Andrew Wilkinson
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea., covering product design, startup building, and AI product work.
Episode
I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
Summary
Co-founder of Tiny, who has built and acquired 75+ businesses, argues that most entrepreneurs choose the wrong ideas by pursuing glamorous, crowded markets instead of boring niches. He walks through Charlie Munger's 'fish where the fish are' principle, explains why he bootstrapped to nearly $300M in revenue without VC, and shares how he built an elaborate AI agent system using Lindy to manage his inbox, calendar, and decisions.
Key Takeaways
Follow Munger's 'fish where the fish are': find niches where almost nobody wants to compete (pest control software, government forms) rather than glamorous markets where everyone plays.
First-time entrepreneurs should build small, simple businesses to develop operational muscle before swinging at big ideas.
You don't need VC funding to build a large business. Tiny bootstrapped to nearly $300M in revenue by choosing businesses that don't require burning millions before profitability.
Andrew's multi-agent email system reduces his inbox by 50% through a chain of agents: one filters noise, one flags urgencies, one summarizes decisions, one drafts replies.
AI is like having the world's most reliable employee for $200/month who works 24/7. Companies and individuals who embrace this aggressively will have a massive advantage.
Notable Quotes
“Well, it goes back to my gym analogy of if you're going to deadlift 300 pounds, trained for 15 years, you should have already had three startups and they should have worked and you've really built up the reps. And I think that if I was going to start Instacart, that's different than someone who's 20 starting it. Not that I would be good at it, but at least I would know what I'm getting into.”
“Well, I've also found people will shoot themselves in the foot. If I tell them an idea in a board meeting and I say, "I really need you to try this," it never works because usually they sandbag it, right? They don't really put their heart into it or they're just placating me and they don't want it to work. They want their idea to work. And so I've learned not to do that.”
“Okay. So it'd say, "Okay, you email Lenny, he lives in Marin." It puts in the database you live in Marin. And then next time I travel to the Bay Area, the agent will see two weeks before and it'll say, "I saw you're going to San Francisco. Here's all the people in San Francisco you should try and have coffee with." Right? So just all these things that-”