#26 - Barista to Billionaire: Andrew Wilkinson on Tiny, ADHD & Raising Money: When to Stop Chasing
Description
I loved this one. Andrew Wilkinson (co-founder of Tiny and author of Never Enough) and I ended up covering so much—business and life, habits and mental models. We talk about “enough,” when to raise VC vs. bootstrapping, his recent ADHD discovery and how it became a founder superpower, finding the right partner, how he uses AI day-to-day, and legacy. It’s easy to see why Tiny runs the way it does—long-term, buy-and-hold; people often describe it as the “Berkshire Hathaway of the internet.”
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Where to find AndrewTiny: https://www.tiny.comInstagram: https://www.instagram.com/awilkinson/X: https://x.com/awilkinson
What we cover– Two Truths & a Lie (including a chance meeting with Steve Jobs)– Leaving a web-design job and starting anyway– Bootstrapped vs. VC: which path, when, and why– ADHD (recently discovered) → how he works– The feeling of “never enough”—and reframing it– Building Tiny with Chris (why partnerships need real work)– AI in Andrew’s daily workflow– Legacy & giving—letting go– Lightning round: books, newsletters, habits
Timestamps00:00 Intro01:49 Two Truths & a Lie – Meeting Steve Jobs10:39 What Now – Current Focus15:47 How to Start a Business: Bootstrapping vs. VC25:26 Having Enough & ADHD33:19 Chris and Zoe — The People on the Journey40:56 How Andrew Uses AI49:29 Legacy & Letting Go57:48 Lightning Round
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About the show
I’m Lydia—ex-banker turned climate-tech founder and podcast host. Escape 9-to-5 explores stories of people who left the default path to build lives of freedom, impact and authenticity. Thanks for listening! 🌱
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