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.
Husk at besøge podcastens hjemmeside og støtte skaberen: sidehustleschool.com
Forfatter
Chris Guillebeau
Kategori
Podcastens hjemmeside
Seneste episode
4. nov. 2026
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Episoder
#2074 - First $1,000: “You can’t sell anything until you list it…” 05.09.2022 7:48
In this week’s First $1,000 segment, we hear from the owner of an Etsy shop called The Blue Breakfront. After making a few rookie mistakes, she leveled-up and began getting steady 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...
#2073 - Q&A: “How can I compete with unfair Etsy sellers?” 04.09.2022 4:32
We had an episode recently with an Amazon seller who had a competitor posting lots of fake reviews. Today’s caller has been dealing with a similar issue: unfair Etsy sellers who mass-manufacture their products, contrary to the platform’s seller policy. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Thi...
#2072 - Q&A: “How to best use a time of unemployment?” 03.09.2022 5:33
Today’s caller faces a big decision: during a time of unemployment, does she stretch her side hustle into a career, or go back to traditional 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...
#2071 - Failure Friday: “I thought I’d set up the website incorrectly…” 02.09.2022 5:36
In this week’s Failure Friday segment, we hear from a middle-school principal from Pennsylvania. When he starts a blog for high-school volleyball players, it doesn’t get off to a smashing 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 liste...
#2070 - TBT: Mochi-Making Classes Transition Online 01.09.2022 8:08
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of KaorisKitchen.com. She started teaching mochi-making classes in the Bay Area, but pivoted to a new business selling mochi donuts locally. 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 inc...
#2069 - Q&A: “Too many coaches! I know I need to ‘choose a niche,’ but how?” 31.08.2022 4:13
Today’s listener is a life coach who’s heard me say that the way to succeed with this kind of personal service is to choose a focus or niche. Fair enough … but how do you do that? 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...
#2068 - College Friends Start Utah Fulfillment Center 30.08.2022 6:48
Two friends learn the logistics of running a fulfilling business. In their first month of operation, they handled 3,000 orders for a Kickstarter 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 not...
#2067 - First $1,000: Lutheran Pastor Sells & Ships “Consecrate” Boxes 29.08.2022 9:16
In this week’s First $1,000 segment, we hear from the creator of Consecrate, a subscription box for pastors and ministers. She sends more than 500 boxes out each month! 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...
#2066 - Q&A: “How do you forecast earnings for a side hustle?” 28.08.2022 5:20
A listener came across my back-of-the-napkin spreadsheet template and is wondering something: if a business or side hustle is new, how can you forecast earnings for it? It’s a good question, but there’s also a good answer. 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...
#2065 - Q&A: "They asked for a refund after three hours of coaching..." 27.08.2022 3:48
After completing two long sessions with a client, a new coach received a request for a refund. Should she revise her policy of “money back with no questions asked”? 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 wee...
#2064 - Failure Friday: “This is super embarrassing looking back…” 26.08.2022 7:13
In this week’s Failure Friday segment, we hear from an Atlanta designer. In addition to her full-time day job, she’s the owner of a stationary brand called Lucky Dog Design. Selling her products on Amazon seemed like a logical idea, but turned into a costly mistake. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitti...
#2063 - TBT: Baseball Training School Slides Into Growth 25.08.2022 8:47
In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of a baseball training academy. During the pandemic, he opened an additional business selling training gear on Amazon. 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 less...
#2062 - Q&A: “Can I sell the same thing with two business names?” 24.08.2022 4:14
Today’s caller is wondering if she can sell the same line of products with two different brand names. Is this clever or unethical? 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.c...
#2061 - TV Producer Invents Sustainable Toothpaste Alternative 23.08.2022 7:09
After traveling non-stop for a busy job, a TV producer aims to reduce her plastic consumption. 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 B...
#2060 - First $1,000: “We began with a single sports team…” 22.08.2022 7:21
In this week’s First $1,000 segment, we hear from the founder of a sports leadership coaching business. He got his start by volunteering at a local school, and it quickly grew into something more. 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 liste...
#2059 - Q&A: “Amazon Prime Day, but for side hustlers…” 21.08.2022 4:50
Today’s listener is wondering about a side hustle version of Prime Day. Can there be such a thing, or should the smaller sellers of the world simply piggyback on what Amazon has done since everyone is shopping anyway? 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...
#2058 - Q&A: “How do I transition from Etsy to Shopify?” 20.08.2022 4:58
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 6:54
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 6:48
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 4:27
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 6:51
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 5:16
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 4:10
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 5:13
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 8:43
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...
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