

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

Sep 18, 2025 • 5min
Ep. 3183 - TBT: Creator Builds Instagram Mastermind Pod
Discover how a social media strategist created a private mastermind pod to enhance Instagram engagement. Learn about the initial testing, the rules set for participation, and how it transformed into a paid program with onboarding. Dive into the strategies for sharing likes and comments, boosting visibility, and leveraging algorithms. This insightful discussion not only offers tips for creators but also showcases the potential for side hustles in the social media landscape.

Sep 17, 2025 • 8min
Ep. 3182 - STORY: Personal Trainer Pumps Up Breakfast
A dedicated personal trainer transforms breakfast with her high-protein pancake mix, reaping an impressive $25,000 monthly. Her inspiring journey showcases the challenges of building a healthy brand, utilizing social media for growth, and fostering community engagement. The joy of pancakes serves as a gateway to entrepreneurship, proving that a passion for wellness can lead to both personal fulfillment and financial success.

Sep 16, 2025 • 6min
Ep. 3181 - Q&A: “Should my first info product be $30 or $300?”
Should you price your first info product at $30 or $300? The discussion dives into the psychology behind perceived value and the consequences of attracting budget-conscious customers. It emphasizes the fine balance between low and premium pricing strategies. Listeners gain actionable insights into creating effective pricing that resonates with their target audience. Learn how to navigate these challenges and confidently launch your digital product.

Sep 15, 2025 • 5min
Ep. 3180 - First $1,000: Foot Traffic Nerd Turns Public Data Into Paid Service
Discover how a data enthusiast turned public information into a profitable service that aids local businesses in navigating foot traffic trends. Learn about the practical steps taken to rapidly generate revenue while mastering the art of packaging insights. This engaging tale highlights curiosity-driven entrepreneurship and the power of data, showcasing how informed decisions can lead to substantial financial gains.

Sep 14, 2025 • 7min
Ep. 3179 - Weekend Workshop: Building Systems That Sell Themselves
Discover how to turn your frustrations into income by creating tools that solve real problems. Learn about the Guest Post Tracker, a successful innovation born from a challenging experience. The podcast emphasizes the role of curiosity in entrepreneurship and presents practical guidance for validating market needs. Each week offers actionable advice to help you transform everyday challenges into thriving side hustles. Join the journey of making money on the side without quitting your job!

Sep 13, 2025 • 5min
Ep. 3178 - Q&A: “How do I stop every freelance project from starting in chaos?”
Freelancers, ever start a project in chaos? Discover how to transform your client onboarding process into a seamless experience. Learn about constructing a standardized system that includes welcome packets, contracts, and effective communication strategies. By streamlining this process, you can boost productivity and minimize stress. Say goodbye to panic-mode and hello to organized success!

Sep 12, 2025 • 4min
Ep. 3177 - Q&A: “How can I make money by renting out houseplants?”
Can houseplants become a source of income? Discover the innovative concept of renting out indoor plants for styling and events. One hobbyist shares their journey of turning a rare plant collection into a profitable venture. Learn about market demand, pricing strategies, and how to manage plant rentals. This burgeoning trend highlights a unique way to turn a passion for greenery into a thriving side business.

Sep 11, 2025 • 6min
Ep. 3176 - TBT: Helping High School Dropouts Start Plumbing Careers
Discover how a unique program is helping high school dropouts kickstart rewarding careers in plumbing by providing essential skills and paid apprenticeships. Learn about the innovative business model bridging the skills gap between eager students and employers. Delve into the traits that make side hustlers successful, focusing on the importance of curiosity and proactive choices. Also, find out how platforms like ShipStation can streamline operations for small business owners. This engaging discussion offers both inspiration and practical insights!

Sep 10, 2025 • 7min
Ep. 3175 - STORY: Movie Industry Friends Rewrite the Credits, Earn $20,000/Month
In a fascinating twist, two friends modify the tedious process of movie credits, leading to a successful side hustle. Their innovative software, InCrawl, changes the game for film producers. It streamlines credit sequences and boosts efficiency. This venture generates an impressive $20,000 each month, showcasing how creativity can transform mundane tasks into lucrative opportunities.

Sep 9, 2025 • 5min
Ep. 3174 - Q&A: “How can a first-time author stand out in a market of 4,500 books per day?”
Navigating the book market is a challenge for first-time authors, with thousands of titles released daily. Effective marketing is crucial for standing out amid the competition. The discussion emphasizes the importance of engaging with audiences and building a strong platform. Concrete strategies are provided to help authors gain visibility and achieve success in a crowded landscape.