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
Web del podcast
Último episodio
18 de oct. de 2026
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Episodios
Ep. 3553 - Q&A: “Would you join an introvert's networking club?” 23.09.2026 4:53
With introverts getting a lot of attention these days, might it be worth it to create some type of networking club for them—or is this exactly the thing they don’t want? 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 eac...
Ep. 3552 - Q&A: “Can you really fly for free as an airline courier?” 22.09.2026 4:32
Today’s caller has seen ads about becoming an independent airline courier. It sounds fun—but is this a viable business opportunity, a scam, or perhaps something else? 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 w...
Ep. 3551 - First $1,000: “My roommate threw a wad of hundred-dollar bills on the table…” 21.09.2026 9:43
In this week’s First $1,000 segment, we hear from Silver Picker, a college student turned coin reseller who makes $10,000 one summer from coins and metals he finds at estate sales. 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...
Ep. 3550 - STORY: It’s No Joke: Prank Musical Greeting Card Earns $36,000/Month 20.09.2026 7:13
What starts as a silly idea to make a musical greeting card with no off-switch turns into a multiple six-figure, nonstop success for two brothers. 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 note...
Ep. 3549 - Q&A: “Should I hire a graphic designer?” 19.09.2026 4:47
This listener runs an online health coaching company. Her course content needs detailed illustrations, and she’s not an artist. What should she do? 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: &n...
Ep. 3548 - Failure Friday: Supplier Problem Harms Client Relationship 18.09.2026 5:26
In this week’s Failure Friday segment, we hear from an attorney who sells cork sunglasses (not at the seashore…). When a client placed a large order, a long delay in China caused the relationship to break 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 less...
Ep. 3547 - TBT: Bumblebee Linens Builds a New Hive 17.09.2026 6:52
In this week’s “Throwback Thursday” segment, we hear about the rise, fall, and rise of Bumblebee Linens. Choose wisely: your honey or your life! 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. 3546 - Q&A: “Where are my customers coming from?” 16.09.2026 4:46
This listener sells a video tutorial series for students taking the MCAT—but she’s not sure where her customers are coming from. How can she aquire this valuable information? 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 day...
Ep. 3545 - Q&A: “How can I publish my Army enlistment guide?” 15.09.2026 6:09
An Army veteran wants to help new military enlistees get a leg up in training. What’s the best format for his material? 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.c...
Ep. 3544 - First $1,000: “I have 3 clients and $4,000/month in retainer fees…” 14.09.2026 5:11
In this week’s First $1,000 segment, we hear from a Social Media Manager from Toronto. She has a day job she enjoys but—naturally—also has a side hustle that’s bringing in $4,000 a month. 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...
Ep. 3543 - STORY: Professor Starts Marvel-ous YouTube Channel 13.09.2026 6:56
A university professor manages depression by sharing his gift for gaming and community building on YouTube. 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 Ema...
Ep. 3542 - Q&A: “Can you still get paid to post pins on Pinterest?” 12.09.2026 5:05
An early Side Hustle School episode featured a woman who earned $40,000 pinning images on Pinterest. Is this business model still feasible? 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...
Ep. 3541 - STORY: American Woman Starts International Whisky Brand 11.09.2026 7:14
A graphic designer falls in love with scotch—building an international whisky brand with money she’d originally saved for couples counseling. 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: &n...
Ep. 3540 - TBT: Blogger Explores Affiliate Marketing in India 10.09.2026 7:01
In this week’s “Throwback Thursday” segment, we hear from a blogger in India who helps readers with financial products, earning commissions along the way. 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. 3539 - Q&A: “How about a directory of garage and yard sales?” 09.09.2026 5:01
Today’s caller has an idea to create a directory of garage and yard sales. She thinks it’s a winner because so many people are trying to buy and resell items. What’s the best way to 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...
Ep. 3538 - Q&A: “I have 20 years of experience—how do I pick a niche?” 08.09.2026 5:44
Today’s caller draws on a lot of experience in production, branding, and more. She now wants to strike out on her own, but feels overwhelmed by all the options. Can we help her find the right focus? 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 an...
Ep. 3537 - First $1,000: “I wanted to be the guy with a laptop on the beach…” 07.09.2026 6:41
In this week’s First $1,000 segment, we hear from the founder of Maid This, a cleaning company that grows to millions of dollars in sales and allows the founder to work remotely. 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...
Ep. 3536 - STORY: BBQ Catering Hustle Smokes Out Competitors 06.09.2026 7:10
They loved smoked BBQ—and one day, they realized doing it for a living was the dream. So they jumped in full-force to the idea, heading straight for disaster. 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 wee...
Ep. 3535 - Q&A: “I’m getting too many inquiries…” 05.09.2026 4:26
Today’s caller has a different sort of problem than most people who struggle to get off the ground: her business is going so well that she’s feeling overwhelmed with the work. 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 seve...
Ep. 3534 - Failure Friday: “My anniversary sale was an epic fail…” 04.09.2026 4:30
In this week’s Failure Friday segment, we hear from the founder of a membership site that’s going very well—until the founder stops giving it the attention it deserves. 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...
Ep. 3533 - TBT: “Chewable Energy” Gum Sticks With Customers 03.09.2026 5:38
In this week’s “Throwback Thursday” segment, we hear from an athlete who sets out to create chewable energy gum. It’s gum-believable! 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...
Ep. 3532 - Q&A: “I want to be a broker for overseas web developers…” 02.09.2026 5:38
A caller has an idea to connect overseas web developers with clients in the U.S. How would this work, and how can they profit from 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. Show notes: SideHustl...
Ep. 3531 - Q&A: “Can I pursue public speaking as a side hustle?” 01.09.2026 5:52
This listener wants to get paid for public speaking, and he’s got a good story to share—but does he need a more specific topic? 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...
Ep. 3530 - First $1,000: “I help people get back their hacked accounts…” 01.09.2026 5:25
In this week’s First $1,000 segment, we hear from a coder with an unusual side hustle: he helps clients recover their hacked or lost Facebook accounts. In his first month, he’s already served fifteen 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...
Ep. 3529 - STORY: Anchors Aweigh! Designer Leads Guided Sailing Tours 30.08.2026 7:49
A graphic designer packs his bags to see the world, then stumbles into a new line of work leading guided sailing tours. 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.c...
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