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

#2782 - Q&A: “How to prepare for a side hustle while incarcerated?” 13.08.2024

In this episode, we discuss legal side hustles for prisoners, as well as how they can build the right kinds of skills to succeed upon release. Bravo to our listener for raising this question! 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&...

#2781 - First $1,000: Transforming Homes to Sell Faster in Pittsburgh 12.08.2024

In this week’s “First $1K” segment, we hear from Emma in Pittsburgh, who transformed her talent for decorating into a profitable home staging business. Learn how she earned her first $1,000 by helping homeowners and realtors prepare properties for sale. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countri...

#2780 - Q&A: “What types of social media ads are most effective?” 11.08.2024

In this episode, we break down the most effective types of social media ads and what makes them successful. Learn about targeting, content creation, and key strategies to boost your side hustle—without wasting money! 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 guide...

#2779 - Q&A: “How does the funnel system work for selling info products?” 10.08.2024

In this episode, we break down the funnel system for selling info products. Learn the different stages of the funnel and how to use this approach to maximize your sales, starting with a low-cost product to bring people in. 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...

#2778 - Failure Friday: How a $20,000 Mastermind Led Me Astray 09.08.2024

In this week’s “Failure Friday” segment, we hear from an eager coach-in-training who spent $20,000 to join a mastermind group that focused on ecommerce businesses, leaving her lost and overwhelmed as she tried to start her new business. Discover how she navigated this setback and began working more strategically towards her goals. Side Hustle School features a new episode EVERY DAY, featuring deta...

#2777 - TBT: Solar Panel Sales Pro Earns $120,000+ 08.08.2024

In this week’s “Throwback Thursday” segment, we hear from a solar panel sales rep in Utah who earns all his income through commissions. Discover how he rose from a newbie to a top performer, now earning over $100,000 a year working part-time in the competitive solar market. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without q...

#2776 - Q&A: “How can I get my documentary funded?” 07.08.2024

In this episode, we explore the best ways to fund a documentary, including grants, crowdfunding, and sponsorships. Learn how to secure the budget you need to bring a creative project 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&...

#2775 - Q&A: “Can small content creators succeed with affiliate marketing?” 06.08.2024

In this episode, we explore how smaller content creators can compete in the affiliate marketing space dominated by big companies. Learn realistic strategies to stand out and attract the search traffic you need to 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...

#2774 - First $1,000: Oakland Car Detailing Hustle Waxes On, Off 05.08.2024

In this week’s “First $1K” segment, we visit Oakland, California, where a side hustler with a passion for car racing creates a successful detailing biz. 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 note...

#2773 - Q&A: “What are the best time-tracking tools?” 04.08.2024

In this episode, we explore the best time-tracking tools and share some side hustle ideas for helping others manage their time more effectively. 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...

#2772 - Q&A: ”What’s the wildest side hustle idea you’ve ever heard of?” 03.08.2024

In this episode, we explore some of the wildest side hustle ideas ever featured on the show. Discover how people are making extra money with chickens, air, and goats! Also: are these unconventional ideas more likely to 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...

#2771 - Failure Friday: Executive Function Coach Experiences Burnout 02.08.2024

In this week’s Failure Friday segment, we hear from a coach who works with families on executive function issues. Business is growing—a bit too fast, it turns out. 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...

#2770 - TBT: “Reviews to Riches” with Nutrition School Promotion 01.08.2024

In this week’s “Throwback Thursday” segment, we hear from an affiliate for a nutrition school who turns her reviews and videos into a lucrative business, earning up to $20,000/month. 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 sev...

#2769 - Q&A: “How can I use TikTok to promote my side hustle?” 31.07.2024

In this episode, we explore how to leverage TikTok to promote your side hustle. Learn the best strategies for creating engaging content, using TikTok’s features to your advantage, and building a loyal audience. 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...

#2768 - Q&A: “What’s the best posting frequency for social media?” 30.07.2024

In this episode, we explore the best posting frequency for social media and how to adapt to changing algorithms. Learn how to balance quality and quantity to maximize engagement and grow your online presence. 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 lesson...

#2767 - First $1,000: From Trade Show Model to Auto Show Specialist 29.07.2024

In this week’s “First $1K” segment, we hear from an Atlanta side hustler who transitioned from being a trade show model to running her own agency specializing in providing models for auto shows. 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...

#2766 - Q&A: “Membership site vs. one-time product purchase—what’s best?” 28.07.2024

In this episode, we explore the pros and cons of creating a membership site versus offering a one-time product purchase. Learn which model might be more sustainable for your business, as well as the best fit for 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. This year, the show includes...

#2765 - Q&A: “Should I hire a vanity publisher for my book?” 27.07.2024

In this episode, we explore the best publishing options for your book and why you should avoid vanity presses. Instead, learn about the benefits of self-publishing and traditional publishing to ensure your book reaches its audience effectively. 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,...

#2764 - Failure Friday: A Cautionary Tale of Blog Monetization 26.07.2024

In this week’s Failure Friday segment, we hear from a nomadic blogger who grows her business to a sustainable level, but then sees a big drop in numbers after an algorithmic update. 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...

#2763 - TBT: Boosting Craft Sales and Community Through YouTube 25.07.2024

In this week’s “Throwback Thursday” segment, we hear from a creator who took her DIY craft kit business to the next level by starting a YouTube channel. Discover how she diversified her revenue streams with engaging video content. 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...

#2762 - Q&A: “What are the challenges and opportunities in the cannabis industry?” 24.07.2024

In this episode, we explore the challenges and opportunities in the legalized cannabis industry. A few years in, profits are surprisingly elusive! 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...

#2761 - Q&A: “How can I ensure my crowdfunding campaign gets funded?” 23.07.2024

In this episode, we explore effective strategies to ensure your crowdfunding campaign gets fully funded and attracts attention. Learn how to create a compelling campaign page, engage backers, and leverage social media for maximum visibility. 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...

#2760 - First $1,000: Mastering Spotify’s Algorithm with Bulk Uploads 22.07.2024

In this week’s “First $1K” segment, we hear from a music producer who found success on Spotify by writing and uploading niche songs across multiple accounts. Discover how this unconventional approach helps him earn several thousand dollars a month in royalties. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

#2759 - Q&A: “ Building community through parasocial relationships…” 21.07.2024

In this episode, we explore how parasocial relationships can impact your side hustle. Learn how to cultivate and leverage these relationships—ethically—to build a loyal audience and drive business growth. 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 an...

#2758 - Q&A: “How are influencers using ManyChat to grow their business?” 20.07.2024

In this episode, we explore how influencers are using ManyChat to engage their audiences and drive sales. Learn from case studies and discover key strategies and best practices for running successful campaigns. 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...

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