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Inside Podcasting


Sep 25, 2019

In this episode, Skye interviews entrepreneur and angel investor Jason Calacanis. Jason, who is Skye's boss, also hosts two podcasts, This Week in Startups and Angel. Before this interview was recorded, Jason told Skye she could ask him anything — and she took him up on that. The pair discuss: 

  • Jason's rollercoaster childhood;
  • What drove him to get out of Brooklyn;
  • The wild ups and downs of his entrepreneurial career;
  • How he got into podcasting;
  • Why a network TV show featuring Jason was axed;
  • Why Skye thinks Jason is just a teensy bit Trumpian;
  • His favorite podasts.

Watch Jason practice Taekwondo as a wee young man here

And get in touch:

Host Skye Pillsbury on Twitter @skyepillsbury

Guest Jason Calacanis on Twitter @Jason

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