Side Hustle School

Chris Guillebeau / Onward Project
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Nov 11, 2025 • 5min

Ep. 3237 - Q&A: “Will professionals trade hours instead of cash?”

In this episode, Paula, a web developer from Milwaukee, dives into the fascinating world of bartering services. She shares her innovative idea of creating a local skill-swap cooperative based on a time-bank model. The conversation explores how professionals might trade skills instead of cash, utilizing a simple one hour equals one credit system to streamline exchanges. Chris provides valuable insights on building trust and logistics, emphasizing the importance of vetting members and starting small. This insightful dialogue sparks ideas for collaborative economies!
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Nov 10, 2025 • 6min

Ep. 3236 - First $1,000: Turning Cable Chaos into Magnetic Profit

Tired of messy cables? Discover how one innovator turned a TikTok clip into a lucrative side hustle by designing magnetic cable rails. Learn about the quick manufacturing process and clever marketing that skyrocketed sales through engaging video demonstrations. The thrill of hitting that first $1,000 profit mark highlights the potential for simple ideas to become successful ventures. Chris also shares valuable lessons on starting low-cost manufacturing projects, encouraging everyone to take small steps toward their entrepreneurial dreams.
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Nov 9, 2025 • 8min

Ep. 3235 - Weekend Workshop: The Wandering Teacher's Global Classroom

Discover the fascinating journey of a language hacker who turned his passion for teaching into a global side hustle. Learn how Benny Lewis’s month-long Spanish immersion sparked rapid fluency and inspired his popular course, 'Fluent in 3 Months.' Explore his unique marketing strategies, including playful YouTube videos and performances that attracted eager students. Gain insights on building a digital lifestyle business while solving personal challenges and proving effective methods for success. Let these lessons inspire your own hustle!
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Nov 8, 2025 • 6min

Ep. 3234 - Q&A: “What’s a fair founder-investor deal between friends?”

Tessa, a designer and college friend, dives into the intricacies of founder-investor relationships when seeking a $25,000 investment for her travel accessory prototype. Chris provides insight on balancing cash and sweat equity, suggesting a fair 75/25 equity split. They also discuss the nuances of managing passive investors, advocating for a one-year cliff and monthly vesting to keep motivations aligned. This episode offers a practical guide for navigating financial partnerships among friends.
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Nov 7, 2025 • 5min

Ep. 3233 - Q&A: “Where do I find my first paying customer?”

Discover effective strategies for landing your first paying customer. Learn how to position your products where buyers naturally congregate. Get inspired by the idea of turning your home into an Airbnb while you're away. Explore the benefits of selling at farmer's markets, with practical advice on securing those initial sales. Chris emphasizes that making sales is more valuable than compliments, pushing you to take meaningful action. Tune in for insights that can kickstart your side hustle!
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Nov 6, 2025 • 6min

Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital

A fitness enthusiast turned a passion for gym equipment into a thriving media business. Discover how he transformed scavenged gear into quick flips, making impressive profits. Faced with burnout, he pivoted to sharing his expertise through a practical guide for home gym setups. Utilizing social media for marketing, he launched a successful newsletter that generated recurring affiliate income. Hear how his work not only boosted his finances but also helped others build their ideal home gyms.
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Nov 5, 2025 • 8min

Ep. 3231 - STORY: The Coffee Grinder That Made $300,000

A petroleum engineer stumbles upon a lucrative side hustle reselling coffee grinders on Amazon. He starts small but quickly scales his venture to over $300,000 in revenue. The journey includes tackling a product disaster with a 90% return spike, which he resolves through stellar customer service. By redesigning the grinder and emphasizing loyalty, he transforms early customers into devoted fans. Ultimately, he leaves his corporate job to expand his brand even further, showcasing the power of research, creativity, and customer care.
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Nov 4, 2025 • 5min

Ep. 3230 - Q&A: “How do I test Facebook vs. free traffic?”

Free traffic methods may feel safe, but paid ads could boost your hustle faster—if the numbers align. Discover how to set up a two-week ad experiment on a budget of $200, focusing on clear metrics to measure success. Learn to create different ad variants and assess lead quality through email engagement. Chris emphasizes the importance of knowing when to stop spending on ineffective ads and provides actionable tips to help you navigate the world of traffic generation.
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6 snips
Nov 3, 2025 • 7min

Ep. 3229 - First $1,000: Shopify Library Becomes Paid Subscription

A developer found a clever way to address common Shopify theme frustrations by bundling quick fixes into a subscription service. With over 170 store owners signing up, he generated $2,500 monthly in recurring revenue. The launch strategy relied on straightforward marketing tactics and community engagement. Retention strategies, including regular updates and engaging content, kept churn rates low. This innovative approach transformed his freelance work, allowing him to focus on developing high-value snippets instead of repetitive tasks.
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Nov 2, 2025 • 7min

Ep. 3228 - Weekend Workshop: When Getting Fired Becomes Your Best Break

Explore how losing a job can spark unexpected opportunities. Hear Michael's journey from layoff to launching a mattress business from an empty car showroom. Discover how innovative marketing strategies, like bicycle delivery, helped him stand out. Learn why embracing change and continuous education can lead to long-term success. Michael's story emphasizes viewing setbacks as stepping stones to freedom and new ventures. Tune in for actionable insights on starting your own side hustle!

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