Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau sidehustleschool.com
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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Episodes

#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 solved. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you'r...

Sep 17, 20216 minEp. 1721

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every single...

Sep 16, 20217 minEp. 1720

#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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along!...

Sep 15, 20216 minEp. 1719

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and ha...

Sep 14, 20218 minEp. 1718

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published e...

Sep 13, 20216 minEp. 1717

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every si...

Sep 12, 20216 minEp. 1716

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been publis...

Sep 11, 20215 minEp. 1715

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're ...

Sep 10, 20218 minEp. 1714

#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 label wine. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the...

Sep 09, 20216 minEp. 1713

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every single day si...

Sep 08, 20216 minEp. 1712

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and h...

Sep 07, 20218 minEp. 1711

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very gratefu...

Sep 06, 20215 minEp. 1710

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has...

Sep 05, 20217 minEp. 1709

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every si...

Sep 04, 20215 minEp. 1708

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been p...

Sep 03, 20218 minEp. 1707

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every single day since ...

Sep 02, 20216 minEp. 1706

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com If you're enjoying the show, please pass it along! It's free and has been published every single day since...

Sep 01, 20215 minEp. 1705

#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 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@sidehustleschool.com Be on the show: SideHustleSchool.com/q...

Aug 31, 20219 minEp. 1704

#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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chris's main site: ChrisGuillebeau.com Side Hustle School features a new episode EVERY DAY, featuring detailed ca...

Aug 30, 20216 minEp. 1703

#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 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: ...

Aug 29, 20217 minEp. 1702

#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 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@sidehustleschool.com Be ...

Aug 28, 20216 minEp. 1701

#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 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@sidehustleschool....

Aug 27, 20217 minEp. 1700

#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 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@sidehustleschool.com Be on the show: Sid...

Aug 26, 20219 minEp. 1699

#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 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitt...

Aug 25, 20215 minEp. 1698

#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 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@sidehustleschool.com Be on the show: SideHustleSchool.c...

Aug 24, 20218 minEp. 1697

#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 free guided lessons and listener Q&A several days each week. 🎧 Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @19...

Aug 23, 20216 minEp. 1696

#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 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questi...

Aug 22, 20218 minEp. 1695

#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 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Con...

Aug 21, 20215 minEp. 1694

#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 crack. 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 n...

Aug 20, 20217 minEp. 1693

#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 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@sidehustlesc...

Aug 19, 20219 minEp. 1692
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