
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 S... more
| Publishes | Daily | Episodes | 3526 | Founded | 10 years ago |
|---|---|---|---|---|---|
| Number of Listeners | Category | Business | |||

Today’s caller is starting a *second* side hustle and wants to know where to find the best virtual assistants and other contractors.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money... more
Today’s listener is inspired to learn more about the “core emotional needs” of a potential customer, but isn’t sure how to do it or what to do with the info. Are these needs always the same, or do they vary?
Side Hustle School features a new episod... more
In this week’s First $1,000 segment, we hear from the self-described “Wordpress Girl,” who starts a service helping female entrepreneurs get set up with a website.
Side Hustle School features a new episode EVERY DAY, featuring detailed case studies ... more
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: Sid... more
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I understand you need to monetize the podcast, and I respect that.
But lately the balance feels way off — it honestly sounds like 70% ads and only 30% real content. The constant and lengthy ad segments are overwhelming and make it hard to stay engaged.
I’m saying this as someone who genuinely enjoys the show. But if this doesn’t change and the ad load stays this heavy, I’ll probably stop listening.
Great quick tips. But like 50% of the entire thing is ads. Super disappointing money grab :(
Thank you, it’s the little things we don’t think of!
It could be way better if they didn’t have that many ads on very short episodes.
I love the format of this podcast. Short, bite-size episodes full of great information.
Key themes from listener reviews, highlighting what works and what could be improved about the show.
How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.
Apple Podcasts | #239 | |
Apple Podcasts | #178 |
Recent interactions between the hosts and their guests.
Listeners, social reach, demographics and more for this podcast.
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A daily show focused on ordinary people starting side projects alongside regular jobs. Episodes spotlight real-world journeys—from turning hobbies into products, to bootstrapping services, to leveraging marketplaces and online platforms. Listeners hear practical, actionable steps, failures to learn from, and tangible outcomes, often framed as concise, story-driven lessons that stay useful for immediate application. A notable strength is the breadth of industries featured, with frequent emphasis on validating ideas, pricing, customer relationships, and scalable paths from first sale to ongoing revenue. The format tends to be short, high-signal, and highly actionable, making it a good fit for aspiring entrepreneurs seeking quick inspiration p... more
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These podcasts share a similar audience with Side Hustle School:
1. The Side Hustle Show
2. The Smart Passive Income Online Business and Blogging Podcast
3. Side Hustle Pro
4. Money Girl
5. The Koerner Office - Business Ideas and Deep Dives with Chris Koerner
Side Hustle School launched 10 years ago and published 3526 episodes to date. You can find more information about this podcast including rankings, audience demographics and engagement in our podcast database.
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Recent guests on Side Hustle School include:
1. Rupert Hunt
2. Sean Ogle
3. Dan Kurzrock
4. Andrew Molina
5. Alexandra Kennan
6. Evan Oxhorn
7. Shayna Hartman
8. Kyle Bergman
To view more recent guests and their details, simply upgrade your Rephonic account. You'll also get access to a typical guest profile to help you decide if the show is worth pitching.