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

#2857 - Q&A: “How do I price my first workshop??” 27.10.2024

In this episode, we explore how to price your first workshop. Learn tips for calculating costs, researching the market, and finding the right pricing strategy to make your workshop a success. 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&...

#2856 - Q&A: “What pitfalls should you avoid when monetizing a passion?” 26.10.2024

In this episode, we discuss the common pitfalls to avoid when turning a passion into an income-generating side hustle. First up: not everything you enjoy should be monetized. 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...

#2855 - Failure Friday: Translation Mishap Derails Import Business 25.10.2024

In this week’s “Failure Friday” segment, we hear from an entrepreneur who ran into a major issue with a Japanese translation while running an importing 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....

#2854 - TBT: Acupressure Mats Are a Big Seller on Amazon! 24.10.2024

In this Throwback Thursday story, we revisit the story of an Amazon FBA seller who navigated the ups and downs of product selection. One surprisingly popular category: acupressure mats! 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...

#2853 - Q&A: “How to create and sell custom Shopify themes?” 23.10.2024

In this episode, we explore how to create and sell custom Shopify themes for e-commerce businesses. This is a big market! 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:...

#2852 - Q&A: “Tips for building a fitness brand on TikTok…” 22.10.2024

In this episode, we explore how to create and market niche workout videos on TikTok. Learn strategies for engaging content, optimizing for the algorithm, and growing your following in a competitive space. 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 an...

#2851 - First $1,000: Forager Uncovers Truffles for High-End Restaurants 21.10.2024

In this week’s First $1,000 segment, we hear from a Connecticut forager who hunts down expensive truffles and herbal delicacies for high-end restaurants in the area. 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...

#2850 - Q&A: “How to monetize a podcast without traditional sponsorships?” 20.10.2024

In this episode, we explore how to launch a podcast without relying on traditional sponsorships. A new podcaster has a topic that most advertisers won’t want to touch—so what can he 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...

#2849 - Q&A: “Best way to launch a book in 2025?” 19.10.2024

In this episode, we discuss the best strategies for launching a book in 2025. From building your platform to using a multi-phase launch plan, learn how to prepare for success. 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 da...

#2848 - Failure Friday: Why My “Alt MBA” Program Flopped 18.10.2024

In this week’s “Failure Friday” segment, we hear from a college teacher who attempted to start an online “Alt MBA” program but faced unexpected challenges. Discover what went wrong and what we can 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 fre...

#2847 - TBT: Mixing Drinks and Making Money in Aspen 17.10.2024

In this week’s “Throwback Thursday” segment, we hear from a bartender who moved from Michigan to Aspen, Colorado, to take advantage of the lucrative opportunities in the high-end resort town.  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...

#2846 - Q&A: “"How can I transition from finance to my creative side hustle career?” 16.10.2024

In this episode, we'll explore practical strategies for a listener looking to transition a side hustle into a new full-time career, even while working a demanding day job. 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 e...

#2845 - Q&A: “How to start a small marketing agency?” 15.10.2024

In this episode, we explore the steps to building a successful small marketing agency, including how to decide on an area of specialization. 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...

#2844 - First $1,000: Hospice Nurse Helps Families Prepare for Final Days 14.10.2024

In this week’s First $1,000 segment, we meet a former hospice nurse who launched a unique side hustle as a “death doula.” She shares how her compassionate approach to end-of-life care is changing how families navigate their final days with loved ones. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This...

#2843 - Q&A: "How can I explain reiki more effectively to potential clients?" 13.10.2024

In this episode, we'll explore how alternative wellness practitioners can build awareness and educate potential clients about their services, so they can spend more time actually providing treatments. 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 li...

#2842 - Q&A: “How to start a reselling business with limited storage?” 12.10.2024

In this episode, we explore how to start a reselling business when you have limited storage space. Can you avoid the issue of inventory altogether?  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...

#2841 - Failure Friday: The Corporate Gig Where I Undersold Myself 11.10.2024

In this week’s “Failure Friday” segment, we hear from an industry expert who was invited to give a corporate talk at an oil company conference in Halifax. Just one problem: he didn’t know how much to charge, so he asked for much less than the company would have paid. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...

#2840 - TBT: Austin Event Planner Goes Hard for SXSW 10.10.2024

In this week’s “Throwback Thursday” segment, we hear from an event planner in Austin who books many of the city’s tech parties and events, especially during the popular SXSW festival. 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...

#2839 - Q&A: "When is the right time to quit your job and go all-in?” 09.10.2024

In this episode, we'll explore the key milestones and financial targets that can signal when it's time to transition your side hustle into a full-time 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. S...

#2838 - Q&A: “How can I diversify my side income streams?” 08.10.2024

In this episode, we discuss how to diversify your freelance income to create a more resilient business or side hustle. 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: tea...

#2837 - First $1,000: NYC Exotic Petsetter Cares for Bearded Dragons 07.10.2024

In this week’s First $1,000 segment, we hear from a New York City exotic petsetter who sees everything from bearded dragons to chinchillas to axolotls—and 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 listener Q&A several days each week. S...

#2836 - Q&A: “How to reduce newsletter churn?” 06.10.2024

In this episode, we tackle high churn rates in subscription-based newsletters. Learn how to keep subscribers engaged and active! 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...

#2835 - Q&A: “How to start a successful membership site?” 05.10.2024

In this episode, we explore how to create AND sustain a successful membership site. Learn about choosing the right platform, pricing strategies, and the best types of content to keep your members engaged. 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 an...

#2834 - Failure Friday: The Challenges of Helping Smokers Switch to Vaping 04.10.2024

In this week’s “Failure Friday” segment, we hear from a tech employee who tried to start a business helping smokers transition to vaping and other smokeless tobacco alternatives. Unfortunately, he struggled to attract paying clients. 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 in...

#2833 - TBT: Building a Cross-Atlantic Real Estate Business 03.10.2024

In this week’s “Throwback Thursday” segment, we hear from a British real estate agent who found success selling Bermuda condos to buyers in Florida.  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:...

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