I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny)
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What is the main topic discussed in this episode?
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 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 CEO of Tiny, a holding company that's often called the Berkshire Hathaway of the Internet. They own over 40 businesses, ranging from Dribbble to WiiCommerce to the AeroPress Coffee Maker, and they focused 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 $1 billion a week. 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.
What is Andrew Wilkinson’s “fish where the fish are” framework for spotting high‑margin niches?
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.com. 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, misgrowth. 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 big 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, Incident I.O. and Zip use Sauce. One enterprise uncovered a product gap that unlocked $16 million ARR. Another caught a spiking issue and prevented millions insurance. You can too at sauce.app slash. 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 CXN 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.
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Chapters
8 chapters
1
What is the main topic discussed in this episode?
0:00–1:46
2
What is Andrew Wilkinson’s “fish where the fish are” framework for spotting high‑margin niches?
1:46–20:09
3
How can founders avoid the common mistake of chasing overly‑crowded business ideas?
20:09–31:57
4
Why does Andrew say that boring, low‑competition ideas are often the most profitable?
31:57–45:10
5
What are the pros and cons of bootstrapping versus raising venture capital according to Andrew?
45:10–55:28
6
How does Tiny evaluate and acquire companies in under 15 minutes using Buffett‑style moats?
55:28–1:09:09
7
What lessons has Andrew learned about hiring and managing people in his portfolio companies?
1:09:09–1:22:17
8
Which AI tools and agents does Andrew use daily to automate his work and life?
1:22:17–1:28:24
Speakers
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