We share why Jesse Itzler’s nonlinear path—music, aviation, endurance, ownership—works because it’s guided by better questions, not a stricter plan. The takeaway is simple: stack experiences, build culture before profit, and design a life that lets you choose.
• unconventional career arcs that compound into advantage
• running business like an ultra marathon
• culture as a performance multiplier
• humility as an operating system for learning
• identity stacking across work, family, sport, creativity
• freedom and optionality over status and valuation
• permissionless action through small, repeatable experiments
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