Podcast Archive | Side Hustle School

Weekend Workshop: Sell Like a Girl Scout

What It’s About

Today’s episode comes from Day 18, which is all about the art of natural selling!

Notes from Chris

Episode 3039

It’s Weekend Workshop, and it’s new!

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Skillshare is giving Side Hustle School listeners 2 months of unlimited access—for $0.99! Join the 2 million students learning everything from street photography to SEO on Skillshare today!
Get Started Here!

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Q&A: “When is it worth spending money on your side hustle?”

What It’s About

Side hustles keep getting cheaper…

Notes from Chris

Episode 3038

Starting a side hustle often means getting creative with limited resources—using what you have, borrowing what you don’t, and learning to do more with less. But as your hustle grows, the question of when to invest in tools or services becomes critical.

Today’s question comes from Clara in Toronto, who launched her business with just $50 and a borrowed camera. She wants to know how to balance staying scrappy with making smart investments to scale. Let’s dive into how to decide where to spend and where to save.

“Hi Chris, this is Clara calling from Toronto. My side hustle kicked off with just $50, a borrowed camera, and a lot of DIY spirit. Over time, I’ve seen some success, and now I’m torn about when—and where—to start spending real money. I love the creativity that comes from working with almost nothing, but I also know I might be missing out on growth if I don’t invest in the right tools or services. How do I figure out what’s absolutely worth paying for, and what I should keep hacking together on my own so I don’t lose the scrappy approach that got me here?”

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Q&A: “How do I turn being an industry outsider into an advantage?”

What It’s About

Turn your weakness into a strength, right?

Notes from Chris

Episode 3037

Breaking into an industry where you don’t have formal training can feel intimidating, but sometimes, that fresh perspective is exactly what sets you apart.

Today’s question comes from Beatrice in Berlin, who launched a collection of statement scarves with zero professional background in textiles. While her unconventional approach has been a selling point, she’s worried about how to reassure customers that her products are high-quality and worth their trust. Let’s talk about how to balance creative freedom with building credibility as an outsider.

“Hi Chris, Beatrice here. I decided to launch a collection of statement scarves—despite having zero professional background in textiles. Surprisingly, my lack of training has become an unexpected selling point: it’s given me a fresh, unconventional style that stands out. But I also worry about potential customers who might question my credibility: why buy from someone who hasn’t studied fashion or worked in the industry? How can I keep leveraging the creative freedom that comes from being an outsider, while reassuring buyers that I’m serious, committed, and can deliver a top-notch product—despite not being a so-called ‘expert’?”

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

TBT: Missoula Videographer Redefines Remote Filming

What It’s About

Remote filming allows this traveling videographer to stay home.

Notes from Chris

Episode 3036

Welcome to Throwback Thursday / “Where are they now?” where we take an in-depth look at someone who’s story has evolved considerably since we first featured them.

Last week, we heard from a side hustler who builds a spring break site that soars to $8,000 during peak months by combining ad networks with carefully edited AI content.

Today, in our latest feature, we’ll hear from a pro videographer who ditches travel hassles by mailing filming kits worldwide and directing online course shoots entirely from afar.

Listen to today’s episode to hear more…

SEE ALSO:

Raver Turns LED-Powered Gloves Into Bright Future: When a raver-turned-salesperson falls in love with an underground art form, he turns it into a successful side business.
Bright Idea Leads Chicago Woman to Million-Dollar Hustle: A Chicago-based plastic recycling sales rep overcomes her fears and doubts to transform her love for DIY lamp shades and $10 in supplies into a multi-million dollar business.
3D Printing Brings Cosplay Into 21st Century: With a 3D printer and sense of imagination, a California natural gas industry worker takes superhero DIY cosplay to a whole new level.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

GET YOUR FIRST 1,000 EMAIL SUBSCRIBERS

Social media is nice, but building an email list is still the single best way to get customers and clients for your hustle. It's not hard to get started—sign up for a 30-day trial and join the list-building challenge! You’ll be up and running in no time. Learn More

Sponsors & Gratitude

Don't Do Business Without It

Side Hustle School is brought to you by American Express.

No matter what you do in business, from working nine-to-five to working five-to-nine, it’s easier when you don’t go it alone. Get the powerful backing of American Express—don't do business without it! Visit American Express

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Frozen Yogurt Dog Treats Are No Barking Matter

What It’s About

Dogs love this canine-friendly ice cream.

Notes from Chris

Episode 3035

In today’s story…

… frozen yogurt dog treats are on the menu today … the side hustle menu.

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Q&A: “How can I incorporate activism into my brand without seeming performative?”

What It’s About

An interesting question! How can you show you care (as a brand) without virtue signaling?

Notes from Chris

Episode 3034

Incorporating values like sustainability or activism into a business can be powerful, but it also comes with the challenge of staying authentic.

Today’s question comes from Ellie, who wants to align her skincare brand with her commitment to environmental activism while avoiding the pitfalls of performative marketing. Let’s explore how to weave purpose into a business model in a way that feels genuine and impactful.

“Hi Chris, I’m Ellie. I’ve been thinking about starting a business that focuses on skincare products. Sustainability and environmental activism are really important to me, and I want those values to be part of my brand. But I’ve seen other businesses get criticized for being performative, and I don’t want to fall into that trap. How can I incorporate activism into my side hustle in a way that feels authentic, meaningful, and genuinely makes an impact, without it seeming like a marketing gimmick?”

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

3033First $1,000: Feeding the Neighborhood, One Block at a Time

What It’s About

A Brooklynite feeds her neighborhood with local produce boxes.

Notes from Chris

Episode 3033

Today’s episode is part of a feature we call ‘Your First $1,000.’ As you might surmise from the title, this is all about how someone made their first $1,000.

How did they get to that point? Not their first $100,000—that’s cool, but it would probably be a long story.

But what about their first $1,000—how did they make that happen, what did it feel like, and what did they learn?

Let’s hear today’s story. I’ll be back at the end to wrap us up.

SEE ALSO:

Military Spouse Starts Subscription Box Mission:When an HR Director’s husband is away on military deployment, she uses the alone time to march toward a subscription box.
Think Inside the Subscription Box:Looking for more community, a North Carolina web agency owner starts a subscription box for female entrepreneurs. It’s supposed to be a referral tool for her agency, but it ends up becoming a full-time business of its own.
Nature-Loving Neighbors Create Kids Subscription Box: When two couples can’t figure out how to get their kids outdoors and away from electronics in the winter, a personal challenge blossoms into an unbeLEAFable side hustle.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

WEB HOSTING @ $2.49/MONTH

Want to build any kind of website for your hustle? If so, you'll need somewhere to host it! This is the reliable company I've used for many websites. It's cheap, flexible, and offers support 24-7.

Get your own hosting plan for just $2.49 a month!
Learn More

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

Sponsors & Gratitude

Don't Do Business Without It

Side Hustle School is brought to you by American Express.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.
Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Weekend Workshop: Launch Before You’re Ready

What It’s About

Today’s episode comes from Day 17, which is all about which is all about publishing your offer.

Notes from Chris

Episode 3032

It’s Weekend Workshop, and it’s new!

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Q&A: “How do I create and sell a premium online course?”

What It’s About

If you want to sell a course with a high ticket price, what do you need to know?

Notes from Chris

Episode 3031

Online courses have become one of the most popular ways for professionals to share their expertise, but standing out in a crowded market takes careful planning.

Today’s question comes from Kevin, a leadership coach who wants to create a premium online course that feels worth the investment. Let’s explore what makes a course successful, how to structure it for maximum value, and strategies to position it as a must-have resource.

“Hey Chris, this is Kevin. I’ve been working as a professional in leadership coaching for several years, and I want to take my expertise to a broader audience by creating a premium online course. I’m not sure how to structure it, though, or what makes an online course stand out when so many are already out there. How do I create something that feels worth the high price point, and what’s the best way to position it as a valuable resource in a crowded market?”

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

Q&A: “How do I prepare for tech failures without overloading my setup?”

What It’s About

A near Failure Friday story! But fortunately this side hustler manages to recover.

Notes from Chris

Episode 3030

Even the best-laid plans can be thrown off by an unexpected glitch, especially when running a side hustle. Today’s question comes from Neil in Brisbane, who experienced a payment system failure at a recent event and wants to know how to better prepare for these hiccups without overloading his setup. Let’s explore simple, effective ways to safeguard your operations and keep your reputation intact during minor crises.

“Hey hey, Chris! Nice to meet you. My name is Katie and I am a freelance copywriter in Chicago, Illinois. I often juggle multiple projects at once, and occasionally, deadlines overlap unexpectedly when clients request revisions at the last minute. This makes it hard to manage my time and deliver quality work consistently. For example, last week, I had two clients simultaneously requesting same-day edits on projects I thought were finished. I’m unsure how to build more buffer time into my schedule or set better expectations with clients to avoid these crunch periods. What strategies can I use to prevent this from happening in the future?”

Listen to today’s episode to learn more…

SEE ALSO:

Catholic Designer Creates Stylish Apparel Line: What shall it profit a man to gain the whole world but not sell any t-shirts? This designer cast his bread upon the waters and ended up with a profitable fashion line.
Seattle Couple Creates New “Income LiveStream”: When a married couple runs into logistical problems at their wedding, it leads to an innovative service that other engaged couples need during the pandemic.
Role-Playing Pastor Rolls The Dice On $2800/Month Hustle: Listener success story! This Presbyterian minister turns to his lifelong interest in role-playing games to set up a sustainable second income source.

Inspiration is good; inspiration combined with action is better. Now get back to work!

Yours in the revolution,

cg-sig-newsletter

Download Episodes By Months:

Season 9 (2025): JAN | FEB | MAR |

Season 8 (2024): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 7 (2023): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 6 (2022): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 5 (2021): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 4 (2020): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 3 (2019): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 2 (2018): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Season 1 (2017): JAN | FEB | MAR | APR | MAY | JUN | JUL | AUG | SEP | OCT | NOV | DEC |

Resources

GET $625 IN FREE TRAVEL

Earn 50,000 travel rewards points (enough for 2 round-trip plane tickets or $625 in travel credit). You'll also earn 2x points on all travel and dining spend, with zero foreign transaction fees.

I use this card every day all over the world! Learn More

CREATE YOUR ONLINE STORE

Create your online store with Shopify using an exclusive discount for Side Hustle School listeners. For a limited time, get a free 21-day trial and a 10% discount for a whole year.

Many Side Hustle School listeners are building sites using Shopify's easy-to-learn platform. Try it free today! Learn More

Sponsors & Gratitude

Learn More With Skillshare!

Supporting the sponsors keeps the show free. Today’s episode of Side Hustle School is brought to you by Skillshare.

Like the Show? Leave a Rating!

Side Hustle School is for you! If you’re enjoying it, please take a quick moment to leave a rating or write a quick review. It's really easy and it makes a difference!

It also makes a huge difference when you tell your friends about the show. Remember, it's 100% free and listener-supported.

Here's How

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

To infinity and beyond,

Chris Guillebeau

What It’s About

Today’s episode comes from Day 18, which is all about the art of natural selling!

Notes from Chris

Episode 3039

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

Email

Say Hi

What It’s About

Side hustles keep getting cheaper…

Notes from Chris

Episode 3038

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

Email

Say Hi

What It’s About

Turn your weakness into a strength, right?

Notes from Chris

Episode 3037

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

Email

Say Hi

What It’s About

Remote filming allows this traveling videographer to stay home.

Notes from Chris

Episode 3036

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

Email

Say Hi

What It’s About

Dogs love this canine-friendly ice cream.

Notes from Chris

Episode 3035

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

Email

Say Hi

What It’s About

An interesting question! How can you show you care (as a brand) without virtue signaling?

Notes from Chris

Episode 3034

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

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Say Hi

What It’s About

A Brooklynite feeds her neighborhood with local produce boxes.

Notes from Chris

Episode 3033

Resources

Sponsors & Gratitude

Keep in Touch

There’s a new story every single day on Side Hustle School. Episodes are produced to be short and to the point—I know you’re busy. Be sure you subscribe to get instant notification of the day’s broadcast!

Follow

Email

Say Hi

What It’s About

Today’s episode comes from Day 17, which is all about which is all about publishing your offer.

Notes from Chris