This story appears in the May 2016 issue of Playboy. Subscribe

I grew up in southeastern Connecticut, two and a half hours from New York City. I always romanticized New York and obsessed about it in a way I now reserve for the look on my baby daughter’s face. My parents would take my siblings and me into the city maybe once or twice a year, but if I had to trace my fascination with New York to one thing it was the Tom Hanks movie Big. I had it on VHS and would play it on repeat. Here was this kid who miraculously turned into an adult but had the brain of a child, and by maintaining his youthful spirit he was able to succeed in this gigantic playground that was New York City. Playing piano with his feet got him a promotion. To me, that movie was fucking gospel.

I moved to New York when I was 20. I was a bike messenger that first summer, which was horrible. This was 2001, so you had to pay for your cell phone minutes. I lived in a 12-by-12-foot room on the Upper West Side for $370 a month. The building was partly filled with people who’d recently been let out of jail. I shared a wall with a family who had a hot plate, and I could smell whatever it was they were cooking, through the wall, all day, every day.

I was always making videos. Always. I had a little table with my pink, bulbous iMac that I edited on. The way I distributed videos was through something called iDisk, which was essentially an early Dropbox. I would give people my user name and password so they could log in to my account and download my QuickTime videos.

No matter how poor I was, nothing could upset me. No matter how rough my living situation was, I wasn’t a victim. I put myself in that situation. If I couldn’t find success with my videos, it was no one’s fault but my own. And even when I was struggling under the harshest of conditions, all I had to do was step outside and look up and see these big magnificent buildings.

Most places in this country, you’re taught that if you follow the rules, listen to your superiors and do as you’re told, everything will be all right. I’m of the conviction that it won’t be. I believe in defining my own rules. If there’s 27 inches of snow on the ground and I know I can safely snowboard behind a truck, good fucking luck convincing me I shouldn’t. New York City encourages and embraces that kind of thinking. In fact, if you come here and think you can’t think like that, you’ll most likely fail.

Forty-four million people watched that snowboarding video. The next night, they played it in Madison Square Garden at a Rangers game, and the crowd burst into applause. The fact that I make a living at this…man, it’s fucking Tom Hanks in Big!