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Artwork for Side Hustle School

Side Hustle School

Chris Guillebeau
Side Hustle
Side Hustle School
Entrepreneurship
Etsy
Side Hustles
E-Commerce
Affiliate Marketing
Youtube
Pricing Strategies
Amazon
Social Media Marketing
Small Business
Reselling
Facebook Marketplace
Social Media
Kettlebell Kings
Personal Finance
Passive Income
Craigslist
Resilience

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

PublishesDailyEpisodes3526Founded10 years ago
Number of ListenersCategory
Business

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Artwork for Side Hustle School

Latest Episodes

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

Key Facts

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Recent Guests

Rupert Hunt
Founder of spareroom.co.uk (flat-sharing platform)
spareroom.co.uk
Episode: Ep. 3466 - STORY: Music Graduate Makes Spare Change Filling Spare Rooms
Sean Ogle
Founder of Location Rebel; expert in building small, location-independent businesses
Location Rebel
Episode: Ep. 3464 - Failure Friday: “We accept your proposal… to resign”
Dan Kurzrock
Co-founder and chief grain officer of ReGrain
ReGrain
Episode: Ep. 3463 - TBT: Beer Made from “Upcycled” Grain TBT: Blogger Explores Affiliate Marketing in India
Andrew Molina
Hawaiian ukulele musician featured in the story
Self-employed
Episode: Ep. 3459 - STORY: Hawaiian Native Teaches Virtual Ukulele Lessons
Alexandra Kennan
Founder of Urban Hiker San Francisco
Urban Hiker San Francisco
Episode: Ep. 3456 - TBT: Urban Hiker Leads Tours in San Francisco
Evan Oxhorn
Musician who licenses songs for TV shows
stockmusicmusician.com
Episode: Ep. 3453 - First $1,000: “My music was played on a Romanian TV show…”
Shayna Hartman
PhD turned embodied writing coach; owner of Synergy Wellness
Synergy Wellness
Episode: Ep. 3450 - Failure Friday: “I decided to give money to Meta…”
Kyle Bergman
Creator of The Great Fantastic; founder of Swoveralls
The Great Fantastic / Swoveralls
Episode: Ep. 3449 - TBT: These “Sweatpant Overalls” Produce Joy and Extra Pockets
Tanya Smith
Boudoir photographer and educator who built a studio-based business
Self-employed photographer; founder of profitableportraits.com
Episode: Ep. 3445 - STORY: Divorce Leads Banker To Boudoir Photography Empire

Host

Chris Guillebeau
Host and creator of the show; writes and presents practical, story-driven side-hustle content.

Reviews

4.7 out of 5 stars from 4.4k ratings
  • 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.

    Podcast Addict
    1
    nathan
    4 months ago
  • Good content, annoying ads

    Great quick tips. But like 50% of the entire thing is ads. Super disappointing money grab :(

    Apple Podcasts
    2
    SquareLover
    United Statesa year ago
  • Good stuff!

    Thank you, it’s the little things we don’t think of!

    Apple Podcasts
    5
    54321AK
    United Statesa year ago
  • Too many ads

    It could be way better if they didn’t have that many ads on very short episodes.

    Apple Podcasts
    4
    Vdfhbddgvxrg
    Australiaa year ago
  • I love the format of this podcast. Short, bite-size episodes full of great information.

    Audible
    5
    Mimi Gray
    United Statesa year ago

Listeners Say

Key themes from listener reviews, highlighting what works and what could be improved about the show.

A not-insignificant portion notes heavy advertising; content quality varies with ad load.
Many find daily episodes motivating and easy to consume, with consistent inspiration and practical steps.
Listeners appreciate concise, actionable tips and real-world stories.

Chart Rankings

How this podcast ranks in the Apple Podcasts, Spotify and YouTube charts.

Apple Podcasts
#239
United States/Business
Apple Podcasts
#178
New Zealand/Business

Talking Points

Recent interactions between the hosts and their guests.

Ep. 3413 - Q&A: “How can I sell my own crossword puzzles?”
Q: How can you make and sell your own crossword puzzles?
Jessica outlines her passion for crosswords and her plan to design her own puzzles, while the host guides her toward selling them by targeting niche communities, learning their language, and exploring platforms beyond the major newspapers to build an audience.
Ep. 3465 - Q&A: “Help! I’m stuck trying to find my ‘ah-ha’ idea”
Q: Hi Chris, this is Monica from Los Angeles, California. Thanks for this show and sharing so much valuable information on starting a side hustle, especially in such an unsettling economy as the one we're currently facing. My question is about starting that side hustle. I really know I want a side hustle, but I can't find the side hustle to start. I think about it, I keep my eyes open for opportunities, I've inventoried my skills, but nothing has crossed my path that gives me that aha moment. The concept of do what you love and the money will follow is not a guarantee, but certainly you have to at least value or be interested in the thing about which you're hustling, right? So my question is, what do you do when you really want a profitable side hustle, but you just can't come up with that aha idea? Thanks, and I hope you and your team stay safe.
The host suggests that you don't need the perfect, lifetime-defining idea to start a profitable side hustle. Start with something that has value, that you can actually do, and then use the experience to pivot toward the next opportunity. A successful initial project can come from testing, learning, and staying motivated by the possibility of discovering something better as you go.
Ep. 3462 - Q&A: “I stopped delivering for my Patreon…”
Q: What would you suggest for a Patreon creator who has stopped delivering, but can't afford to lose the funds?
Start with transparent communication: acknowledge the situation, allow cancellations, and provide a concrete plan with timelines for upcoming content. Offer updated content promises and show that you're actively working toward delivering, which can preserve loyalty and reduce churn.
Ep. 3447 - Q&A: “How can I sell flash cards to pharmacy students?”
Q: How do I find and market to a very specific and small audience?
The host suggests first validating the product with feedback from the exact target users, then focusing on organic discovery by ranking for terms like 'pharmacy study aid' or 'drug memorization guide' and exploring targeted channels beyond platforms like Etsy to reach pharmacy students and technicians.
Ep. 3451 - Q&A: “’Spaced repetition' practice with outsourced tutors from overseas?”
Q: Didn't you have a story about that once? My question is, how would I validate the need for this idea, and how could I put together a working model?
There is value in examining prior, similar ventures and in gauging real user interest before building. Start by studying a comparable platform, assess what worked and where they faced missteps, then validate demand through concrete signals (interest, willingness to pay, trial signups) and outline a lean model that can be tested with minimal risk.

Audience Metrics

Listeners, social reach, demographics and more for this podcast.

Listeners per Episode
Gender Skew
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Frequently Asked Questions About Side Hustle School

What is Side Hustle School about and what kind of topics does it cover?

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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How many listeners does Side Hustle School get?

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Which podcasts are similar to Side Hustle School?

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

How many episodes of Side Hustle School are there?

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.

How do I contact Side Hustle School?

Our systems regularly scour the web to find email addresses and social media links for this podcast. We scanned the web and collated all of the contact information that we could find in our podcast database. But in the unlikely event that you can't find what you're looking for, our concierge service lets you request our research team to source better contacts for you.

Where can I see ratings and reviews for Side Hustle School?

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What guests have appeared on Side Hustle School?

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.

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