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

Overview

Andrew Wilkinson, co-founder of Tiny, shares his journey from running 75+ businesses to building a $300M revenue portfolio without venture capital. He discusses strategies for identifying high-margin niches, leveraging AI for productivity, and navigating personal challenges like anxiety and ADHD. The episode also explores the future of work in an AI-driven world and the pursuit of happiness beyond financial success.

Notable Quotes

- Fish where the fish are. Walk off into the forest and find a small fishing hole with lots of fish and very little competition. – Andrew Wilkinson, on finding profitable niches.

- It's like having the world's most reliable employee who costs $200 a month and works 24/7. – Andrew Wilkinson, on the transformative power of AI agents.

- Easy choices, hard life. Hard choices, easy life. – Andrew Wilkinson, on making tough decisions for long-term success.

🎯 Finding the Right Business Idea

- Avoid Overcrowded Markets: Wilkinson emphasizes the importance of targeting niches with low competition. He advises against starting trendy businesses like cafes or bars, which are often over-saturated and low-margin.

- Start Small and Simple: First-time entrepreneurs should focus on straightforward businesses to build confidence and skills. Wilkinson’s first success was a web design agency, which provided immediate positive feedback.

- Boring is Profitable: Businesses like pest control or form-filling software may seem dull but often have high margins and low competition.

🤖 Leveraging AI for Productivity

- AI Stack: Wilkinson uses tools like Lindy for automating email and scheduling, Replit for coding, and Limitless for recording and analyzing daily interactions.

- Custom AI Agents: He has built workflows to manage emails, schedule meetings, and even suggest people to meet when traveling. These agents have replaced his assistant and streamlined his operations.

- AI in Personal Life: Wilkinson uses AI to track promises, manage his calendar, and even analyze arguments with his partner for better communication.

💡 Lessons from Acquiring and Managing Businesses

- Focus on Moats: When acquiring companies, Wilkinson looks for strong brands, network effects, or high switching costs that make businesses resilient. Examples include Letterboxd and Aeropress.

- Lazy Leadership: He advocates for delegating tasks you dislike and hiring CEOs whose instincts align with the business’s needs.

- People Problems: Wilkinson stresses the importance of hiring the right people and quickly addressing toxic behavior. He uses AI to screen for potential red flags in candidates.

📉 The Future of Work and AI’s Impact

- Job Displacement: Wilkinson predicts significant changes in knowledge work as AI becomes more advanced. He believes most jobs could eventually be reduced to a single prompt.

- Advice for New Grads: Focus on mastering AI tools to stay competitive. He compares the current phase of AI to the Palm Pilot era before the iPhone revolutionized mobile tech.

- Emerging Opportunities: In a world of abundance, new jobs may emerge around human connection, creativity, and unique skills like humor or companionship.

🧠 Mental Health and the Pursuit of Happiness

- Money ≠ Happiness: Wilkinson shares how achieving financial success didn’t alleviate his anxiety. He reframed his goals to focus on philanthropy and reduced his material possessions.

- Medication for Mental Health: Diagnosed with ADHD and anxiety, Wilkinson found relief through SSRIs and ADHD medication, which he credits for transforming his mental state.

- ADHD in Entrepreneurs: He highlights the prevalence of ADHD among entrepreneurs and encourages others to get tested, as understanding the condition can improve both work and personal life.