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

#2866 - Q&A: "How can I use A/B testing to improve my website conversion rate?"

In this episode, we explore how to use A/B testing to boost your website conversion rate. Sometimes the simplest changes make a huge improvement! 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 on the show: SideHustleSchool.com/questions Con...

Nov 05, 20246 minEp. 2866

#2865 - First $1,000: From Spreadsheets to Secret Shopping

In this week’s “First $1K” segment, we hear from an accountant who turned her attention to detail and data collection skills into a side gig as a mystery shopping evaluator. 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 on the show: SideHu...

Nov 04, 20246 minEp. 2865

#2864 - Q&A: “How to assess market demand for your side hustle?”

In this episode, we discuss how to assess the market demand for your side hustle idea. Can you know in advance if your idea will 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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on ...

Nov 03, 20245 minEp. 2864

#2863 - Q&A: “What are some good business ideas for teens?”

In this episode, we explore business ideas for teens and pre-teens, from pet sitting to digital services. Learn how to guide your kids in starting and managing their own ventures without overwhelming 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: SideHustleSchool.com Email: team@sidehustles...

Nov 02, 20245 minEp. 2863

#2862 - Failure Friday: Stock Photo Platform Lowers Commissions

In this week’s Failure Friday segment, we meet a landscape photographer whose thriving side hustle on Shutterstock comes crashing down after a sudden policy change: a classic case of “don’t put all your stock photos in one basket.” 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...

Nov 01, 20246 minEp. 2862

#2861 - TBT: An Architect’s Side Hustle in 3D Real Estate Modeling

In this week’s “Throwback Thursday” segment, we hear from an architect who turned his skills in 3D modeling and rendering into a successful side hustle, helping real estate agents bring their listings to life. 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...

Oct 31, 20245 minEp. 2861

#2860 - Q&A: “Launching a silent disco service!”

In this episode, we discuss how to start a silent disco service for events and corporate clients. What are the essential equipment requirements, logistics, and ways to find your first 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 includes free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be ...

Oct 30, 20246 minEp. 2860

#2859 - Q&A: “How do I find my ‘zone of genius’ for a side hustle?”

In this episode, we explore how to identify your unique skills or ‘zones of genius’ and turn them into profitable side hustles. 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 on the show: SideHustleSchool.com/questions Connect on Instagram:...

Oct 29, 20245 minEp. 2859

#2858 - First $1,000: Mastering the Art of Product Launches

In this week’s First $1,000 segment, we follow a side hustler’s journey from marketing enthusiast to launch specialist. He shares how he built a new marketing agency helping entrepreneurs and authors make a splash with their product releases. 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...

Oct 28, 20247 minEp. 2858

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

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be o...

Oct 27, 20245 minEp. 2857

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

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 days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideH...

Oct 26, 20245 minEp. 2856

#2855 - Failure Friday: Translation Mishap Derails Import Business

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.c...

Oct 25, 20246 minEp. 2855

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the ...

Oct 24, 20247 minEp. 2854

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

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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193c...

Oct 23, 20246 minEp. 2853

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

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 and listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustlesc...

Oct 22, 20245 minEp. 2852

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

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 week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleScho...

Oct 21, 20247 minEp. 2851

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the ...

Oct 20, 20245 minEp. 2850

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

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 days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: Side...

Oct 19, 20246 minEp. 2849

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

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

Oct 18, 20246 minEp. 2848

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

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be o...

Oct 17, 20246 minEp. 2847

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

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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHust...

Oct 16, 20246 minEp. 2846

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect ...

Oct 15, 20245 minEp. 2845

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

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 year, the show includes free guided lessons and listener Q&A several days each week. Show notes...

Oct 14, 20246 minEp. 2844

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

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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool...

Oct 13, 20245 minEp. 2843

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

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: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions C...

Oct 12, 20245 minEp. 2842

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

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 their job. This year, the show includes free guided lessons and listener Q&A several days each ...

Oct 11, 20247 minEp. 2841

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

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the sh...

Oct 10, 20247 minEp. 2840

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.co...

Oct 09, 20246 minEp. 2839

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

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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193coun...

Oct 08, 20246 minEp. 2838

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

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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.co...

Oct 07, 20247 minEp. 2837