Side Hustle School

By Chris Guillebeau / Onward Project

Business Careers

What's Side Hustle School about?

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.

4.7

3,001 ratings

Download our free app to listen on your phone

LAST EPISODE

#1728 - Failure Friday: “Ev...

09.24.2021

In this week’s Failure Friday segment, we hear from Jonathan Fields (!), author of Sparked. The morning his popular yoga studio received a VIP guest, the sound system broke down. He ran out to get a new one just in ...

Side Hustle School episodes:

09.24.2021 #1728 - Failure Friday: “Everyone in the room said ‘Turn it off!’…” In this week’s Failure Friday segment, we hear from Jonathan Fields (!), author of Sparked. The morning his popular yoga studio received a VIP guest, the sound system broke down. He ran out to get a new one just in ...
09.23.2021 #1727 - TBT: “ColorHype” Owner Sells 8,000 Painting Kits In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of ColorHype. Initially a local painting class business based in Texas, ColorHype adapted during the pandemic and sold more than 8,000 painting kits to ...
09.22.2021 #1726 - Q&A: Is it still a good idea to sell Merch by Amazon? Two years ago, one of our listeners made $30,000 selling t-shirts on Amazon without stocking any inventory. Opportunities come and go, however, and today’s caller is wondering if the Merch by Amazon program is still viable. Show notes: SideHustleSchool.com Email: ...
09.21.2021 #1725 - “Big Dinosaur Podcast” Generates Dino-mite Profits A dinosaur loving couple starts a podcast about their favorite ancient reptiles, hosting more than 350 episodes and now bringing in a full-time income. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on ...
09.20.2021 #1724 - Q&A: Can I use OnlyFans for PG-rated content? Today’s caller wants to recruit supporters on OnlyFans, but she doesn’t provide “adult” services. Is it possible to use this platform for PG-related patronage? Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on ...
09.19.2021 #1723 - Utah Dad Makes a Splash with Paddleboard Rentals Pandemic demand for outdoor activities helped this seasonal side hustle—but what really allowed it to thrive was the owner’s use of Google Maps. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: ...
09.18.2021 #1722 - Q&A: Can I sell travel insurance packages as an affiliate? The airlines make millions of dollars pushing useless travel insurance policies. How can you get in on the racket?? Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main ...
09.17.2021 #1721 - Failure Friday: “A bad hire will set you back six months…” In this week’s Failure Friday segment, we hear from the founder of a consulting training firm. As his business grew, he went against his intuition and hired an overseas virtual assistant. Unfortunately, this new employee created more problems than they ...
09.16.2021 #1720 - TBT: Local Comic Book Store Expands to National Subscription Box In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the Sacramento-based co-owner of Comic Crate, a monthly comic book subscription box service. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: ...
09.15.2021 #1719 - Q&A: Our listener won a contest to live in Airbnbs for a year! Amazing story: one of our listeners in the UK won a contest (with 315,000 entrants) to live anywhere with Airbnb for a whole year. Awesome, right? He’s now wondering how to maximize the publicity his family is getting. Show notes: ...
09.14.2021 #1718 - The $30,000/Month Women’s Fitness Website When a mom of two wants to avoid returning to full time employment, she starts freelance writing. An assignment for a women’s fitness website leads to much more when she adapts their model for herself. Show notes: SideHustleSchool.com Email: [email protected] ...
09.13.2021 #1717 - Q&A: “I want to write the German immigrant's guide to the U.S…” A listener from Germany immigrated to the U.S. several years ago. He found the legal process to be confusing, and now wants to help guide other German-speakers through the experience. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions ...
09.12.2021 #1716 - Houseplant Biz Blossoms for Hong Kong Transplant A Washington, D.C. resident originally from Hong Kong uses Facebook Marketplace to cultivate a $4,000/month houseplant hustle, all based on the Chinese principles of Feng Shui. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau ...
09.11.2021 #1715 - Q&A: Reselling for others: should I charge a flat fee or percentage? 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. Show notes: SideHustleSchool.com Email: [email protected] Be on ...
09.10.2021 #1714 - Failure Friday: Dating Profile Ghostwriter Struggles to Launch App In this week’s Failure Friday segment, we hear from Meredith Golden, the founder of an app that provides transparency and truth in dating. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: ...
09.09.2021 #1713 - TBT: Wine Tour Business Pivots During Pandemic In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of Heathen Wines. After hosting tours all over Europe, he changed his business model during the pandemic to offer virtual tours and sell private ...
09.08.2021 #1712 - Q&A: Is there a way to trade plane tickets for profit? Today’s listener has a creative idea, but also some sky-high problems to solve. Is it possible to trade unused plane tickets between passengers with different names? Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau ...
09.07.2021 #1711 - P.E. Teacher Livestreams Lessons to 50,000 Students When her school district goes remote, this P.E. Teacher (and former pro volleyball player!) begins teaching daily on YouTube. Within two months, she starts a new business and quits her job to go all-in. Show notes: SideHustleSchool.com Email: [email protected] Be ...
09.06.2021 #1710 - Q&A: “I’d like to be a financial advisor for Gen Z…” This Gen Z listener wants to become a financial advisor for her generation. How can she build her authority and platform? Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit ...
09.05.2021 #1709 - No Code, No Problem: Easy-to-Build Apps for Everyone While waiting in line at a food truck, this Miami man discovers a way to build professional looking apps without learning how to code. He now earns a substantial side income building them for clients. Show notes: SideHustleSchool.com Email: [email protected] ...
09.04.2021 #1708 - Q&A: What are the ethics of paid referrals to therapists? 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? Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on ...
09.03.2021 #1707 - Failure Friday: “Hundreds of people were shut out of my webinar…” In this week’s Failure Friday segment, we hear from a boudoir photographer who diligently planned for her first webinar with 400 excited attendees—but the platform could only handle 50 of them. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: ...
09.02.2021 #1706 - TBT: Extra-Strong Coffee Supports Firefighters Nationwide In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Muertos Coffee. This coffee is strong enough to raise the dead! Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on ...
09.01.2021 #1705 - Q&A: How does a side hustle fit into a savings plan? How does a side hustle fit into your overall savings plan? That’s what our listener wants to know, in response to some recent comments on different asset classes. Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on ...
08.31.2021 #1704 - The Six-Figure Belly Dancing Course A digital marketer is determined to make a career out of her true passion: belly dancing! She now sells a course that brings in more than $100,000 a year. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
08.30.2021 #1703 - Q&A: How many social platforms should I post to? A listener has an active YouTube channel and is trying to keep up with a lot of different networks, but he’s not seeing the traction and growth that he’d like. Should he specialize or diversify? Show notes: SideHustleSchool.com Email: [email protected] ...
08.29.2021 #1702 - Accountant Sells $20,000 in Knitting Kits This DIYer made $20,000 in 2020 selling knitting kits on Etsy. Why did she succeed when so many other craft sellers struggle? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra ...
08.28.2021 #1701 - Q&A: “I’d like to be a medical claims adjustor, but for weddings" A listener has an idea to become a wedding consultant who is effectively a claims adjustor, negotiating with vendors to help couples to pay less. It’s an interesting idea, but is it viable? Side Hustle School features a new episode ...
08.27.2021 #1700 - Failure Friday: “I didn’t know my business partner was a convicted felon…” In this week’s Failure Friday segment, we hear from Alan Perlman, the founder of a drone training company. His business now brings in seven figures a year, but it started with a rocky partnership. Side Hustle School features a new ...
08.26.2021 #1699 - TBT: Matchsticks Made in Heaven (and Georgia) In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a former H.R. manager who now sells matchsticks full-time. That’s right—it’s a perfect match. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
08.25.2021 #1698 - Q&A: Is there an easier way to start reselling? Reselling is quick and simple—but it’s also a lot of work, and today’s caller is looking for a shortcut. Does such a thing exist? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ...
08.24.2021 #1697 - Lawyer Moonlights Music Production Tutorials When a lawyer’s after-hours hobby of music production draws interest, he creates a series of video tutorials that leads budding producers to an online course. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
08.23.2021 #1696 - Q&A: How to start a meal prep side hustle? Today’s listener seeks help in monetizing his experience with weekly meal prepping. 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 ...
08.22.2021 #1695 - Finance Worker Strikes Gold with Custom Jewelry When the daughter of a jewelry maker discovers how profitable the industry can be, she uses her skills from corporate finance to build her own brand. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
08.21.2021 #1694 - Q&A: Is there a limit to how high I can price my service? Today’s caller believes in the idea of raising prices, but is worried about losing customers if he raises them too much. How high is too high? Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of ...
08.20.2021 #1693 - Failure Friday: “We made a ton of investment … then we decided to close.” In this week’s Failure Friday segment, we hear from Nate Martin, the founder of America’s original escape room. His business, Puzzle Break, now has locations worldwide—but an early expansion to San Francisco turned out to be a puzzle he couldn’t ...
08.19.2021 #1692 - TBT: App Helps 60,000 Women Get Paid More In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Meggie Palmer, founder of PepTalkHer, an app that has helped more than 60,000 users (mostly women) negotiate a pay raise. Side Hustle School features a new ...
08.18.2021 #1691 - Q&A: How to become a travel agent? Today’s listener is interested in becoming a travel agent—and yes, those still exist! Modern travel agents tend to work on specialized, boutique trips for select clients. How can our listener get certified and find her market? Side Hustle School features ...
08.17.2021 #1690 - Product Manager Starts “Airbnb for Dungeons and Dragons” This product manager has achieved the dream of many kids born in the 80s and 90s: he gets paid to host and run his favorite tabletop roleplaying games. Side Hustle School features a new episode EVERY DAY, featuring detailed case ...
08.16.2021 #1689 - Q&A: "My sister made $5,000 but feels guilty..." A caller poses an unusual question: their sister has been doing well in a new art restoration service, but feels guilty about getting paid for it. What’s the best answer for this? Side Hustle School features a new episode EVERY ...
08.15.2021 #1688 - ESL Teacher Resells Furniture for Big Profits When a Missouri ESL teacher sells a couple of barstools on a whim, she begins a furniture flipping journey that leads to a full-time income. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ...
08.14.2021 #1687 - Q&A: How can I make a course delivered by text messages? After taking my new Idea to Income course that’s taught through text messaging, a listener wants to make their own. Good for them! Here’s how they—or you—can do it. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
08.13.2021 #1686 - Failure Friday: Ice Glass Event Business Melts Down In this week’s Failure Friday segment, we hear from the inventor of a mug made out of ice. During a big event on an unseasonably warm Minnesota day, he watches in horror as his product literally melts down. Side Hustle ...
08.12.2021 #1685 - TBT: Small 3D Printing Site Competes With Etsy In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Nikko Mendoza, who sells 3D printing templates. After he lost his job last year, he started taking his side gig more seriously—and business took off. Side ...
08.11.2021 #1684 - Q&A: How to launch a set of unique enamel pins? A listener makes enamel pins with brain imagery on them. These pins are loved by neuroscientists and other professionals who work with the brain—but how can she break into the larger wholesale market? Side Hustle School features a new episode ...
08.10.2021 #1683 - Designer Makes Magnificent Menswear A menswear designer and new mom goes in search of flexibility and freelancing. After quitting her stable job, she pitches direct-to-consumer brands and ends up with plenty of work. Side Hustle School features a new episode EVERY DAY, featuring detailed ...
08.09.2021 #1682 - Q&A: Is there a better way to offer discounts to customers? Today’s caller is seeking advice on managing the discount process. Her side hustle is growing, and she’s using a smart strategy of offering a discount after the first purchase—but she needs a better process for managing this. Side Hustle School ...
08.08.2021 #1681 - Management Consultants Create Travel-Themed Digital Art Two friends who work as consultants create an online shop offering digital and print-on-demand travel-themed art prints. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. ...
08.07.2021 #1680 - Q&A: How do I actually sell an NFT?? WFT is an NFT? It’s a non-fungible token, also known as digital art that’s for sale to the highest bidder. In today’s extra-special Q&A episode, a listener provides the question and the answer. That’s right, one of our featured artists ...
08.06.2021 BONUS: Last Day of “Idea to Income” Course Discount Heads up! The “Idea to Income” course discount ends this weekend. If you haven’t signed up yet, use code IDEA at https://courses.sidehustleschool.com. The course takes ten minutes a day, with all lessons delivered directly to your phone. Side Hustle School ...

Older episodes