
Side Hustle School
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/
Latest episodes

Mar 25, 2025 • 4min
Ep. 3006 - Q&A: “How do I set the right hourly rate for my side hustle?”
Learn how to set a fair hourly rate for your side hustle, especially if you're a social media manager. Discover tips for balancing your skills with market demands to confidently price your services. Explore how freelancers can analyze their costs and income goals while considering project complexity. Regularly reviewing your rates based on experience can enhance your earnings and sustainability in your side hustle.

Mar 24, 2025 • 6min
Ep. 3005 - First $1,000: This “Crypto Tax Whisperer” Takes On the IRS
Explore the fascinating journey of an accountant who evolved from traditional practices to becoming a go-to expert in cryptocurrency tax management. Discover how she transformed chaos into a thriving business with custom software and training programs. Navigate the complexities of IRS regulations surrounding crypto taxes and learn essential strategies to avoid costly mistakes. This engaging tale shows how adaptability can lead to both personal growth and financial success.

4 snips
Mar 23, 2025 • 7min
Ep. 3004 - Weekend Workshop: Create a Side Hustle Shopping List
Discover the essentials for launching a successful side hustle in 2025! Learn how to create a side hustle shopping list that prioritizes simplicity and efficiency. Explore key tools and resources while budgeting effectively. Get practical tips on aligning your passions with entrepreneurial goals. Tune in for a free guided lesson that transforms ideas into action!

Mar 22, 2025 • 5min
Ep. 3003 - Q&A: “How can I get clients to provide more accurate information?”
Discover how service-based businesses can enhance client communication to prevent costly mistakes. Explore the struggles of a custom clothing designer dealing with remote clients. Learn effective strategies like visual guides and standardized forms to ensure accurate measurements. Dive into proactive techniques for clearer interactions that will lead to better outcomes and satisfied clients. This insightful discussion is packed with practical tips to refine your service approach and protect your business!

5 snips
Mar 21, 2025 • 5min
Ep. 3002 - Q&A: “How can I stand out in a world of AI-generated content?”
How can creators stand out in an age of AI-generated content? The discussion highlights the importance of authenticity and personal storytelling. Strategies for maintaining uniqueness include building genuine connections with audiences. Emphasizing personal branding, the conversation provides practical tips for leveraging individual perspectives to grow side hustles effectively. In a digital world, staying true to oneself is the key to differentiation.

Mar 20, 2025 • 6min
Ep. 3001 - TBT: Food Blog Grows to Thriving Culinary Ecosystem
In this week’s Throwback Thursday segment, learn how a recipe blogger moved beyond one-off cookbook sales to form a culinary community, offering seasonal meal plans, live demos, and valuable kitchen tool discounts. 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.

Mar 19, 2025 • 8min
Ep. 3000 - STORY: “Pocket Monkey” Tool Sells 500,000 Units
After getting locked out of his apartment, a software engineer creates a pocket tool that goes on to sell 500,000 units and employ 17 people. 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.

Mar 18, 2025 • 5min
Ep. 2999 - Q&A: “How to prioritize tasks and to-do items without getting overwhelmed?”
In today’s episode, we explore neurodivergent-friendly strategies to tackle an overwhelming to-do list. Learn how to work with your energy, build momentum, and stay productive without burnout. 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.

Mar 17, 2025 • 6min
Ep. 2998 - First $1,000: From Malibu Bartender to At-Home Bar Designer
In this week’s First $1,000 segment, discover how a Malibu bartender began designing home bars, added a line of custom bar tools, and launched virtual cocktail classes to reach $150,000 a year. 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.

Mar 16, 2025 • 7min
Ep. 2997 - Weekend Workshop: Finding the Right Price
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: finding the right price. 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.