The year was 2000.
The web was becoming a cultural and financial phenomenon.
Crazy new internet companies were being funded and old traditional companies were racing to get established online.
Old media was starting to panic as new media patterns were taking over.
Napster nodes were spreading and the paradigm of entertainment was changing.
But even as the web was taking over, we didn’t really have any “Web Stars” rising out of the pixels. There were viral stars like Mahir, the “I kiss you!” guy, the weird dude who dressed up like Peter Pan, and Jennicam.
But there were no YouTube stars. There was no YouTube! Even MySpace was years away.
Meanwhile, I had been passionately exploring self-expression on the web since 1996.
I created a personal site called “CockyBastard.com” as a hub for all my photos, writing, gif animations, html design experiments and Flash experiments.
And in 2000, when the Webby Awards introduced the “Best Personal Site” Category, I won.
The Webby Awards at the time was a huge production. Red carpet, televised, famous people.
Judges that year included Patrick Stewart, Matt Groening, Laurie Anderson, and David Bowie.
When my name was called, I jumped to the stage wearing a full-length monster fur coat, bare chest and my hair in pippi-longstocking braids.
It was glorious.
The next day, my inbox was full of congrats and a number of business pitches. I was also contacted by World of Wonder, a production company. They were behind RuPaul and helping turn her into cultural phenomenon. They wanted to fly me to LA and talk about my future.
They could see the convergence of Television and Web and were looking for a personality they could mold into a star. I had the charisma and presence for it, they said. But they had one important question, “Could I sing?”
I dropped a few lines of rap at a dorm party in college. Does that count?
The meeting was good. But my non-singing was definitely an obstacle for the plan they had in store. We agreed to stay in touch and see what project ideas might come up. A limo drove me back to the airport.
In the months that followed, the 1st Internet bubble burst. The inevitability of the new entertainment paradigm shift came into question — or at least was postponed. And my position as the golden boy of Web/TV convergence lost its luster, as well.
Thank god. What if I went to Hollywood? I would have missed out on the wacky chapters of my life that helped me grow into the person I am today.
I took the road less famous…and that has made all the difference.
BONUS: The Webbies made a hilarious Mockumentary “Behind The Website” about my fall from grace. (Starring my mom and brother!)
POSTSCRIPT: Later that year I moved into a webcam house and started broadcasting my own DIY shows…one of which became “Hug Nation.”