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Side Hustle School

Chris Guillebeau / Onward Project

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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.
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In this episode, we explore alternatives to eBay for starting a reselling business. Learn about the pros and cons of platforms like Facebook Marketplace, Mercari, and OfferUp. 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 f…
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In this episode, we help a listener seeking to monetize their fan fiction while navigating copyright issues. Expecto Patronum! 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 …
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In this week’s “Failure Friday” segment, we hear from a tech-savvy course creator who tried to save money by building their own platform—and why using a turnkey service might have been the better choice. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th…
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In this week’s “Throwback Thursday” segment, we hear from a seller of productivity guides who has evolved his business over the years. Discover how he transitioned from a single popular guide and now sells a range of products, earning over $100,000 a year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of peopl…
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In this episode, we explore how to handle the ethical dilemma of charging subscribers without fully delivering a service. What do you do if you stop providing something—but buyers keep paying?? 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…
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This listener needs help discovering his skills! In this episode, we discuss how ANYONE can identify and develop skills for a successful side hustle. 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 lis…
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In this week’s “First $1K” segment, we hear from a tag-team duo in Nashville who starts a personal branding agency. Discover how they earned their first $1,000 by helping entrepreneurs and influencers build their personal brands through digital marketing. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people…
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In this episode, we explore the factors to consider when deciding whether to invest in a trade show booth. These booths don’t come cheap … are they worth it? 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…
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In this episode, we explore how to turn organizational skills into a profitable consulting service. Learn how to define your niche, build a portfolio, and market your services to attract clients and grow your business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin…
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In this week’s “Failure Friday” segment, we hear from an enterprising seller who faced a setback when their anime-themed T-shirts were de-listed after an IP owner filed a complaint. 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 incl…
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In this week’s “Throwback Thursday” segment, we hear from an Ohio man who turned his experience with aquariums into a maintenance service for homes and offices. 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…
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In this episode, we explore creative ways to monetize a property rental beyond Airbnb. We’ll consider event rentals, setting up a co-working space, or even urban farming to maximize a property’s potential. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. …
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In this episode, we explore how to get paid for drone piloting. That’s right—drone skills are valuable! 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: …
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In this week’s “First $1K” segment, we hear from an aspiring entrepreneur in Baltimore who starts a seasonal pop-up coffee cart. 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 day…
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In this episode, we explore effective strategies to improve a non-profit membership drive. Learn how to attract more members and ensure growth with actionable tips and insights. 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…
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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 …
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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. T…
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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 quittin…
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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 …
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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 less…
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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 e…
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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…
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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 quitt…
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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 wh…
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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 list…
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