing crew are great at putting on an organized contest with consistently great courses, regardless of the resort. I did my first of their events this year at Seymour and placed third. Eventsing's Andrew Singleton motivated me to do the rest of the stops by dangling a surf trip to El Salvador in front of me, so I took to the road. Luckily, I won the Sun Peaks stop to cover my travel costs for the rest of the season. At the last stop at Mt. St. Louis, the course was really icy during practice. I landed on my back and had a costochondral separation of my rib. It kept popping out all day, but I safely made it through the event and placed second, winning the series overall.

Surfs up then?
Ironically, I tried to go surfing in Tofino a few weeks ago, and it was extremely uncomfortable due to that rib injury; hopefully, it'll be good to go for El Salv.

How do you make traveling to contests a reality?
I always try to kill two birds (or ten) with one stone. I link trips together so that I can pay for three flights instead of four, and I am an ultimate couch surfer. For the past couple of seasons I have been spending a couple weeks in Ontario to film rails. This year I planned this around the Billabong Flaunt It contest thinking I could win some money to subsidize my travel costs. This idea was successful and essentially made the filming trip free.

Endeavor Snowboards has been my biggest supporter (aside from Starbucks). Their program is a bit different than the average snowboard company in that if I work hard and have coverage in web videos, magazines, snowboard videos, and contests, I am rewarded as such. It's a really well built program that pushes me to fuel my own snowboard career.

(keep reading for Gillian's report from Ms. Superpark and her guilty pleasures)