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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)

Overview

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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)

Lenny's Podcast: Product | Career | Growth

2025/07/03
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

2025/07/03
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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...

Highlights

Andrew Wilkinson, co-founder of Tiny, has built a diverse portfolio of profitable businesses without venture capital, including well-known brands like Dribbble and AeroPress. Starting from humble beginnings as a barista and web designer, he's grown his ventures into a business generating close to $300 million in annual sales. In this conversation, he shares valuable insights on entrepreneurship, productivity, leadership, and the future of AI.
00:00
Andrew Wilkinson discusses AI's potential in transforming knowledge work
04:12
The best startup idea is something you're genuinely interested in, not just a popular trend.
10:07
Entrepreneurs should embrace 'lazy leadership' and focus only on what they love.
14:54
Startup ideas should connect to one's unique skills for an unfair advantage.
19:36
Entrepreneurs can now use AI to evaluate business ideas effectively.
25:32
'Bootstrap businesses can grow large without burning money, like my company reaching $300M revenue'
34:05
Serato is a leading DJ software firm with a unique unfair advantage
36:47
A sign to fire someone is having even one thought of doing so
45:10
Lindy.ai helps automate complex calendar tasks and reduces inbox volume by 20%.
49:30
The Limitless device helps with self-reflection in relationships and parenting by recording daily interactions.
55:37
By 2027, AI models will be smarter than all PhDs
58:22
AI prompting may replace traditional coding, opening new career paths
1:05:29
Wealth doesn't guarantee happiness as even billionaires struggle with anxiety and comparison
1:12:44
Starting an SSRI was described as turning down the volume on a negative inner voice and going from a chaotic to a quiet mind.
1:24:41
Andrew recounts approaching Steve Jobs at 17 and getting candid advice.

Chapters

Introduction to Andrew Wilkinson
00:00
Finding the right business idea
04:07
Avoiding common business pitfalls
07:18
Finding your unfair advantage
11:58
Fish where the fish are
17:08
Why boring is good
20:08
Bootstrapping vs. venture capital
25:30
Lessons from acquiring and managing businesses
31:20
Avoiding people problems
36:47
Leveraging AI in business and life
42:39
The Limitless device
49:30
Job displacement and AI’s future impact
53:13
Advice for new grads
58:20
Parenting in the age of AI
1:02:50
The pursuit of happiness beyond wealth
1:05:26
Mental health and medication
1:10:10
Lightning round and final thoughts
1:16:45

Transcript

Andrew Wilkinson: You don't want to walk into the gym on day one and try and deadlift 300 pounds. So when someone comes to me and they're a first-time entrepreneur and they say, I'm going to make the next great AI company, I think that is the equivalent. ...