I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
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:
- The “fish where the fish are” framework for spotting high‑margin niches no one else notices
- The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)
- How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”
- Telltale signs you should shut down (or never start) that startup idea
- His journey from crippling anxiety to clarity through SSRIs and ADHD medication
- His prediction that most knowledge work will be automated—and the skills to teach your kids now
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Where to find Andrew Wilkinson:
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Where to find Lenny:
- Newsletter: https://www.lennysnewsletter.com
- X: https://twitter.com/lennysan
- LinkedIn: https://www.linkedin.com/in/lennyrachitsky/
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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
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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-
