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.

Hosted on Acast. See acast.com/privacy for more information.

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Episodes

#1871 - First $1,000: “I had literally zero intention of running a business…”

In this week’s First $1,000 segment, we hear from Lindsay Gordon, who left a career at Google to become a career coach for analytically-minded people. 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/question...

Feb 14, 20229 minEp. 1871

#1870 - Q&A: Is the directory website model outdated?

A caller from Massachusetts has a small moving business and is thinking about adding a directory website that provides listings to movers from around the country. Is this business model outdated, or might it still have potential? 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...

Feb 13, 20226 minEp. 1870

#1869 - Q&A: “I’m building the world's most difficult scavenger hunt…”

A scavenger hunt that takes place across state lines and requires weeks to complete? That’s what our listener is putting together! 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...

Feb 12, 20225 minEp. 1869

#1868 - Failure Friday: “What you didn’t hear was how unfocused I was…”

In this week’s Failure Friday segment, we hear from Chelsea Raehl, who sells 3D printed cookie cutters. After starting out strong, she quickly became unfocused and exhausted in trying to do too many things at once. 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@si...

Feb 11, 20228 minEp. 1868

#1867 - TBT: Catholic Designer Updates T-Shirts for New Generation

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Joe Kim, founder of PAL Campaign. Seeking to advance what he calls “the dog days of Christian t-shirt design,” he introduced a fresh, updated style that teenagers in youth groups would actually wear. 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 severa...

Feb 10, 20227 minEp. 1867

#1866 - Q&A: What kind of side hustle can I start with a chronic illness?

Today’s caller has an autoimmune disease that limits her energy. When it’s hard to commit in advance to a schedule of tasks, what kind of side hustle should you consider? 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: SideHustl...

Feb 09, 20226 minEp. 1866

#1865 - “Free Prep Course” Site Generates 7-Figure Income

A former educator schools the system, offering his test prep guides for free but generating a massive return through online advertising. 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 T...

Feb 08, 20228 minEp. 1865

#1864 - First $1,000: “It was the Super Bowl of professional fishing…”

In this week’s First $1,000 segment, we hear from Pete Robbins, a government lawyer who gets paid to go fishing and write about it. His best advice: “Press the damn send button.” 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: S...

Feb 07, 20228 minEp. 1864

#1863 - Q&A: How can my tour business earn recurring revenue?

Today’s caller is a tour operator who hosts visiting Americans and other tourists in his home city of Barcelona. Is there a way he can shift from being paid for single tours to a recurring revenue 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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustlesch...

Feb 06, 20225 minEp. 1863

#1862 - Q&A: How can I get med students to buy my flash cards?

This listener has made a set of flash cards to help med students memorize part of the body and other terminology. How can they reach their target market? 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/quest...

Feb 05, 20224 minEp. 1862

#1861 - Failure Friday: “My Facebook page with 150,000 fans was taken over by hackers…”

In this week’s Failure Friday segment, we hear from the world’s leading expert on tailgating. When his popular Facebook page got hacked, he lost thousands of followers and it took more than a month to resolve. 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@sidehus...

Feb 04, 20227 minEp. 1861

#1860 - TBT: “Walking Dead” Sugar Cookies Provide Sustenance for Apocalypse

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from Carrie Buchanan, founder of the Bombshell Baking Company. This full-time social worker earns up to $4,000/weekend selling themed cookies at conventions. 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....

Feb 03, 20227 minEp. 1860

#1859 - Q&A: Should I sell guides for software application training?

A listener in Ireland wonders about selling e-books or other tools to help users with software applications like Microsoft Word or Google Docs. What does she 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 week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHust...

Feb 02, 20225 minEp. 1859

#1858 - Online Resume Templates Scale Recruiter’s Expertise

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 the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram: @1...

Feb 01, 20227 minEp. 1858

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

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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.co...

Jan 31, 20227 minEp. 1857

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

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sideh...

Jan 30, 20226 minEp. 1856

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect ...

Jan 29, 20225 minEp. 1855

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

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehus...

Jan 28, 20227 minEp. 1854

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

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 lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@s...

Jan 27, 20226 minEp. 1853

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

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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleS...

Jan 26, 20225 minEp. 1852

#1851 - Conservation Scientist Designs & Sells Nonbinary Stickers

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect...

Jan 25, 20226 minEp. 1851

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

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be o...

Jan 24, 20229 minEp. 1850

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

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, the show includes free guided lessons and listener Q&A several days each week. Show notes: SideHust...

Jan 23, 20224 minEp. 1849

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

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 week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSc...

Jan 22, 20226 minEp. 1848

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

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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.co...

Jan 21, 20228 minEp. 1847

#1846 - TBT: Aussie Dental Blog Turns Brushheads

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Co...

Jan 20, 20228 minEp. 1846

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the ...

Jan 19, 20225 minEp. 1845

#1844 - Nurse Quits Job for Six-Figure Parenting Blog

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 days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHus...

Jan 18, 20227 minEp. 1844

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

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. This year, the show includes free guided lessons and listener Q&A several days each week. Show ...

Jan 17, 20228 minEp. 1843

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: S...

Jan 16, 20225 minEp. 1842
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