Today’s guest, Jason Calacanis, joins host Chuck Feerick to talk about his new book “Angel”, what it takes to be a successful angel investor, and a variety of other topics.

Jason is a technology entrepreneur, angel investor, and the host of two very popular podcasts, This Week in Startups and Angel. He got his start in the world of startups in New York and his second company, Weblogs inc., was sold to AOL in 2005, after which Jason became a “scout” for top-tier Silicon Valley venture capital firm Sequoia Capital. Since then, Jason has gone on to launch numerous ventures and is currently the founder of a series of conferences that bring entrepreneurs together with potential investors, frequently appears in the media, and most notably is a successful angel investor in over 100 companies, including both Thumbtack and Uber.

In this episode, Chuck and Jason discuss:

  • Jason’s earliest role in New York with Silicon Alley reporter and what he learned about entrepreneurship in that process
  • Jason’s first angel investment
  • Why Jason decided to write a book, why now, and why he wants to give away all his best practices and secrets
  • Where Jason says it is most important to be located geographically to be a great angel investor
  • When meeting with a founder, what Jason believes are the most important things an aspiring angel should ask
  • What Jason feels is the best way that angel investors can be helpful to their portfolio companies
  • If Jason thinks that angel investors should stick to investing in the industries they know (e.g. should a doctor only invest in healthcare)?
  • Regarding startup crowdfunding platforms, whether or not Jason feels these platforms are the best place for an angel investor to start and if some are better or safer than others
  • What Jason thinks about ICOs
  • What book, besides Angel, Jason thinks everyone should read
  • Which of Jason’s investments he is most excited about right now

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Episode 40: Bonus Episode – Jason Calacanis: Entrepreneur, angel investor, and author of “Angel”


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