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June 8, 2026 • 62 mins

Zane Caplansky opened what's considered Toronto's first pop-up restaurant — a deli inside a dive bar in Little Italy — and turned it into one of the city's most beloved institutions. Along the way he appeared on Dragon's Den three times, got featured on Diners, Drive-Ins and Dives and You Gotta Eat Here, ran a food truck, a catering empire, and a College Street restaurant that had lineups for years.

Then his landlord locked him out at midnight — rent paid, no warning — and it cost him $100,000 in legal fees and nearly broke him.

But that gut punch turned out to be the pivot that changed everything.

Zane joins Phil and Kenny to talk about the full arc: the scrappy pop-up beginnings, the Dragon's Den pitches (including Jim Treliving famously not understanding what a food truck was), the public humiliation of the lockout, closing the deli, moving to Tofino, becoming a dad at 53 — and why reviving the Caplansky's mustard brand as a CPG product might be the smartest thing he's ever done.

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