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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:

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

Some of my biggest takeaways:

1. Fish where the fish are, not where the fishermen are. The best opportunities are in boring industries everyone ignores—like form-filling software that makes $30M/year helping people access government grants. Sexy businesses (cafes, restaurants, news) attract infinite competition and razor-thin margins.

2. AI has already replaced entire job categories—but only for the technically savvy. Andrew’s AI agents handle 100% of what his full-time assistant did for $200/month. But we’re in the “Palm Trio phase”—functional but clunky. The iPhone moment (when everyone can do this) is still five years away.

3. ADHD affects 30% of entrepreneurs (vs. 5% of the general population). Andrew discovered that his ADHD explained his “inch-deep, mile-wide” approach and difficulty with routine tasks. Medication transformed his brain from “Times Square to a quiet library.” Many entrepreneurs’ superpowers and struggles stem from undiagnosed ADHD.

4. If you ever think “Should I fire this person?” even once—fire them immediately. In Andrew’s experience, superstars are irreplaceable and you’d be lost without them. But the moment doubt creeps in, it’s already over. You have 6 to 12 months before it implodes; cut now and save everyone the pain.

5. Bootstrapped businesses can become huge companies. The only difference between bootstrapping and VC is tolerance for burning money. If you choose businesses with natural moats and patient growth, you can build massive companies without giving up equity or control.

6. Money is just “Europe for your anxiety.” At 20, Andrew thought moving to Europe would fix his problems—but he was still anxious, just in Europe. Same with money: whether he had $20M or $300M in revenue, the stress was identical. Even multi-billionaires compare themselves to Bezos and feel poor.

7. In an AI-abundant future, being funny might be a job. As AI handles all knowledge work, uniquely human skills become valuable—humor, connection, taste. The person who can make you laugh or motivate you to exercise might be the new high-status profession. We’re already seeing this with OnlyFans, but for human connection.

8. Hire for what people already are, not what you hope to coach them into. “To a man with a hammer, everything looks like a nail.” When Andrew hired a CEO who loved enterprise sales for a business that needed organic marketing, guess what happened? People do what they tell you they’ll do.

9. Money doesn’t fix anxiety—brain chemistry does. After reaching billionaire status, Andrew was “still just as anxious as ever.” A tiny SSRI did more for his mental state than any amount of success. If you’d take Tylenol for a headache, why not treat the anxiety that’s actually ruining your life?

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

• 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.