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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...

Episodes

20 of 3,653 episodes

Ep. 3594 - Q&A: “Is it better to offer more ways of accepting payment?”

This listener is wondering about adding new options for accepting payment, including checking debits and cryptocurrency. Is more always bett...

4:43Nov 3, 2026

Ep. 3593 - First $1,000: “I had to spend $20,000 to make $1,000…”

In this week’s “First $1,000” segment, we hear from the creator of Metaphor Dice, the writing tool that plays like a game and helps you thin...

6:33Nov 2, 2026

Ep. 3592 - STORY: Friends Foster Korean Face Mask Frenzy

When several friends and colleagues discover the consumer craze over Korean face masks, they team up to create their own subscription box si...

7:05Nov 1, 2026

Ep. 3591 - Q&A: “How to market spooky savory pastries?”

Happy Halloween! In the spirit of the holiday, we have a listener in Canada who’s making a spooky treat for sale. What’s the best way she ca...

4:54Oct 31, 2026

Ep. 3590 - Failure Friday: “I dropped out of Stanford and left my business…”

In this week’s Failure Friday segment, we hear from Bryan Quoc Le, a scientist and food blogger. His early days of selling vegan banana ice...

5:45Oct 30, 2026

Ep. 3589 - TBT: “Recovering Attorney” Operates 7-Figure Podcast Service

In this week’s “Throwback Thursday” segment, we hear from a former attorney and White House aide who starts a service helping businesses wit...

8:13Oct 29, 2026

Ep. 3588 - Q&A: “How to become an affiliate manager for large launches?”

Some product launches have an “affiliate manager” who coordinates promotion efforts. How can our listener learn to offer this service on a f...

5:28Oct 28, 2026

Ep. 3587 - Q&A: “How to approach a company about a partnership?"

Today’s listener has an interesting challenge: he wants to reach out to a company he bought a product from and offer to partner with them. H...

5:28Oct 27, 2026

Ep. 3586 - First $1,000: Tarot and TikTok Become Winning Combo

In this week’s First $1,000 segment, we hear from a tarot card reader who was profitable in one month, all thanks to savvy use of TikTok and...

5:44Oct 26, 2026

Ep. 3585 - STORY: Artistic Cartographer Maps Out Successful Side Hustle

A designer with an enthusiasm for both maps and art merges the two to create hand-printed mazes that zig-zag through the hearts of iconic ci...

8:25Oct 25, 2026

Ep. 3584 - Q&A: “Should I create a pre-order campaign for my book launch?”

Today’s listener is self-publishing a book on personal finance—and he’s wondering about the launch process. Should he make the book availabl...

4:55Oct 24, 2026

Ep. 3583 - STORY: Maniac Pumpkin Carving!

Get paid up to $700 each for carving pumpkins?? Only on Side Hustle School: a love of all things Halloween leads two friends to carve out a...

8:09Oct 23, 2026

Ep. 3582 - TBT: Aussie Sketches Old Homes for New Money

In this week’s “Throwback Thursday” segment, we hear from a designer in Australia who sketches and sells illustrations of houses. Her side h...

9:02Oct 22, 2026

Ep. 3581 - Q&A: “Can you deduct side hustle losses from income taxes?”

This listener’s new side hustle lost money this year. Hopefully that will change in the future, but for now—is there a silver lining in bein...

4:11Oct 21, 2026

Ep. 3580 - Q&A: “Is there an easier way to start reselling?”

Reselling is quick and simple—but it’s also a lot of work, and today’s caller is looking for a shortcut. Does such a thing exist? Side Hustl...

4:51Oct 20, 2026

Ep. 3579 - First $1,000: New Podcaster Sets Up Joint Venture Deals

In this week’s First $1,000 segment, we hear from a new podcaster with a business model of setting up joint venture (JV) deals. How does it...

7:05Oct 19, 2026

Ep. 3578 - Un-Tours Of Myanmar Offer Adventure and Unpredictability

His friends kept asking him to lead tours of Myanmar, and he finally agreed. But he wasn’t going to stick to the usual sights—his ‘un-tours’...

7:56Oct 18, 2026

Ep. 3577 - Q&A: “Can I get paid to help iPhone owners switch to Android?”

Today’s listener wants to serve the masses of people who buy Apple products but would shop for Android and PC devices if they knew what to b...

6:49Oct 17, 2026

Ep. 3576 - Failure Friday: “Amazon permanently banned my seller account…”

In this week’s Failure Friday segment, we hear from Kelan from TheSavvyCouple.com. In his early days, he sold on eBay and Amazon. It was all...

7:17Oct 16, 2026

Ep. 3575 - TBT: The 7-Figure Dachshund Apparel Business

In this week’s “Throwback Thursday” segment, we hear from the co-founder of Bean Goods, which sells dachshund-themed apparel for dogs and hu...

7:45Oct 15, 2026