5 • 1.5K Ratings
🗓️ 3 July 2025
⏱️ 88 minutes
🧾️ Download transcript
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
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Where to find Andrew Wilkinson:
• LinkedIn: https://www.linkedin.com/in/awilkinson/
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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-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/
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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
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Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email [email protected].
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Lenny may be an investor in the companies discussed.
Click on a timestamp to play from that location
0:00.0 | You don't want to walk into the gym on day one and try and deadlift 300 pounds. |
0:05.0 | So when someone comes to me and they're a first-time entrepreneur and they say, |
0:08.0 | I'm going to make the next great AI company, I think that is the equivalent. |
0:13.0 | I feel like you've actually started and run more companies than maybe anyone else in the world. |
0:17.0 | What is your best advice for coming up with a great startup idea? |
0:24.7 | Charlie Munger, Warren Buffett's longtime business partner, has this amazing quote, |
0:30.3 | Is where the fish are? The biggest mistakes I've made have been going into business models where other people have repeatedly failed and thinking, I can do this better. It's so funny to watch you |
0:35.4 | on Twitter. Clearly, you've become AI-obsessed. |
0:37.9 | It's like having the world's most reliable employee who costs $200 a month and works 24-7. |
0:43.9 | So many knowledge work jobs are going to change massively. |
0:48.0 | I think the fundamental question is, do all jobs just become a single prompt? |
0:53.7 | Today, my guest is Andrew Wilkinson. |
0:56.2 | Andrew is the co-founder and CEO of Tiny, a holding company that's often called the Berkshire |
1:00.6 | Hathaway of the Internet. |
1:02.1 | They own over 40 businesses ranging from dribble to Wee Commerce to the Aeropress Coffee Maker, |
1:07.3 | and they focused on buying profitable businesses from founders and holding them for the long term. |
1:11.6 | Andrew and his co-founder bootstrapped the business from zero to hundreds of millions of dollars in value, |
1:16.6 | and Andrew personally was worth over $1 billion at one point. |
1:19.6 | In our wide-ranging conversation, we cover a bunch of strategies for coming up with a good business idea, |
1:24.6 | what common business ideas you should avoid, his experience automating much of his work and life using AI, and what that means for employment |
1:32.6 | in the near future. |
1:34.0 | Also what he's learned about happiness and money and how they are not directly related, |
... |
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