I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | 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.

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 $200 a month and works 24/7. 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 CEO of Tiny, a holding company that's often called the Berkshire Hathaway of the internet. They own over 40 businesses ranging from Dribble to WeCommerce 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 bootstrapped 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 LennysNewsletter.com and click Bundle. With that, I bring you Andrew Wilkinson. This episode is brought to you by Sauce. The way teams turn feedback into product impact is stuck in the past. Vague reports, static taxonomies, unactionable insights that don't move business metrics. The result? Churn, lost deals, missed growth. Sauce is the AI product co-pilot that helps CPOs and product teams uncover business impact and act faster. It listens to your sales calls, support tickets, churn reasons, and lost deals, surfacing the biggest product issues and opportunities in real time. It then routes them to the right teams to turn signals into PRDs, prototypes, and even code that drives revenue, retention, and adoption. That's why whatnot, Linktree, IncidentIO, and Zip use Sauce. One enterprise uncovered a product gap that unlocked 16 million dollars ARR. Another caught a spiking issue and prevented millions in churn. You can too at sauce.app/lenny. Sauce, built for AI product teams. Don't get left behind. This episode is brought to you by Interpret. Interpret is a customer intelligence platform used by leading CX and product orgs like Canva, Notion, Perplexity, Strava, Hinge, and Linear. To leverage the voice of the customer and build best in class products, Interpret unifies all customer conversations in real time, from Gong recordings to Zendesk tickets, to Twitter threads, and makes it available for your team for analysis and for action. What makes Interpret unique is its ability to build and update a customer specific knowledge graph that provides the most granular and accurate categorization of all customer feedback, and connects that customer feedback to critical metrics like revenue and CSAT. If modernizing your voice of customer program to a generational upgrade is a 2025 priority, like customer centric industry leaders like Canva, Notion, Perplexity, and Linear, reach out to the team at interpret.com/lenny. That's E-N-T-E-R-P-R-E-T.com/lenny. Andrew, thank you so much for being here, and welcome to the podcast.