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

#2632 - Q&A: “What are the single most important marketing tasks?” 16.03.2024

Today’s episode zeroes in the essential marketing strategies ideal for any side hustle. Discover how to effectively engage your audience, establish a strong online presence, and grow your customer base. 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...

#2631 - Failure Friday: Lost in the Code of Education 15.03.2024

In this week’s Failure Friday segment, we bring you the story of "EduAI," an AI-driven tutoring platform whose technological complexity led to its downfall, underscoring the balance between innovation and usability in EdTech. 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 f...

#2630 - TBT: The Mentor's Guide to Patenting 14.03.2024

In this week’s “Throwback Thursday / Where are they now?” segment, we meet the semi-retired inventor who's now demystifying the patent process for new creators. 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...

#2629 - Q&A: “How many subscription boxes do I need to sell to be sustainable?” 13.03.2024

Join us in this episode as we help a listener find the magic number for her subscription box business. Learn how to calculate the number of subscriptions you need to be sustainable! 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 seve...

#2628 - Q&A: “What, Apple takes 30% of all app payments”? 12.03.2024

In this episode, we discuss strategies for app developers to navigate Apple's 30% in-app purchase fee. Discover how alternative payment methods, subscription models, and cross-platform development can help maximize your app's revenue while staying within Apple's policy framework. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money wit...

#2627 - First $1,000: The College Greek Life Alumni Mentorship Network 11.03.2024

In this week’s First $1,000 segment, we delve into the story of a college grad who creates a mentorship platform, connecting fraternity and sorority members with alumni for career guidance. 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&am...

#2626 - Q&A: “Should my online course be live or on demand?” 10.03.2024

In this episode, we explore the pros and cons of live versus on-demand online courses, including some specific resources for course creation. Tune in to learn how to perfectly blend your teaching style with your audience's needs for the best learning experience. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting thei...

#2625 - Q&A: “How can I 3x my subscription service?” 09.03.2024

In this episode, we explore the journey from steady growth to rapid expansion for a caller’s cozy home goods subscription service. Discover the secrets of growth hacking and learn how to *triple* your subscriber base with creativity and data-driven decisions. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their j...

#2624 - Failure Friday: Organic Cosmetics Line Breaks Down 08.03.2024

In this week’s Failure Friday segment, a venture into organic cosmetics faces unexpected challenges, highlighting the importance of product testing in natural beauty products. 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...

#2623 - TBT: New England Soapmaker Makes Clean Start 07.03.2024

In this week’s “Throwback Thursday / Where are they now?” segment, we revisit the story of a New England soapmaker who turned a small, artisanal craft into a thriving 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 d...

#2622 - Q&A: “Should I make an ebook, online course, or something else?” 06.03.2024

In today's episode, we guide a listener through the decision between creating an ebook or an online course for expanding their digital presence. Tune in to learn how to match your content with your unique strengths and audience needs. 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 i...

#2621 - Q&A: “How to maintain momentum for daily projects?” 05.03.2024

In this episode, we tackle the challenge of keeping daily creative projects fresh and engaging. Learn how to reinvigorate your routine with themes, collaborations, and audience interaction—all of which can increase interest and attention. 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 sh...

#2620 - First $1,000: AI-Powered TikTok Accounts Earn Passive Income 04.03.2024

In this week’s First $1,000 segment, we hear from a tech-savvy TikTok user, who creates multiple, AI-powered accounts to promote affiliate products. Very impressive! 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...

#2619 - Q&A: “How can I find sponsors for my podcast and YouTube channel?” 03.03.2024

In this episode, we delve into the art of attracting sponsors for your podcast and YouTube channel. Discover how to identify potential sponsors, craft a compelling pitch, and build lasting partnerships that align with your brand and engage your audience. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. T...

#2618 - Q&A: “Should I use the ProfitFirst model?” 02.03.2024

In this episode, we delve into whether the Profit First model (from our friend Mike Michalowicz) is a viable financial strategy for a freelance graphic designer. 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....

#2617 - Failure Friday: The Great Salt Lake Brewery Blunder 01.03.2024

In this week’s Failure Friday segment, a plan to start a brewery brand dissolves before launch, due to mismatched commitment levels and challenging state alcohol regulations. 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...

#2616 - TBT: Fiver Voice Actor Breaks Into Gaming Industry 29.02.2024

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from a voice actor who uses Fiver to build his portfolio before trying his hand at the booming video game industry. 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...

#2615 - Q&A: “Can I franchise my side hustle?” 28.02.2024

A listener from Georgia wants to franchise her culinary tours. In this episode, we dive into the essential steps for transforming a local side hustle into a nationwide franchise. 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...

#2614 - “Balancing ads and membership models…” 27.02.2024

A caller with a wellness blog wants to get paid two ways: both from advertising AND a membership model. Can she do this without alienating her longtime followers? 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....

#2613 - First $1,000: Real Estate Adviser Gets Real 26.02.2024

In this week’s First $1,000 segment, we hear from a former real estate agent who now operates an educational platform to advise potential investors.  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:...

#2612 - Q&A: “How can I give a TED talk?” 25.02.2024

In this episode, discover how to turn your passion into a powerful message for the TED stage. Get the next steps for crafting a compelling talk, applying to TEDx events, and enhancing presentation skills—all crucial for anyone aspiring to share an idea with the world. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin...

#2611 - Q&A: “How long do you stick with a losing project?” 24.02.2024

Join us as we help a caller with her online store dilemma. Should she keep pushing her line of fashion badges, patches, and stickers, or is it time to consider something new? 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...

#2610 - Failure Friday: “I abandoned a growing email list…” 23.02.2024

In this week’s Failure Friday segment, we hear from an online retailer who started a promising email list but faltered in maintaining it. Consistency matters! 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. Sho...

#2609 - TBT: Social Media Agency Connects Brands with Creators 22.02.2024

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of a social media agency who works as a matchmaker between online creators and brands who pay for coverage. 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...

#2608 - Q&A: “Why has YouTube outlasted so many platforms?” 21.02.2024

Today's episode delves into the reasons behind YouTube's enduring success. Learn crucial lessons for content creators and digital marketers on building a lasting presence on the one platform that’s outlived many 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 gu...

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