Andrew Wilkinson
Co-Founder & CEO at Tiny
Co-founder and CEO of Tiny, a holding company often called the 'Berkshire Hathaway of the internet' that owns 40+ businesses including Dribbble and AeroPress, bootstrapped from zero to hundreds of millions in value.
Dimension Profile
Key Themes
Episode Summary
Andrew Wilkinson, who built Tiny into a 40+ business holding company worth hundreds of millions, shares strategies for selecting good business ideas, including 'fishing where the fish are' and starting simple. He discusses his AI obsession and how it's transforming knowledge work, the disconnect between money and happiness he discovered after becoming a billionaire, and how getting diagnosed with ADHD and taking SSRIs had more impact on his happiness than wealth.
Leadership Principles
- → Fish where the fish are — don't enter business models where others have repeatedly failed thinking you'll be different
- → Don't try to deadlift 300 pounds on day one — first-time founders should start with simpler businesses
- → AI is like having the world's most reliable employee who costs $200/month and works 24/7
Notable Quotes
"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."
— On why first-time founders should start with simpler, more achievable businesses
"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."
— On the importance of choosing markets with proven success patterns
"It's like having the world's most reliable employee who costs $200 a month and works 24/7. So many knowledge work jobs are going to change massively."
— On AI's impact on knowledge work and business operations
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