Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau / Onward Projectsidehustleschool.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.

Sales and Distribution by Lemonada Media https://lemonadamedia.com/  

Episodes

#1645 - Q&A: Is there a market for online stand-up paddleboard lessons?

Is there a limit to what can be done online? Today’s caller is testing it! Let’s consider if there’s a way she can teach stand-up paddleboarding from behind a screen. 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: [email protected] Be on the show: SideHustle...

Jul 03, 20215 minEp. 1645

#1644 - Failure Friday: Antiracism Interest Grows, But What Do Clients Want?

In this week’s Failure Friday segment, we hear from the founder of an agency that supports workplace inclusion and antiracism. Her business experienced major growth in the past year—but clients aren’t always sure what they really want. 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: SideHustleS...

Jul 02, 20217 minEp. 1644

#1643 - TBT: Sexual Wellness Site Revs Up Reviews

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a sex-positive blogger who publishes a site that reviews toys and other products for sexual wellness. 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: [email protected] Be on the s...

Jul 01, 20218 minEp. 1643

#1642 - Q&A: Does it matter which email list software I choose?

Today’s listener just got her website up (whoo hoo!) and now she’s wondering about the next step: which company to use for her email list. 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect...

Jun 30, 20216 minEp. 1642

#1641 - Social Studies Teacher Gains 1.5 Million TikTok Followers

When a teacher looks for a way to connect with her students during lockdown, she starts her own TikTok account and goes to the head of the class with her viral videos. 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: [email protected] Be on the show: SideHustl...

Jun 29, 20219 minEp. 1641

#1640 - Q&A: How does "yield farming" work?

Did you know you can earn interest (sometimes at very high rates) for “staking” digital currencies? It’s a wild world full of risk, volatility, and—for some—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 Email: [email protected] Be on the show: SideHustl...

Jun 28, 20216 minEp. 1640

BONUS: The Post-Pandemic Economy

In this special episode, Chris Guillebeau talks with Tim Welsh, Vice Chair of Consumer and Business Banking at U.S. Bank. Tim tells us how small businesses are leading the way in the economy's recovery, as well as how banks can help address historic inequities and disparities. Spoiler: Tim does NOT recommend investing your entire savings portfolio in Dogecoin. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting thei...

Jun 28, 20219 min

#1639: Graduate Uses Equestrian Art to Canter Out of Debt

When a psychology graduate wants to pay off $65,000 in debt, she takes life by the reins and learns to scale her equestrian art 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect ...

Jun 27, 20217 minEp. 1639

#1638 - Q&A: How to sell a podcast as a paid subscription?

Apple Podcasts, Spotify, and presumably some other networks are all jumping on the premium podcast train. If you want to start one—a podcast as a paid subscription–how do you do 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: SideHustleSchool.com Email: [email protected] Be on the s...

Jun 26, 20216 minEp. 1638

#1637 - Failure Friday: “It took me way too long to bounce back…”

In this week’s Failure Friday segment, we hear from a personal finance blogger who gets zero response to a coaching program he’s excited about—and then takes two years to recover. Lots of good lessons 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 days each week. 🎧 Show notes: SideHustleSchool.com Email: team@sidehus...

Jun 25, 20217 minEp. 1637

#1636 - TBT: When the Pandemic Hit, This Product Went Up 70x

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-inventor of a device that allows public restroom users to open the door with their foot. Their business increased 70x at the start of the global pandemic! 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...

Jun 24, 20219 minEp. 1636

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

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: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/question...

Jun 23, 20216 minEp. 1635

#1634 - Peace Corps Alum Tutors U.S. Military Recruits

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 notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/que...

Jun 22, 20218 minEp. 1634

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

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: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Conne...

Jun 21, 20216 minEp. 1633

#1632 - Food Scientist Cooks Up Juicy Profits

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. 🎧 Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.c...

Jun 20, 20218 minEp. 1632

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

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. 🎧 Show notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.c...

Jun 19, 20216 minEp. 1631

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

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 guided lessons and listener Q&A several days each week. 🎧 Show notes: SideHustleSchool.com Email: t...

Jun 18, 20218 minEp. 1630

#1629 - TBT: Rosemary Beads Count Off Extra Income

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 notes: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questio...

Jun 17, 20218 minEp. 1629

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

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 days each week. 🎧 Show notes: SideHustleSchool.com Email: [email protected] Be on the show:...

Jun 16, 20217 minEp. 1628

#1627 - Teen Blogger Draws Up Design Company

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 Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @c...

Jun 15, 20216 minEp. 1627

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

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: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect o...

Jun 14, 20217 minEp. 1626

#1625 - Zen Master Makes Mindful Moola

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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connec...

Jun 13, 20219 minEp. 1625

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

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: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twit...

Jun 12, 20215 minEp. 1624

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

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 Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @c...

Jun 11, 20216 minEp. 1623

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

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 several days each week. 🎧 Show notes: SideHustleSchool.com Email: [email protected] Be on t...

Jun 10, 20218 minEp. 1622

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

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 several days each week. 🎧 Show notes: SideHustleSchool.com Email: [email protected] Be on the ...

Jun 09, 20216 minEp. 1621

#1620 - Savvy Couple Grows Finance Blog into Six Figure Business

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: SideHustleSchool.com Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect...

Jun 08, 20219 minEp. 1620

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

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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chrisguillebeau Connect on Instagram:...

Jun 07, 20215 minEp. 1619

#1618 - Accountant Shifts Gears To Renting Out Cars

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 Email: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Twitter: @chri...

Jun 06, 20218 minEp. 1618

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

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&A several days each week. 🎧 Show notes: SideHustleSchool.com Email: [email protected] Be...

Jun 05, 20216 minEp. 1617