Jim Cressman poses with country star Alan Jackson.

Jim Cressman sees opportunity where others don’t think to look. The head of British Columbia-based Invictus Entertainment Group has carved a unique niche in Canada by promoting shows in secondary markets, bringing major acts like John Cougar Mellencamp and Bob Dylan to towns that aren’t used to short drives for A-list concerts.

“It’s been exciting for me, but it’s also one of those things where you get th...

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