Glue Guys

Earning the Right to Take Risks - [Glue Guys, EP.50]

68 snips
Aug 14, 2025
Risk-taking is an art, and the discussion dives into how to assess when to go for it versus playing it safe. With insights from the NBA and venture capital, they explore how to earn the right to take risks while avoiding financial pitfalls. Listeners learn why standing still can be the riskiest choice of all. Personal stories delve into navigating career changes, the psychological barriers of loss aversion, and the importance of viewing identity beyond job titles. Plus, practical tips on embracing calculated risks and the art of storytelling make this a thought-provoking listen.
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INSIGHT

Earn The Right Before Big Swings

  • Earn the right to swing big by building education, skills, or downside protection first.
  • Realistically model your fallback earnings and avoid catastrophizing the worst-case scenario.
ADVICE

Model The Downside Realistically

  • Calculate how much you would realistically earn if a new risky move fails and plan accordingly.
  • Treat big moves as reversible moves rather than permanent exits to reduce fear and improve decision-making.
ANECDOTE

Draft Capital Buys Leeway

  • Shane used draft status and guaranteed contracts as runway to expand his game early in his career.
  • Lower draft capital or shorter leash requires proving value before taking risky plays on court.
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