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

Ep. 3231 - STORY: The Coffee Grinder That Made $300,000 05.11.2025

Rise and shine! A petroleum engineer finds the perfect item to resell on Amazon. He goes on to sell $300,000 worth of the humble coffee grinder.  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:...

Ep. 3230 - Q&A: “How do I test Facebook vs. free traffic?” 04.11.2025

Free traffic feels safe, but paid ads might unlock a faster lane—IF the math checks out. Let's design a two-week, $200 ad test with clear “go / no-go” numbers so this side hustler can see truth, not guesswork. 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...

Ep. 3229 - First $1,000: Shopify Library Becomes Paid Subscription 03.11.2025

Shopify merchants kept begging forums for the same quick theme fixes.  One developer bundled all his proven snippets behind a $15 monthly paywall—and 170 store owners are happily copying, pasting, and 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 gu...

Ep. 3228 - Weekend Workshop: When Getting Fired Becomes Your Best Break 02.11.2025

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: if he hadn't been pushed, he wouldn't have made the leap. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without qui...

Ep. 3227 - Q&A: “Why won’t TikTok followers join my newsletter?” 01.11.2025

TikTok, Snap, and Instagram fame is fun, but e-mail tends to pay the bills. Today we lay out the follower-to-inbox conversion math, including the moment a list becomes non-negotiable. 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 se...

Ep. 3226 - Q&A: “Can I legally profit from salvaging barn wood?” 31.10.2025

Old barns can be gold mines—or legal landmines. Today we cover permits, insurance, and realistic margins for turning reclaimed boards 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. This year, the show includes free guided lessons and listener Q&A several days each week. Show note...

Ep. 3225 - TBT: A Guided Journal, a Friend in Need, and 1,000+ Sales 30.10.2025

In this week's Throwback Thursday segment, learn how a creative project for a friend in recovery became a business, eventually leading to a partnership with a Washington, DC nonprofit. 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. 3224 - STORY: Line Chef Makes Millions Cooking Up Apron Empire 29.10.2025

A chef sets out to reinvent the humble apron, growing it to a multi-million-dollar company while still working in restaurants at night.  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: SideHust...

Ep. 3223 - Q&A: “When does a logo actually matter?” 28.10.2025

Today's caller wonders whether to polish the package or finish the product. We'll set a two-checkpoint rule that keeps creativity flowing, without turning branding into busywork. 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. 3222 - First $1,000: “CRM Makeovers” for Real Estate Agents 27.10.2025

In this week's First $1,000 segment, meet the HubSpot whiz who charges Realtors $500 for a three-hour CRM detox—merging duplicates, tagging leads, and automating follow-ups before lunch. 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. 3221 - Weekend Workshop: The Premium Pricing Paradox 26.10.2025

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: the $100 Alaska coupon book that sells over and over. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quittin...

Ep. 3220 - Q&A: “When is business coaching worth the cost?” 25.10.2025

Coaching can fast-track growth—or drain a lot of money from your bank account. In this short episode, you'll learn a simple metric to decide whether a pricey mentor is a smart bet or a motivational luxury. 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 les...

Ep. 3219 - Q&A: “Can I sell carbon-offset checks to small brands?” 24.10.2025

Green-washing headlines have everyone nervous, and for good reason. Today we design a “quick-check” carbon-audit service small brands will pay for—and keep the workload under two hours per client. 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...

Ep. 3218 - TBT: I Built a Supplement Guide People Actually Trust 23.10.2025

In this week's Throwback Thursday segment, learn how a side hustler built a trustworthy supplement guide from one TikTok video, turning it into a $40,000 affiliate 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...

Ep. 3217 - STORY: Aussie Stretches Out with Online Store for Tall Women 22.10.2025

Tall women everywhere rejoice as an eCommerce side hustle brings new meaning to ‘top shelf.'   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@sidehu...

Ep. 3216 - Q&A: “How do I avoid a garage full of unsold kits?” 21.10.2025

Should you spend months growing followers or risk cash on inventory right away? Today we outline a “test-then-preorder” strategy that proves demand in weeks, pays for production up front, and builds your email list as you go. 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 sho...

Ep. 3215 - First $1,000: Board-Game Date Nights in a Café Basement 20.10.2025

In this week's First $1,000 segment, hear how a board-game collector transformed an unused café basement into a candle-lit playground for couples. 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 not...

Ep. 3214 - Weekend Workshop: From Spreadsheets to Six Figures 19.10.2025

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: the original spreadsheet king. 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. 3213 - Q&A: “Can I monetize a college scholarship database?” 18.10.2025

Obscure college scholarships are gold, at least if parents trust your data. In this episode we design a subscription, ROI guarantee, and tech stack that can turn a spreadsheet into monthly 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...

Ep. 3212 - Q&A: “Will people pay for AI-optimized resumés?” 17.10.2025

Cheap resumé bots and pricey human writers leave a gap. We'll show how an AI-plus-expert service can fill it, both profitably and credibly. 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...

Ep. 3211 - TBT: Built in a Weekend, Used by Thousands 16.10.2025

In this week's Throwback Thursday segment, hear how a side project built over a single weekend turned into a surprisingly steady income stream, all thanks to a clunky but useful Chrome extension with 5,000 loyal users. 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...

Ep. 3210 - STORY: Canadian Bidets Modernize Bathroom Life 15.10.2025

In several parts of the world, bidets are used in lieu of toilet paper—but why not in Canada? One man sets out to change that, flushing away discouragement and banking profits.  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&amp...

Ep. 3209 - Q&A: “How do I use exit pop-ups?” 14.10.2025

A well-timed nudge can rescue sales, but only if it feels like service, not a race to the bottom. Let's design a polite “please stay” offer that boosts revenue without creating coupon addicts. 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...

Ep. 3208 - First $1,000: Vintage Sewing Machine Rehab Workshops 13.10.2025

In this week's First $1,000 segment, meet the maker who buys twenty-dollar thrift-store sewing machines, teaches students to revive them, and lets each participant leave with a fully functioning vintage Singer.  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...

Ep. 3207 - Weekend Workshop: The Global Photography Pivot 12.10.2025

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: a nomadic photography 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...

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