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:*
1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices
2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)
3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”
4. Telltale signs you should shut down (or never start) that startup idea
5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication
6. His prediction that most knowledge work will be automated—and the skills to teach your kids now
*Transcript:* https://www.lennysnewsletter.com/p/ive-run-75-businesses-andrew-wilkinson
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*Where to find Andrew Wilkinson:*
• X: https://x.com/awilkinson
• 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
…References continued at: https://www.lennysnewsletter.com/p/ive-run-75-businesses-andrew-wilkinson
*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/._
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Lenny may be an investor in the companies discussed.
