Chris Guillebeau

Side Hustle School

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. Hosted on Acast. See acast.com/privacy for more information.

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Autor

Chris Guillebeau

Categoría

Business

Web del podcast

sidehustleschool.com

Último episodio

18 de oct. de 2026

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Episodios

Ep. 3528 - Q&A: “Is it still possible to start a blog?” 29.08.2026

Jon is wondering if he’s missed out on the golden age of blogging. He wants to start a blog, but is it too late? 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...

Ep. 3527 - STORY: Cake Artist’s Confections Whisk Up Delicious Profits 28.08.2026

This pastry chef starts by baking on the side, then grows her hustle into a full-time business selling more than $100,000 worth of wedding and custom cakes 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...

Ep. 3526 - TBT: Tap Dance Teacher Offers Worldwide Lessons 27.08.2026

In this week’s “Throwback Thursday” segment, we hear from Bill Simpson, chief tap dancer of HowtoTapDance.com. From his homebase of Melbourne, Australia, he teaches the art of the tap to students all over 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...

Ep. 3525 - Q&A: “Should I self-publish a mental health guidebook on Kindle?” 26.08.2026

A listener in Mexico is starting a podcast on mental health, and also wants to publish a book. Should she put it out on Kindle even though she doesn’t have a lot of followers yet? 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 severa...

Ep. 3524 - Q&A: “I’d like to be a financial advisor for Gen Z…” 25.08.2026

This Gen Z listener wants to become a financial advisor for her generation. How can she build her authority and platform? 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...

Ep. 3523 - First $1,000: “I wanted to explore AI-generated art…” 24.08.2026

In this week’s First $1,000 segment, we hear from a real estate professional who makes and sells design elements that come from AI-generated art.  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...

Ep. 3522 - STORY: Lather, Rinse, Recycle: Soapy Problem Leads to Clean Solution 23.08.2026

An account manager solves the pondering question of “What happens to soap after it’s used in a hotel room?”—and turns it into a sustainable 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. Sho...

Ep. 3521 - Q&A: “How do I find customers as a digital personal assistant?” 22.08.2026

Today’s listener is in search of his first customer! He wants to become a digital personal assistant to help people with tech support. How should he proceed? 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...

Ep. 3520 - Failure Friday: “After I was hit by a car, things got worse…” 21.08.2026

In this week’s Failure Friday segment, we hear from an affiliate marketer who encountered an unusual problem: after he was hit by a car, the public knowledge of his business was used against 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 l...

Ep. 3519 - TBT: Bridesmaid-for-Hire Keeps Walking Down the Aisle 20.08.2026

In this week’s “Throwback Thursday” segment, we hear from the woman behind “Bridesmaid-for-Hire,” one of our most popular episodes in year one. Her business has grown a lot since then, but she’s also learned some lessons in simplifying.  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, th...

Ep. 3518 - Q&A: “Where do I begin if I want to make an app?” 19.08.2026

This listener wants to make an app, but needs some help knowing where to start. 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...

Ep. 3517 - Q&A: “Should I start a new site for my food business?” 18.08.2026

This listener has an older food blog that she hasn’t updated in a while, and now she wants to convert it to an ecommerce site. Is that the best approach, or should she start all over? 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...

Ep. 3516 - First $1,000: “I built an Airbnb rental in my backyard…” 17.08.2026

In this week’s First $1,000 segment, we hear from a serial side hustler who builds an ADU in his backyard, allowing him to earn $1,500/month in passive rentals. He then uses the profits to buy another property. 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 less...

Ep. 3515 - STORY: Hair Braiding Workshops Help Trans-Racial Adoptive Families 16.08.2026

A Chicago woman uses her side hustle to support her life, then adapts it to help more than 1,000 children in trans-racial adoptive families.  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: &nb...

Ep. 3514 - Q&A: “How to make a board game from start to finish?” 15.08.2026

Today’s listener wants to make a board game. There are many steps involved, and he’ll need to learn a lot along the way. But that shouldn’t stop him! Let’s see if we can help him out.  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&am...

Ep. 3513 - STORY: Teacher Flips Sports Gear For $8,000/Month 14.08.2026

A teacher uses his love for sports memorabilia to bridge the financial gap between his teaching contracts—then goes on to create a highly profitable 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 ea...

Ep. 3512 - TBT: Southern Transplant Creates Watercolor Brand 13.08.2026

In this week’s “Throwback Thursday” segment, we revisit a graphic designer who creates a watercolor brand that is sold in retailers throughout South Carolina and beyond.  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 da...

Ep. 3511 - Q&A: “Do I have to sell as a SAAS?” 12.08.2026

A listener is trying to decide how to price a new online service. Should she use the common SAAS (“software as a service”) model, or are there alternatives?  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....

Ep. 3510 - Q&A: “How many tech tools do I need to master?” 11.08.2026

This listener has a side hustle teaching data analytics, and wants to grow—but he’s feeling overwhelmed with all the necessary tools. How can he choose the right resources without becoming fixated on them? 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 a...

Ep. 3509 - First $1,000: Paralegal Assists U.S. Immigrants to Canada 10.08.2026

In this week’s First $1,000 segment, we hear from a Canadian paralegal who helps American immigrants learn to navigate the bureaucracy of migration.  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...

Ep. 3508 - STORY: “SwitchPod” Camera Tool Raises $415,748 on Kickstarter 09.08.2026

When two friends spot an opportunity to create a practical camera accessory, the crowdfunding campaign exceeds their wildest expectations.  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: &nbsp...

Ep. 3507 - Q&A: “How to convert non-paying students into customers?” 08.08.2026

Today’s listener (from Egypt!) is teaching software development through an apprenticeship model, but most of his students aren’t paying. How can he convert some of these free students into 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 lis...

Ep. 3506 - Failure Friday: “I had tears in my eyes reading the response…” 07.08.2026

In this week’s Failure Friday segment, we hear from a jewelry seller who almost gets taken out of commission by a highly negative review.  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:  ...

Ep. 3505 - TBT: Family Affirmation Cards Go Global 06.08.2026

In this week’s “Throwback Thursday” segment, we hear from the co-founder of a Canadian business that helps kids and families with self-worth. 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:  Si...

Ep. 3504 - Q&A: “How do you forecast earnings for a side hustle?” 05.08.2026

A listener came across my back-of-the-napkin spreadsheet template and is wondering something: if a business or side hustle is new, how can you forecast earnings for it? It’s a good question, but there’s also a good answer. 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...

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