Home Podcasts Side Hustle School
Side Hustle School

Side Hustle School

Chris Guillebeau 3496 Episodes Sep 20, 2026

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 hear a different story of someone who's started a side hustle, including what went well, how they 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 and other books.

Episodes

Ep. 3550 - STORY: It’s No Joke: Prank Musical Greeting Card Earns $36,000/Month
Ep. 3550 - STORY: It’s No Joke: Prank Musical Greeting Card Earns $36,000/Month Sep 20, 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 notes:
Ep. 3549 - Q&A: “Should I hire a graphic designer?”
Ep. 3549 - Q&A: “Should I hire a graphic designer?” Sep 19, 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:&nbsp
Ep. 3548 - Failure Friday: Supplier Problem Harms Client Relationship
Ep. 3548 - Failure Friday: Supplier Problem Harms Client Relationship Sep 18, 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 lesso
Ep. 3547 - TBT: Bumblebee Linens Builds a New Hive
Ep. 3547 - TBT: Bumblebee Linens Builds a New Hive Sep 17, 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: Si
Ep. 3546 - Q&A: “Where are my customers coming from?”
Ep. 3546 - Q&A: “Where are my customers coming from?” Sep 16, 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 days
Ep. 3545 - Q&A: “How can I publish my Army enlistment guide?”
Ep. 3545 - Q&A: “How can I publish my Army enlistment guide?” Sep 15, 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.comE
Ep. 3544 - First $1,000: “I have 3 clients and $4,000/month in retainer fees…”
Ep. 3544 - First $1,000: “I have 3 clients and $4,000/month in retainer fees…” Sep 14, 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 Q
Ep. 3543 - STORY: Professor Starts Marvel-ous YouTube Channel
Ep. 3543 - STORY: Professor Starts Marvel-ous YouTube Channel Sep 13, 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.comEmail:
Ep. 3542 - Q&A: “Can you still get paid to post pins on Pinterest?”
Ep. 3542 - Q&A: “Can you still get paid to post pins on Pinterest?” Sep 12, 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: SideHus
Ep. 3541 - STORY: American Woman Starts International Whisky Brand
Ep. 3541 - STORY: American Woman Starts International Whisky Brand Sep 11, 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:&nbsp
Ep. 3540 - TBT: Blogger Explores Affiliate Marketing in India
Ep. 3540 - TBT: Blogger Explores Affiliate Marketing in India Sep 10, 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 note
Ep. 3539 - Q&A: “How about a directory of garage and yard sales?”
Ep. 3539 - Q&A: “How about a directory of garage and yard sales?” Sep 9, 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&am

Recommended