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Side Hustle School

Side Hustle School

Chris Guillebeau 3496 Episodes Oct 14, 2026

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 hear a different story of someone who's started a side hustle, including what went well, how they 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 and other books.

Episodes

Ep. 3574 - Q&A: “Can I use another author's work in my book?”
Ep. 3574 - Q&A: “Can I use another author's work in my book?” Oct 14, 2026 4:33 Today’s listener has a legal question that I can actually answer with some confidence: what are the rules about quoting or referencing someone else’s work in something you offer for sale?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
Ep. 3573 - Q&A: “How do I focus on retaining clients?”
Ep. 3573 - Q&A: “How do I focus on retaining clients?” Oct 13, 2026 4:24 Today we’re going to hear from a CPA in the midwest who wants to focus on retaining clients. This is more important than finding new 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 includes free guided lessons and listener Q&A several days each week.Show notes: SideH
Ep. 3572 - First $1,000: “I succeeded by following contradictory advice…”
Ep. 3572 - First $1,000: “I succeeded by following contradictory advice…” Oct 12, 2026 7:41 In this week’s “First $1,000” segment, we hear from the seller of Pretty Old Books. What started as an idea to sell vintage book sets on Etsy turned into an entirely different business model. 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. 3571 - STORY: Guitar Player Chalks Up Success By Enjoying The Process
Ep. 3571 - STORY: Guitar Player Chalks Up Success By Enjoying The Process Oct 11, 2026 7:39 A systems administrator and lifelong guitar player generates thousands per month writing about his musical hobby. 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.comEmail:
Ep. 3570 - Q&A: “Can I offer a permanent price discount?”
Ep. 3570 - Q&A: “Can I offer a permanent price discount?” Oct 10, 2026 4:19 Our listener has seen furniture stores offer non-stop sales. Is there any reason they can’t have a sale that never ends in their 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 days each week.Show notes: Si
Ep. 3569 - STORY: Hand Lettering Artist Upgrades Photo Booth Props
Ep. 3569 - STORY: Hand Lettering Artist Upgrades Photo Booth Props Oct 9, 2026 7:42 An illustrator gives boring wedding photo booth props a much-needed upgrade, creating an alternative to greeting cards at the same time.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
Ep. 3568 - TBT: Physician Designs Plush Toys to Teach Anatomy
Ep. 3568 - TBT: Physician Designs Plush Toys to Teach Anatomy Oct 8, 2026 7:25 In this week’s “Throwback Thursday” segment, we hear from a doctor who makes plush toys in the shape of human organs to teach kids about the body. 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:
Ep. 3567 - Q&A: “Can I resell items I get for free?"
Ep. 3567 - Q&A: “Can I resell items I get for free?" Oct 7, 2026 4:08 Today’s listener received some free display equipment at a trade show. Can he resell it without worrying, or does this create an ethical dilemma? 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:&
Ep. 3566 - Q&A: “An English-language anime club in Japan…”
Ep. 3566 - Q&A: “An English-language anime club in Japan…” Oct 6, 2026 4:20 Today’s caller wants to start an English-speaking anime club in Japan. With the country recently re-opened for visitors, let’s get this party started!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:&n
Ep. 3565 - First $1,000: “I got paid to walk dogs while on work calls…”
Ep. 3565 - First $1,000: “I got paid to walk dogs while on work calls…” Oct 5, 2026 5:36 In this week’s First $1,000 segment, we hear from a Chicago native who starts “Day Job Dogwalking” during the pandemic. While juggling work calls with her employer, she gets paid (and eventually hires someone) to walk dogs in her neighborhood. 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. 3564 - STORY: Physical Therapist Sells 57,000 “Neck Hammocks”
Ep. 3564 - STORY: Physical Therapist Sells 57,000 “Neck Hammocks” Oct 4, 2026 7:29 In trying to remedy his own workout injuries, this physical therapist invents a portable device to relieve pain. He then patents the device and sells 57,000 of them.  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
Ep. 3563 - Q&A: “What’s the 80/20 rule of side hustling?”
Ep. 3563 - Q&A: “What’s the 80/20 rule of side hustling?” Oct 3, 2026 4:23 Today’s listener is wondering about applying the Pareto principle to the world of side hustles. What can we learn—and what should we do differently as a result of this knowledge?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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