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PODCAST

Side Hustle School

Chris Guillebeau / Onward Project

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. Sales and Distribution by Lemonada Media

business entrepreneurship

All Episodes

4:34

Ep. 3399 - Q&A: “Is my business idea a pyramid scheme?”

Side Hustle School ·

2026/04/22

It’s not often that someone calls in and says, “Am I running a pyramid scheme?” … but that’s basically what we’ve got here today. 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@sidehustleschool.com Be on the show:

en

6:07

Ep. 3398 - Q&A: “How to go from prototype into...

Side Hustle School ·

2026/04/21

This listener wants to sell non-screen entertainment kits for kids. How can she go from concept to on-the-shelf product? 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram:

en

8:08

Ep. 3397 - First $1,000: Lutheran Pastor Sells &...

Side Hustle School ·

2026/04/20

In this week’s First $1,000 segment, we hear from the creator of Consecrate, a subscription box for pastors and ministers. She sends more than 500 boxes out each 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&A several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

7:38

Ep. 3396 - STORY: Loan Officer Charts New Course With...

Side Hustle School ·

2026/04/19

A mortgage loan officer combines her nautical roots with a love of design to create geographically personalized jewelry. 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram:

en

4:50

Ep. 3395 - Q&A: “My crazy idea to launch a new...

Side Hustle School ·

2026/04/18

This caller wants to start a print publication—nothing digital! What’s the business model of this potential business magazine? 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on

en

5:47

Ep. 3394 - Failure Friday: “I had to issue refunds...

Side Hustle School ·

2026/04/17

In this week’s Failure Friday segment, we hear from a successful Shopify store owner who sells party favors. Everything was going great, until disaster struck in the form of a misplaced change to her order panel. 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:

en

6:09

Ep. 3393 - TBT: Natural Deodorant Becomes Beauty Line

Side Hustle School ·

2026/04/16

In this week’s “Throwback Thursday” segment, we hear from a CPA who turns natural deodorant made from apple cider vinegar into a beauty and skin-care line. 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@sidehustleschool.com Be on the show:

en

4:14

Ep. 3392 - Q&A: “Should I use Etsy's platform or...

Side Hustle School ·

2026/04/15

A listener with an Etsy shop wants to open her own site as well. What’s the best way to branch 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit

en

5:34

Ep. 3391 - Q&A: “Should I quit my job when the...

Side Hustle School ·

2026/04/14

Lately I’ve been hearing from a lot of people in a time of transition one way or another. Here’s an example: when the economy is in a downturn, is this is a bad time to quit your 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. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be

en

6:07

Ep. 3390 - First $1,000: “I cold-pitched 10 brands...

Side Hustle School ·

2026/04/13

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 several days each week. Show notes: SideHustleSchool.com Email: team@sidehustleschool.com Be on the show:

en

7:44

Ep. 3389 - STORY: Three Friends Step Up, Pull In...

Side Hustle School ·

2026/04/12

After three co-workers notice their colleagues using paper towels to open restroom doors, they invent a simple solution that’s a step above the rest. 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@sidehustleschool.com Be on the show:

en

4:53

Ep. 3388 - Q&A: “Someone left me a bad review! What...

Side Hustle School ·

2026/04/11

Oh no! Today’s listener received a bad review on Etsy through no fault of their own. Is there anything they can do to appeal? 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram:

en

8:12

Ep. 3387 - STORY: Two Women Create Swimwear Brand for...

Side Hustle School ·

2026/04/10

After getting fed up with poorly-fitting swimwear, two friends realize that women with larger bust sizes are just an afterthought when swim brands design suits—so they set out to create an alternative. 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:

en

6:47

Ep. 3386 - TBT: Texas Marimba Rentals Hit Noteworthy...

Side Hustle School ·

2026/04/09

In this week’s “Throwback Thursday” segment, we hear from Texas’s leading provider of marimba rentals. 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram:

en

4:35

Ep. 3385 - Q&A: “What if a company hires you and...

Side Hustle School ·

2026/04/08

After a friend had a negative experience working for a company that didn’t pay up, our caller wants to make sure this doesn’t happen to him. What can he do to be proactive about invoicing and collecting payment? 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:

en

5:48

Ep. 3384 - Q&A: “I’m running the numbers on a...

Side Hustle School ·

2026/04/07

Today’s listener is trying to forecast profits for her subscription service, and wants to know what seems like a reasonable expectation. 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on

en

5:15

Ep. 3383 - First $1,000: Anime Artist Offers...

Side Hustle School ·

2026/04/06

In this week's First $1,000 segment, a talented artist capitalizes on their love for anime by offering personalized art commissions. Learn how they navigated pricing strategies, portfolio creation, and keeping up with 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 each week. Show notes: SideHustleSchool.com Email:

en

7:29

Ep. 3382 - STORY: Cigar Subscription Box Delivers...

Side Hustle School ·

2026/04/05

A software engineer creates a premium subscription box service for savvy cigar smokers. 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@sidehustleschool.com Be on the show: SideHustleSchool.com/questions Connect on Instagram: @193countries Visit Chris's main site:

en

3:33

Ep. 3381 - Q&A: “Driving an RV across the country—can...

Side Hustle School ·

2026/04/04

Everyone, let’s pack all of our stuff up in an RV and hit the road. We just need a tripod for all those #vanlife photos we’re going to be taking! (Also, our caller wants to know how she can get sponsored for her own RV adventure.) 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:

en

5:46

Ep. 3380 - Failure Friday: “Perfect SAT Score” Tutor...

Side Hustle School ·

2026/04/03

In this week’s Failure Friday segment, we hear from the founder of a standardized test prep service. Before he started his business, he earned a perfect score on the SAT—and then pitched a book that was rejected by more than 100 literary agents and publishers. 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

en

1,477 results

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