Lead with Love® Podcast

Creativity. Business. Life.

Living the unconventional life with Chris Guillebeau

SUBSCRIBE   Apple Podcasts | Spotify | Amazon Music | Stitcher

If you’ve ever found yourself pursuing the unconventional path in life, this episode is for you.

In today’s conversation, I talk with Chris Guillebeau, the New York Times bestselling author of The $100 Startup (one of my favorite books), Side Hustle, and other books. During a lifetime of self-employment that included a four-year commitment as a volunteer executive in West Africa, he visited every country in the world (193 in total) before his 35th birthday. His daily podcast, Side Hustle School, is downloaded more than two million times a month.

Chris is someone that I really look up to in terms of the books he’s written (a total of 5, holy guacamole!) and how he shows up in the world. Giving a keynote at his World Domination Summit Event was one of the most impactful moments for me on my own entrepreneurial journey.

“Ideas don’t have value until you do something with them.”


What you'll hear (and don't want to miss!)

  • [5:28] How Chris developed the thread of non-conformity in his life and business
  • [7:58] Why he doesn’t like the word “balance” – and what he uses instead
  • [12:28] He says it’s an ongoing process, but what Chris does to stop comparing himself to others
  • [14:03] What inspired him to share openly about his breakdown
  • [18:28] How he feels about balancing criticism and connection – and why not everything you write has to land with everyone
  • [23:10] The way World Domination Summit started and his recommendations for someone looking to build a community from scratch
  • [25:58] How his podcast has contributed to the growth of his business, and what’s surprised him most about it
  • [33:58] The role that accountability has played in Chris becoming a published author and how it affects what he does today
  • [36:59] How and why he implements a live, in-person element to his book marketing strategy
  • [39:53] What Chris really wanted to be when he grew up and how it’s led to him leading an unconventional life
  • [46:42] What his team looks like today and why he’s unconventional in his approach with this too
  • [49:35] Why Chris says he never “unplugs” and what’s next for him in his journey
  • [52:16] The path to take if you want to speak at an event like World Domination Summit – and the one thing you should never ask

Resources + links mentioned:

» Chris Guillebeau

» Books

» World Domination Summit

» Side Hustle School Podcast

» Connect with Chris on Facebook, Instagram and Twitter!

» The Importance of Having a Breakdown

» Loving the Process Not the Product with Jonathan Fields

» 5 Simple Rules to Build Your Community with Heart with Jadah Sellner

» World Domination Summit Keynote with Jadah Sellner

» Love is the Killer App by Tim Sanders

» Playing Big by Tara Mohr

Key Quotes:

  • “It’s not like I’m anti-capitalist in any way, but I think there’s certainly room for, or even a necessity for, looking at different kinds of metrics.” [7:05]
  • “Just hearing about this convergence between something I’ve done and what other people are doing, that to me is motivating.” [9:53]
  • “Ideas don’t have value until you do something with them.” [19:26]
  • “I believe if you have the people, you can figure everything else out.” [22:44]
  • “As a young adult I felt like I had something to share, but it took a little while to figure out what was the medium and how I was going to do it.” [40:47]
  • “I tend to be much more successful when I’m doing most things on my own, and that’s what I keep doing.” [46:33]

Show some love

Did you love this episode? Reviews are like warm hugs, high fives, and happy dance all in one. Leave an honest review over on Apple Podcasts.

Back to Top