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. 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 no...

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 ...

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]...

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: ...

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...

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: team@sidehustlesc...

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 ...

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 se...

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: team@sidehustleschoo...

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 Connec...

Apr 09, 20257 minEp. 3021

Ep. 3020 - Q&A: “How do I manage last-minute requests without burning out?”

In this episode, we explore how service-based freelancers can manage last-minute client requests without sacrificing quality or burning out. Learn how to build buffer time into your schedule and set clear project boundaries. 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 Emai...

Apr 08, 20255 minEp. 3020

Ep. 3019 - First $1,000: Miami Divorce Planner Offers “Freedom Celebrations”

In this week’s First $1,000 segment, discover how a former wedding planner in Miami pivoted to organizing “freedom celebrations” for newly divorced clients, landing her first thousand dollars from two high-end events. 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: SideHustleScho...

Apr 07, 20257 minEp. 3019

Ep. 3018 - Weekend Workshop: Design Your First Workflow

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: creating clear, repeatable systems for running your business efficiently. 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 li...

Apr 06, 20257 minEp. 3018

Ep. 3017 - Q&A: “How do I balance transparency with professionalism?”

In this episode, we tackle the tricky balance of being transparent with your audience while maintaining professionalism. How can you build trust without oversharing or compromising your credibility? 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 05, 20255 minEp. 3017

Ep. 3016 - Q&A: “Is there still room to start a podcast in 2025?”

Is it too late to start a podcast in 2025? In this episode, we tackle how to stand out in a crowded field and grow an audience for a niche topic. 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 Con...

Apr 04, 20254 minEp. 3016

Ep. 3015 - TBT: Bringing Tokyo’s Best Stationery to Global Audiences

In this week’s Throwback Thursday segment, learn how a stationery-lover in Tokyo began shipping curated paper goods and writing supplies abroad—all while championing small artisan shops. 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 03, 20256 minEp. 3015

Ep. 3014 - STORY: Accountant Earns $233,751 Reselling Items He Buys at Walmart

A young accountant learns the art of reselling, purchasing textbooks, dental floss, and Cheerios from retail stores in bulk—then earns hundreds of thousands of dollars in profit by selling it online. 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@sidehustles...

Apr 02, 20258 minEp. 3013

Ep. 3013 - Q&A: “How do I find my first clients without paid advertising?”

In this episode, we help a new business owner attract their first paying clients without spending a dime on ads. Learn grassroots strategies for networking, social media, and building momentum from scratch. 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@sidehustle...

Apr 01, 20255 minEp. 3013

Ep. 3012 - First $1,000: Stay-at-Home Dad’s Virtual Garage Sale Venture

In this week’s First $1,000 segment, find out how a stay-at-home dad turned his neighbors’ forgotten items into steady online income, taking a cut of each sale. 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: SideHus...

Mar 31, 20255 minEp. 3012

Ep. 3011 - Weekend Workshop: Make It Easy to Get Paid

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: make it easy to get paid. 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 note...

Mar 30, 20259 minEp. 3011

Ep. 3010 - Q&A: “How to set better boundaries with clients?”

In this episode, we explore how to manage client expectations when emotions get in the way. Learn how to set clear boundaries, navigate tough conversations, and keep your business running smoothly—even when clients slow down the process. 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: SideHu...

Mar 29, 20256 minEp. 3010