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

#2757 - Failure Friday: Lost Contract Leads to 50% Revenue Drop 19.07.2024

In this week’s Failure Friday segment, we hear from an employee training consultant who lands a big contract—only to become too dependent on 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: SideH...

#2756 - TBT: Charging Higher Rates Through Content Strategy Consulting 18.07.2024

In this week’s “Throwback Thursday” segment, we hear from a freelance writer who transformed her business by shifting to content strategy consulting. Learn how she leveraged AI tools to provide stronger insights, resulting in higher-paying work and more consistent client relationships. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon...

#2755 - Q&A: “What are creative ways to monetize YouTube and Instagram?” 17.07.2024

In this episode, we explore innovative ways to monetize YouTube and Instagram content beyond ad revenue and sponsorships.  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:...

#2754 - Q&A: “How to balance teaching and side hustling?” 16.07.2024

In this episode, we explore strategies to help a listener balance his full-time teaching job with a side hustle. How can he manage his time effectively and avoid burnout? 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 ea...

#2753 - First $1k: Woodworker Breathes New Life into Old Lumber 15.07.2024

In this week's First $1,000 segment, we meet a woodworker who discovers the beauty and potential of reclaimed lumber—and then sells 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: SideHustleScho...

#2752 - Q&A: “How to handle negative reviews on Etsy?” 14.07.2024

In this episode, we explore how to handle negative reviews and maintain a positive reputation for your online shop. This caller needs some help! 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...

#2751 - Q&A: “What are the best passive income opportunities?” 13.07.2024

In this episode, we explore the best passive income projects for side hustlers right now. Discover how to choose the best projects, validate your idea, and 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 severa...

#2750 - Failure Friday: ADHD Diagnosis Helps Frazzled Consultant 12.07.2024

In this week’s Failure Friday segment, we hear from an educational consultant whose struggles with focus led to a period of burnout. 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....

#2749 - TBT: Athlete Turned Mindfulness Coach Shares Winning Strategies 11.07.2024

In this Throwback Thursday episode, we catch up with a former pro athlete who becomes a sought-after mindfulness coach. Discover how they're helping athletes harness the power of the mind to elevate their game. 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...

#2748 - Q&A: “Can you buy and resell digital products??” 10.07.2024

In this episode, we explore the world of digital product flipping. Discover how to buy, improve, and resell websites, domains, and other digital assets for profit. 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...

#2747 - Q&A: “Can I turn negotiating discounts into a side hustle?” 09.07.2024

In this episode, we explore a unique side hustle idea: negotiating subscription discounts on behalf of others. Tune in to learn how to turn your negotiation skills into a profitable venture! 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...

#2746 - First $1k: Urban Farmer Grows Aquaponics Consulting Business 08.07.2024

In this week's First $1,000 segment, we meet a farming enthusiast who helps urban dwellers and restaurants create their own self-sustaining ecosystems. 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...

#2745 - Q&A: "What are some unique pet side hustles?" 07.07.2024

In this episode, we explore unique pet-related side hustle ideas that go beyond pet sitting and dog walking. Discover innovative services you can offer, and effective marketing strategies to stand out in the pet 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...

#2744 - Q&A: “How to get started as an audiobook narrator?” 06.07.2024

In this episode, we explore how to transform a great voice into a side hustle in voice acting and audiobook narration. How can you get going, and where do you find your first gigs? 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 sever...

#2743 - Failure Friday: A Lego Reseller's Lesson in Integrity 05.07.2024

In this week's Failure Friday segment, we hear from a Lego reseller who learns the hard way that if a deal seems too good to be true, it pro 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...

#2742 - TBT: Detroit Food Truck Owner Revs Up Ghost Kitchen 04.07.2024

In this Throwback Thursday episode, we catch up with a Motor City food truck owner who expands their culinary reach by venturing into the mysterious world of ghost kitchens.  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...

#2741 - Q&A: “What does ‘working on your business’ mean?” 03.07.2024

In this episode, we dive into the distinction between working on your business and working in your business, as popularized by Michael Gerber in "The E-Myth Revisited." 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...

#2740 - Q&A: "What's the easiest way to build a landing page?” 02.07.2024

In this episode, we explore the best and easiest ways to build a website or landing page for your side hustle. Don’t get bogged down in technical complexities! 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. Sh...

#2739 - First $1k: Braille Translator Dots the Way to Success 01.07.2024

In this week's First $1,000 segment, we meet a linguist who combines their love for language and passion for accessibility to start a side hustle translating written content into Braille. 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&...

#2738 - Q&A: “How many digital products should I sell?” 30.06.2024

In this episode, we help a side hustler navigate the decision-making process for structuring her digital information product offerings. We'll explore the pros and cons of selling one, three, or five 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 lesso...

#2737 - Q&A: “I’m getting too many chargebacks!” 29.06.2024

In this episode, we tackle the common challenge of chargebacks in e-commerce side hustles. We'll explore practical strategies to help you prevent and minimize chargebacks, protect your business from fraudulent activity, and keep more of your money in your pocket. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting the...

#2736 - Failure Friday: The SEO Consultant's Outsourcing Oversight 28.06.2024

In this week's Failure Friday, we explore the story of an SEO consultant who learned the hard way the dangers of outsourcing to unvetted agencies. 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: Sid...

#2735 - TBT: Teacher Earns Extra Credit from Returned Items 27.06.2024

In this week’s “Throwback Thursday” segment, we meet a savvy schoolteacher who discovers a lucrative side hustle in reselling returned goods on Amazon. Learn how he navigates bulk auctions, inventory management, and product selection to turn a profit and supplement his teaching income. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mon...

#2734 - Q&A: “What should I *do* with my email list?” 26.06.2024

In this episode, we dive into the world of email marketing and explore best practices for engaging with your subscribers and converting them into loyal customers. Once you have an email list set up—what do you actually do with 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 inclu...

#2733 - Q&A: “Six months in, and I need more life / work balance...” 25.06.2024

In this episode, we tackle the challenges of avoiding burnout while growing a side hustle. Discover techniques for staying motivated, managing stress, and maintaining alignment—as much as possible! 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...

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