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. 3281 - TBT: After 1,700 Years, I Outsourced Christmas 25.12.2025

In this week's Throwback Thursday segment, hear how the North Pole's most iconic founder finally pivoted from production to licensing—earning passive income while keeping the magic alive. 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. 3280 - STORY: The Rise and Fall of BirdSupplies.com 24.12.2025

Before the boom of online shopping, this bird lover struggled to find quality products for her feathery friends. She decided to take flight herself, earning up to $250,000/year reselling supplies. Squawk! 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. 3279 - Q&A: “Do I have to be loud to sell my service?” 23.12.2025

Today's caller dreads the spotlight but still needs clients. We'll outline three low-noise, high-trust tactics that bring work to you without daily dancing on social media. 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. 3278 - First $1,000: Helping Creators Migrate Course Content 22.12.2025

In this week's First $1,000 segment, four course creators feared ripping their content out of their current system. One weekend migration specialist moved every video and quiz to Kajabi—pocketing a paycheck while their students never missed a lecture. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job...

Ep. 3277 - Weekend Workshop: The Sculptor Who Thrived on Disaster 21.12.2025

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 New York sculptor creates their own market in selling custom firebowls. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra m...

Ep. 3276 - Q&A: “Can I I force myself to ship something every two weeks?” 20.12.2025

Today's caller is stuck in study-hall mode. We'll set a simple “learn 30%, build 70%” rule and a launch checkpoint, so that progress finally outruns podcast listening. 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 severa...

Ep. 3275 - Q&A: “How do I talk about pricing when it feels impolite?” 19.12.2025

Today's caller feels guilty just naming a price. We'll reframe selling from “asking for money” to “offering a structured service,” and use a script to make the conversation automatic. 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...

Ep. 3274 - TBT: I Reverse-Engineered Google-Form Hacks 18.12.2025

In this week's “Throwback Thursday” segment, who says Google Forms has to stay boring and purple?  One tinkerer unlocked timers and custom branding, then charged nightly Zoom rates that carried him past a thousand dollars before anyone at Google even noticed. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without...

Ep. 3273 - STORY: London Photographer Rents Camera Gear 1,100 Times 17.12.2025

A London receptionist rents out his photography equipment on a peer-to-peer sharing site… over and over and over. 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: t...

Ep. 3272 - Q&A: “How do I avoid a bad review on my first client job?” 16.12.2025

The first paying client feels like a high-wire act without a net. We'll put a small safety net underneath: clear scope, midpoint check-in, and a simple “fix it fast” promise that keeps reviews in good shape. 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. 3271 - The Ski-Lodge Lost-and-Found Hustle 15.12.2025

In this week's First $1,000 segment, a self-described ski bum buys two trash bags of unclaimed lodge gear for fifty bucks each. Three chilly weeks later, clean goggles and bright jackets melted into more than a grand in 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...

Ep. 3270 - Weekend Workshop: From Rock Bottom to Business Empire 14.12.2025

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 British woman goes from living in a shelter to running a million-dollar business. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who ea...

Ep. 3269 - Q&A: “What do I do if my partner doesn’t believe in my business?” 13.12.2025

In this episode, a listener wants support at home without abandoning a dream. We'll address the emotional core—safety, trust, respect—then add a simple structure so the business proves itself without turning the relationship into collateral damage. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

Ep. 3268 - Q&A: “Are Instagram links killing my reach?” 12.12.2025

A listener worries external links are throttling her posts. We'll use Instagram-native tools, light automation, and a simple test to keep reach high while still sending people to purchase. 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. 3267 - TBT: Hand-Written Recipes Become Kitchen Wall Art 11.12.2025

In this week's Throwback Thursday segment, discover how one maker rescued stained recipe cards and transformed them into framed kitchen art. Her sentimental side hustle—complete with a done-for-you option—has already brightened 150 homes and counting. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting the...

Ep. 3266 - STORY: Marathon Runner Earns Full-Time Income Trying On Shoes 10.12.2025

A decade-long “marathon distance” project earns six-figures in affiliate commissions for this patient runner.  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 E...

Ep. 3265 - Q&A: “Should I add shipping to my Marketplace listings?” 09.12.2025

A local-only seller is debating shipping. We'll cover when it's worth it, the safest ways to get paid, and a simple two-week pilot that won't put you at risk. 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. Sho...

Ep. 3264 - First $1,000: Flipping Rolling Carts & Filing Cabinets 08.12.2025

In this week's First $1,000 segment, dull beige cabinets became hot pastel storage after one coat of paint and the right Facebook group. In just nineteen days, that makeover hustle rolled past a thousand dollars in profit—no moving truck required. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. Th...

Ep. 3263 - Weekend Workshop: The Never Boss Philosophy 07.12.2025

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: “never have a boss, never be a boss.” Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting th...

Ep. 3262 - Q&A: “Should I raise my coaching rates or add more clients?” 06.12.2025

Today's caller has two levers—charge a bit more or work a bit more. We'll test both in plain numbers, then show why nudging the price usually wins for a solo coach. 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 ea...

Ep. 3261 - Q&A: “Is my struggling side hustle worth saving?” 05.12.2025

A listener wants to know if a slow start is normal, or a warning sign that another business might be better. We'll set a simple 90-day experiment to decide whether to double down, redesign, or walk away. 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...

Ep. 3260 - TBT: Campaign Scheduling Tool Turns Out Voters 04.12.2025

In this week's Throwback Thursday segment, find out how a small campaign tool turned into a software product now licensed by multiple counties. 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: SideHu...

Ep. 3259 - STORY: Accountant Earns Six-Figures Selling Spreadsheets to Etsy Sellers 03.12.2025

She was burned out being a CPA, so she turned her efforts to an Etsy business—but it wasn't long before she was hitting the books again, just in a more creative way. Her new spreadsheets help Etsy sellers and earn a six-figure income for her. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This ye...

Ep. 3258 - Q&A: “Can I profit from flipping open-box customer returns?” 02.12.2025

Today's listener wants to turn store returns into cash. We'll cover how to evaluate a pallet, estimate true margins, and avoid getting stuck with dead inventory. 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....

Ep. 3257 - First $1,000: DIY Headshot Stations for University Job Fairs 01.12.2025

In this week's First $1,000 segment, campus recruiters needed polished LinkedIn photos—but photographers were booked solid. One creative grad built a plug-and-play headshot booth, rented it four times in a month, and snapped up his first grand without clicking the shutter himself. Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mo...

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