Small Bets, Big Follow-Through

A discussion on investment strategy focusing on making initial small bets but going all-in when you spot winners, inspired by Chris Sacca's approach.

Core Investment Philosophy

• Make small initial bets to test opportunities
• When you find a winner, follow-on aggressively
• In technology, winners get extremely big
• Better to have amazing returns or zero than mediocre returns

Chris Sacca Example

• Started with $25k law school money
• Day traded during dotcom boom
• Turned $25k into $10M, then lost $4M
• Key insight: When he spotted Twitter's potential
  • Quit his job to focus on Twitter's growth
  • Personally fundraised despite not being part of the company
  • Bought $1B of Twitter stock pre-IPO
  • Became one of largest shareholders at IPO

Risk Tolerance Approaches

• Conservative Approach (Sam Parr)

  • Higher chance of being "pretty good"
  • More balanced portfolio
  • Lower risk tolerance

• Aggressive Approach (Shaan Puri)

  • Higher chance of being "amazing or zero"
  • Makes larger bets
  • Comfortable with potential losses
  • Philosophy: "If I went to zero today, I'd be back in 3 years"

Mindset Shift

• Act like someone with $100M
• Make decisions without money worry
• Take larger bets than your current bankroll
• Be more active in investing
• Remove "invisible handcuffs" limiting bold moves
• When you see something works, be aggressive in approach