The Pathless Path with Paul Millerd

Billy used to be an avid skier, working odd jobs and traveling between the northern and southern hemispheres trying to catch the best skiing. In 2018 he e-mailed Ryan Holiday and pitched him on doing some work for him for free. In a couple of months, he was hired as Ryan's research assistant.  Billy is one of the most curious people I know and we dive into his journey.

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⌛TIMESTAMPS
  • (00:56) - The scripts Billy grew up with
  • (13:45) - Reaching out to Ryan Holiday
  • (17:52) - The research process and learning from Ryan
  • (25:21) - Skiing, Australia and finding his own voice
  • (40:23) - Animal courtship
  • (43:42) - How Ryan Holiday manages his team
  • (51:42) - Ambition and learning from past models
  • (01:03:10) - Downsides to fame
  • (01:04:01) - Where can we find Biilly?

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What is The Pathless Path with Paul Millerd?

The Pathless Path is hosted by Paul Millerd - a writer, creator, and consultant. He has conversations with freelancers, self-employed entrepreneurs, creators, and vagabonds who share their perspectives on their relationship with work, burnout, bootstrapping, indie hacking, remote work, reinvention, creativity, sabbaticals, leisure, self-employment, unconventional living, and digital nomadism. Past guests include Ali Abdaal, Russ Roberts, Kevin Kelly, Khe Hy, David Senra, Derek Sivers, Joe Hudson, Luke Burgis, Ben Hunt, Dan Vassallo, Steph Smith, Alex Pang, Visakan Veerasamy, Michael Ashcroft, Kyla Scalon, Trung Phan, Justin Welch, and more.