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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

PublishesDailyEpisodes3338Founded9 years ago
Number of ListenersCategories
EntrepreneurshipCareersBusiness

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Artwork for Side Hustle School

Latest Episodes

Today’s caller undercuts her own price before the client even speaks. Let’s help her overcome this pattern of self-sabotage!

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without... more

Inflation climbs and workload grows, but rates stay frozen—sound familiar? Today we’ll run a quick value check, set a price-rise timeline, and craft a client email that keeps loyalty high.

Side Hustle School features a new episode EVERY DAY, featur... more

In this week’s Throwback Thursday segment, hear how the North Pole’s most iconic founder finally pivoted from production to licensing—earning passive income while keeping the magic alive.

Side Hustle School features a new episode EVERY DAY, featuri... more

Before the boom of online shopping, this bird lover struggled to find quality products for her feathery friends. She decided to take flight herself, earning up to $250,000/year reselling supplies. Squawk!

Side Hustle School features a new episode E... more

Key Facts

Accepts Guests
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Recent Guests

Santa Claus
The cultural figure known for delivering gifts on Christmas, innovator in the toy business.
Episode: Ep. 3281 - TBT: After 1,700 Years, I Outsourced Christmas
Rachel K. Vargas
A resilient sculptor who has transformed her life's disasters into entrepreneurial success
Episode: Ep. 3277 - Weekend Workshop: The Sculptor Who Thrived on Disaster
Antonio Salvani
A receptionist and part-time photographer from London
Episode: Ep. 3273 - STORY: London Photographer Rents Camera Gear 1,100 Times
Naomi Dunford
A successful entrepreneur and former teenage mother who founded IttyBiz
Episode: Ep. 3270 - Weekend Workshop: From Rock Bottom to Business Empire
Erika Kosminski
A parent and former HR professional who transitioned to starting her own transcription service.
Episode: Ep. 3256 - Weekend Workshop: Building Teams Without Hiring Employees
Nev Lapwood
Entrepreneur and founder of Snowboard Addiction
Snowboard Addiction
Episode: Ep. 3249 - Weekend Workshop: From Ski Bum to Six-Figure Teacher
Sean Markham
A side hustler based in Chicago who works in marketing and copywriting.
Episode: Ep. 3246 - TBT: Recruiters Pay Me to Tear Apart Their Emails
Brett Kelly
Expert in digital documentation and creator of the Evernote Essentials guide
Episode: Ep. 3242 - Weekend Workshop: “Digital Documentation” Earns Passive Income
Unnamed Designer
A user experience designer focusing on workspace organization through a cable management invention.
Episode: Ep. 3236 - First $1,000: Turning Cable Chaos into Magnetic Profit

Host

Chris Guillebeau
Chris Guillebeau is an entrepreneur, author, and speaker known for his focus on promoting the idea of unconventional entrepreneurship. He is the author of multiple bestselling books and hosts this daily podcast aimed at aspiring side hustlers and those seeking to create new income opportunities.

Reviews

4.7 out of 5 stars from 4.4k ratings
  • 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 States6 months ago
  • Good stuff!

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

    Apple Podcasts
    5
    54321AK
    United States6 months 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
  • Great information

    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.

Listeners value the motivation and inspiration drawn from real-life side hustle stories.
Many appreciate the actionable insights and practical advice offered by the host.
Reviewers often highlight the show's ability to instill a sense of community among side hustlers, fostering connection among like-minded individuals.
There are consistent complaints regarding the high volume of advertisements throughout episodes, impacting listener experience.

Chart Rankings

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

Talking Points

Recent interactions between the hosts and their guests.

Ep. 3279 - Q&A: “Do I have to be loud to sell my service?”
Q: Are there marketing approaches, maybe authority building or quiet outreach, that work for someone who hates being loud online?
Yes, there are low-noise, high-trust marketing tactics that can be effective, such as building a referral system and creating evergreen content instead of relying on daily social media presence.
Ep. 3282 - Q&A: “I’m ready to raise prices … but how?”
Q: How do I analyze current value, decide on a new rate, and communicate the change without triggering a mass exodus?
Focus on the value you provide to clients and do market research to set a new rate. Communicate the increase clearly and with adequate notice while emphasizing the ongoing value offered.
Ep. 3275 - Q&A: “How do I talk about pricing when it feels impolite?”
Q: How do you get comfortable asking for fair payment when every instinct says it's impolite?
By externalizing prices, creating a rate sheet, and practicing responses to bring confidence when discussing fees.
Ep. 3272 - Q&A: “How do I avoid a bad review on my first client job?”
Q: How do experienced side hustlers handle the risk of disappointing an early customer?
You need to get some experience, and then you will see that most customers are good.
Ep. 3269 - Q&A: “What do I do if my partner doesn’t believe in my business?”
Q: What do I do if my partner doesn't believe in my business?
Discuss your partner's fears, propose a trial period for your side hustle, and ensure you have dedicated time for your relationship.

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?

Focusing on the journeys of everyday individuals who have successfully launched side hustles, this podcast offers stories that engage and inspire listeners seeking financial independence or creative outlets outside their principal jobs. Each episode highlights a different entrepreneur's experience, delving into their motivations, strategies, and the adversities faced as they cultivated their projects. Themes include innovative business strategies, financial planning, and work-life balance, making it a practical resource for those eager to explore entrepreneurship while managing full-time careers.

Listeners can expect a wealth of actionable insights, particularly regarding the creative use of skills and resources to start small, low-risk ve... 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. All the Hacks: Money, Points & Life
4. Entrepreneurs on Fire
5. The Startup Ideas Podcast

How many episodes of Side Hustle School are there?

Side Hustle School launched 9 years ago and published 3338 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?

Rephonic pulls ratings and reviews for Side Hustle School from multiple sources, including Spotify, Apple Podcasts, Castbox, and Podcast Addict.

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What guests have appeared on Side Hustle School?

Recent guests on Side Hustle School include:

1. Santa Claus
2. Rachel K. Vargas
3. Antonio Salvani
4. Naomi Dunford
5. Erika Kosminski
6. Nev Lapwood
7. Sean Markham
8. Brett Kelly

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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