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
Podcast website
Latest episode
Jul 11, 2026
Where to listen?
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Episodes
#2832 - Q&A: “How to build an authentic personal brand?” 02.10.2024 4:52
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. Sh...
#2831 - Q&A: “How to build and manage a remote team?” 01.10.2024 4:55
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 no...
#2830 - First $1,000: Passive Income with YouTube Toy Reviews 30.09.2024 4:54
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...
#2829 - Q&A: “Best practices for automated follow-up emails?” 29.09.2024 5:15
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: team@s...
#2828 - Q&A: “What’s the best way to organize a meetup?” 28.09.2024 5:57
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:...
#2827 - Failure Friday: Lessons from a Candle Subscription Box 27.09.2024 5:36
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...
#2826 - TBT: Turning Small Items into Big Profits 26.09.2024 6:10
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...
#2825 - Q&A: “When can I start getting paid for YouTube views?” 25.09.2024 4:30
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 list...
#2824 - Q&A: “How can I monetize my content on Threads?” 24.09.2024 4:46
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 Ema...
#2823 - First $1,000: Artisan Chocolatier Hits Sweet Milestone 23.09.2024 5:54
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....
#2822 - Q&A: “Can you start a reselling business without using eBay?” 22.09.2024 5:06
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 da...
#2821 - Q&A: “Can I make money from writing fan fiction?” 21.09.2024 4:22
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 Em...
#2820 - Failure Friday: The Downside of DIY Platforms 20.09.2024 5:39
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...
#2819 - TBT: Building a Range of Productivity Tools 19.09.2024 5:01
In this week’s “Throwback Thursday” segment, we hear from a seller of productivity guides who has evolved his business over the years. Discover how he transitioned from a single popular guide and now sells a range of products, earning over $100,000 a year. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job....
#2818 - Q&A: “My subscribers are paying for nothing…” 18.09.2024 5:27
In this episode, we explore how to handle the ethical dilemma of charging subscribers without fully delivering a service. What do you do if you stop providing something—but buyers keep paying?? 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...
#2817 - Q&A: “How can I identify and develop side hustle skills?” 17.09.2024 5:11
This listener needs help discovering his skills! In this episode, we discuss how ANYONE can identify and develop skills for a successful 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:...
#2816 - First $1,000: Nashville Branding Agency Gets Personal 16.09.2024 6:27
In this week’s “First $1K” segment, we hear from a tag-team duo in Nashville who starts a personal branding agency. Discover how they earned their first $1,000 by helping entrepreneurs and influencers build their personal brands through digital marketing. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job....
#2815 - Q&A: “Should I get an expensive booth at a trade show?” 15.09.2024 4:30
In this episode, we explore the factors to consider when deciding whether to invest in a trade show booth. These booths don’t come cheap … are they worth 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...
#2814 - Q&A: “How can I turn organizational skills into a business?” 14.09.2024 4:16
In this episode, we explore how to turn organizational skills into a profitable consulting service. Learn how to define your niche, build a portfolio, and market your services to attract clients and grow your 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 gui...
#2813 - Failure Friday: IP Complaint Ends Anime T-Shirt Venture 13.09.2024 6:32
In this week’s “Failure Friday” segment, we hear from an enterprising seller who faced a setback when their anime-themed T-shirts were de-listed after an IP owner filed a complaint. 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...
#2812 - TBT: Aquarium Maintenance Business Makes Splash 12.09.2024 4:51
In this week’s “Throwback Thursday” segment, we hear from an Ohio man who turned his experience with aquariums into a maintenance service for homes and offices. 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....
#2811 - Q&A: “Creative ways to monetize a property rental…” 11.09.2024 4:36
In this episode, we explore creative ways to monetize a property rental beyond Airbnb. We’ll consider event rentals, setting up a co-working space, or even urban farming to maximize a property’s potential. 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 a...
#2810 - Q&A: “How can I monetize my drone piloting skills?” 10.09.2024 4:54
In this episode, we explore how to get paid for drone piloting. That’s right—drone skills are valuable! 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...
#2809 - First $1,000: Coffee Cart Business Brews Up Baltimore 09.09.2024 5:42
In this week’s “First $1K” segment, we hear from an aspiring entrepreneur in Baltimore who starts a seasonal pop-up coffee cart. 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...
#2808 - Q&A: “How can we improve a non-profit membership drive?” 08.09.2024 4:43
In this episode, we explore effective strategies to improve a non-profit membership drive. Learn how to attract more members and ensure growth with actionable tips and insights. 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...
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