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PODCAST

Side Hustle School

Chris Guillebeau / Onward Project

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. Sales and Distribution by Lemonada Media

business entrepreneurship

All Episodes

5:42

Ep. 3290 - Q&A: “What if you don't want to use social...

Side Hustle School ·

2026/01/03

This listener makes motion videos and backgrounds for churches, but he dislikes social media (#notafan). Should he just get over his resistance, or can his business succeed in another way? 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@sidehustleschool.com Be on the

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7:34

Ep. 3289 - STORY: Rent the Chicken! An Egg-Cellent...

Side Hustle School ·

2026/01/02

This Pennsylvania couple rents out 2,000 chickens to people interested in urban homesteading. It’s a side hustle worth clucking about! 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on

en

7:52

Ep. 3288 - Side Hustle School Season 10 Starts TODAY

Side Hustle School ·

2026/01/01

We’re back with an all-new season! Here’s how year ten (!) of Side Hustle School will work. Introducing new features, music, and another 365 days of episodes. 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@sidehustleschool.com Be on the show:

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9:13

Ep. 3287 - STORY: Military-Themed Teddy Bears Help...

Side Hustle School ·

2025/12/31

An in-house ad executive turned teddy bear manufacturer creates a military-grade sleep system for children, earning six figures in sales and making a lot of people beary happy. 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@sidehustleschool.com Be on the show:

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4:45

Ep. 3286 - Q&A: “After nine years of daily episodes,...

Side Hustle School ·

2025/12/30

A longtime listener inquires about the future of Side Hustle School. Don’t worry, we’re not done! 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit

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5:18

Ep. 3285 - First $1,000: A Discord Server That Pays...

Side Hustle School ·

2025/12/29

In this week’s Throwback Thursday segment, discover how one creative learner built a thriving online community—and why most of its value has nothing to do with algorithms or ads. 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@sidehustleschool.com Be on the

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6:09

Ep. 3284 - Weekend Workshop: From Wedding Dresses to...

Side Hustle School ·

2025/12/28

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 young entrepreneur builds her way to the Nebraska State Legislature. 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

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4:48

Ep. 3283 - Q&A: “How can I keep from negotiating...

Side Hustle School ·

2025/12/27

Today’s caller undercuts her own price before the client even speaks. Let’s help her overcome this pattern of self-sabotage! 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on

en

5:22

Ep. 3282 - Q&A: “I’m ready to raise prices … but how?”

Side Hustle School ·

2025/12/26

Inflation climbs and workload grows, but rates stay frozen—sound familiar? Today we’ll run a quick value check, set a price-rise timeline, and craft a client email that keeps loyalty high. 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@sidehustleschool.com

en

6:40

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

Side Hustle School ·

2025/12/25

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 Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

8:30

Ep. 3280 - STORY: The Rise and Fall of BirdSupplies.com

Side Hustle School ·

2025/12/24

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 and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

5:24

Ep. 3279 - Q&A: “Do I have to be loud to sell my...

Side Hustle School ·

2025/12/23

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 each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

6:59

Ep. 3278 - First $1,000: Helping Creators Migrate...

Side Hustle School ·

2025/12/22

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. This year, the show includes free guided lessons and listener Q&A several days each week

en

5:53

Ep. 3277 - Weekend Workshop: The Sculptor Who Thrived...

Side Hustle School ·

2025/12/21

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 money without quitting their job. This year, the show includes free guided lessons and

en

4:28

Ep. 3276 - Q&A: “Can I I force myself to ship...

Side Hustle School ·

2025/12/20

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on

en

4:47

Ep. 3275 - Q&A: “How do I talk about pricing when it...

Side Hustle School ·

2025/12/19

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 and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

6:22

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

Side Hustle School ·

2025/12/18

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 quitting their job. This year, the show includes free guided lessons and listener Q&A several days

en

7:35

Ep. 3273 - STORY: London Photographer Rents Camera...

Side Hustle School ·

2025/12/17

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: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram:

en

4:11

Ep. 3272 - Q&A: “How do I avoid a bad review on my...

Side Hustle School ·

2025/12/16

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 guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com Email:

en

6:19

Ep. 3271 - The Ski-Lodge Lost-and-Found Hustle

Side Hustle School ·

2025/12/15

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 free guided lessons and listener Q&A several days each week. Show notes: SideHustleSchool.com

en

1,388 results

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