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.

Bezoek zeker de website van de podcast en steun de maker: sidehustleschool.com

Auteur

Chris Guillebeau

Categorie

Business

Website van de podcast

sidehustleschool.com

Nieuwste aflevering

31 okt. 2026

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Afleveringen

Ep. 3318 - Q&A: “How can I sell on a platform like NextDoor?” 31.01.2026

NextDoor is not primarily designed as a platform for you to go crazy and sell a bunch of stuff. So if you DO want to sell there—what do you need to know?  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 we...

Ep. 3317 - STORY: Jiu-Jitsu Instructor Pins Down Mobile Workout Tool 30.01.2026

An unconventional workout tool becomes a hit on Kickstarter, then goes on to earn $20,000 a month for its creator.  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 Email: t...

Ep. 3316 - TBT: Designer Scales Personalized Wedding Products to $1M+ 29.01.2026

In this week's “Throwback Thursday” segment, we hear from a graphic designer who does custom illustrations for weddings and other events. It's now a seven-figure 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 se...

Ep. 3315 - Q&A: “How do I transition from Etsy to Shopify?” 28.01.2026

A listener has been selling on Etsy and wants to make the switch to Shopify. What's the best way to do this? 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 Email: team@sidehust...

Ep. 3314 - Q&A: “What's the best software to write a non-fiction book?” 27.01.2026

Today's caller wants to know about the easiest and most helpful tools to write a non-fiction book. Unfortunately, books do not write themselves, but we'll give him three resources that might make it easier.   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...

Ep. 3313 - First $1,000: “I still remember the day I hit the goal…” 26.01.2026

In this week's First $1,000 segment, we hear from Jodi Carlson, who sells resources and materials for Girl Scout troop leaders.  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...

Ep. 3312 - STORY: The Clothes Dryer That Changed a Family Forever 25.01.2026

When this government employee is let go from his job, he stumbles upon a reselling opportunity that would end up helping his family ride the coming recession—and eventually earn six figures in a single 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 gu...

Ep. 3311 - Q&A: “Get paid to help brands with their Terms & Conditions?” 24.01.2026

Today's caller wants to help brands improve their Terms & Conditions, also known as T&C. Can she design and license a template that companies will pay for? 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. 3310 - Failure Friday: “We were incredibly disappointed…” 23.01.2026

In this week's Failure Friday segment, we hear from the founder of Kettlebell Kings, an ecommerce shop. When a big early order from a supplier went terribly wrong, he had to regroup and learn resilience.  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...

Ep. 3309 - TBT: “MomBox” Expands to Popular Subscription Box Service 22.01.2026

In this week's “Throwback Thursday” segment, we hear from Kate Westervelt, the founder of MomBox. She's gone from frustrated new mom to CEO of a growing startup! 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...

Ep. 3308 - Q&A: “What are the ethics of paid referrals to therapists?” 21.01.2026

A listener with a YouTube channel about quitting smoking wants to earn commissions by referring viewers to therapists. What are the ethical and practical concerns of this idea? 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. 3307 - Q&A: “Should I charge a flat fee or percentage?” 20.01.2026

A listener and her teenager have been getting off to a good start selling on Facebook Marketplace. They now have the chance to sell for others, and are wondering about some best practices.  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. 3306 - First $1,000: “The pre-launch brought in $1,000 on day one…” 19.01.2026

In this week's First $1,000 segment, we hear from the founder of Brave Count, a subscription box for military spouses.  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 Emai...

Ep. 3305 - STORY: Engineer Makes $80,000/Year Handing Out Free Maps 18.01.2026

A former sound engineer in Texas maps out a successful career by providing free information guides for hotel guests. Advertisers pay for their business to get in front of out-of-town guests. 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. 3304 - Q&A: “Is it better to have more projects or a single focus?” 17.01.2026

It's the age-old question: how many side hustles should you try to tackle at once—and is there any process-driven way to make this decision?  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 note...

Ep. 3303 - STORY: Food Tour Guide Chomps Down on $100,000 Profit 16.01.2026

After first beginning with private cooking lessons, this former marketer discovers an even bigger opportunity in the world of food tours. 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: SideHustleSc...

3302 - TBT: Mystery Trip Biz Doubles Down on Thrills 15.01.2026

In this week's “Throwback Thursday” segment, we hear from Dave Green, the founder of Mystery Trip. His in-person event planning service has adjusted well to a hybrid world. 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 s...

Ep. 3301 - Q&A: “How do songs get licensed for background music?” 14.01.2026

An independent musician seeks advice on skipping out on Spotify. Royalties for most artists are dismal on streaming services—is corporate licensing for background music a better option?  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 liste...

Ep. 3300 - Q&A: “How many ‘wine-of-the-month’ clubs are there??” 13.01.2026

Today's caller has seen many “of-the-month” clubs, ranging from wine, plants, and even all the way to pickles. With so many of them out there, does that mean the market is saturated? 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. 3299 - First $1,000: Fashion Affiliate Earns $10,000/Month 12.01.2026

In this week's First $1,000 segment, we hear from a fashion lover who uses affiliate campaigns to earn commissions. This new business is taking off! 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...

Ep. 3298 - STORY: Rehearsal App for Actors Earns $500,000 11.01.2026

Not satisfied with the iPhone's built-in Voice Recorder, a radio host and acting coach creates his own app to help actors rehearse. It goes on to earn more than $500,000. 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 ea...

Ep. 3297 - Q&A: “Should I pay $2,000 for a domain name I really want?” 10.01.2026

Today's listener has found the perfect domain for her new website and YouTube channel, but it's already been registered and the seller wants $2,000 for it. What should she do? 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 da...

Ep. 3296 - Failure Friday: “Apple rejected my game before it even launched…” 09.01.2026

In this week's Failure Friday segment, we hear from a mobile game developer with an ambitious idea—so ambitious that it never got off the ground.  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...

Ep. 3295 - TBT: Best Guitar Lessons in the Universe 08.01.2026

In this week's “Throwback Thursday” segment, we hear from a university administrator who creates a sustainable full-time income from teaching guitar.  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...

Ep. 3294 - Q&A: “I’m offering executive coaching at a high price…” 07.01.2026

Today's caller is on their second attempt with a coaching service for busy executives. It's a big-ticket item, but the first round didn't go very well. What should they change for take two? 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&am...

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