

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

Oct 9, 2025 • 5min
Ep. 3204 - TBT: The Secret Author Behind Your Favorite Romance Novel
Discover how a fanfiction writer transformed her passion into a lucrative ghostwriting career. Earning five figures per project, she now pens bestselling romance novels under various pen names. Learn about her journey from a $5,000 co-write to earning $10,000 for full-length novels. She shares insights on payment structures, working with multiple romance subgenres, and the tools that support her thriving business. It's a fascinating look at balancing creativity with the demands of a fast-paced publishing world.

Oct 8, 2025 • 7min
Ep. 3203 - STORY: Underwear Side Hustle Turns Into $500,000/Month Business
Two women turned a side hustle into a $500,000/month underwear brand. They thrived after a successful Kickstarter campaign, focusing on inclusive designs. With no fashion background, they researched and tested products diligently. Adapting their advertising and building an Instagram community helped them connect with customers. Their journey exemplifies how a simple idea can evolve into a multi-million dollar business, showcasing the diverse outcomes that side hustles can achieve.

Oct 7, 2025 • 4min
Ep. 3202 - Q&A: “Can a ‘tech deals’ newsletter really make money?”
Discover how tech discounts can turn into profitable newsletters. Explore strategies for building trust with your audience and the importance of niche focus. Learn about effective list-building techniques using social media and referral programs. Chris breaks down the economics of affiliate marketing, revealing how weekly emails can lead to significant earnings. Plus, find out why treating each deal with care is crucial for maintaining reader loyalty.

Oct 6, 2025 • 5min
Ep. 3201 - First $1,000: Weekend ASL Crash Courses for Hospitality Staff
Discover how a certified ASL interpreter transformed empty hotel conference rooms into quick and effective training sessions for hospitality staff. Inspired by a mishap at check-in, they created a practical four-hour workshop. Learn about their unique promotional tactics, like filming participants for social media. Witness their rapid growth, landing multiple bookings and generating significant earnings. The interpreter shares vital advice on solving specific problems and balancing this venture with regular work, all while enhancing guest experiences.

6 snips
Oct 5, 2025 • 6min
Ep. 3200 - Weekend Workshop: From Utah Piano Teacher to Digital Nomad
Discover how frustrations in music teaching turned into a booming online business. A piano teacher automated his scheduling and billing, creating a tool that ultimately earned him $360,000 a year. Learn about his journey to a location-independent lifestyle in Costa Rica with a remote team. Explore the fantastic concept of addressing common pain points to develop viable solutions across various professions. This transformation showcases how one problem can open doors to freedom and entrepreneurial success.

Oct 4, 2025 • 5min
Ep. 3199 - Q&A: “How do I handle a non-compete that hurts my side hustle?”
A promotion with strings attached can stall a thriving side hustle. Today we’ll walk through reading the fine print, negotiating carve-outs, and keeping both your boss and your business on the road. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Read A Year of Mental Health: yearofmentalhealth.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 See omnystudio.com/listener for privacy information.

Oct 3, 2025 • 5min
Ep. 3198 - Q&A: “I went viral, but now I can’t meet demand!”
What happens when your product goes viral and orders skyrocket? Discover a four-step plan to manage overwhelming demand while keeping customers happy. Learn how to pause sales, communicate honestly, and potentially hire short-term help to meet production needs. Get insights on canceling orders selectively and celebrating this unexpected success. It's all about turning chaos into a sustainable opportunity!

6 snips
Oct 2, 2025 • 6min
Ep. 3197 - TBT: Turning Property Management Experience Into Digital Products
A former apartment manager turned her real estate expertise into a successful template shop for DIY landlords. She created a toolkit of 25 essential documents, addressing common pain points. Through strategic pricing and savvy marketing, she averages $1,500 a month, with peaks up to $3,000. Additionally, she offers consulting services to improve onboarding processes. The host also shares tips on monetizing idle spaces, like hosting on Airbnb, while emphasizing the value of serving niche markets.

5 snips
Oct 1, 2025 • 8min
Ep. 3196 - STORY: Google Employee Makes $100,000 Using Fiverr
A Google product manager raked in an extra $100,000 by leveraging Fiverr's platform for marketing services. Discover his unique strategy of using Fiverr Pro to offer premium pricing and high-quality consultations. The discussion highlights the importance of customer reviews and how to navigate Fiverr's low-cost culture. Tips for standing out include building a strong portfolio and maintaining persistence. This success story serves as inspiration for those looking to dive into side hustles while maintaining a full-time job.

7 snips
Sep 30, 2025 • 6min
Ep. 3195 - Q&A: “Which passive-income model fits a consultant best?”
Discover how consultants can break free from the billable hour with three innovative passive income models. Learn to create flagship courses and automate sales for lasting revenue. Explore the potential of evergreen articles that generate affiliate earnings over time. Chris also highlights the value of a micro-asset portfolio, showcasing how small, diverse revenue streams can lead to financial stability. Plus, get guidance on selecting the best income path tailored to your personality and goals!