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. 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: team@sidehustleschool.com 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: team@sidehustleschool.c...

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: team@sidehustleschool.com 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

Ep. 3009 - Q&A: “How can I work fewer hours without losing income?”

In this episode, we help a web developer reduce his work hours while keeping his income steady. Learn how to raise rates, outsource tasks, and restructure service packages to build a smarter, more sustainable 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: tea...

Mar 28, 20256 minEp. 3009

Ep. 3008 - TBT: Pet Furniture Maker Adds Digital Blueprints for DIYers

In this week’s Throwback Thursday segment, see how shifting from physical products to digital plans and online classes helped a woodworker reach more customers and streamline his business model. 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...

Mar 27, 20256 minEp. 3008

Ep. 3007 - STORY: Florida Woman Gets Paid to Remove Poisonous Frogs

In this ribetting feature, a high school science teacher earns an extra $3,000/month removing an invasive species of toads throughout Florida. 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 Connec...

Mar 26, 20257 minEp. 3007

Ep. 3006 - Q&A: “How do I set the right hourly rate for my side hustle?”

In today’s episode, we help a social media manager set a fair hourly rate. Learn how to balance your skills and market demands to price your services confidently. 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: SideHustleS...

Mar 25, 20254 minEp. 3006

Ep. 3005 - First $1,000: This “Crypto Tax Whisperer” Takes On the IRS

In this week’s First $1,000 segment, discover how an unassuming accountant turned a chaotic batch of crypto trades into a full-scale practice, complete with custom software and national training programs. 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@sidehu...

Mar 24, 20256 minEp. 3005

Ep. 3004 - Weekend Workshop: Create a Side Hustle Shopping List

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: create a side hustle shopping list. 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....

Mar 23, 20257 minEp. 3004

Ep. 3003 - Q&A: “How can I get clients to provide more accurate information?”

In this episode, we explore how service-based businesses can guide clients through providing accurate information. Learn how to reduce costly mistakes and protect your 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: Si...

Mar 22, 20255 minEp. 3003

Ep. 3002 - Q&A: “How can I stand out in a world of AI-generated content?”

In today’s episode, we tackle a growing concern for creators: how to stand out in a world increasingly dominated by AI-generated content. If you’re worried about keeping your work authentic and engaging, you’re not alone. 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...

Mar 21, 20255 minEp. 3002

Ep. 3001 - TBT: Food Blog Grows to Thriving Culinary Ecosystem

In this week’s Throwback Thursday segment, learn how a recipe blogger moved beyond one-off cookbook sales to form a culinary community, offering seasonal meal plans, live demos, and valuable kitchen tool discounts. 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: t...

Mar 20, 20256 minEp. 3001

Ep. 3000 - STORY: “Pocket Monkey” Tool Sells 500,000 Units

After getting locked out of his apartment, a software engineer creates a pocket tool that goes on to sell 500,000 units and employ 17 people. 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...

Mar 19, 20258 minEp. 3000

Ep. 2999 - Q&A: “How to prioritize tasks and to-do items without getting overwhelmed?”

In today’s episode, we explore neurodivergent-friendly strategies to tackle an overwhelming to-do list. Learn how to work with your energy, build momentum, and stay productive without burnout. 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.c...

Mar 18, 20255 minEp. 2999

Ep. 2998 - First $1,000: From Malibu Bartender to At-Home Bar Designer

In this week’s First $1,000 segment, discover how a Malibu bartender began designing home bars, added a line of custom bar tools, and launched virtual cocktail classes to reach $150,000 a year. 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....

Mar 17, 20256 minEp. 2998

Ep. 2997 - Weekend Workshop: Finding the Right Price

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: finding the right price. 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...

Mar 16, 20257 minEp. 2997

Ep. 2996 - Q&A: “Can I legally sell t-shirts with retro images of celebrities?”

In today’s episode, we help an aspiring side hustler navigate the tricky world of copyright and likeness rights. Can you legally sell products featuring old-school celebrity images? Let’s break it down. 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@si...

Mar 15, 20255 minEp. 2996

Ep. 2995 - Q&A: “How to organize leads without getting overwhelmed?”

In this episode, we help a small business owner organize client leads without getting overwhelmed. Learn simple, affordable ways to track inquiries, follow-ups, and deadlines—even if you’re not ready for a big CRM system. 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...

Mar 14, 20255 minEp. 2995

Ep. 2994 - TBT: Streamlining Standardized Test Preparation

In this week’s Throwback Thursday segment, learn how one test prep tutor goes from juggling individual clients to running a membership platform filled with guided lessons, practice tests, and group 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: team@side...

Mar 13, 20257 minEp. 2994

Ep. 2993 - STORY: Homemade Art Tutorials Turn Struggling Artist Into YouTube Star

A struggling painter and sculptor uploads a drawing video to YouTube and discovers a massive audience for tutorials on hand-drawing, generating over 50 million views in 6 years. 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: Si...

Mar 12, 20257 minEp. 2993

Ep. 2992 - Q&A: “How do I handle indecisive event planning clients?”

In this episode, we help an aspiring event planner manage indecisive clients who keep changing their event themes. Learn how to set clear expectations, avoid delays, and charge for extra work—without coming across as pushy. 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...

Mar 11, 20256 minEp. 2992

Ep. 2991 - First $1,000: My Life as a Proposal Planner

In this week’s First $1,000 segment, find out how one Bay Area event planner turns suitors’ dreams into carefully choreographed reality, complete with hidden photographers and heartfelt surprises. 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@sidehust...

Mar 10, 20255 minEp. 2991

Ep. 2990 - Weekend Workshop: Assemble the Nuts and Bolts

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: assemble the nuts and bolts. 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 n...

Mar 09, 20257 minEp. 2990

Ep. 2989 - Q&A: “What should I do if a brand uses my photo without permission?”

In this episode, we help a content creator navigate what to do when a brand uses their photo without permission. Learn how to approach the situation professionally—or when it might be better to let it go and move forward. 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 E...

Mar 08, 20255 minEp. 2989

Ep. 2988 - Q&A: “How do I create passive income from a skill-based service?”

In this episode, we help a freelance marketing consultant explore ways to turn her expertise into passive income. Learn how to create scalable products that generate revenue—even when you’re not working one-on-one with clients. 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...

Mar 07, 20255 minEp. 2988

Ep. 2987 - TBT: Solo Nutrition Practice Offers Corporate Wellness Service

In this week’s Throwback Thursday segment, discover how a freelance nutritionist transitioned from personal meal plans to comprehensive corporate wellness programs, creating ongoing value for employees and stable income for herself. 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: SideHustleS...

Mar 06, 20256 minEp. 2987