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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

6:45

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

Side Hustle School ·

2025/10/12

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

en

4:51

Ep. 3206 - Q&A: “How do I fight piracy without...

Side Hustle School ·

2025/10/11

You can’t stop every pirate, but you can slow them down—and keep real customers smiling. Today we cover low-cost deterrents, “soft DRM,” and community perks that make stealing less attractive. 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

4:48

Ep. 3205 - Q&A: “How do I license calming coloring...

Side Hustle School ·

2025/10/10

Trade $2 one-time sales for four-figure B2B deals. We build the pitch, pricing, and contract essentials for licensing art to wellness platforms. 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

5:20

Ep. 3204 - TBT: The Secret Author Behind Your...

Side Hustle School ·

2025/10/09

In this week’s Throwback Thursday segment, hear how one fanfiction writer went pro—now earning five figures per project ghostwriting for bestselling romance authors who don’t want their names published. 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

7:00

Ep. 3203 - STORY: Underwear Side Hustle Turns Into...

Side Hustle School ·

2025/10/08

Two women launch an underwear brand in their spare time. It grows from an early Kickstarter campaign to a multi-million dollar company with more than a dozen employees. 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

3:49

Ep. 3202 - Q&A: “Can a ‘tech deals’ newsletter really...

Side Hustle School ·

2025/10/07

Tech discounts can pay the bills, at least if you treat them like a product, not a hobby. Today we map out list-building, trust, and revenue math for a profitable deal newsletter. 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

4:59

Ep. 3201 - First $1,000: Weekend ASL Crash Courses...

Side Hustle School ·

2025/10/06

In this week’s First $1,000 segment, hear how a certified interpreter turned empty hotel conference rooms into a training ground for quick, practical American Sign Language (ASL). 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

5:09

Ep. 3199 - Q&A: “How do I handle a non-compete that...

Side Hustle School ·

2025/10/04

A promotion with strings attached can stall a thriving side hustle. Today we’ll walk through reading the fine print, negotiating carve-outs, and keeping both your boss and your business on the road. 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

5:23

Ep. 3198 - Q&A: “I went viral, but now I can’t meet...

Side Hustle School ·

2025/10/03

A viral spike is great—until it breaks your capacity. Today we map a four-step triage plan to pause the chaos, satisfy customers, and turn overwhelm into long-term buzz. 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

5:32

Ep. 3197 - TBT: Turning Property Management...

Side Hustle School ·

2025/10/02

In this week’s Throwback Thursday segment, learn how one former apartment manager turned their real estate experience into a template shop for landlords, helping them boost revenue without buying new properties. 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

7:32

Ep. 3196 - STORY: Google Employee Makes $100,000...

Side Hustle School ·

2025/10/01

In just one year, this Google product manager earned an extra $100,000 by providing marketing services on Fiverr.com. Learn his tips to hack the platform for yourself! 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

6:13

Ep. 3195 - Q&A: “Which passive-income model fits a...

Side Hustle School ·

2025/09/30

Want to escape the billable-hour treadmill? Today we map out three proven paths—courses, content, and compounding cashflows—that turn one-time effort into long-term 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 listener Q&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

5:11

Ep. 3194 - First $1,000: Marketer Sells Simple Fixes...

Side Hustle School ·

2025/09/29

In this week’s First $1,000 segment, hear how a digital marketer gets paid for cleaning up Google listings for orthodontists—fixing visibility problems most offices didn’t even realize they had. 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

8:01

Ep. 3193 - Weekend Workshop: The Art of Electronics...

Side Hustle School ·

2025/09/28

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: buy low, sell high, repeat! 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

5:39

Ep. 3192 - Q&A: “How can a freelancer pay herself a...

Side Hustle School ·

2025/09/27

Feast-or-famine income doesn’t have to mean feast-or-famine life. Today we build a simple three-bucket system that turns lumpy freelance revenue into a steady, predictable paycheck. 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

4:23

Ep. 3191 - Q&A: “What KPIs should I track for my...

Side Hustle School ·

2025/09/26

Fifty customers, fifty metrics—too many for a two-person team. Today we boil micro-SaaS analytics down to the three numbers that actually move the needle. 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

4:47

Ep. 3190 - TBT: Helping Aspiring Film Professionals...

Side Hustle School ·

2025/09/25

In this week’s Throwback Thursday segment, learn how a London-based side hustler launched a service to help aspiring film crew members get their first jobs and union credentials—and how they’re now planning to expand to Los Angeles and Vancouver. 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

6:45

Ep. 3189 - STORY: College Grad Shares “More than Mac...

Side Hustle School ·

2025/09/24

When a college student learns to cook, she documents her recipes online, earning more than $1,000/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 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

4:15

Ep. 3188 - Q&A: “Can you run a YouTube channel with...

Side Hustle School ·

2025/09/23

Can a faceless, AI-voiced show win viewers and ad dollars? Today we break down platform rules, audience psychology, and the tiny legal print you can’t ignore when the “host” is synthetic. 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

5:47

Ep. 3186 - Weekend Workshop: Design Disruption in...

Side Hustle School ·

2025/09/21

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: an astrology calendar for modern times. 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

1,325 results

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