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.

Author

Chris Guillebeau

Category

Business

Podcast website

sidehustleschool.com

Latest episode

Jul 11, 2026

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Episodes

#34: Real Estate Project Manager Fills Apartment Buildings With Original Artwork 03.02.2017

How a Seattle real estate project manager connects apartment properties with local artists for site-specific custom art installations. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Shown...

#33: GE Engineer Sells Hand-Crafted Slate Artwork to All 50 States 02.02.2017

A GE engineer uses his skills to make and sell hand-crafted slate artwork to all 50 states. In addition to bringing in a great side income, it’s also given him more courage and security to make decisions at his day job. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along...

Extended Cut #1: The Power of Observation 01.02.2017

Bonus episode! Where do hustle ideas come from? Short version: they're everywhere! This episode was recorded live from Johannesburg, South Africa and shows you how to do two things to start coming up with ideas: first, pay attention. Second, ask questions. Before your day is over, make a list of possibilities based on everything you've learned so far. Let me know what you come up with! Share: #Sid...

#32: Make $4,000/Month Renting Out Cars You Don't Own 01.02.2017

How a Los Angeles man has been able to bring in over $4,000/month leasing and releasing a fleet of cars he leased from the manufacturer. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Sho...

#31: A Visit To The Ballpark Inspires a Unique Fashion Item 31.01.2017

A couple learns to manufacture novelty baseball sweaters after receiving a lot of attention at the stadium. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Shownotes: SideHustleSchool.com...

#30: Ohio IT Director Earns $31,000 Helping Others Set Up Wordpress Sites 30.01.2017

How an Ohio IT director earned more than $31,000 by referring clients to the tools and resources they needed to set up their own websites. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool S...

#29: Hospital Database Programmer Outsources His Skills 29.01.2017

How a hospital employee utilizes skills that he learned from work to help others work with and process complex computer programs and information earning up to $125/hour. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hus...

Weekly Recap #4: Good Fortune Favors the Prepared 28.01.2017

In our fourth weekly recap, we'll highlight the lessons learned in this week of Side Hustle School, and you'll also learn why fortune favors those who come prepared. Bonus: I’m starting a traveling workshop series! Tell me where I should go. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they ove...

#27: Stressed-Out Mom Gives Up TV To Launch Her Side Hustle 27.01.2017

How a San Diego accountant coping with the struggles of new motherhood launched her own private label wine hustle for stressed out parents like herself. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #Side...

#26: These Resume Templates Make $462/Month In Passive Income 26.01.2017

A student creates a visual resume service to make extra cash, then transitions that service to work smarter, not harder. It now brings in $462 in month in completely passive income. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Yo...

#25: Pottery Barn Commissions Art From Independent Photographer 25.01.2017

How an independent photographer explored several different options for selling her art, and ended up creating a hustle that brings in a third of her total income. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Sh...

#24: Honeymoon In Nepal Becomes Fashion Accessories Hustle 24.01.2017

A multinational love affair turns into a global side hustle that raises money to invest in the community where their product is made. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Showno...

#23: Guitar Teacher Sells Lessons On Craigslist And Makes $80/Hour 23.01.2017

How a busy new father created a part-time hustle teaching guitar lessons and now earns $5,000-6,000 a month, working 20-25 hours a week. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Sho...

#22: 17-Year Old Canadian Makes $7,000 From a Holiday Pop-Up Shop 22.01.2017

How a high-school student started a holiday pop-up shop at a mall and made more than $7,000 in profit in a month. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Shownotes: SideHustleSchoo...

Weekly Recap #3: Why Some Hustles Are Better Than Others 21.01.2017

In this third weekly recap, we'll highlight the lessons learned in this week of Side Hustle School, and you'll also learn why some side hustles are better than others. Bonus: I’m starting a traveling workshop series! Tell me where I should go. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they o...

#20: Engineer Creates “Inertia Project” For Women 20.01.2017

How a former engineer loses in Las Vegas and redesigns the trajectory of her life, creating an impressive hustle along the way. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Shownotes: S...

#19: Government Analyst Builds Six-Figure Reselling Hustle 19.01.2017

How a government analyst goes from collecting Frequent Flyer miles to collecting money through a reselling side hustle creating a six-figure income! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHust...

#18: College Student Generates 50m Views On Youtube, Hires 13 Employees 18.01.2017

After seeking a method to conquer her own skin issues, one woman takes to YouTube to help others shed their skin insecurities as well. Five years later, she has her own skincare line serving people all over the world! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along t...

#17: Airbnb For Dogs: Woman Hosts Pets For $200/Day 17.01.2017

After moving to the states to be with her new husband, a nutritionist from Spain finds a way to make a steading income hosting other people's pets in her home. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share...

#16: Homemade Gin Kit Sells 75,000 Units 16.01.2017

After encountering a roadblock in starting their own distillery, two friends create a side hustle that allows others to make gin in the comfort of their own home—no bathtub required! Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. Y...

#15: Graphic Designer Draws Caricatures For $250/Hr 15.01.2017

How a graphic designer went from $8 an hour to $250 an hour in her side business. She now earns more than $100,000 working part-time—and she has some great advice that applies to a lot of hustles. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the...

Weekly Recap #2: What Makes a Good Hustle? 14.01.2017

We look back at this week’s lessons and identify the qualities of a good hustle. Bonus: I’m starting a traveling workshop series! Tell me where I should go. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #...

#13: Waldorf Teacher Designs Curriculum for Other Educators 13.01.2017

A teacher uses what she knows to help other teachers save time and teach more effectively. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Shownotes: SideHustleSchool.com Twitter: @chrisgu...

#12: 40,000 People Use This Web Developer's Side Hustle Every Day 12.01.2017

How a San Francisco commuter became part of the original iPhone launch with a hustle that now helps more than 40,000 people every day. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You’ll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle! Share: #SideHustleSchool Shown...

#11: Ketogenic Cookbook Author Makes $1,000 the First Day 11.01.2017

How a specialized diet led to an eager fan base and a $2,000 / month side hustle, all from someone who never intended to make money from her project. Side Hustle School features a new story EVERY DAY of someone who started a hustle without quitting their job. You'll learn how they got the idea, how they overcame challenges along the way, and what the results are. You need a hustle!  Share: #S...

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