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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 share game-changing strategies to grow a Poshmark side hustle. Learn how to source smarter, spot trending items, and expand your reach to skyrocket 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 includ…
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In this week’s Failure Friday segment, we hear from a longtime hustler who dives into the competitive world of wearable tech with a custom fitness tracker idea, only to face the tough reality of product development and market demands. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money…
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In this week’s “Throwback Thursday / Where are they now?” segment, we catch up with a home baker who went from selling cookies at local farmers' markets to landing a nationwide distribution deal with a major grocery chain. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qui…
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In this episode, we help a Chicago-based graphic designer kick off her side hustle while working full-time. Tune in for actionable insights and at least one practical tip. :) 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 fr…
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In this episode, we share tips and tactics to help a Charleston-based wedding photographer use Pinterest to attract more clients and book more gigs. 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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In this week’s First $1,000 segment, we hear from a genealogical detective who pieced together a successful business by unraveling the mysteries of family histories. 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…
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In this episode, we help a Colorado-based entrepreneur come up with guerrilla marketing tactics to launch a bike repair 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 listener Q&A several…
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In this episode, we help an Aussie side hustler launch an international snack box subscription on a tight budget. 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…
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In this week’s Failure Friday segment, we hear from a side hustler who built his business on personalized tech tutorials and code reviews, only to find his services rendered obsolete by the rise of AI, particularly Microsoft's CoPilot. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mone…
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In this week’s “Throwback Thursday / Where are they now?” segment, we reconnect with a part-time wedding officiant who has found success by focusing on personalizing ceremonies and crafting memorable stories. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their jo…
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In this episode, we help a marketing consultant define her niche, create a compelling service offering, and attract clients to grow her 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 list…
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In this episode, we explore flexible, low-cost side hustle ideas perfect for a stay-at-home mom looking to earn extra income during nap times and after bedtime. 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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From clandestine operations to cyber education, this week's First $1,000 segment features an ex-spy who turned a unique skillset into a thriving business on staying safe in a world of surveillance. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This yea…
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In today's episode, we're investigating Tokyo's gaming scene, specifically how to boost a caller’s custom avatar designs with influencer marketing. How can he find the right people to help him grow? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye…
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In this episode, we explore side hustle ideas tailored to serving the unique needs of seniors, and share tips on how to market these services effectively to the growing senior population. 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 sho…
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In this week’s Failure Friday segment, we hear from a freelancer who sought community and collaboration in a coworking space, only to find isolation and unmet expectations. Her story reveals the gap between the promise of coworking spaces and the reality of solitary office rental. Side Hustle School features a new episode EVERY DAY, featuring detai…
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In this week’s “Throwback Thursday / Where are they now?” segment, we check in with a Boston-based personal organizer who pivoted from online media to focus on transforming homes and lives in her local community. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting thei…
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In this episode, we share strategies to help a virtual assistant level up their side hustle, attract high-paying clients, and command premium rates. 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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In today's episode, we step into the studio of a digital illustrator turning passion into profession. Discover how unique art meets strategic marketing to create a flourishing online 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, th…
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In this week’s First $1,000 segment, we hear from a creative reseller who purchases bulk items on Temu, then resells them (also in bulk!) to local businesses. 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 lesson…
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In today’s episode, we investigate how a language learning method is making waves worldwide. What can we learn from it, and how can the creator be even more successful? 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…
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In today’s episode, let’s dance our way to South Florida, where a listener hopes to expand her Miami workout method to a group far beyond her local gym. 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 …
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In this week’s Failure Friday segment, we hear from an aspiring tech entrepreneur who dreams of opening a short-term housing network in Bali—only to discover that Airbnb kind of has that covered. 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,…
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In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a big box store employee who side hustles as a custom PC builder. 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 listene…
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In today's episode, we're stirring the pot of tradition and technology, exploring how a Neapolitan cook's love for local cuisine can transform into a successful food blog. 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 …
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