A Visit with Charles Trippy of We the Kings

In Summer of 2007, twelve eager online entrepreneurs made their way to Northern Colorado to participate in what was to become a ground-breaking effort; my reality show titled The Next Internet Millionaire.

The contestants selected to for the competition were varied. Six men and six women from the U.S., Canada, U.K., and Costa Rica. Over the two week period, twelve episodes were filmed and history was made. It was the very first competitive Internet reality show and I still can’t believe we pulled it off. (Huge nod to Eric Holmlund and the team with whom it never would have happened.)

I still get emails about the show to this date and new life is being breathed into it as the series will soon be appearing on Hulu.

Amongst the interesting and talented contestants, one stood out as an already up-and-coming star in his own right.

Charles Trippy had already begun amassing a significant following via his YouTube channel. His daily videos featuring his real-life antics and clever editing drew a loyal fan-base that has continued to multiply over the years.

On the set of the show, he was young and little cocky, but very kind and likable. Plus, he was incredibly creative and knew his stuff. He ended up as the runner-up by developing a product teaching people how to make video for fun and profit.

Yesterday morning I posted a shout-out on Facebook for the contestants of the show. It had been a long time since I had communicated with any of them and I wanted to do a “where are they now?”

I can’t remember how it happened, but as a coincidence someone online posted that Charles’ band, We the Kings, was appearing in Denver that very night.

I immediately shot off a text to Charles and he responded with backstage guest passes for myself and a friend.

The place was packed with screaming young girls. If I had been a single man between the age of fifteen and twenty-five, this would have been the place to be!

We the Kings is a tight band with a very loyal following. Clearly, the guys are having a ton of fun playing their music and adjusting to their fame. I’ve no doubt that their popularity will increase. There was also no shortage of CTFxC (Charles Trippy Family x Core) signs being held up at the show.

I had an opportunity to visit with Charles both before and after the show. Of course, since video brought us together it would have seemed ludicrous to not take a few minutes to film an interview.

Having matured some since the show (he’s twenty-nine now), Charles is still an incredibly nice guy, down-to-earth, funny, humble and generous. I’m pleased to say that success has not spoiled Charles Trippy. He has earned every bit of his raving following and I expect that the best is yet to come for he and his wife, Alli.

Check out the interview below, as well as footage from the concert at Summit Music Hall in Denver, CO.

And for a laugh, here is Charles’ audition video for the reality show from 2006. Gotta love that hair!

Are you a Charles Trippy or We the Kings fan? I’d love your feedback below!