In 2011, my team and I produced The Bootleggers’ Ball as a 25th-anniversary fundraiser for the Vancouver Police Museum—a speakeasy-themed evening at the Biltmore Cabaret that leaned hard into the Prohibition era with period burlesque, vintage jazz, a costume contest, and a crowd that showed up ready to play along.

The lineup included The Vaudevillians (a troupe of tap-dancing seniors, their oldest member in his nineties), burlesque performers Lola Frost, Darla DeVine, and Lacey L’Amour, and The Creaking Planks billing themselves as “the jugband of the damned.” The room filled with flappers, gangsters, feather boas, and more tattooed women in fringe than you’d see anywhere outside Burning Man.

Midway through the evening, a vice squad in long dark coats and fedoras raided the joint. Fortunately, the real Chief of Police was our guest of honour—he called off his men with a wink, and the party continued.

The event raised nearly $10,000 for the museum. More than that, it demonstrated something that shaped much of my later programming work: fundraising works best when it’s designed as experience, not as an ask. Give people something worth participating in—whether that’s dressing in costume, stepping into a story, or supporting a place they care about—and the transaction becomes secondary to the relationship.