Side Hustle School

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Episodes

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Side Hustle School

Chris Guillebeau / Onward Project•sidehustleschool.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. 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, 2025•6 min•Ep 3008•Transcript available on Metacast

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, 2025•7 min•Ep 3007•Transcript available on Metacast

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, 2025•4 min•Ep 3006•Transcript available on Metacast

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, 2025•6 min•Ep 3005•Transcript available on Metacast

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, 2025•7 min•Ep 3004•Transcript available on Metacast

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, 2025•5 min•Ep 3003•Transcript available on Metacast

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, 2025•5 min•Ep 3002•Transcript available on Metacast

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, 2025•6 min•Ep 3001•Transcript available on Metacast

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, 2025•8 min•Ep 3000•Transcript available on Metacast

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, 2025•5 min•Ep 2999•Transcript available on Metacast

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, 2025•6 min•Ep 2998•Transcript available on Metacast

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, 2025•7 min•Ep 2997•Transcript available on Metacast

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, 2025•5 min•Ep 2996•Transcript available on Metacast

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, 2025•5 min•Ep 2995•Transcript available on Metacast

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, 2025•7 min•Ep 2994•Transcript available on Metacast