The Pathless Path with Paul Millerd

This episode is with Sky King, the founder of Modern Stoa, a podcast advertising company for podcasters.  His path is fascinating - he grew up in Hawaii, rarely wore shoes, was heavily influenced by Asian culture, had a father who was retired, and somehow ended up in a massive corporation right after college.  In 2016. he became fascinated by how the media was shaping the 2016 US election and decided it was time to act.  From a cold email to Ryan Holiday to helping build Aubrey Marcus' podcast, Sky was on his way.  His long-term vision is to build an alternative to traditional advertising in audio.
We talk about this and a lot more including:
  • Why he quit a good job to work at a smoothie bar
  • How a cold email to Ryan Holiday changed his life
  • Growing up in Hawaii
  • Serendipitous events that lend to him moving to Austin
  • The future of Audio
Links Mentions
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Timestamps
  • 1:41: Intro to Sky and where his name came from
  • 5:03: Sky's influences growing up
  • 11:34 Why he went to the corporate world
  • 17:12 Cold emailing Ryan Holiday & vision for 
  • 19:47 Sky's "quake moment"
  • 25:15 Moving to Austin and working for Aubrey Marcus
  • 30:44 Sky's desire to help people 
  • 32:55 Growing up in Hawaii
  • 36:10 Going to China at 10
  • 39:30 Everything anywhere all at once reflections
  • 44:40 The "true default path"
  • 47:30 Hiring someone & responsibility
  • 48:30 "what are you uniquely positioned to do?"
  • 49:20 Advertising Subsidy & Media incentives
  • 57:20 Meme farming & future of audio
  • 1:01:30 Bucky Fuller & specialization
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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.