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?
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Episodes
#2807 - Q&A: “Should I write for Forbes for free?” 07.09.2024 4:59
In this episode, we critically examine the pros and cons of writing for a prestigious platform like Forbes without getting paid. Discover whether the potential benefits truly outweigh the significant downsides. 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 less...
#2806 - Failure Friday: Coder’s App Flops on Product Hunt 06.09.2024 6:03
In this week’s “Failure Friday” segment, we hear from a hacker who develops an app to solve a common coding problem, but launches before conducting proper market research. Oops! Back to the drawing board. 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 a...
#2805 - TBT: A Gamer’s Journey from Twitch to YouTube 05.09.2024 6:00
In this week’s “Throwback Thursday” segment, we hear from a gaming Twitch streamer who discovered he could make more money by uploading popular streams to YouTube. Learn how he optimized his content for both platforms. 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 gui...
#2804 - Q&A: “Turning a viral video into income…” 04.09.2024 5:40
In this episode, we discuss how to turn viral fame into a potential income stream. Can one big video create an all-new career? 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 Em...
#2803 - Q&A: “Once you make a game or app, how can you distribute it?” 03.09.2024 5:16
In this episode, we explore how to distribute a new game or app effectively. Once you’ve made it—how can you get it in the hands of as many players as possible? 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. S...
#2802 - First $1,000: Turning Passion into Profit with Fantasy Maps 02.09.2024 5:32
In this week’s “First $1K” segment, we hear from an artist who turned their passion for creating fantasy maps into a profitable business. Discover how they earned their first $1,000 by selling custom maps to tabletop gamers and fantasy authors. 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,...
#2801 - Q&A: “How can I sell clothes on Depop?” 01.09.2024 5:04
In this episode, we explore tips for successfully selling on Depop and why it’s become so popular with a younger audience. Learn how to make your listings stand out and attract buyers in this trendy marketplace. 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...
#2800 - Q&A: “How does anyone profit on Temu? 31.08.2024 5:25
In our 2,800th episode (!), we explore how to succeed on the competitive marketplace of Temu. Learn about selecting the right products, creating standout listings, and leveraging marketing techniques to boost your sales. 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 g...
#2799 - Failure Friday: Bouncing Back After Two Years of Discouragement 30.08.2024 6:40
In this week’s “Failure Friday” segment, we hear from an aspiring small business owner who got discouraged when an early side hustle idea didn’t work out and stopped trying for two years—but when he finally tries again, a new idea takes off right away! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi...
#2798 - TBT: Project Manager Boosts Local Food Truck Owners 29.08.2024 5:13
In this week’s “Throwback Thursday” segment, we hear from a project manager who specializes in coordinating operations for local food truck vendors. 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: S...
#2797 - Q&A: “How to create engaging and profitable webinars?” 28.08.2024 5:29
In this episode, we explore how to create engaging and profitable webinars. Even after many years and “shiny new things,” this model still works! 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: Side...
#2796 - Q&A: “How can Pinterest drive traffic to an e-commerce store?” 27.08.2024 5:15
In this episode, we explore how to use Pinterest to drive traffic to your e-commerce store and boost sales. Learn to create engaging pins, optimize your profile, and leverage Pinterest’s features to attract more visitors. 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...
#2795 - First $1,000: Asian-Inspired Popcorn Delights in Vancouver 26.08.2024 5:01
In this week’s First $1,000 segment, we hear from a digital marketer in Vancouver, BC, who turned her love for Asian flavors into a popular side hustle. Discover how they earned their first $1,000 by specializing in gourmet popcorn. 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...
#2794 - Q&A: “What’s the difference between dropshipping and FBA?” 25.08.2024 5:33
In this episode, we explore the differences between dropshipping and Fulfilled by Amazon (FBA). Which e-commerce model is best for beginners? 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...
#2793 - Q&A: ”How do I monetize a podcast and grow my listener base?” 24.08.2024 5:34
In this episode, we explore effective strategies to monetize a podcast and grow a loyal listener base. Learn how to attract sponsors, engage your audience, and boost your podcast’s visibility. 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...
#2792 - Failure Friday: The Case of the Disappearing Developer 23.08.2024 6:17
In this week’s “Failure Friday” segment, we hear from a small business owner who hired someone to update their website, only to be locked out during a crucial sales period when the developer disappeared. 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...
#2791 - TBT: Boosting Biotech Startups with Creative Ad Strategies 22.08.2024 6:47
In this week’s “Throwback Thursday” segment, we hear from an advertising consultant focused on biotech startups in Southern California who found success with a flat fee structure. He now earns over $150,000/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 le...
#2790 - Q&A: “How can I manage multiple side hustles without burning out?” 21.08.2024 5:02
In this episode, we explore how to manage multiple side hustles without burning out. Learn practical strategies to prioritize tasks, stay organized, and maintain your sanity while juggling several projects. 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...
#2789 - Q&A: “How can I monetize my blog beyond ad placements?” 20.08.2024 5:29
In this episode, we explore effective ways to monetize your blog beyond traditional ad placements. Learn about affiliate marketing, sponsored content, creating digital products—and more! 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...
#2788 - First $1K: 3D Modeling Skills Leads to International Business 19.08.2024 6:37
In this week’s “First $1K” segment, we hear from an engineer who used his skills in 3D modeling and rendering to offer services on Upwork. Discover how he leveraged his expertise in a growing freelance market. 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 lesso...
#2787 - Q&A: “How to market a unique contact management app?” 18.08.2024 4:22
In this episode, we explore an idea for a contact management app. A caller needs help defining the ideal audience and getting it to market. 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: SideHustle...
#2786 - Q&A: “Can you make money reselling airline amenity kits?” 17.08.2024 5:21
In this episode, we explore the unique idea of collecting and reselling airline amenity kits. Is it a viable side hustle, or will the idea fail to take flight? 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...
#2785 - Failure Friday: A Year Spent Writing the Wrong Book 16.08.2024 7:17
In this week’s “Failure Friday” segment, we hear from a programmer who spent a year writing a 300-page book of life lessons only to realize it was overly generic and unappealing. 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...
#2784 - TBT: A Clothing Reseller’s Transition from Poshmark to Depop 15.08.2024 7:08
In this week’s “Throwback Thursday” segment, we hear from a clothing reseller who shifted her focus from Poshmark to Depop, now making more than half her sales on the Gen-Z focused platform. 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...
#2783 -Q&A: “How can I scale my art business using social media?” 14.08.2024 4:42
In this episode, we explore how artists can scale their businesses using social media and targeted ads, and other effective strategies. Special case study: a listener in Miami! 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 d...
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