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August 27, 2025 74 mins

Bec first heard Derek Sivers on the Tim Ferriss podcast, and was immediately interested in this countercultural person who sold a multimillion dollar company and then moved to New Zealand to do something completely different. He’s interested in learning and iterating, and he did say he would answer every email — so we decided to test him. He answered right away.

Derek has been a musician, a circus performer, an entrepreneur, and a speaker. He’s a slow thinker, an explorer, a xenophile, and loves a different point of view. In New Zealand, he lives in a house that he designed himself, based off the notion that houses should grow from how people actually live, not from a master plan — so he waits to add walls until he figures out what he needs. That’s just one of his more radical ways of thinking. We were pleased and he was pleased that we asked him questions that he had never been asked before about how to live, about spirituality, parenting, and architecture. This conversation is full of surprises, and we hope you enjoy it.

Links:

Useful Not True

How to Live

For more from Derek, check out his website or follow him on Instagram and Twitter


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