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

#1958 - TBT: Boise Woodworking Team Upgrades Toolkit 12.05.2022 7:12

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from an Idaho woodworker. As more people have moved to the area, his business has taken off. 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...

#1957 - Q&A: “I have a tricky ethical situation with my day job…” 11.05.2022 5:02

What happens when your day job brings you a lead for your side hustle? This caller faces an ethical dilemma, as well as a practical one. 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: SideHustleSc...

#1956 - College Student Turned Fashion Influencer Earns $140,000 10.05.2022 7:32

Fascinated by the influencer life, a university student creates a fashion blog that earns real money, thanks to SEO and Pinterest. 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....

#1955 - First $1,000: Digital Art Reaches Physical Homes Worldwide 09.05.2022 5:55

In this week’s First $1,000 segment, we hear from the co-founders of Wandercolors. Together, they produce digital art of iconic travel destinations. 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: S...

#1954 - Q&A: “I’m giving lots of consultations, but making few sales…” 08.05.2022 5:42

Today’s listener is experiencing lots of demand for the free version of her coaching offer, but not the paid one. Let’s see if we can help her! 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. Side Hustle School...

#1953 - Q&A: “I think my client ghosted me…” 07.05.2022 4:37

We’ve all been there—ghosted by someone we liked. In this case, a designer nearly lands the perfect client, but then the client goes AWOL. What can we learn from the experience? 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...

#1952 - Failure Friday: “I naively thought the influencers would bring sales…” 06.05.2022 5:28

In this week’s Failure Friday segment, we hear from an Australian who owns an ecommerce business offering mindful toys and gifts. Following a rebrand, she pays Instagram influencers to create interest—but mostly they just took her 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 s...

#1951 - TBT: “Mozart for Munchkins” Gives Encore Performance 05.05.2022 7:07

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Mozart for Munchkins. The group produces concerts and musical experiences for children of all ages in New York City. 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...

#1950 - Q&A: “Can you really just right-click and save an NFT?!” 04.05.2022 5:40

Today’s caller wants to know: can you really right-click and save someone else’s NFT to your computer? And if you can, can you then sell it yourself? (I love the thinking here!) 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...

#1949 - Travel Membership Program Earns $300,000/Year 03.05.2022 6:59

This travel writer found the ticket to a thriving membership site, helping families book airfare for less. Wheels up! 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: te...

#1948 - First $1,000: “I took a salary cut of fifty per cent…” 02.05.2022 7:38

In this week’s First $1,000 segment, we hear from a globetrotting Australian who owns an ad agency. He took a 50% salary cut to learn about the early model of pay-per-click advertising, but the decision paid off well. 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...

#1947 - Q&A: “I’m overwhelmed with too many inquiries…” 01.05.2022 5:07

Today’s caller has a different sort of problem than most people who struggle to get off the ground: her business is going so well that she’s feeling overwhelmed with the work. 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 d...

#1946 - Q&A: “’Spaced repetition’ practice with overseas tutors?” 30.04.2022 5:49

Today’s listener has an intriguing idea: to aid in memory retention using spaced repetition—but with outsourced tutors from other countries. Think of it like “Upwork meets Coursera.” Will it work? 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 listen...

#1945 - Failure Friday: “They just weren’t interested in what we were selling…” 29.04.2022 7:29

In this week’s Failure Friday segment, we hear from the co-owner of a business that livestreams weddings. When Covid struck, they thought they had the perfect opportunity to expand to a new market—but buyer interest fizzled. 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...

#1944 - TBT: Upcycled Journals Provide Renewable Income 28.04.2022 7:40

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of Just My Type, a creative bookbinding business based in Missoula, Montana. 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 w...

#1943 - Q&A: “I’d like to start a Supreme Court fan club…” 27.04.2022 5:10

This judicial fan club will provide updates, commentary, and memorabilia in the form of a subscription box. How can our listener ensure a fair ruling? 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:...

#1942 - Ottawa Teacher Finds “Unexpected Journey” After Retirement 26.04.2022 7:46

A newly retired teacher capitalizes on the unique spots around Canada’s capital city. 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 t...

#1941 - First $1,000: “My roommate threw a wad of hundred-dollar bills on the table…” 25.04.2022 9:17

In this week’s First $1,000 segment, we hear from Silver Picker, a college student turned coin reseller who earned $10,000 one summer from coins and metals he finds at estate sales. 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 sev...

#1940 - Q&A: “How can I grow my podcast without social media?” 24.04.2022 6:15

A high school student has been hosting a podcast and wants to reach more people—but without using social media. What should she try next, and how can we support her? 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 we...

#1939 - Q&A: “Has my apprenticeship gone on for too long?” 23.04.2022 4:47

The right kind of apprenticeship can work well for both parties. The wrong kind can be, well, terrible. How do you know the difference, and how can you find a graceful exit ramp when it’s time to leave? 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...

#1938 - Failure Friday: “My app kept crashing during the big pitch…” 22.04.2022 7:56

In this week’s Failure Friday segment, we hear from the founder of iGoal.io, a project management tool. An early pitch to a major investor got off to a rough start. 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 w...

#1937 - TBT: Mural Painter Follows Signs to New Career 21.04.2022 6:53

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a land surveyor who changes careers when he discovers an accidental side hustle painting signs and murals. It’s now a full-time, six-figure business! 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 includ...

#1936 - Q&A: “Can I file a small claims suit against a big business?” 20.04.2022 4:37

Today’s caller is having a frustrating experience: they aren’t getting paid for work they’ve completed! Can they take their client to small claims court? 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 not...

#1935 - Orthodontic Marketer Knows the Drill 19.04.2022 7:26

This marketer puts his money where his mouth is, striking gold by helping orthodontists market their business. 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...

#1934 - First $1,000: Running Coach Strides to Finish Line 18.04.2022 6:28

In this week’s First $1,000 segment, we hear from Jason Fitzgerald, a fitness coach and founder of StrengthRunning.com. Two years after starting his side hustle, Jason went full-time. 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 se...