Chris Guillebeau
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. Hosted on Acast. See acast.com/privacy for more information.
Author
Chris Guillebeau
Category
Podcast website
Latest episode
Jul 11, 2026
Where to listen?
Podcasts in the app Replaio Radio Coming soonPodcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts
Episodes
Ep. 3007 - STORY: Florida Woman Gets Paid to Remove Poisonous Frogs 26.03.2025 7:08
In this ribetting feature, a high school science teacher earns an extra $3,000/month removing an invasive species of toads throughout Florida. 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: SideHus...
Ep. 3006 - Q&A: “How do I set the right hourly rate for my side hustle?” 25.03.2025 4:16
In today's episode, we help a social media manager set a fair hourly rate. Learn how to balance your skills and market demands to price your services confidently. 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....
Ep. 3005 - First $1,000: This “Crypto Tax Whisperer” Takes On the IRS 24.03.2025 5:52
In this week's First $1,000 segment, discover how an unassuming accountant turned a chaotic batch of crypto trades into a full-scale practice, complete with custom software and national training programs. 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 an...
Ep. 3004 - Weekend Workshop: Create a Side Hustle Shopping List 23.03.2025 6:58
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: create a side hustle shopping list. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This...
Ep. 3003 - Q&A: “How can I get clients to provide more accurate information?” 22.03.2025 4:40
In this episode, we explore how service-based businesses can guide clients through providing accurate information. Learn how to reduce costly mistakes and protect your business! 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...
Ep. 3002 - Q&A: “How can I stand out in a world of AI-generated content?” 21.03.2025 5:23
In today's episode, we tackle a growing concern for creators: how to stand out in a world increasingly dominated by AI-generated content. If you're worried about keeping your work authentic and engaging, you're not alone. 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...
Ep. 3001 - TBT: Food Blog Grows to Thriving Culinary Ecosystem 20.03.2025 6:10
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...
Ep. 3000 - STORY: “Pocket Monkey” Tool Sells 500,000 Units 19.03.2025 7:27
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: SideHust...
Ep. 2999 - Q&A: “How to prioritize tasks and to-do items without getting overwhelmed?” 18.03.2025 5:21
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...
Ep. 2998 - First $1,000: From Malibu Bartender to At-Home Bar Designer 17.03.2025 5:47
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...
Ep. 2997 - Weekend Workshop: Finding the Right Price 16.03.2025 6:49
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 s...
Ep. 2996 - Q&A: “Can I legally sell t-shirts with retro images of celebrities?” 15.03.2025 4:51
In today's episode, we help an aspiring side hustler navigate the tricky world of copyright and likeness rights. Can you legally sell products featuring old-school celebrity images? Let's break it down. 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...
Ep. 2995 - Q&A: “How to organize leads without getting overwhelmed?” 14.03.2025 5:00
In this episode, we help a small business owner organize client leads without getting overwhelmed. Learn simple, affordable ways to track inquiries, follow-ups, and deadlines—even if you're not ready for a big CRM system. 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...
Ep. 2994 - TBT: Streamlining Standardized Test Preparation 13.03.2025 6:56
In this week's Throwback Thursday segment, learn how one test prep tutor goes from juggling individual clients to running a membership platform filled with guided lessons, practice tests, and group support. 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...
Ep. 2993 - STORY: Homemade Art Tutorials Turn Struggling Artist Into YouTube Star 12.03.2025 6:56
A struggling painter and sculptor uploads a drawing video to YouTube and discovers a massive audience for tutorials on hand-drawing, generating over 50 million views in 6 years. 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...
Ep. 2992 - Q&A: “How do I handle indecisive event planning clients?” 11.03.2025 5:44
In this episode, we help an aspiring event planner manage indecisive clients who keep changing their event themes. Learn how to set clear expectations, avoid delays, and charge for extra work—without coming across as pushy. 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 includ...
Ep. 2991 - First $1,000: My Life as a Proposal Planner 10.03.2025 4:35
In this week's First $1,000 segment, find out how one Bay Area event planner turns suitors' dreams into carefully choreographed reality, complete with hidden photographers and heartfelt surprises. 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 listen...
Ep. 2990 - Weekend Workshop: Assemble the Nuts and Bolts 09.03.2025 7:14
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: assemble the nuts and bolts. 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, t...
Ep. 2989 - Q&A: “What should I do if a brand uses my photo without permission?” 08.03.2025 5:06
In this episode, we help a content creator navigate what to do when a brand uses their photo without permission. Learn how to approach the situation professionally—or when it might be better to let it go and move forward. 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...
Ep. 2988 - Q&A: “How do I create passive income from a skill-based service?” 07.03.2025 5:12
In this episode, we help a freelance marketing consultant explore ways to turn her expertise into passive income. Learn how to create scalable products that generate revenue—even when you're not working one-on-one with clients. 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 in...
Ep. 2987 - TBT: Solo Nutrition Practice Offers Corporate Wellness Service 06.03.2025 5:54
In this week's Throwback Thursday segment, discover how a freelance nutritionist transitioned from personal meal plans to comprehensive corporate wellness programs, creating ongoing value for employees and stable income for herself. 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 inc...
Ep. 2986 - STORY: Itchy Honeymoon Shaves Way To Pubic Oil Kingdom 05.03.2025 8:05
Three friends embrace the reality of pubic area discomfort and build a pubic oil businesses from scratch, turning it into a six-figure side hustle despite the skepticism of literally every person they talked to. 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 les...
Ep. 2985 - Q&A: “How can I relaunch a product that didn’t sell well the first time?” 04.03.2025 5:17
In this episode, we help a small business owner decide whether to relaunch a product that didn't perform well the first time. How can she turn a past flop into a future success? 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...
Ep. 2984 - First $1,000: Hitting the Highway for RV Deliveries 03.03.2025 5:25
In this week's First $1,000 segment, discover how one retiree used his CDL experience to deliver RVs cross-country, getting paid while exploring the open 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. Sh...
Ep. 2983 - Weekend Workshop: Create an Origins Story 02.03.2025 5:57
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: creating a powerful origins story. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This y...
Similar podcasts
Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.