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 22, 2025 • 5min
Ep. 3187 - First $1,000: Typography Lover Turns Letters Into Revenue
Discover how a font designer transformed their passion for typography into a thriving side hustle with a subway-inspired typeface. After launching just two fonts on Creative Market, they quickly made over $1,000 in under a month! The discussion highlights the importance of curiosity, persistence, and action for side hustlers. Get practical tips on designing and marketing fonts, along with valuable insights on building a sustainable creative business.
Sep 21, 2025 • 6min
Ep. 3186 - Weekend Workshop: Design Disruption in Traditional Markets
Explore the fascinating world of design disruption as outdated industries get a modern makeover. Hear the inspiring story of Julie Wilder, who transformed astrology calendars with fresh aesthetics, launching her successful Etsy store and seeing organic growth. Discover practical steps to identify and redesign traditional products for today's market. Get ready to spot opportunities in dated industries and take action toward your next side hustle!
4 snips
Sep 20, 2025 • 5min
Ep. 3185 - Q&A: “How can I sell an Amazon-only FBA brand for top dollar?”
Thinking of selling an Amazon-only FBA brand? Discover how to enhance your business valuation by adding a Shopify channel and capturing customer emails. Learn about reducing channel risk and the impact a 90-day tune-up can have on your sale price. This discussion is packed with actionable insights for maximizing profits on your venture.
Sep 19, 2025 • 5min
Ep. 3184 - Q&A: “How can a coast-to-coast road trip pay for itself?”
Ever thought a road trip could pay for itself? Discover five creative side hustles that can transform your journey into a money-making adventure. From portable income to gigs on the go, learn how to turn your travels into a revenue stream. Dive into innovative ways to monetize your experiences through content creation and stock photos. The open road doesn’t have to break the bank when you're smart about it!
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!
