By Michael Cayley
Geeks On Planes, Automobiles, and Now Trains

In 1970, The Grateful Dead, Janis Joplin, The Band and a train full of “insane people” took a train tour across Canada.  Now that same kind of historic magic is lighting up the connections to Canada’s startup scene. What’s up with this trainiac behavior?

“Geeks on a Train?  Geeks on things are my thing!  I gotta jump on board to make sure they do it right.” says Dave McClure, who developed Geeks on a Plane, presumably to build global connections and access deal valuations outside of the Valley.  McLure, along with a cast of other Silicon Valley rock stars are flying up to Portland on August 21st to catch the Geeks on a Train as it sweeps through the northwest tech community enroute to the Grow2012 conference in Vancouver.

“I wasn’t alive when Festival Express happened but I can imagine how awesome that trip must have been.” says Brydon Gilliss, the founder behind the startup train tour, starting in Kitchener, ON on July 11th and winding its way through Guelph and Toronto heading to the International Startup Festival in Montreal.

“I often talk about the loneliness of being an entrepreneur.” says Gilliss. “More and more of us are going it alone these days but we need each other to succeed.”

This trip captures the excitement of the startup scene in Canada right now. Brydon is leading the community straight through the geography where 87% of of Angel investing happens in this country.

While these trains have all of the excitement of the Festival Express, don’t count on them having the same baggage.  Outsiders may view these hype machines as signs of irrational exuberance but changes last March to Section 116 in Canadian tax law have removed barriers that previous discouraged US investors from looking at Canadian startups, and the well known shortage of Canadian risk capital means that great startups can be found at a steep discount to Silicon Valley valuations.

“The roadtrip will be a great conference-within-the-conference.” says Brian Kobus, Toronto VP of Summerhill Ventures on the tour’s website.

With a pitch competition, DemoCamp and Mentor Speed Dating all on-board, there won’t be time for dulling moments.