The Wealthy Barber Podcast

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#41 — Chris Guillebeau: How to Start a Side Hustle

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Jan 27, 2026

Guest

Chris Guillebeau

Chris Guillebeau, author and entrepreneur behind The $100 Startup and Side Hustle, shares bite-sized lessons on turning hobbies and skills into income. He champions reselling and farmers’ markets as low-risk tests. Action beats overplanning, and he discusses when to quit, enjoying work over scaling, and neurodiversity including ADHD and Time Anxiety.

34:40

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ANECDOTE

Manifesto Launched His Platform

Chris Guillebeau published a free manifesto called A Brief Guide to World Domination and it reached about 100,000 downloads in months.
That reach convinced him a small online document could become the start of an ongoing project.

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ADVICE

Start With Reselling To Learn Fast

Try reselling as a low-risk way to learn business fundamentals like marketing, pricing and photos.
Expect small losses but gain practical experience transferable to other ventures.

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ADVICE

Test Early, Iterate Often

Launch quickly instead of overplanning; use simple websites or marketplaces to test demand.
Iterate from live feedback rather than waiting for perfection.

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Chris’s unconventional early career

02:20 • 3min

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How the blog manifesto launched his audience

04:54 • 14sec

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Why he wrote The $100 Startup

05:07 • 3min

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Turning hobbies and skills into income

07:38 • 3min

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Start small: reselling and testing

10:30 • 3min

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Getting your first customers

13:06 • 2min

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Traits of successful side‑hustlers

14:48 • 2min

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When to quit versus persist

17:10 • 6min

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Farmers' markets as product testing

23:38 • 2min

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Enjoyment over scale for side hustles

25:42 • 2min

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Time Anxiety explained

27:24 • 2min

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Neurodiversion event and neurodiversity focus

29:10 • 1min

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ADHD, schooling and entrepreneurial strengths

30:23 • 3min

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Follow‑ups: Side Hustle books and touring

• Mentioned in 2 episodes

100 Side Hustles

Chris Guillebeau

In '100 Side Hustles,' Chris Guillebeau presents a colorful idea book filled with inspiration for your next big idea. The book features startup stories of regular people launching side businesses that almost anyone can do, such as an urban tour guide, an artist inspired by maps, a travel site founder, and more. These case studies, distilled from Guillebeau's popular 'Side Hustle School' podcast, include insights, takeaways, and photography that reveal the human element behind the hustles. The book covers every important step of launching a side hustle, from identifying underserved markets to crafting unique products and services that spring from your passions.

#1672

• Mentioned in 23 episodes

Time Anxiety

The Illusion of Urgency and a Better Way to Live

Chris Guillebeau

#3061

• Mentioned in 14 episodes

The Art of Non-Conformity

Set Your Own Rules, Live the Life You Want, and Change the World

Chris Guillebeau

Based on Chris Guillebeau's popular online manifesto 'A Brief Guide to World Domination,' this book encourages readers to challenge conventional norms and live unconventional, remarkable lives. It explores creative self-employment, radical goal-setting, contrarian travel, and embracing life as a constant adventure. The book is organized into three parts: The Remarkable Life, Reclaiming Work, and The Power of Convergence, providing practical advice and inspiring stories to help readers design their own path to success and make a meaningful impact.

#1221

• Mentioned in 29 episodes

Side hustle

From Idea to Income in 27 Days

Chris Guillebeau

This book provides a detailed roadmap for creating an additional stream of income without quitting your day job. It guides readers through brainstorming ideas, selecting the best concept, launching, and refining their side hustle to generate income quickly. The book emphasizes that anyone can start a side hustle without needing extensive entrepreneurial experience or resources.

#2628

• Mentioned in 16 episodes

The $100 startup

Chris Guillebeau

In this book, Chris Guillebeau shares insights from 1,500 individuals who have built businesses earning $50,000 or more from minimal investments. He focuses on 50 intriguing case studies, highlighting how people with no special skills turned their passions into profitable ventures. The book emphasizes the importance of finding the intersection between your expertise and what others are willing to pay for, and it provides practical advice on starting and growing a business without needing an MBA, a business plan, or employees. Guillebeau stresses key principles such as the importance of action over planning and the value of selling solutions rather than teaching skills.

#962

• Mentioned in 35 episodes

The Wealthy Barber

David Chilton

In 'The Wealthy Barber', David Chilton provides straightforward and accessible advice on managing personal finances. The book uses a fictional story to illustrate key financial concepts, making it easy for readers to understand and apply the principles to their own lives. It covers topics such as budgeting, investing, and long-term financial planning.

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

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