I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)Andrew Wilkinson shares how he used AI to replace his assistant, why boring businesses beat sexy ideas, why you need to fish where the fish are, and how he lost $10m
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Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital. In this conversation, you’ll learn:
Some of my biggest takeaways:
Where to find Andrew Wilkinson: • LinkedIn: https://www.linkedin.com/in/awilkinson/ Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ In this episode, we cover: (00:00) Introduction to Andrew Wilkinson (04:07) Finding the right business idea (07:18) Avoiding common business pitfalls (11:58) Finding your unfair advantage (17:08) Fish where the fish are (20:08) Why boring is good (25:30) Bootstrapping vs. venture capital (31:20) Lessons from acquiring and managing businesses (36:47) Avoiding people problems (42:39) Leveraging AI in business and life (49:30) The Limitless device (53:13) Job displacement and AI’s future impact (58:20) Advice for new grads (01:02:50) Parenting in the age of AI (01:05:26) The pursuit of happiness beyond wealth (01:10:10) Mental health and medication (01:16:45) Lightning round and final thoughts Referenced: • Andrew’s post on X with the Charlie Munger quote: https://x.com/awilkinson/status/1265653805443506182 • Metalab: https://www.metalab.com/ • Letterboxd: https://letterboxd.com/ • AeroPress: https://aeropress.com/ • Brian Armstrong on X: https://x.com/brian_armstrong • Warren Buffett’s quote: https://quotefancy.com/quote/931119/Warren-Buffett-I-am-a-better-investor-because-I-am-a-businessman-and-a-better-businessman • Flow: https://www.getflow.com/ • Instacart: https://www.instacart.com/ • Things: https://culturedcode.com/things/ • Dustin Moskovitz on LinkedIn: https://www.linkedin.com/in/dmoskov/ • Salesforce: https://www.salesforce.com/ • Serato: https://serato.com/ • Chris Sparling on X: https://x.com/_sparling_ • Lindy: https://www.lindy.ai/ • Replit: https://replit.com/ • Behind the product: Replit | Amjad Masad (co-founder and CEO): https://www.lennysnewsletter.com/p/behind-the-product-replit-amjad-masad • David Ogilvy: https://en.wikipedia.org/wiki/David_Ogilvy_(businessman) • Malcolm Gladwell’s website: https://www.gladwellbooks.com/ • Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder and CEO of StackBlitz): https://www.lennysnewsletter.com/p/inside-bolt-eric-simons • Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder): https://www.lennysnewsletter.com/p/building-lovable-anton-osika • Limitless: https://www.limitless.ai/ • Perplexity: https://www.perplexity.ai/ • Claude: https://claude.ai/ • ChatGPT: https://chatgpt.com/ • Gemini: https://gemini.google.com/app • William Gibson’s quote: https://www.goodreads.com/quotes/681-the-future-is-already-here-it-s-just-not-evenly • Palm Treo: https://en.wikipedia.org/wiki/Palm_Treo • Sam Altman on X: https://x.com/sama • Dario Amodei on X: https://x.com/darioamodei • Anthropic’s CPO on what comes next | Mike Krieger (co-founder of Instagram): https://www.lennysnewsletter.com/p/anthropics-cpo-heres-what-comes-next • Challengers on AppleTV+: https://tv.apple.com/us/movie/challengers/umc.cmc.53cuz33n4e74ixj8whccj87oc • Matic vacuum: https://maticrobots.com/ • Jerzy Gregorek’s quote: https://www.goodreads.com/quotes/8652595-hard-choices-easy-life-easy-choices-hard-life • Tiny: https://www.tiny.com/ • Dribbble: https://dribbble.com/ Recommended books: • The Laws of Human Nature: https://www.amazon.com/Laws-Human-Nature-Robert-Greene/dp/0525428143 • How to Get Rich: One of the World’s Greatest Entrepreneurs Shares His Secrets: https://www.amazon.com/How-Get-Rich-Greatest-Entrepreneurs/dp/1591842719 Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com. Lenny may be an investor in the companies discussed. You're currently a free subscriber to Lenny's Newsletter. For the full experience, upgrade your subscription. |
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