

Side Hustle School
Chris Guillebeau / Onward Project
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/
Sales and Distribution by Lemonada Media https://lemonadamedia.com/
Episodes
Mentioned books

Nov 21, 2025 • 5min
Ep. 3247 - Q&A: “Instagram, TikTok, or LinkedIn—how do I choose?”
Choosing the right platform for a side hustle can make all the difference. Instead of spreading yourself thin by posting everywhere, focus on where potential customers are most active. Native content is key—videos might shine on one platform while photos excel on another. Instagram is highlighted as a top choice for quickly driving sales, especially for custom products. The episode wraps up with a reminder to embrace experimentation, discard what doesn’t work, and keep well-being in mind.

Nov 20, 2025 • 6min
Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails
Sean Markham, a marketing and copywriting expert, shares how he transformed a collection of standout recruiter outreach emails into a profitable business. He reveals the inspiration behind creating an organized swipe file of these emails, which he marketed as a subscription service. Transitioning to selling verified contact lists, he highlights the importance of targeting the right leads rather than merely offering templates. His journey exemplifies how a clever side hustle can flourish with the right approach and insights.

Nov 19, 2025 • 7min
Ep. 3245 - STORY: Six-Figure Beekeeping Biz Buzzes for Minnesota Couple
Discover the inspiring story of a Minnesota couple transforming their passion for beekeeping into a six-figure business. Kiara's sustainability project sparked her interest in bees, while Travis dove in after caring for her hives. They cleverly built their inventory through trades and tackled winter survival challenges for their bees. By selling hives and honey, they found success and even reinvested profits to grow. Their journey highlights the rewards of following your passion and creating value.

Nov 18, 2025 • 4min
Ep. 3244 - Q&A: “How do I upsell without sounding pushy?”
Discover how to upsell without coming off as pushy! Learn key principles such as timing and clear outcomes to make your offers feel natural. Hear a real-life dilemma from a copywriter about spotting client issues while fearing pressure tactics. Unlock a two-step framework that helps you diagnose problems before proposing solutions. It's all about making the upsell a win-win for both you and your clients!

Nov 17, 2025 • 6min
Ep. 3243 - First $1,000: Cozy Reading Gadget Turns Pages and Profit
A bedtime reader turns a simple paperclip into a cozy reading gadget. Struggling to read one-handed, she sketches a page holder and finds a manufacturer to bring her idea to life. After launching on Amazon, a viral video skyrockets sales, leading to improvements based on customer feedback. She now sells 40 units weekly without spending on ads, relying on creative content and engagement to drive her success. This journey highlights the power of innovation and responding to customer needs.

5 snips
Nov 16, 2025 • 8min
Ep. 3242 - Weekend Workshop: “Digital Documentation” Earns Passive Income
This segment reveals how a simple PDF guide generated $120,000 in its first year. It explores the gap in the market for comprehensive documentation, showcasing how Brett created a detailed Evernote guide. The story includes a pivotal moment when a $10,000 sales goal allowed his wife to quit her job, leading to daily passive income. The discussion emphasizes the model's success due to clear user needs and accessible pricing, encouraging listeners to apply similar tactics to their own projects.

Nov 15, 2025 • 6min
Ep. 3241 - Q&A: “Is remote-worker visa consulting a real business?”
The rise of digital nomad visas is creating opportunities and confusion in equal measure. Turning visa expertise into a concierge service invites exciting possibilities. Pricing tiers range from budget checks to comprehensive assistance, making it accessible for various clients. Key strategies for liability protection are highlighted, emphasizing the importance of framing services correctly. Marketing avenues like Reddit and co-working spaces are great for attracting initial clients. This niche could flourish as a boutique side hustle with smart packaging.

Nov 14, 2025 • 5min
Ep. 3240 - Q&A: “Should I tell my clients I’m using AI?”
Explore the intriguing dilemma of disclosing AI use to clients. Discover the widespread adoption of AI tools across various fields and how it reshapes client expectations. Learn to emphasize outcomes rather than tools, ensuring value takes center stage in proposals. Chris offers practical tips for maintaining transparency without compromising trust, including using a brief contract statement. Lastly, consider providing a premium human-only option for clients hesitant about AI, while recognizing that most will still appreciate the benefits of technology.

Nov 13, 2025 • 6min
Ep. 3239 - TBT: This Tiny Spreadsheet Tool Pays the Rent
Discover how a simple browser-based spreadsheet tool turned into a side hustle that pays rent! A developer created EasyCSVFixer to clean messy CRM exports, launching quickly with a drag-and-drop interface. With innovative monetization strategies, including subscriptions and white-label licenses, his tool gained traction through community marketing. He achieved consistent revenue, proving that solving specific problems can lead to a reliable side income. Plus, learn tips on leveraging your home for extra cash!

7 snips
Nov 12, 2025 • 7min
Ep. 3238 - STORY: Agricultural Teacher Earns $200,000 Selling Lesson Plans
An agricultural teacher turned entrepreneur developed a thriving business by creating and selling educational materials for fellow educators. After initially crafting a simple $50 FFA review game, she saw immense demand and expanded her offerings. Her focus on a niche market led to $200,000 in annual revenue, enabling her to pursue this venture full-time. The journey highlights the importance of recognizing needs in specialized communities and acting on creative ideas to generate extra income.


