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.

Husk at besøge podcastens hjemmeside og støtte skaberen: sidehustleschool.com

Forfatter

Chris Guillebeau

Kategori

Business

Podcastens hjemmeside

sidehustleschool.com

Seneste episode

6. nov. 2026

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Episoder

#2026 - This Canadian Cleaning Service Earns $2 Million/Year 19.07.2022

A university lab technician cleans up with a local service business that grows to $2 million in revenue and 500 5-star reviews—all without quitting his job.     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. S...

#2025 - First $1,000: The Las Vegas Ghostwriting Service 18.07.2022

In this week’s First $1,000 segment, we hear from a Las Vegas ghostwriter. After writing a novel of his own, he branches out to write for casino bosses and other 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 e...

#2024 - Q&A: "I'm opening a hair salon in a new area. How can I build my clientele?” 17.07.2022

A hair stylist is leaving her job to start her own salon. Whoo hoo! What are some simple things she (or any service provider) can do to kickstart the client 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...

#2023 - Q&A: “How can I land paid speaking gigs?” 16.07.2022

Our caller recently gave a talk at a women’s leadership event, and it went well. Now she wants to level-up and give more speeches—preferably paid ones. How can she break into this market?  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&amp...

#2022 - Failure Friday: “We opened the box and it was a totally different product…” 15.07.2022

In this week’s Failure Friday segment, we hear from the founder of Kettlebell Kings, an ecommerce shop. When a big early order from a supplier went terribly wrong, he had to regroup and learn resilience.    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...

#2021 - TBT: “Styles for Kidz” Goes Global with Video Classes 14.07.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the founder of Styles for Kidz, a Chicago organization that helps parents and kids with hair care.  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...

#2020 - Q&A: “Does it really cost $100,000 to make an app??” 13.07.2022

How much does it cost to make an app? One of our listeners was quoted $100,000 from a local design studio, and they’re looking for a second opinion. 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: S...

#2019 - Adobe Expert Digitizes Millions of Family Photos 12.07.2022

A longtime Adobe employee creates the picture-perfect business by helping families store and digitize memories across generations.   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....

#2018 - First $1,000: “I quickly raised my price to $50 an hour…” 11.07.2022

In this week’s First $1,000 segment, we hear from a Returned Peace Corps Volunteer (RPCV) who starts a tutoring business on the side. After starting out at $20 an hour, he learns to specialize and raise his rates. 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 l...

#2017 - Q&A: “What is 'growth hacking’?” 10.07.2022

Is “growth hacking” just a fancy marketing term or is something anyone can apply? Hack into this episode to find 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&A several days each week. Show notes: SideHustleSchool.com Email: team...

#2016 - Q&A: “How do you profit from DeFi in a bear market?” 09.07.2022

Is decentralized finance the future … or the past? After a huge two years, many DeFi projects have fallen 90% or more. How can you profit during “crypto winter”? 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....

#2015 -Failure Friday: “Amazon permanently banned my seller account…” 08.07.2022

In this week’s Failure Friday segment, we hear from the co-founder of TheSavvyCouple.com. In his early days, he sold on eBay and Amazon.com. It was all going well, until a supplier problem led to him getting banned—permanently!  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 include...

#2014 - TBT: Cayenne Pepper Throat Lozenges Spice Up Flu Season 07.07.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the creator of an all-natural organic throat lozenge made with cayenne pepper. This cold remedy is on fire! 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&...

#2013 - Q&A: “I’m making an alarm clock that costs money if you oversleep…” 06.07.2022

That’s right, this alarm clock debits your bank account if you don’t get up in time. It’s sure to be a hit! The only problem: our caller isn’t sure how to make it. 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...

#2012 - Office Assistant Profits from Anime Imports 05.07.2022

After noticing a derth of anime items in the United States, this long-time lover of Japanese culture creates a thriving 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. Show notes: SideHustleSchoo...

#2011 - First $1,000: “I cold-pitched 10 brands and got my first 2 clients…” 04.07.2022

In this week’s First $1,000 segment, we hear from a freelance apparel designer who specializes in menswear. After having her first child, she set out to learn to work on her own.  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...

#2010 - Q&A: “How can a travel website earn commissions?” 03.07.2022

Today’s listener wants to earn commissions on travel bookings by creating a website that funnels visitors to big agencies like Expedia. Is this a viable 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...

#2009 - Q&A: “Should I pay $3,000 for my friend's mastermind??” 02.07.2022

A listener has a friend who’s part of a pricey “mastermind” group—and now our listener is experiencing FOMO. Are these groups worth the high price tag? 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...

#2008 - Failure Friday: “The experience of hearing rejection was important…” 01.07.2022

In this week’s Failure Friday segment, we hear from the founder of KindRoot, “hard candy gone good,” plant-powered lozenges for mind and body wellness. In her early days, she experienced rejection from multiple manufacturers and had to learn to trust herself.   Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their...

#2007 - TBT: Brooklyn Clothing Boutique Scales Up 30.06.2022

In this week’s “Throwback Thursday / Where are they now?” segment, we hear from the owner of two businesses in New York City: a clothing line *and* a fashion boutique that features 25+ BIPOC-owned brands.  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...

#2006 - Q&A: “How many ‘wine-of-the-month’ clubs are there??” 29.06.2022

Today’s caller has seen many “of-the-month” clubs, ranging from wine, plants, and even all the way to pickles. With so many of them out there, does that mean the market is saturated? 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 sev...

#2005 - Bam! Pow! Crash! The Comic Book Reselling Hustle 28.06.2022

Drawing on a childhood affection for comic books, this mechanical engineer smashes his student loan debt with an online collectibles 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: Side...

#2004 - First $1,000: “My music was played on a Romanian TV show…” 27.06.2022

In this week’s First $1,000 segment, we hear from a musician who licenses songs for placement in TV shows worldwide. When he gets a check in the mail for a TV show he’s never heard of, he starts taking it more seriously.  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...

#2003 - Q&A: “Jumping into Twitch streaming…” 26.06.2022

A caller is getting into Twitch, the popular live streaming platform. How can she bring over her large Instagram audience?  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...

#2002 - Q&A: "I tried donation-only yoga, but no one donated..." 25.06.2022

Today we hear from a yoga teacher who offers a class at a nearby community center. It went well, except for one problem: her donation-only model didn’t produce much in the way of donations.  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...

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