Side Hustle School - podcast cover

Side Hustle School

Chris Guillebeau / Onward Projectsidehustleschool.com

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 https://lemonadamedia.com/  

Episodes

Ep. 3050 - TBT: Lawn Sign Biz Expands to Wedding Décor Rentals

This week’s Throwback Thursday feature tells the story of a third-grade teacher who grew her creative lawn sign business into a go-to source for wedding décor. 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: [email protected] Be on the show: SideHustleSchool.com...

May 08, 20255 minEp. 3050

Ep. 3049 - STORY: Internet Trolls Eat Their Words In This Comedic Cake Hustle

After seeing a mean comment on Dolly Parton’s Facebook page, a woman realizes the absurdity of internet trolling and bakes up a hilarious and ironic side hustle. 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: [email protected] Be on the show: SideHustleSchool.c...

May 07, 20257 minEp. 3049

Ep. 3048 - Q&A: “Best practices for Meta ads?”

Are Meta ads worth the investment? In this episode, we explore the best practices for running profitable campaigns on Facebook and Instagram in 2025. 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: [email protected] Be on the show: SideHustleSchool.com/questions...

May 06, 20255 minEp. 3048

Ep. 3047 - First $1,000: Pop-Up Cosplay Salon Takes Con-Goers by Surprise

In this week’s First $1,000 story, discover how a Seattle hairstylist unofficially sets up shop near comic conventions—charging cosplayers for last-minute wig rescues and hair touch-ups. 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: [email protected] Be on the...

May 05, 20257 minEp. 3047

Ep. 3046 - Weekend Workshop: Ask 10 People for Help

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: building your support network. 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: SideHustle...

May 04, 20257 minEp. 3046

Ep. 3045 - Q&A: “Should I switch my business to a subscription model?”

Is switching to a subscription model the right move for your business? In this episode, we explore the pros, cons, and strategies for making the transition without alienating your customers. 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: [email protected] Be on...

May 03, 20255 minEp. 2045

Ep. 3044 - Q&A: “Why do authors offer pre-order bonuses?”

Why do so many authors offer pre-order bonuses? In this episode, we explore whether these perks drive sales or just create extra work—and how to decide if they’re right for your book launch. 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: [email protected] Be on...

May 02, 20256 minEp. 3042

Ep. 3043 - TBT: From Cracked Screens to Tech Buyback Business

In this week’s “Throwback Thursday” segment, we hear from a college student who scaled from fixing cracked screens to creating a buyback platform that turns over $20,000 in inventory each 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: [email protected] B...

May 01, 20256 minEp. 3043

Ep. 3042 - STORY: Fashion Buyer Creates Quirky Comfort Craze

Kyle Bergman has always had a unique and edgy taste in fashion. Then, thanks to one viral Buzzfeed article, he was able to create a brand that appeals to other people like him. 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: [email protected] Be on the show: Sid...

Apr 30, 20256 minEp. 3042

Ep. 3041 - Q&A: “Should I expand the services I offer?”

How do you decide which new opportunities to pursue without overloading yourself? In this episode, we help a listener navigate expanding their business while staying focused and strategic. 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: [email protected] Be on t...

Apr 29, 20255 minEp. 3041

Ep. 3040 - First $1,000: Flipping Phones and Tablets for Fun and Profit

In this week’s First $1,000 segment, see how a simple promise of secure data wiping and refurbishment helped a tech-savvy neighbor earn thousands of dollars by flipping outdated electronics. 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: [email protected] Be on...

Apr 28, 20256 minEp. 3038

Ep. 3039 - Weekend Workshop: Sell Like a Girl Scout

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 art of natural selling! 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: SideHustleSch...

Apr 27, 20256 minEp. 3039

Ep. 3038 - Q&A: “When is it worth spending money on your side hustle?”

When is it time to start spending real money on your side hustle? In this episode, we explore how to balance scrappiness with strategic investments to fuel growth. 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: [email protected] Be on the show: SideHustleSchool...

Apr 26, 20256 minEp. 3038

Ep. 3037 - Q&A: “How do I turn being an industry outsider into an advantage?”

How do you turn being an industry outsider into a strength? In this episode, we explore how to practice creativity while building trust and credibility with customers. 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: [email protected] Be on the show: SideHustleSc...

Apr 25, 20254 minEp. 3037

Ep. 3036 - TBT: Montana Videographer Redefines Remote Filming

In this week’s Throwback Thursday segment, discover how a pro videographer ditched travel hassles by mailing filming kits worldwide and directing online course shoots entirely from afar. 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: [email protected] Be on the...

Apr 24, 20256 minEp. 3036

Ep. 3035 - STORY: Frozen Yogurt Dog Treats Are No Barking Matter

A Colorado couple creates a side hustle that gives dogs and their owners a way to enjoy their frozen treats from their own bowls. 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on Instagra...

Apr 23, 20256 minEp. 3035

Ep. 3034 - Q&A: “How can I incorporate activism into my brand without seeming performative?”

How do you build a business that aligns with your values without coming across as performative? In this episode, we help a listener navigate authenticity in sustainability and activism. 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: [email protected] Be on the ...

Apr 22, 20255 minEp. 3034

Ep. 3033 - First $1,000: Feeding the Neighborhood, One Block at a Time

In this week’s First $1,000 segment, learn how a backyard gardener in Brooklyn joined forces with neighbors to create hyper-local produce boxes, quickly earning $1,000 with minimal overhead. 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: [email protected] Be on...

Apr 21, 20256 minEp. 3033

Ep. 3032 - Weekend Workshop: Launch Before You’re Ready

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: publishing your offer! 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.c...

Apr 20, 20257 minEp. 3032

Ep. 3031 - Q&A: “How do I create and sell a premium online course?”

In today’s episode, we explore how to create a standout premium online course. Learn how to structure it, position it for a high price point, and stand out in a competitive market. 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: [email protected] Be on the show:...

Apr 19, 20255 minEp. 3031

Ep. 3030 - Q&A: “How do I prepare for tech failures without overloading my setup?”

What happens when a tech glitch disrupts your side hustle? In this episode, we tackle how to prepare for unexpected challenges without overcomplicating your operations. 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: [email protected] Be on the show: SideHustleS...

Apr 18, 20256 minEp. 3030

Ep. 3029 - TBT: Travel Blog Becomes Spring Break Powerhouse

In this week’s Throwback Thursday segment, discover how this side hustler built a spring break site that soars to $8,000 during peak months by combining ad networks with carefully edited AI content. 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: [email protected]...

Apr 17, 20256 minEp. 3029

Ep. 3028 - STORY: College Student Hacks Into $40,000 A Month Side Hustle

When this student found himself in thousands of dollars worth of debt, he made a simple $40 investment that would go on to transform his life and reach tens of thousands of people around the world. 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: [email protected]...

Apr 16, 20258 minEp. 3028

Ep. 3027 - Q&A: “How do side hustle ‘power laws’ work?”

Why do a few things in your business drive most of your results? In this episode, we break down how power laws work and how to focus on what truly moves 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: [email protected] Be on the show: SideHustleSchoo...

Apr 15, 20256 minEp. 3027

Ep. 3026 - First $1,000: From Text Messages to Digital Concierge

In this week’s First $1,000 segment, discover how one meticulous organizer built an online concierge service, offering tiered subscriptions for routine tasks and real-time support. 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: [email protected] Be on the show:...

Apr 14, 20256 minEp. 3026

Ep. 3025 - Weekend Workshop: Making Time for What Matters

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: how to spend 10% more time on your most important tasks. 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 we...

Apr 13, 20257 minEp. 3025

Ep. 3024 - Q&A: “What’s the ROI of renting out equipment or tools?”

In this episode, we explore the ins and outs of running a tool rental business. Learn how to manage inventory, minimize risks, and maximize profits in this potentially lucrative side hustle. 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: [email protected] Be on...

Apr 12, 20255 minEp. 3024

Ep. 3023 - Q&A: “Could selling templates for AI tools be a business?”

AI tools like ChatGPT are exploding in popularity, but can creating templates for these tools become a profitable side hustle? In this episode, we explore the opportunities, challenges, and potential pitfalls of this idea. 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:...

Apr 11, 20255 minEp. 3023

Ep. 3022 - TBT: When Selling Prints Wasn’t Enough

In this week’s Throwback Thursday feature, discover how pivoting from digital art prints to creating mockups for Etsy and Shopify turned an underperforming side hustle into a high-demand service. 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: [email protected] ...

Apr 10, 20256 minEp. 3022

Ep. 3021 - STORY: Immigrant Couple Translates Heritage Into Children’s Flash Cards

Two immigrants from Laos meet the needs of an underserved community, creating a series of dual-language flash cards and other resources. 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: [email protected] Be on the show: SideHustleSchool.com/questions Connect on I...

Apr 09, 20257 minEp. 3021
For the best experience, listen in Metacast app for iOS or Android
Open in Metacast