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Festival curation and arts management in Vancouver is challenging at the best of times. One is always competing for money, audiences, equipment, and skilled production staff. These issues are only magnified when a “Big Show” like the Olympics comes to town, especially if its premiere cultural events coincide precisely with one’s own normal programming time slot. In this essay I reflect on what the PuSh International Performing Arts Festival, held every January–February in Vancouver, did to face the challenges and mitigate the risks of both competing against and collaborating with the 2010 Cultural Olympiad. I also offer some thoughts on what, if anything, has changed in the cultural landscape of Vancouver as a result of this mega-event.