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

07/03/25
Source: Lenny’s Newsletter by Lenny Rachitsky. Read the original article

TL;DR Summary of Andrew Wilkinson’s Business and AI Insights

Andrew Wilkinson built a $300 million portfolio without venture capital by focusing on underrated, high-margin niches. He leverages AI agents to boost productivity and replace traditional assistants. His experience with ADHD medication transformed his mental clarity, highlighting the importance of brain chemistry over wealth. Looking ahead, human skills like humor will become valuable as AI automates knowledge work.

Optimixed’s Overview: Key Lessons from Andrew Wilkinson on Building Profitable Businesses and Embracing AI

Strategic Business Insights

Andrew Wilkinson, co-founder of Tiny, demonstrates how to build a successful business empire by focusing on overlooked markets rather than trendy sectors. His “fish where the fish are” philosophy advises entrepreneurs to target boring industries with high margins and little competition, such as software that streamlines government grant applications.

  • Bootstrapping over Venture Capital: Patient growth and natural business moats can create massive companies without sacrificing equity or control.
  • Hiring Philosophy: Employ people for their existing strengths rather than attempting to mold them, avoiding misaligned leadership and wasted resources.
  • People Management: If doubt arises about an employee’s fit, immediate action prevents long-term issues and team disruption.

Harnessing AI and Productivity Tools

Wilkinson embraces AI to replace traditional roles, using a stack of agents including Lindy, Replit, and Limitless that handle his full-time assistant’s tasks for a fraction of the cost. However, he notes the current AI tools are still in a “functional but clunky” phase, with mainstream adoption expected within five years.

  • AI Automation: Entire job categories are already being replaced, rewarding those skilled in technology.
  • Future Skills: As AI handles knowledge work, uniquely human traits such as humor, connection, and taste will gain prominence and economic value.

Mental Health and Personal Growth

Wilkinson candidly shares his journey overcoming anxiety and ADHD with the help of medication, which significantly improved his focus and productivity. He emphasizes that financial success alone does not cure anxiety; brain chemistry plays a crucial role in well-being.

  • ADHD Awareness: Approximately 30% of entrepreneurs have ADHD, influencing their working style and challenges.
  • Mental Health Management: Medication can transform mental clarity, likened to turning a “Times Square” brain into a “quiet library.”
  • Perspective on Wealth: Money is likened to “Europe for anxiety”—it relocates but does not eliminate stress.