Published, by Tim Shore

Navigate the Streets

Feb 17, 2026
∙ Paid

After deciding that starting a non-profit water company wasn't going to work, I started thinking about other business ideas. I heard about an event called Urban Challenge, inspired by "The Amazing Race." Teams of two would run around a city on foot. You'd get clues that led you to specific locations called checkpoints. At each checkpoint, you'd take a photo to prove you'd found it. The first team to visit all checkpoints and reach the finish line wins.

Urban Challenge was already in many cities across the U.S. but wasn't in Canada yet. I thought I could create a version in Toronto. But first, I wanted to see how it actually worked.

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