My First Million
The best business ideas come from noticing what's working and doing it better, faster, or for a different audience.
Risk Perception Changes with Experience
Experienced entrepreneurs perceive less risk in activities they've done repeatedly, while others see the same activities as highly risky
Decision Rule
When evaluating 'risky' opportunities, ask whether your risk assessment is based on inexperience or genuine danger
How It Works
Repeated exposure to business acquisition, deal-making, or specific industries creates pattern recognition that reduces perceived uncertainty
Failure Modes
Overconfidence from past success in different contexts
Dismissing legitimate new risks due to familiarity bias
Assuming others share your risk tolerance
Example Decision
“Experienced acquirer sees buying 10 magazines for $5M as low-risk because they know the value unlock playbook, while first-time buyer sees it as extremely risky”