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

You don't want to walk into the gym on day one and try and deadlift three hundred pounds. So when someone comes to me and they're a first time entrepreneur and they say, I'm gonna make the next great AI company, I think that is the equivalent I feel like you've actually started and run more companies. Than maybe anyone else in the world. What is your best advice for coming up with a great startup idea? Charlie Munger, Warren Buffett's longtime business partner, has this amazing quote Fish where the fish are. 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. It's so funny to watch you on Twitter. Clearly you've become AI obsessed. It's like having the world's most reliable employee who costs two hundred dollars a month and works twenty-four-seven. So many knowledge work jobs are going to change massively. I think the fundamental question is do all jobs just become a single prompt? Today my guest is Andrew Wilkinson. Andrew is the co-founder and CO of Tiny, a holding company that's often called the Berkshire Hathaway of the Internet. They own over 40 businesses, ranging from dribble to Wommer to the AeroPress Coffee Maker. And they focus on buying profitable businesses from founders and holding them for the long term.

Andrew and his co-founder bootstrap the business from zero to hundreds of millions of dollars in value, and Andrew personally was worth over one billion dollars at one point. In our wide ranging conversation, we cover a bunch of strategies for coming up with a good business idea, what common business ideas you should avoid, his experience automating much of his work and life, Using AI and what that means for employment in the near future. Also what he's learned about happiness and money and how they are not directly related. And also how getting diagnosed with ADHD and then taking SSRIs was the thing that most impacted his happiness in life. This is both a powerful and also a very tactically useful conversation, and I'm really excited for you to hear it. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you get a year free of a bunch of amazing products.

Including Bolt. Linear, superhuman, notion, perplexity, granola, and more. Check it out at Lenny's Newsletter dot com and click bundle. With that. I bring you. Andrew Wilkinson.

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