Chris Guillebeau – Taking Your Side Hustle from Idea to Income


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Chris’s Wild Idea: To interview people who have had successful side hustles, and to publish a book and podcast about it.

Chris Guillebeau is the New York Times bestselling author of The $100 Startup, The Art of Non-Conformity, Born For This, and The Happiness of Pursuit. His latest book, Side Hustle, which debuts September 19th, shows how to take your side hustle from an idea to a profitable business.

In addition to being an incredible writer, Chris visited all 193 countries by age 35. He is all about living the life you want, and not the life others expect you to have. He shares why he doesn’t believe you have to quit your job unless you want to, plus his favorite productivity tools.

Listen to this Episode if

  • You want to quit your job.
  • You have or have thought about starting a side hustle.
  • You want to travel the world.
  • You’ve read The $100 Startup or any of Chris’s other books.
  • You want to monetize your hobby.

Key Takeaways

  • 4:30 – The first step to starting your side hustle.
  • 6:40 – What side hustles actually make money.
  • 8:30 – How to monetize a blog.
  • 11:40 – How to make your side hustle bigger.
  • 13:30 – What tools Chris uses to be extra productive.
  • 15:20 – What techniques Chris uses to move on from anxiety or sadness.
  • 17:20 – How to decide what’s next.
  • 20:00 – What other countries Chris would live in.
  • 21:45 – What stuff Chris always takes with him when he travels.
  • 22:40 – Why book tours are awesome.
  • 25:40 – Chris’s favorite books.
  • 27:00 – The struggle of Chris’s teenage years.

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