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Ever wonder how someone goes from brewing coffee to running 40+ businesses? Andrew Wilkinson did just that. In this conversation, he reveals why chasing “enough” nearly burnt him out—and how ADHD became his founder superpower. Andrew is the co‑founder of Tiny and author of Never Enough. We explore his journey from barista to building a global portfolio, when to bootstrap vs. raise capital, the mental models he lives by, and how he thinks about partnership, AI and legacy. By the end, you’ll see why Tiny is often called “the Berkshire Hathaway of the internet.” If you enjoyed this, you might also like our conversation with Derek Sivers on reinventing yourself. • Whatever Scares You—Go DO It | Derek Siver... Listen on Spotify: https://open.spotify.com/show/2DOHX3D... Follow us on Instagram: / escape9to5_pod Where to find Andrew: Tiny (Andrew’s company): https://www.tiny.com Andrew on Instagram: https://www.instagram.com/awilkinson/... Andrew on X: https://x.com/awilkinson on YT: @NeverEnoughPod Timestamps 00:00 Intro 01:49 Two Truths & a Lie – Meeting Steve Jobs 10:39 What Now – Current Focus 15:47 How to Start a Business: Bootstrapping vs VC 25:26 Having Enough & ADHD 33:19 Chris and Zoe — The People on the Journey 40:56 How Andrew Uses AI 49:29 Legacy & Letting Go 57:48 Lightning Round Take the 30-second “Escape 9-to-5” quiz: https://tally.so/r/nG7ZbQ I’m Lydia — ex-banker turned climate-tech founder and podcast host. Escape 9-to-5 is where we explore stories of people who left the default path to build lives of freedom, impact and authenticity. 🌱 #AndrewWilkinson #Tiny #BoringBusinesses #ADHD #VC #Bootstrapped #Entrepreneurship #Escape9to5 🎙 Tools Used to Record This Episode 🎙 Record with Riverside: https://www.riverside.fm/?via=lydia-chen 🎥 DJI Camera: https://dji-retail.co.uk/r?id=38ff4g 🎬 Edit with CapCut Pro (7-day free trial): https://www.capcut.com/capcut_pc_web/... 🎵 Epidemic Sound (free music trial): https://www.epidemicsound.com/campaig... 🧠 Notion for episode planning: https://www.notion.com/product?utm_so... --- 🌱 Other Tools I Recommend 📚 Part-Time YouTuber Academy (PTYA): https://go.aliabdaal.com/ptya?ref=lyd... 🧠 LifeOS by Ali Abdaal: https://aliabdaal.com/lifeos/ref/lydi... 🧘♀️ Psycle London Starter Kit: https://psyclelondon.com/pages/regist... 🚲 SoulCycle Invite: https://www.soul-cycle.com/r/7mBwe8c8/ 💪 ClassPass (£1 trial + 20 credits): https://classpass.com/refer/STTVGMC52... (Some of these are affiliate links — thank you for supporting my channel!) --- 🌍 **Website**: https://www.lydiaclinzi.com 📸 **Instagram**: / lydiachenlinzi 🎯 About the Podcast Escape 9 to 5 is for people who’ve left corporate life behind and never looked back. We talk about risk, reinvention, and what it takes to build a life you don’t need a vacation from. Let’s grow and glow together 🌱✨ © 2025 Lydia C. Linzi. All Rights Reserved.