
Side Hustle School
A daily show for everyone who works a regular job and wants to start an income-earning project on the side. In each episode, listeners will hear a different story of someone who's started a side hustle—along with what went well, how that person overcame challenges, and what happened as a result. The show is written and hosted by Chris Guillebeau, the New York Times bestselling author of The $100 Startup, The Happiness of Pursuit, and other books.
Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Latest episodes

Dec 7, 2024 • 6min
#2898 - Q&A: “What are the hardest side hustles to start and operate?”
Exploring the tough terrain of side hustles, listeners discover which ventures pose the biggest challenges. The fashion and food industries face significant hurdles like inventory headaches and high overhead costs. The discussion emphasizes the need to align passion with practical opportunities, encouraging manageable projects that balance fulfillment with minimal risk. Tune in for insights that can help navigate the complexities of starting and running a side hustle successfully.

Dec 6, 2024 • 7min
#2897 - Failure Friday: "Good Political News" Channel Runs Out of Stories
In this Failure Friday, a content creator shares the rollercoaster ride of launching a channel dedicated to uplifting political stories. Inspired by good news trends, they encounter the tough reality of finding enough positive narratives. This leads to some serious challenges, including burnout and reevaluation of their goals. The conversation dives into the importance of strategic planning in side hustles and how aligning projects with personal skills can make or break your success.

Dec 5, 2024 • 6min
#2896 - TBT: Home Gym Affiliate Earns $80,000
Discover an inspiring tale of turning a passion for fitness into a thriving affiliate marketing blog. Learn how one individual earned over $80,000 by sharing home gym equipment insights, flourishing especially during the pandemic. Delve into the secrets of successful selling with tips on reducing cart abandonment and the importance of niche selection for maximizing affiliate commissions. Get ready to unlock the potential of your side hustle!

Dec 4, 2024 • 4min
#2895 - Q&A: “Should I record my videos in portrait or landscape mode?”
The discussion dives into whether to record videos in portrait or landscape mode, focusing on maximizing engagement across platforms like YouTube, TikTok, and Instagram. Tips on content repurposing show how to streamline video production effectively. Listeners can learn about the different requirements for each platform and how to create versatile content that works everywhere. It's all about making the most of your efforts while catering to diverse audience preferences!

Dec 3, 2024 • 5min
#2894 - Q&A: “Can I do Substack, TikTok, podcast, and a paid membership?”
A solo travel creator grapples with the choice between focusing on a single platform or branching out to multiple channels like Substack and TikTok. The discussion highlights the creator's dilemma of balancing several content formats while maximizing audience engagement. Listeners can absorb valuable tips on navigating this challenge and learn from successful examples of creators who have effectively integrated different platforms. It's a practical guide for anyone looking to expand their content reach!

Dec 2, 2024 • 7min
#2893 - First $1,000: Building a Business One Signature at a Time
Discover the intriguing world of signature gathering for ballot initiatives. A California entrepreneur shares how he turned this unique side hustle into a profitable business, earning more than $1 per signature. Learn about the challenges faced in kickstarting the venture and how community engagement fueled its growth. This story highlights the intersection of entrepreneurship and civic involvement, showing how one can build a successful enterprise while contributing to the electoral process.

Dec 1, 2024 • 5min
#2892 - Q&A: “How will a new presidential administration impact side hustlers?”
Explore how a change in presidential administration could shake things up for small business owners and side hustlers. Delve into expected tax changes and regulatory adjustments that might affect your hustle. Discover the importance of staying adaptable in an unpredictable political landscape, and learn how access to funding could shift. This insightful discussion uncovers the potential hurdles and opportunities on the horizon for those looking to earn extra income.

Nov 30, 2024 • 5min
#2891 - Q&A: “How to conduct competitor analysis for free?”
Explore cost-effective strategies for analyzing your competition without breaking the bank. Discover how simple Google searches and free tools can provide invaluable insights. Learn to leverage social media platforms to stay ahead in your side hustle. This episode equips you with practical methods that enhance your competitive edge, especially for entrepreneurs on a tight budget.

Nov 29, 2024 • 7min
#2890 - Failure Friday: Sugar-Coated Advice Crumbles Cake Dreams
A passionate baker shares her journey from startup success to painful failures. Misguided pricing strategies and well-meaning advice led to her business struggles. She emphasizes the need to value one’s skills and shift focus when necessary, discovering a newfound passion for digital marketing. The discussion also highlights the pitfalls of relying on friends and family for business advice, urging listeners to seek informed guidance from external resources instead.

Nov 28, 2024 • 7min
#2889 - TBT: From House Flipper to Rental Property Guru
A side hustler transforms from house flipping to specializing in helping families secure rental properties in distressed areas. Their journey showcases the growth of a consulting business that empowers new real estate investors. By offering structured services, they positively impact communities. Additionally, the discussion highlights the joys of language learning during the festive season, emphasizing how it can enrich personal connections and experiences.