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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

8:15

Ep. 3235 - Weekend Workshop: The Wandering Teacher's...

Side Hustle School ·

2025/11/09

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: an early language hacker starts “Fluent in 3 Months.” 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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5:35

Ep. 3234 - Q&A: “What’s a fair founder-investor deal...

Side Hustle School ·

2025/11/08

Cash can launch the product; labor will keep it alive. Today we map out founder-friendly splits, vesting schedules, and a simple “dynamic equity” formula that grows with effort. 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

en

4:56

Ep. 3233 - Q&A: “Where do I find my first paying...

Side Hustle School ·

2025/11/07

One sale beats a hundred compliments. Let’s walk through a low-risk, weekend-ready plan that puts money in this side hustler’s hands within two weeks. 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

6:00

Ep. 3232 - TBT: The Garage Gym Hustle That Went Digital

Side Hustle School ·

2025/11/06

In this week’s Throwback Thursday segment, learn how one fitness fan turned flipping gym equipment into a small media business. He now sells setup guides and curates weekly home gym deals for thousands of subscribers. 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

8:25

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

Side Hustle School ·

2025/11/05

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

en

5:22

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

Side Hustle School ·

2025/11/04

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

en

6:45

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

Side Hustle School ·

2025/11/03

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

en

7:15

Ep. 3228 - Weekend Workshop: When Getting Fired...

Side Hustle School ·

2025/11/02

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 quitting their job. This year, the show includes free guided lessons and listener

en

5:19

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

Side Hustle School ·

2025/11/01

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

en

5:03

Ep. 3226 - Q&A: “Can I legally profit from salvaging...

Side Hustle School ·

2025/10/31

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 notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show: SideHustleSchool.com/questions

en

5:59

Ep. 3225 - TBT: A Guided Journal, a Friend in Need,...

Side Hustle School ·

2025/10/30

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

en

7:41

Ep. 3224 - STORY: Line Chef Makes Millions Cooking Up...

Side Hustle School ·

2025/10/29

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

en

4:37

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

Side Hustle School ·

2025/10/28

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

en

5:56

Ep. 3222 - First $1,000: “CRM Makeovers” for Real...

Side Hustle School ·

2025/10/27

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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com

en

7:19

Ep. 3221 - Weekend Workshop: The Premium Pricing Paradox

Side Hustle School ·

2025/10/26

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

en

5:35

Ep. 3220 - Q&A: “When is business coaching worth the...

Side Hustle School ·

2025/10/25

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

en

5:54

Ep. 3219 - Q&A: “Can I sell carbon-offset checks to...

Side Hustle School ·

2025/10/24

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

en

5:50

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

Side Hustle School ·

2025/10/23

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

en

7:02

Ep. 3217 - STORY: Aussie Stretches Out with Online...

Side Hustle School ·

2025/10/22

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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit

en

5:05

Ep. 3216 - Q&A: “How do I avoid a garage full of...

Side Hustle School ·

2025/10/21

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

en

1,393 results

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