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

#1858 - Online Resume Templates Scale Recruiter’s Expertise 01.02.2022 7:06

Turning her skills into a product allowed this corporate coach to help others at scale. 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...

#1857 - First $1,000: “I knew I had to do SOMETHING…” 31.01.2022 6:40

In this week’s First $1,000 segment, we hear from a “client attraction coach” who decides to start a business sometime in the next 5-10 years. Fortunately, he moves much quicker, finding a creative way to deliver marketing advice. 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 incl...

#1856 - Q&A: “Buy almonds in one state, sell oranges in another…” 30.01.2022 5:38

When we talk about arbitrage, we’re not usually talking about agricultural products—but this listener is! Can they buy almonds in California and oranges in Florida, and then sell each one in the opposite state?? 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 le...

#1855 - Q&A: Get paid to earn airline status for busy executives? 29.01.2022 5:22

Today’s caller describes his business idea as being “truly up in the air.” Can he get paid for helping executives earn airline elite status? 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: SideHustl...

#1854 - Failure Friday: “If I had done any research, I would have picked a different country…” 28.01.2022 7:15

In this week’s Failure Friday segment, we hear from Kassandra Marsh, an Australian graphic designer. When she had a new business idea, she jumped in without doing any research. Lesson learned: do the research. 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 le...

#1853 - TBT: “Not Your Mother’s Resumé” Service Doubles Business 27.01.2022 6:00

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Chelsea Opare-Addo, founder of Not Your Mother’s Resumé. This tech recruiter has doubled her side income since we first told her story! 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...

#1852 - Q&A: Should I buy a McDonald’s franchise? 26.01.2022 4:32

Should you buy into an existing franchise? That’s what our caller is wondering about—they’re looking at investing in a Subway or McDonalds. Is this a $5 foot-long 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 days eac...

#1851 - Conservation Scientist Designs & Sells Nonbinary Stickers 25.01.2022 6:01

Founded by a conservation scientist on a whim, “Nonbeenary Designs” offers amusing and affirming stickers that recognize the nonbinary 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 several days each week. Show notes: SideHu...

#1850 - First $1,000: “I succeeded by following contradictory advice…” 24.01.2022 9:09

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...

#1849 - Q&A: Should I sell this valuable domain name? 23.01.2022 3:58

If you’re like me, you have way too many domains you’ve registered but never put to use. *Unlike* me, however, this listener has a highly valuable one on their hands. Should they cash out to the highest bidder or hold out for a better offer? 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...

#1848 - Q&A: “Square refunded my customer's payment!” 22.01.2022 5:31

One of our listeners recently encountered a negative situation with their new tour guide business: they got a chargeback! How can they appeal and get back their money? 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...

#1847 - Failure Friday: “If I could do it over again, I’m not sure I would…” 21.01.2022 8:07

In this week’s Failure Friday segment, we hear from the founder of a business that transports bicycles to adventure sport locations in Central America. After spending $40,000 to get going, he learned it was harder than he thought! 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 inc...

#1846 - TBT: Aussie Dental Blog Turns Brushheads 20.01.2022 7:32

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Australia’s leading dental blog. Brace yourself! 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: Sid...

#1845 - Q&A: How do songs get licensed for background music? 19.01.2022 4:46

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 listener Q&A...

#1844 - Nurse Quits Job for Six-Figure Parenting Blog 18.01.2022 6:54

She was known as the pregnancy nurse—and she did so well talking to parents that she quit her job to run a popular parenting blog. It brings in multiple six figures 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 day...

#1843 - First $1,000: “Beekeeping is forced zen: be present or get stung!” 17.01.2022 8:07

In this week’s “First $1,000” segment, we hear from Frank Mortimer, the self-described “Bee Man of New Jersey.” In his initial foray into selling honey at a farmers market, he learned several critical lessons. Among others: don’t forget the tasting spoons! Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job....

#1842 - Q&A: Should I hire a designer or do it myself? 16.01.2022 4:54

When should you hire a designer and when should you “just get it done” on your own? In this listener’s case, she’s really not sure—let’s see if we can help her make the 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 sever...

#1841 - Q&A: “The Super Mario Bros. civil war reenactment…” 15.01.2022 4:44

Today’s caller has an idea to remix a historical event for a new generation. Forget about civil war reenactments—they want to create a reenactment of classic video game battles! 🍄 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 sever...

#1840 - Failure Friday: “We spent countless hours making videos no one watched…” 14.01.2022 7:54

In this week’s Failure Friday segment, we hear from the co-founder of Master ABA, a site that helps families and professionals help children with autism. The two founders spent a great deal of time developing a membership that wasn’t compelling to their audience, before realizing their mistake and regrouping. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of p...

#1839 - TBT: Prize Fighter Leaves Ring for Soulful CBD Sales 13.01.2022 8:14

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Mike Lee, the co-founder of Soul CBD. After a successful boxing career, Mike hung up his gloves to enter the small business arena. 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 less...

#1838 - Q&A: “An old-school magazine about old-school businesses…” 12.01.2022 4:44

This caller wants to start a print publication—nothing digital! What’s the business model of this potential business magazine? 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 E...

#1837 - Lifelong Toy Car Fan Becomes Mega Dealer 11.01.2022 8:11

A chance encounter at a funeral leads to a second act reselling vintage toy cars. 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 sh...

#1836 - First $1,000: “I had to spend $20,000 to make $1,000…” 10.01.2022 7:14

In this week’s “First $1,000” segment, we hear from the creator of Metaphor Dice, the writing tool that plays like a game and helps you think more figuratively. How did he make his first $1,000, and what did he learn? 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 guid...

#1835 - Q&A: What if a company hires you and doesn’t pay up?? 09.01.2022 5:22

After a friend had a negative experience working for a company that didn’t pay up, our caller wants to make sure this doesn’t happen to him. What can he do to be proactive about invoicing and collecting payment? 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 l...

#1834 - Q&A: Should I stick to my plan or accept other offers? 08.01.2022 5:17

When you have a particular business model in mind but people want to pay you for something else—what do you 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 days each week. Show notes: SideHustleSchool.com Email: team@side...