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October 30, 2023 62 mins

Two years ago, Jake Lenok couldn't take it anymore. After three years of misery working odd behind-the-scenes jobs at ESPN, Jake took a lifeline from a close friend. An offer to a better life -- a life full of more meaningful work, more work-life balance, more money, and most importantly, more freedom.

Sitting together in his South Beach condo, Jake walks me through the tough decision to leave the industry he loved, how he landed in finance, his decision to move to Miami earlier this year, how he's made the most of his significant salary increase, and more:

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TOPICS:

  • Intro (00:00)
  • Moving to Miami (01:41)
  • How his life has improved since leaving ESPN (06:31)
  • Finance bro life and the stereotypes (21:56)
  • Keeping ambition when you're already winning (27:30)
  • Why you should disregard your family's wishes when making a big decision (30:30)
  • Why flaky people suck (38:38)
  • Saying hi to strangers (40:13)
  • How to have more confidence (47:56)
  • His struggles with complacency (52:30)
  • If I'll consider living in Miami (56:13)


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