Swing Big With Conviction

A discussion about making big moves when you have strong conviction, particularly in investments and business decisions. The key insight is that you only need to be right a few times if you bet big enough when you are.

Core Philosophy

• You'll only be right a few times in life - when you are, swing big
• Don't need to be right often if you make significant moves when you have conviction
• Focus on opportunities where you can see potential others might miss

Real World Example: Bitcoin Investment (2013)

• Recognized Bitcoin's potential early (around $80-90 per coin)
• Made significant investment (~few hundred thousand dollars)
• Held through ups and downs due to strong conviction
• Still holding today based on long-term belief in the technology
• Used tax implications as reason to avoid selling during highs

Decision Making Framework

• Look for opportunities that could be "way bigger"
• Don't need to risk everything - just enough to matter if you're right
• Hold through volatility if core thesis remains intact
• Learn from previous missed opportunities
• Use past experiences to inform future conviction plays

Example: Domain Names in the 90s

• Father recognized potential of domain names early
• Bought family name domain but didn't go further
• Could have bought valuable domains like poker.com, home.com
• Lesson learned: When you see potential, take significant action
• Used this lesson to inform later Bitcoin investment

Key Principles

• Recognize when you have unique insight
• Act decisively when you have strong conviction
• Don't need to risk everything - just enough to matter
• Hold through volatility if core thesis remains intact
• Learn from missed opportunities to inform future decisions