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?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

Ep. 3132 - Q&A: “How can I be persistent … without being pushy?” 29.07.2025

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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...

Ep. 3112 - STORY: “Graphic Design for Dogs” Earns $84,000 09.07.2025

A graphic designer and pet lover unleashes a side hustle that earns $84,000 a year. Dog-ear this episode!  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@sideh...

Ep. 3111 - Q&A: “Is standing in line for cash a legit side hustle?” 08.07.2025

Could standing in line be your next side hustle? In this episode, we explore the strange but real world of paid line-sitting—and whether it's actually a smart use of your time. 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...

Ep. 3110 - First $1,000: Murder Mystery Lover Sells Clues in the Mail 07.07.2025

In this week's First $1,000 segment, meet a crime fiction devotee who built her own “detective-for-hire” game, complete with weekly mailed clues and online reveals. Find out how she used her storytelling skills—and a few vintage stationery props—to turn curious readers into paid participants. Side Hustle School features a new episode EVERY DAY, featuring detailed case studi...

Ep. 3109 - Weekend Workshop: The Fish Tank Review Method 06.07.2025

This segment is all about helping you learn the key steps to a new side hustle, one step or concept per week. It includes activities, examples, and more—and of course it's all free. Today's topic: finding value in what you already know. 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, th...

Ep. 3108 - Q&A: “Can I make money as a film location scout?” 05.07.2025

Is scouting cool locations for film sets a job you can do solo—and without Hollywood ties? In this episode, we explore the surprising ways city explorers can turn their local knowledge into 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 includes free guided lessons and...

Listen to the Side Hustle School podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.