Episode #41 is out now! Our guest this episode is Chris Guillebeau — author, entrepreneur, blogger and speaker best known for “The $100 Startup,” “Side Hustle,” and his latest book, “Time Anxiety.” Chris first rose to prominence through his blog “The Art of Non-Conformity,” where he shared stories of unconventional work, travel and building income on your own terms.

In this conversation, Dave and Chris dive into the world of side hustles and small entrepreneurship — how to turn skills and hobbies into income, why reselling is one of the easiest ways to start and why action always beats overplanning. Chris shares what successful side-hustlers have in common, how to find your first customers, why farmers’ markets are an underrated testing ground for business ideas, and how knowing when to quit can be just as important as knowing when to push forward.

Whether you’re thinking about starting a side hustle, testing a business idea, or just want a fresh perspective on work and time, this episode is full of practical insights and encouragement. Listen now on our website, YouTube, Apple Podcasts, Spotify and all major podcast platforms.

Show Notes

(00:00) Intro & Disclaimer

(00:55) Intro to Chris Guillebeau

(02:05) Chris’s Unconventional Early Career

(05:03) The Why Behind Writing “The $100 Startup”

(08:06) Turning Skills and Hobbies Into Income

(11:04) Reselling is a Great Place to Start for Entrepreneurship

(11:56) Action Beats Overplanning

(13:06) How to Find Your First Customers

(14:45) What Do Successful Side-Hustlers Have in Common?

(21:12) The Impact of “The $100 Startup” 

(22:09) Knowing When to Quit is Vital

(23:40) Farmers’ Markets Are Great for Testing Business Ideas

(25:44) Why Enjoyment Matters More Than Scale for Side Hustles

(27:16) What is Time Anxiety?

(29:02) ADHD & Neurodiversity

(33:16) Conclusion