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.
Be sure to visit the podcast's website and support the creator: sidehustleschool.com
Author
Chris Guillebeau
Category
Podcast website
Latest episode
Oct 24, 2026
Where to listen?
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Episodes
Ep. 3137 - Weekend Workshop: The Art of Professional Networking 03.08.2025 7:35
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: developing your skills as a “connector.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting...
Ep. 3136 - Q&A: “How can I scale my coaching business?” 02.08.2025 4:51
What's the smartest way to grow a coaching business when your calendar is already full? In this episode, we look at sustainable ways to scale without losing your personal touch. 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...
Ep. 3135 - Q&A: “Can you make money from a true crime podcast?” 01.08.2025 5:03
Thinking about launching a true crime podcast? In this episode, we explore what it takes to stand out—and how to build a foundation for growth and monetization from the start. 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...
Ep. 3134 - TBT: How I Sold Curated Pop Culture Packs from Thrifted Merch 31.07.2025 6:05
In this week's Throwback Thursday segment, hear how one side hustler created themed bundles of thrifted pop culture items—turning $10 Goodwill hauls into $60+ nostalgia packs for superfans. 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 listene...
Ep. 3133 - STORY: Metal Detectorist Gets Paid for Finding Lost Jewelry 30.07.2025 6:41
When a full-time data developer starts a detective agency with his kids, it goes on to help people recover over $100,000 worth of jewelry in a casual 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 day...
Ep. 3132 - Q&A: “How can I be persistent … without being pushy?” 29.07.2025 4:15
In this episode, we help a caller explore how to balance persistence and pushiness in sales. She doesn't want to be pushy, but she wants to close the deal! 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 n...
Ep. 3131 - First $1,000: Sleep-Deprived Dad Creates Digital Baby Journal 28.07.2025 5:10
In this week's First $1,000 segment, discover how one new parent turned a 3 a.m. spreadsheet session into a sellable baby tracker. With no ads and no tech background, he reached $1,000 in sales using only parenting groups and a Notion template. 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,...
Ep. 3130 - Weekend Workshop: The Wordpress Revolution 27.07.2025 6:31
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: from doing to teaching. 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...
Ep. 3129 - Q&A: “Would people pay to disappear from the internet?” 26.07.2025 5:34
Could helping people vanish from the internet be a viable business? In today's episode, we explore the growing market for digital privacy services—and what it takes to offer one. 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 s...
Ep. 3128 - Q&A: “Both of my ideas are strong, but I can only do one…” 25.07.2025 4:13
Stuck between two side hustle ideas? In this episode, we'll look at how to choose the right path when both options feel equally strong. 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...
Ep. 3127 - TBT: How Selling $2 Digital Products Earned $185,000 24.07.2025 5:44
In this week's Throwback Thursday segment, discover how one side hustler created a shop selling $2 digital products—and scaled it to $185,000 in revenue by mastering SEO, volume, and a few smart upsells. 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...
Ep. 3126 - STORY: Nerdy Kickstarter Campaign Raises $1 Million 23.07.2025 6:52
This Ohio man loves board games so much that he made his own—and when he tries to raise $6,000 through a Kickstarter campaign, he ends up with much more than he ever imagined. 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...
Ep. 3125 - Q&A: “How do I license my educational materials to a publisher?” 22.07.2025 5:14
A listener has created a valuable educational resource—but doesn't want to handle all the distribution herself. In today's episode, we look at how to license curriculum or teaching materials for broader reach and passive income. 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...
Ep. 3124 - First $1,000: Musician Creates Loop Packs for Video Editors 21.07.2025 5:27
In this week's First $1,000 segment, hear how a freelance musician turned abandoned audio sketches into a product for content creators. With just twelve clean loops and a few community posts, he hit $1,000 in under a 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 fre...
Ep. 3123 - Weekend Workshop: The Most Awesome Guitar Lessons in the Universe 20.07.2025 8:11
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: how a music teacher raised his rates to $120/hour. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting t...
Ep. 3122 - “Can you sell ‘closure as a service??’” 19.07.2025 4:30
Can you get paid to help people walk away from jobs, businesses, or relationships? In this episode, we explore the business of graceful exits—and whether it's a service the world 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 includes free guided lessons and listener Q&...
Ep. 3121 - Q&A: “I want to build an app with ‘vibe coding…’” 18.07.2025 6:18
Can you build an app just by describing your idea to AI? In this episode, we take a closer look at vibe coding—and whether it's ready for side hustlers to use. 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...
Ep. 3120 - TBT: No Snakes, Big Sales, and the Faux-Leather Hustle 17.07.2025 6:13
In this week's Throwback Thursday segment, hear how one side hustler built a passionate following by making “snakeskin” wallets—without using a single animal product, just upcycled materials and a clever story. 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 include...
Ep. 3119 - STORY: Ex-Baseball Players Hit Home Run With Baseball Bat Subscriptions 16.07.2025 6:37
Two former baseball players create a bat rental service, serving thousands of customers across the country. 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@sid...
Ep. 3118 - Q&A: “How can I launch a no-recipe cooking channel?” 15.07.2025 4:30
Do you need step-by-step recipes to build a food business? In this episode, we explore whether teaching kitchen improvisation can become a profitable niche. 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...
Ep. 3117 - First $1,000: From Power Rangers to Profits in Two Weeks 14.07.2025 5:06
In this week's First $1,000 segment, hear how a toy collector used estate sales, eBay, and insider knowledge to flip vintage figures for a profit. By focusing on three collectible categories, he built a low-stress resale system that brings in steady income. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job...
Ep. 3116 - Weekend Workshop: The $3,000/Month Cruise Ship Review Site 13.07.2025 8:10
This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: turning a personal experience into profit. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job...
Ep. 3115 - Q&A: “How much inventory should I keep on hand?” 12.07.2025 4:52
Struggling to strike the right balance between too much inventory and not enough? In this episode, we explore smart ways to manage product stock—especially when space and cash are tight. 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...
Ep. 3114 - Q&A: “Is it okay to use a fake name for my business?” 11.07.2025 4:36
Is it shady to use a fake name for your side hustle—or just smart privacy protection? In this episode, we look at the ethics, risks, and alternatives to staying anonymous. 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...
Ep. 3113 - TBT: How I Flipped Facebook Marketplace Finds Into Tuition Money 10.07.2025 6:10
In this week's Throwback Thursday segment, hear how one college student flipped used furniture from Facebook Marketplace—and paid off half their tuition bill without ever taking out a loan. 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 l...
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