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

Andrew Wilkinson, co-founder and CEO of Tiny (a holding company often called the Berkshire Hathaway of the internet, owning 40+ bootstrapped businesses), discusses how to pick a startup idea, which business models to avoid, and why buying profitable businesses can beat starting them. The conversation also covers his hands-on use of AI agents, what AI might mean for knowledge-work jobs, and his candid experience with money, happiness, ADHD and medication.

01Key learnings

• Choose a business in an area you're genuinely interested in, but look for the unglamorous niche where competition is low, following the 'fish where the fish are' idea.
• Pick a first business that delivers a quick, simple win, since early success builds the confidence and narrative needed to keep going.
• Look for a unique edge (skills, background, or access to audiences) and pivot toward the most profitable customer segment for your idea.
• Avoid markets where many well-funded players have repeatedly failed; a strong team cannot fix a broken business model.
• Bootstrapped companies can scale large; prioritize businesses with moats like brands or network effects, and avoid head-to-head fights with venture-backed rivals.
• When hiring, select for people already fully formed for the role rather than hoping to coach potential, and cut underperformers quickly rather than hoping they improve.
• Use AI agents to automate personal and business workflows such as email triage, scheduling, research prep, and memory of past context, freeing time for higher-value work.
• Get checked for ADHD and anxiety if you struggle with focus or constant worry; treatment can dramatically improve quality of life, which wealth alone did not do for Wilkinson.

02Frameworks mentioned

Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.