Shane Battier and Ravi Gupta dive deep into the art of risk-taking. They explore when to "swing big" versus playing it safe, drawing from Shane's NBA career and Ravi's venture capital experience. The duo discusses earning the right to take risks, avoiding financial and opportunity ruin, and why standing pat can sometimes be the riskiest move of all. From basketball strategy to startup decisions, they break down how to evaluate upside potential, overcome loss aversion, and separate identity from outcomes. Plus, practical advice on lifestyle choices, the "nobody cares" principle, and why great stories never start with "I went home after dinner."