Chris Guillebeau

Side Hustle School

Business EN ↓ 3536 episodes

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.

Author

Chris Guillebeau

Episodes

#1733 - Q&A: Should I become a “miles and points broker”? 29.09.2021 4:49

This listener’s dad has an extra half million Frequent Flyer miles sitting around. The surplus has got them both thinking: is there a way they can get paid by matching discounted miles with budget flyers? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit Chr...

#1732 - “Going Gray” Blog Brings in $6,000/Month 28.09.2021 7:30

When an aerospace manager decides to embrace her gray hair, she starts a blog to help others in similar situations. 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!...

#1731 - Q&A: How do you 'build your platform' if you're selling on Amazon? 27.09.2021 4:57

Today’s caller has an important question: if you use Fulfillment by Amazon, how do you go about building your platform? After all, Amazon controls the entire customer service process and doesn’t even let you know who’s buying. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram:...

#1730 - 7th Grade Teacher Earns 2nd Income Writing Resumes 26.09.2021 6:14

This English teacher has a passion for writing. After a few unexpected twists and turns in his career, he’s using his skills to help others find their dream jobs. 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 yo...

#1729 - Q&A: What separates a $30 course from a $1,000 course? 25.09.2021 5:09

Some online courses cost $30, others cost $1,000 or more. What’s the difference between a lower-priced course and a higher-priced one—are the more expensive ones just “better” or is there more to the story? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @193countries Visit...

#1728 - Failure Friday: “Everyone in the room said ‘Turn it off!’…” 24.09.2021 8:49

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 time, and the problem was solved—or was it? Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisgu...

#1727 - TBT: “ColorHype” Owner Sells 8,000 Painting Kits 23.09.2021 6:43

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 customers nationwide. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @c...

#1726 - Q&A: Is it still a good idea to sell Merch by Amazon? 22.09.2021 4:37

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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @19...

#1725 - “Big Dinosaur Podcast” Generates Dino-mite Profits 21.09.2021 7:08

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: 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 enjo...

#1724 - Q&A: Can I use OnlyFans for PG-rated content? 20.09.2021 5:05

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: 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...

#1723 - Utah Dad Makes a Splash with Paddleboard Rentals 19.09.2021 7:22

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: 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...

#1722 - Q&A: Can I sell travel insurance packages as an affiliate? 18.09.2021 5:34

The airlines make millions of dollars pushing useless travel insurance policies. How can you get in on the racket?? 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! I...

#1721 - Failure Friday: “A bad hire will set you back six months…” 17.09.2021 5:48

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: @chris...

#1720 - TBT: Local Comic Book Store Expands to National Subscription Box 16.09.2021 7:05

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: ChrisGuillebea...

#1719 - Q&A: Our listener won a contest to live in Airbnbs for a year! 15.09.2021 5:31

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: @193coun...

#1718 - The $30,000/Month Women’s Fitness Website 14.09.2021 7:32

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 Chr...

#1717 - Q&A: “I want to write the German immigrant's guide to the U.S…” 13.09.2021 6:11

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: Chri...

#1716 - Houseplant Biz Blossoms for Hong Kong Transplant 12.09.2021 6:18

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: ChrisGuille...

#1715 - Q&A: Reselling for others: should I charge a flat fee or percentage? 11.09.2021 4:51

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:...

#1714 - Failure Friday: Dating Profile Ghostwriter Struggles to Launch App 10.09.2021 8:27

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...

#1713 - TBT: Wine Tour Business Pivots During Pandemic 09.09.2021 6:28

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 Co...

#1712 - Q&A: Is there a way to trade plane tickets for profit? 08.09.2021 6:03

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...

#1711 - P.E. Teacher Livestreams Lessons to 50,000 Students 07.09.2021 7:31

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 Chr...

#1710 - Q&A: “I’d like to be a financial advisor for Gen Z…” 06.09.2021 4:37

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 alo...

#1709 - No Code, No Problem: Easy-to-Build Apps for Everyone 05.09.2021 7:09

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'...