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

Where to listen?

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Episodes

#560 - Retired Couple Sells Digital Art Prints Online 14.07.2018

A retired husband-and-wife team make a shift from handmade art to digital art prints. They now sell more than 100 prints each 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.  Share: #SideHustleSchoolShow notes: SideHustleScho...

#559 - Independent Musician Strikes Chord With Customized Love Ballads 13.07.2018

When she discovers the bottom of her bank account, this singer-songwriter offers to write personalized love songs for $325 each. 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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.c...

#558 - 5-Year-Old’s Frustration Leads to Modern Day Piggy Bank 12.07.2018

When a 5-year-old earns money taking out the trash for neighbors, his mom realizes that piggy banks are more style than function. She then reinvents this classic tool as a “piggy box” that won’t get stuck in the mud. 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 th...

#557 - More Monet, Fewer Problems: Attorney Turns Holiday Prints Into Cash 11.07.2018

This Texas attorney has no Magrittes about starting her easy-to-scale side hustle. 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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeauInstagram: @193coun...

#556 - Underwear Side Hustle Turns Into $500,000/Month Business 10.07.2018

Two women launch an underwear brand in their spare time. It grows from an early Kickstarter campaign to a multi-million dollar company with more than a dozen employees. 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.  Share: #SideHu...

#555 - Pre-Made Meals Bring In $5,500/Month After Layoff 09.07.2018

After losing her job, this digital marketer turns to the kitchen, where she whips up pre-made meals and launches a successful crowdfunding campaign.  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.  Share: #SideHustleSchoolShow note...

#554 - Weekly Recap: Don’t Become Efficient at Doing the Wrong Things 08.07.2018

In our twenty-sixth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A!  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @ch...

#553 - Editor Creates Book Club For Bad People 07.07.2018

In an age of endless distractions, an editor for Superdry found she was reading fewer books. By creating a subscription book club, she now sends new titles to more than 300 people each 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 resu...

#552 - Doctor’s Diagnosis Becomes Food Diary Side Hustle 06.07.2018

A chronic illness diagnosis leads to the “write” side hustle for a full-time communications manager in the UK.  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chris...

#551 - College Students Start Sock-Selling Social Enterprise 05.07.2018

A group of college students learn to sell socks with a cause. In two years they sign up more than 100 educational institutions! 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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.co...

#550 - Canadian Powerlifter Creates Elegant Bow Tie Biz 04.07.2018

This hospital employee and competitive powerlifter wasn’t making enough money on the side as a personal trainer, so he turned to a completely different idea: bow ties! 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.  Share: #SideHus...

#549 - Bean-Lover Grinds Way To $4,000/Month Family Coffee Business 03.07.2018

A love of coffee leads to a family-owned coffee hustle, bringing joy and beans to to loyal customers. Don’t procrastinate; pro-caffeinate!  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.  Share: #SideHustleSchoolShow notes: SideHus...

#548 - Google Employee Makes $100,000 Using Fiverr 02.07.2018

In just one year, this Google product manager earns an extra $100,000 by providing marketing services on Fiverr.com. Learn his tips to hack the platform for yourself!  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.  Share: #SideHus...

# 547 - Weekly Recap: Should You Ever Buy Someone Else’s Business? 01.07.2018

In our twenty-sixth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A!  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @ch...

#546 - What’s In the Box? Low-Carb, Low-Sugar Snacks 30.06.2018

A CPA and Side Hustle School listener learns to start her own subscription box. In less than a year, it brings in more than $5,000/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.  Share: #SideHustleSchoolShow notes: SideHust...

#545 - College Grad Shares “More than Mac & Cheese” Recipes for Students 29.06.2018

When a college student learns to cook, she documents her recipes online, earning more than $1,000/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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguille...

#544 - Oh Snap! Photography Site Turns Into Passive Income Hustle 28.06.2018

A traffic engineer begins shooting wedding photography to make some cash on the side, but it’s his niche tutorial website that earns the real money… at least until it doesn’t.  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.  Share:...

EXTENDED CUT: The $400,000 "Being Boss" Podcast 27.06.2018

Go behind-the-scenes of the mega-popular Being Boss podcast and brand. Lessons include: set partnerships carefully, take a stand for something, and “choose your choices.”  What are YOU working on? Write me at podcast@sidehustleschool.com or @chrisguilllebeau  Share: #SideHustleSchoolShow notes: SideHustleSchool.com/extendedTwitter: @chrisguillebeauInstagram: @193countries To learn more about liste...

#543 - Marriage Inspires Theatre Captioning App & Service 27.06.2018

After marrying a woman who was born deaf, an actor and musician starts a side hustle captioning theater performances.  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter:...

#542 - Graphic Designer Chalks Up Gripping Side Hustle 26.06.2018

Joining Crossfit community changed this stay-at-home dad’s life, so he wanted to give back… and preferably get paid along the way. He finds the solution in sourcing gym chalk from an overseas supplier.  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 wha...

#541 - Personal Trainer Pumps Up Breakfast with $25,000/Month Pancake Hustle 25.06.2018

A full-time personal trainer takes her ‘breakfast of champions’ to the next level with pancakes that put the ‘pro’ in protein.  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.co...

#540 - Weekly Recap: World Domination Arrives in Portland, Oregon 24.06.2018

In our twenty-fifth recap of Season II, we'll highlight the lessons learned in this week. Also: listener Q&A!  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @ch...

#539 - Moonlighting Makeup Artist Earns Extra $25,000/Year 23.06.2018

A young marketing director by day and professional makeup artist by weekend creates a side hustle that could make anyone blush.  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.c...

#538 - Children’s Book Author Turns Page to New Income 22.06.2018

A successful children’s book author pivots from making book trailers to coaching other authors. Along the way she learns to grow her business and spend more time with family.  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.  Share:...

#537 - Brooklyn App Developer Spins All-Natural Cotton Candy 21.06.2018

A mobile app developer gets nostalgic and creates an all-natural cotton candy catering biz.  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.  Share: #SideHustleSchoolShow notes: SideHustleSchool.comTwitter: @chrisguillebeauInstagram...

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