The HigherUp Podcast Jesse Itzler: The Two Rules That Create Life-Changing Opportunities | The HigherUp Podcast Ep. 72
8 snips
Jan 29, 2026 
Jesse Itzler, entrepreneur, investor, endurance athlete and author, shares his annual Masogi challenges and the Ten Inning Game philosophy. He talks about using scary, earned goals to build identity and resilience. He explains time management by seasons, graceful ways to say no, and small gestures that create huge networking edges.
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Handwritten Notes Trump DMs
- Do use handwritten notes and surprising gifts to stand out because they get read and remembered.
- Do allocate minutes daily or yearly for sincere, physical outreach to deepen relationships.
Making Big Meetings Memorable
- Jesse recalled walking into rare, make-or-break meetings fully aware of their magnitude.
- He used memorable stunts, like wearing a wig, to create surprise and be unforgettable in pivotal moments.
Extra Inning Wins Over Time
- The 'ten-inning game' is consistency plus extra effort beyond basics everyone does.
- Small, repeated extra actions compound into a unique reputation and advantage over time.
