Back in the 2010s, Ken Diamond had a booming moccasin business in Vancouver—celebrities wore his shoes, which also secured a hallowed spot on the shelves of Istetan, the Tokyo department store that's home to likely the world's great shoe selection. But at the brand's peak, a bit burned out and seeking something fresh, Ken bailed on it all.

Today, 150km and two ferries from Vancouver on Canada's remote Sunshine Coast, Ken is hand-making stitchdown construction boots, one pair at a time. This episode, Ben chats with Ken about what that moccasin roller coaster ride was like, how he started making boots (with a construction that's just so incredibly different from the moccasins), the meaning and impact of "copying" designs, what perfection means in footwear and if it's even attainable, and what satisfaction truly means to him.

Oh and LOST. That too. WE HAVE TO GO BACK, KEN!!!

https://www.instagram.com/kendiamondboots/

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This episode was sponsored by Standard & Strange

Theme Song: The Road by Punk Rock Opera

This episode was sponsored by Coblr—the business management system powering the repair industry. https://www.coblros.com/

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2025 dates and location for Stitchdown's Boot Camp 3—the world's fair of shoes and boots and leather and more—coming soon.

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Ken Diamond on the Rare Satisfaction of Making Boots by Hand