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Artwork for Side Hustle School

Side Hustle School

Chris Guillebeau
Side Hustle School
Side Hustle
Entrepreneurship
Etsy
Side Hustles
E-Commerce
Youtube
Affiliate Marketing
Amazon
Pricing Strategies
Small Business
Social Media
Kettlebell Kings
Personal Finance
Social Media Marketing
Passive Income
Kickstarter
Sales Slump
Patreon
Marketing Strategies

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

PublishesDailyEpisodes3546Founded10 years ago
Number of ListenersCategory
Business

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Artwork for Side Hustle School

Latest Episodes

Today’s listener wants to make money helping people set up and get the best use out of their new smartwatch. What’s the best course of action?

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn ex... more

In this week’s First $1,000 segment, we hear from Lindsay Gordon, who left a career at Google to become a “career coach for analytically-minded people.” 

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people ... more

When an engineer receives a ridiculously baggy work shirt, he grabs it by the collar and designs a DIY tailoring device. Four years later, he’s sold $150,000 of them. 

Side Hustle School features a new episode EVERY DAY, featuring detailed case stud... more

Today’s listener has an idea to sell a toolkit to help sole proprietors become more efficient. What are the pros and cons of this idea? 

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra mo... more

Key Facts

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Recent Guests

Lindsay Gordon
Career coach for Analytically Minded People
A Life of Options
Episode: Ep. 3488 - First $1,000: “I had literally zero intention of running a business…”
CD Wang
Chemical engineer and inventor of Zip Seam
Zip Seam (inventor)
Episode: Ep. 3487 - STORY: Chemical Engineer Zips Up Solution for Baggy Shirts
Yair Aitzma
Listener who pitched a side-hustle idea to create a toolkit for sole proprietors
Portland, Oregon
Episode: Ep. 3486 - Q&A: “I’d like to sell a toolkit to sole proprietors…”
Jennifer Tomei
Multilingual insurance agent and creator of Turnkey Translator
Turnkey Translator
Episode: Ep. 3484 - TBT: Multilingual Insurance Agent Creates Translation Course
Nick Vitilaro
Co-founder of Hero's Journal
Hero's Journal
Episode: Ep. 3477 - TBT: “Hero’s Journal” Completes Epic Quest
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

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
    5 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
    Australia2 years ago
  • I love the format of this podcast. Short, bite-size episodes full of great information.

    Audible
    5
    Mimi Gray
    United States2 years 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
#90
Ireland/Business

Talking Points

Recent interactions between the hosts and their guests.

Ep. 3489 - Q&A: “I’d like to sell an Apple Watch guide…”
Q: Hi Chris, how much should I sell an Apple Watch guide for?
Keep it affordable at around $10-$15 for the basic guide, perhaps $25 for a premium version, so it remains accessible while still offering value; use AI and YouTube-informed search behavior to find relevant topics that buyers are actually looking for.
Ep. 3486 - Q&A: “I’d like to sell a toolkit to sole proprietors…”
Q: Do you think it is a good idea to pursue this toolkit for sole proprietors, given the uncertainties about reach?
The host suggests that the idea could be valuable if it is feasible and profitable and if there is a clearly defined target market with a plan to reach them; validation and specificity are essential before moving forward.
Ep. 3484 - TBT: Multilingual Insurance Agent Creates Translation Course
Q: What is your number one piece of advice for someone starting a similar side hustle?
Start now regardless of experience; focus on solving a real problem, build sample work to prove capability, and then scale by taking on real clients.
Ep. 3483 - Q&A: Are there any *good* MLM companies?
Q: Hi Chris, can you recommend a few of the better MLMs?
Chris explains there aren't really any good MLMs and that the model itself is flawed, suggesting that exceptions to the rule are unlikely and that people should pursue other approaches.
Ep. 3476 - Q&A: “How to find markets for livestreaming events?”
Q: My question to you today is, do you have any ideas or insight as to the potential niches in these two categories? Niches that I could possibly take advantage of right away and get this hustle up and running.
The host walks through several niche directions (startup product launches, behind‑the‑scenes startup interviews, product demos at events, educational presentations) and emphasizes the need to articulate clear audience needs, a strong marketing position, and a compelling why‑watch angle to differentiate from DIY streaming, plus a turnkey 'done‑for‑you' offering to reduce the client's workload.

Audience Metrics

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

Listeners per Episode
Gender Skew
Location
Interests
Professions
Age Range
Household Income
Social Media Reach

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. The Koerner Office - Business Ideas and Deep Dives with Chris Koerner
5. The Marie Forleo Podcast

How many episodes of Side Hustle School are there?

Side Hustle School launched 10 years ago and published 3546 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. Lindsay Gordon
2. CD Wang
3. Yair Aitzma
4. Jennifer Tomei
5. Nick Vitilaro
6. Rupert Hunt
7. Sean Ogle
8. Dan Kurzrock

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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