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

#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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] 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: [email protected] Be on the show: SideHustleSchool.co...

Oct 07, 20247 minEp. 2837

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

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

Oct 06, 20246 minEp. 2836

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

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

Oct 05, 20246 minEp. 2835

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

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

Oct 04, 20246 minEp. 2834

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

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

Oct 03, 20247 minEp. 2833

#2832 - Q&A: “How to build an authentic personal brand?”

In this episode, learn how to build a personal brand that’s authentic and impactful. Do you just post a bunch of selfies on Instagram, or is there more to 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...

Oct 02, 20245 minEp. 2832

#2831 - Q&A: “How to build and manage a remote team?”

In this episode, we explore how to build and manage a remote team for your growing side hustle. How can you find the best candidates—and keep them around? 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/ques...

Oct 01, 20245 minEp. 2831

#2830 - First $1,000: Passive Income with YouTube Toy Reviews

In this week’s “First $1K” segment, we hear from a YouTuber who starts a toy review channel and gets paid for thousands of views. Might there be a channel waiting for YOU to launch next? 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...

Sep 30, 20245 minEp. 2830

#2829 - Q&A: “Best practices for automated follow-up emails?”

In this episode, we explore how to set up effective automated follow-up email sequences—without being too annoying. 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 Instagram: @193countri...

Sep 29, 20245 minEp. 2829

#2828 - Q&A: “What’s the best way to organize a meetup?”

In this episode, we discuss how to organize and promote a successful meetup or sales presentation on a budget—and how this can help your 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: [email protected] Be on the show: SideHustleSchool.com/questions...

Sep 28, 20246 minEp. 2828

#2827 - Failure Friday: Lessons from a Candle Subscription Box

In this week’s “Failure Friday” segment, we hear from a candle seller who tries to start a subscription box business, but soon discovers a much better business in selling in bulk to restaurants. 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] B...

Sep 27, 20246 minEp. 2827

#2826 - TBT: Turning Small Items into Big Profits

In this week’s “Throwback Thursday” segment, we hear from a woman who turned her passion for designing pins and stickers into a profitable business. Learn how she tackled the challenge of increasing her average order size and now earns $60,000 a year part-time. 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. ...

Sep 26, 20246 minEp. 2826

#2825 - Q&A: “When can I start getting paid for YouTube views?”

In this episode, we discuss how to start earning money from YouTube views. Learn about the requirements for monetization, strategies to grow your channel quickly, and tips to maximize your earnings. 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]...

Sep 25, 20245 minEp. 2825

#2824 - Q&A: “How can I monetize my content on Threads?”

In this episode, we explore how to monetize your presence on Meta’s Threads. More than 100 million users are on to something! 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 Instagram: @...

Sep 24, 20245 minEp. 2824

#2823 - First $1,000: Artisan Chocolatier Hits Sweet Milestone

In this week’s “First $1K” segment, we hear from an artisan chocolatier in Seattle who turns their passion for handcrafted chocolates into a profitable 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.c...

Sep 23, 20246 minEp. 2823

#2822 - Q&A: “Can you start a reselling business without using eBay?”

In this episode, we explore alternatives to eBay for starting a reselling business. Learn about the pros and cons of platforms like Facebook Marketplace, Mercari, and OfferUp. 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: Side...

Sep 22, 20245 minEp. 2822

#2821 - Q&A: “Can I make money from writing fan fiction?”

In this episode, we help a listener seeking to monetize their fan fiction while navigating copyright issues. Expecto Patronum! 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 Instagram: ...

Sep 21, 20244 minEp. 2821

#2820 - Failure Friday: The Downside of DIY Platforms

In this week’s “Failure Friday” segment, we hear from a tech-savvy course creator who tried to save money by building their own platform—and why using a turnkey service might have been the better choice. 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@sidehustlesch...

Sep 20, 20246 minEp. 2820