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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Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billion at one point)—all without ever raising venture capital.

In this conversation, you’ll learn:

1. The “fish where the fish are” framework for spotting high‑margin niches no one else notices

2. The exact agent stack (Lindy, Replit, Limitless, and more) that supercharges Andrew’s day-to-day productivity (and has replaced his assistant)

3. How Andrew evaluates companies in less than 15 minutes using Buffett‑style moats and “lazy leadership”

4. Telltale signs you should shut down (or never start) that startup idea

5. His journey from crippling anxiety to clarity through SSRIs and ADHD medication

6. His prediction that most knowledge work will be automated—and the skills to teach your kids now

Some of my biggest takeaways:

1. Fish where the fish are, not where the fishermen are. The best opportunities are in boring industries everyone ignores—like form-filling software that makes $30M/year helping people access government grants. Sexy businesses (cafes, restaurants, news) attract infinite competition and razor-thin margins.

2. AI has already replaced entire job categories—but only for the technically savvy. Andrew’s AI agents handle 100% of what his full-time assistant did for $200/month. But we’re in the “Palm Trio phase”—functional but clunky. The iPhone moment (when everyone can do this) is still five years away.

3. ADHD affects 30% of entrepreneurs (vs. 5% of the general population). Andrew discovered that his ADHD explained his “inch-deep, mile-wide” approach and difficulty with routine tasks. Medication transformed his brain from “Times Square to a quiet library.” Many entrepreneurs’ superpowers and struggles stem from undiagnosed ADHD.

4. If you ever think “Should I fire this person?” even once—fire them immediately. In Andrew’s experience, superstars are irreplaceable and you’d be lost without them. But