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

#1635 - Q&A: "I want to sell a spreadsheet to track fitness goals…” 23.06.2021 6:16

Our caller today has an idea that’s a combination of old-school and new school: a spreadsheet to track your fitness goals. How much should it cost? 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...

#1634 - Peace Corps Alum Tutors U.S. Military Recruits 22.06.2021 8:20

When a Peace Corps alumnus uses his teaching skills to help a friend, he discovers that many military recruits need help preparing for their entry test. 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...

#1633 - Q&A: “How to start a membership community around self-growth?” 21.06.2021 5:43

Today’s listener wants to start a membership community centered around self-growth. So far, so good—but what’s the best way to introduce it? 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: SideH...

#1632 - Food Scientist Cooks Up Juicy Profits 20.06.2021 8:19

Instead of working in R&D or academia, a PhD picks another path by honing his skills as a freelance writer focused on food science. It pays to specialize! 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. 🎧...

#1631 - Q&A: Is it crazy to run an online bookstore? 19.06.2021 6:03

Today’s listener has a Black-owned independent children's bookstore. Online sales weren’t a priority until the pandemic, but now she’s wondering how to adapt. 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....

#1630 - Failure Friday: “Pitching to executives felt like an awful first date…” 18.06.2021 7:45

In this week’s Failure Friday segment, we hear from a military spouse who sells punny greeting cards. When she’s called to pitch her idea to executives at an incubator, she figures she can wing it. How hard can it be? 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 gui...

#1629 - TBT: Rosemary Beads Count Off Extra Income 17.06.2021 8:21

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a Chicago-based maker of rosary beads and other faith-based jewelry. 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 note...

#1628 - Q&A: “I’m your worst student … what should I do?" 16.06.2021 6:44

Today’s listener is feeling stuck. They’ve tried everything—or at least, a lot of things—and still aren’t sure how to go from idea to income. What’s the best way to get unstuck? 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...

#1627 - Teen Blogger Draws Up Design Company 15.06.2021 6:25

A college student who’s been starting blogs since she was fifteen discovers a talent for design that translates to dollars. 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...

#1626 - Q&A: “I’d like to become a professional ‘complaint coach’” 14.06.2021 7:05

This listener is really good at complaining to big companies when things go wrong. Is there a way he can turn this skill into a service? 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...

#1625 - Zen Master Makes Mindful Moola 13.06.2021 8:41

When a marketing manager gets a pandemic pay cut, he meditates on options and creates a wellness blog. 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@sidehustle...

#1624 - Q&A: “Personal Shark Tank” looks for investors, but with a twist 12.06.2021 4:38

Our caller is seeking direct investors for his big idea. Would you give him money in return for a percentage of potential profits? 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: SideHustleSchoo...

#1623 - Failure Friday: Overwork Leads to 3am Emergency Room Visit 11.06.2021 6:14

In this week’s Failure Friday segment, we hear from the owner of a design studio who works herself into the emergency room. 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...

#1622 - TBT: Tea-riffic Business Holds Up Under Pressure 10.06.2021 7:43

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a hardworking tea brand owner. She’s climbed a steep path through COVID challenges, but sales are way 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...

#1621 - Q&A: Can I get paid in Bitcoin without converting to dollars? 09.06.2021 5:32

PayPal allows you to accept cryptocurrency payments, but then converts those payments into fiat currency (like dollars or pounds). Is there a way to take payments with no conversion? 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...

#1620 - Savvy Couple Grows Finance Blog into Six Figure Business 08.06.2021 9:16

It took nine months to get to $50—but soon afterwards, the tide began to turn for this husband and wife duo who wanted to get out of debt. 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: SideHus...

#1619 - Q&A: “Help! My sister is pressuring me to join her MLM…” 07.06.2021 5:27

Today’s caller is hoping to avoid an awkward family discussion about network marketing. 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...

#1618 - Accountant Shifts Gears To Renting Out Cars 06.06.2021 7:31

When an Atlanta accountant discovers the sharing economy, he wheels and deals his way to owning an entire fleet of 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 Emai...

#1617 - Q&A: Can I get paid to help iPhone owners switch to Android? 05.06.2021 6:08

Today’s listener wants to serve the masses of people who buy Apple products but would shop for Android and PC devices if they knew what to buy. It’s an interesting market—how can he succeed? 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...

#1616 - Failure Friday: “The client ordered the most expensive thing on the menu…” 04.06.2021 6:26

In this week’s Failure Friday segment, we hear from a “Reddit Secret Santa” who builds a whole business around an idea that started as a seasonal project. 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...

#1615 - TBT: Premium Cocktail Pins Offer “Negronis for Your Homies” 03.06.2021 7:57

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of a cocktail pin merchant. Bottoms 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: SideHustle...

#1614 - Q&A: How do income-share agreements work? 02.06.2021 5:44

A listener has learned about income-share agreements, where college tuition or other learning costs aren’t due until after graduation. Is this a good deal? 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. 🎧 Sh...

#1613 - Monogrammed Blanket Etsy Shop Measures Up 01.06.2021 6:59

A simple embroidery shop becomes a six-figure blanket biz, podcast, and 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 o...

#1612 - Q&A: “Help! My lifestyle site is stuck at a plateau…” 31.05.2021 5:38

A listener’s lifestyle site started well, but can’t seem to get past an early-stage plateau. What should she 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...

#1611 - Intern Manages Businesses For Six-Figure Income 30.05.2021 7:57

When a corporate intern searches for an off-ramp, she creates a new job title that leads to a full-time income and new 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: SideHustleSc...