#26 Andrew Wilkinson: Never Enough? Barista → 40+ Businesses & Tiny

Andrew Wilkinson joins Lydia to talk about the philosophy of “enough,” when to raise VC vs bootstrapping, his recent ADHD discovery (and why it became a founder superpower), finding the right partner, how he uses AI day-to-day, and legacy. Andrew built Tiny, the buy-and-hold collection behind Dribbble, AeroPress and 40+ “boring” businesses — often called the Berkshire Hathaway of the internet. This is a conversation about choosing the unsexy path, building with people you trust, and designing a life big enough for both curiosity and contentment.

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