As another Winnipegger, I had no idea companies like this existed in our city. Maybe I'm the isolated one, but how can we spread the word about things going on in the area?
SkullSpace (WIP hackerspace): http://www.skullspace.ca/
Secret Handshake (monthly meetup for freelancers): http://www.meetup.com/secrethandshake/
Winnipeg.rb (Ruby group with a monthly meetup): http://winnipegrb.org/
Winnipeg WordPress Meetup (organized by a local Automattic employee): http://winnipegwpmeetup.wordpress.com/