Chris Guillebeau

Side Hustle School

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

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

Where to listen?

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Episodes

#2058 - Q&A: “How do I transition from Etsy to Shopify?” 20.08.2022

A listener has been selling on Etsy and wants to make the switch to Shopify. What’s the best way to do this? 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@sidehust...

#2057 - Failure Friday: “Then one afternoon I got a call from the police…” 19.08.2022

In this week’s Failure Friday segment, we hear from Dev Chakravarty from the U.K. He had an idea to start a rental car company for electric vehicles. This turned out to be much more difficult than he expected! 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 lesso...

#2056 - TBT: Philly French Toast Bites Take Over 18.08.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Lokal Artisan Foods, offering delicious french toast bites in Philadelphia and beyond.  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...

#2055 - Q&A: "I sold more by raising my prices—is that wrong??” 17.08.2022

Today’s listener has a moral dilemma: they made more money by raising their prices! Wait, what’s wrong with that? Listen to their question to find out. 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...

#2054 - Health-Conscious Coffee Lover Steeps Into Crowded Market 16.08.2022

Taking a cue from her Carda-Mom, a sales professional creates steepable coffee flavoring bags containing organic spices instead of artificial syrups. 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:...

#2053 - First $1,000: “It came from patience and vision boarding…” 15.08.2022

In this week’s First $1,000 segment, we hear from a wedding marketer who makes a vision board and sets out to build a new 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....

#2052 - Q&A: “How to market audio services to Christian filmmakers?” 14.08.2022

Today’s caller seeks help marketing his services to a subset of faith-based filmmakers. Where can he find clients, and what does he offer them?  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...

#2051 - Q&A: “How do creators get paid?” 13.08.2022

There are lots of ways an online creator can get paid. Which are the most common—and which are the most profitable?  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@...

#2050 - Failure Friday: “Kickstarter rejected my project right before launch…” 12.08.2022

In this week’s Failure Friday segment, we hear from the founder of Bad Day Box, offering “snail mail self-care.” She planned to launch on Kickstarter, but was forced to make a last-minute change.  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...

#2049 - TBT: Lightshows Are the Next Big eSport 11.08.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Throwlights, a business that sells gear and training for lightshows. The concept comes from electronic music festivals and is taking off worldwide. 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, th...

#2048 - Q&A: “What are the best niches for affiliate programs?” 10.08.2022

Today’s caller is planning to jump into the world of affiliate promotion, where you can get paid for recommending products on a website. Are some niches or topics more profitable than others? 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&...

#2047 - Busy Mom Cleans Up Debt by Cleaning Car Seats 09.08.2022

A part-time occupational therapist and mom of two in search of a new income stream finds the solution with a gig economy platform focused on cleaning baby equipment.  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...

#2046 - First $1,000: “The pre-launch strategy produced $1,000 on day one…” 08.08.2022

In this week’s First $1,000 segment, we hear from the founder of Brave Count, a subscription box for military spouses.  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...

#2045 - Q&A: “Can I have a career of side hustles?” 07.08.2022

Our caller is thinking of going all-in on the world of multiple small businesses—not just one, but a whole career of side hustles. How 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 listener Q&A several days each week. Show notes: S...

#2044 - Q&A: “Help! The topic I chose is no longer relevant” 06.08.2022

What if you set out to become an expert in a topic—and all of a sudden, or perhaps over time—that topic becomes less and less relevant? That’s what our listener is facing in today’s episode. 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...

#2043 - Failure Friday: “After I was hit by a car, things got worse…” 05.08.2022

In this week’s Failure Friday segment, we hear from an affiliate marketer who encountered an unusual problem: after he was hit by a car, the public knowledge of his business was used against him.    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 list...

#2042 - TBT: Filipino Virtual Assistant Hub Serves Millions 04.08.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of OnlineJobs.ph, a directory of Filipino workers available for remote work. The site now has more than two million profiles! 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...

#2041 - Q&A: “If you had to start over, how would you grow a blog?” 03.08.2022

Blogging can still be profitable and rewarding, but a lot of strategies and tactics have changed over the years. If you’re starting a new blog today, what should 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 ea...

#2040 - Shine Bright Like a Diamond (and Sell Them) 02.08.2022

The manager of an antique jewelry company takes her skills to the open market, eventually establishing a gem of a 7-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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool....

#2039 - First $1,000: “I posted videos on TikTok and started getting paid…” 01.08.2022

In this week’s First $1,000 segment, we hear from viral TikTok sensation Rebecca Rogers, a social studies teacher with millions of followers. She now charges $6,000 for a single video post!  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...

#2038 - Q&A: “How many income streams is best?” 31.07.2022

Today’s caller is diving into the world of side hustling, already earning money from one or two sources with plans to add more. Is there an optimal number to aim for? 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...

#2037 - Q&A: Are there any *good* MLM companies? 30.07.2022

Today’s listener is at risk of falling prey to a shady network marketing (MLM) company. How do we know it’s shady? Because it’s a network marketing company! Listen and 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 guided lessons and listener Q&A several day...

#2036 - Failure Friday: “Despite my best efforts, no one was buying…” 29.07.2022

In this week’s Failure Friday segment, we hear from the creator of a writing program. She wanted to reach more people, so she decided to give Facebook her money. What could go wrong?  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...

#2035 - TBT: The Intersection of Customization and Convenience 28.07.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the co-founder of Happy Box, a service that offers unique care packages for all occasions. 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 ea...

#2034 - Q&A: “I don’t know where my customers are coming from…” 27.07.2022

In today’s episode, a consultant wonders how customers are finding them. If you don’t know the answer to this question, you might be doing the wrong things—but how do you find out? 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...

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