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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

5:44

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

Side Hustle School ·

2025/12/12

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

en

5:56

Ep. 3267 - TBT: Hand-Written Recipes Become Kitchen...

Side Hustle School ·

2025/12/11

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

en

7:29

Ep. 3266 - STORY: Marathon Runner Earns Full-Time...

Side Hustle School ·

2025/12/10

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

en

5:37

Ep. 3265 - Q&A: “Should I add shipping to my...

Side Hustle School ·

2025/12/09

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

en

6:43

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

Side Hustle School ·

2025/12/08

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

en

8:14

Ep. 3263 - Weekend Workshop: The Never Boss Philosophy

Side Hustle School ·

2025/12/07

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

en

5:15

Ep. 3262 - Q&A: “Should I raise my coaching rates or...

Side Hustle School ·

2025/12/06

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

en

5:49

Ep. 3261 - Q&A: “Is my struggling side hustle worth...

Side Hustle School ·

2025/12/05

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

en

5:21

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

Side Hustle School ·

2025/12/04

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

en

7:38

Ep. 3259 - STORY: Accountant Earns Six-Figures...

Side Hustle School ·

2025/12/03

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

en

4:59

Ep. 3258 - Q&A: “Can I profit from flipping open-box...

Side Hustle School ·

2025/12/02

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

en

5:35

Ep. 3257 - First $1,000: DIY Headshot Stations for...

Side Hustle School ·

2025/12/01

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

en

7:51

Ep. 3256 - Weekend Workshop: Building Teams Without...

Side Hustle School ·

2025/11/30

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 small-scale, large-reach transcription 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

en

4:44

Ep. 3255 - Q&A: “When is uneven side-hustle income...

Side Hustle School ·

2025/11/29

Today’s caller makes more money on weekends than at the day job—but their revenue graph looks like a heart monitor. Can they rely enough on their extra income to go all-in? 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

4:31

Ep. 3254 - Q&A: “How do I price my VA work for true...

Side Hustle School ·

2025/11/28

If clients praise your speed but you’re still billing like a beginner, it’s time to level up. Today we pinpoint the three value levers that justify higher VA rates—and a script that keeps loyal clients on board. 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

6:18

Ep. 3253 - TBT: Scarce Lego Sets Build Value Over Time

Side Hustle School ·

2025/11/27

In this week’s Throwback Thursday segment, find out how one patient side hustler stockpiled retired LEGO sets, held them like collectibles, and eventually parlayed the profits into a full-on store. 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

8:02

Ep. 3252 - STORY: Frenchman Says Bonjour to...

Side Hustle School ·

2025/11/26

After relocating to Quebec, this continental creative brings seasonal flavor to an artisanal food retailing biz. 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

en

5:13

Ep. 3251 - Q&A: “Is my burnout a signal to pivot?”

Side Hustle School ·

2025/11/25

Are you just tired—or do you need a bigger break? In this episode, we’ll help a listener take a stress-test to know if they need rest, a redesign, or a full business pivot. 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. 3250 - First $1,000: Digital Window Menu Boards...

Side Hustle School ·

2025/11/24

In this week’s First $1,000 segment, a designer helps food trucks and pop-up restaurants get rid of chalk dust and update to the digital age. 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

7:07

Ep. 3249 - Weekend Workshop: From Ski Bum to...

Side Hustle School ·

2025/11/23

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 online snow-skiing school. 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

1,346 results

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