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I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)

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Jul 3, 2025

Guest

Andrew Wilkinson

Andrew Wilkinson, co-founder of Tiny, shares his journey from teenage barista to billionaire entrepreneur. He discusses the importance of spotting high-margin niche opportunities and emphasizes starting small to build confidence. The conversation highlights his efficient use of AI tools that act as personal assistants, alongside his thoughts on the future of work. Wilkinson openly addresses the link between mental health and happiness, advocating for discussions around ADHD and medication. He even recounts a memorable encounter with Steve Jobs, offering unique entrepreneurial insights.

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Episode notes

00:00 / 00:00

Start Simple to Build Success

Start with simple businesses where you can achieve early success and positive feedback.
Avoid complex, highly competitive businesses as a beginner to build confidence and muscle gradually.

00:00 / 00:00

Bootstrapped Businesses Can Scale Big

Bootstrap businesses can scale to hundreds of millions without venture capital.
Choose businesses with moats and low competition for sustainable growth without burning cash.

00:00 / 00:00

Hire for Ability, Cut Quickly

Hire carefully to avoid difficult people, cutting ties immediately if doubts arise.
Hire for current ability rather than potential; people rarely change fundamentally.

Get the Snipd Podcast app to discover more snips from this episode

Finding Niche Startup Opportunities

04:17 • 18min

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Navigating Business Models: Insights and Missteps

22:38 • 18min

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Navigating Job Roles and Embracing AI for Efficiency

41:07 • 3min

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Harnessing Automation for Efficient Productivity

44:10 • 4min

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Harnessing AI for Productivity and Growth

48:03 • 17min

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Money, Happiness, and Mental Health

01:05:17 • 17min

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Exploring Favorites: Movies, Innovative Products, and Life Lessons

01:22:24 • 2min

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An Unexpected Encounter with Steve Jobs

01:24:08 • 4min

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The Laws of Human Nature

Robert Greene

In 'The Laws of Human Nature,' Robert Greene delves into the complexities of human behavior, identifying 18 laws that govern our actions and motivations. Drawing from historical figures such as Pericles, Queen Elizabeth I, and Martin Luther King Jr., Greene provides insights into how to detach from emotions, master self-control, develop empathy, and see beyond people's masks. The book is designed to help readers become better judges of character, manage their thought patterns, and influence others more effectively. It emphasizes the importance of self-awareness and understanding one's own flaws to make better decisions in personal and professional life.

How to Get Rich

Felix Dennis

In 'How to Get Rich,' Felix Dennis shares his insights and experiences on building wealth. The book is distinct from other self-help or get-rich-quick guides as it emphasizes the importance of hard work, calculated risks, and ownership. Dennis discusses the necessity of execution over great ideas, the role of luck, and the need to overcome fear and embarrassment of failure. He also highlights the importance of maintaining control over one's business and the sacrifices required to achieve significant wealth. The book is known for its blunt and practical advice, reflecting Dennis's own journey from a college dropout to a multi-millionaire.

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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Brought to you by:

Sauce—Turn customer pain into product revenue

Enterpret—Transform customer feedback into product growth

Miro—A collaborative visual platform where your best work comes to life

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Where to find Andrew Wilkinson:

• X: https://x.com/awilkinson

• 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 podcast@lennyrachitsky.com.

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Lenny may be an investor in the companies discussed.

This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe

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