Archives: Podcast

Weekend Workshop: Look for Money Lying Under a Rock

What It’s About

Today’s episode comes from Day 25, which is all about … if you see money, pick it up!

Notes from Chris

Episode 3088

It’s Weekend Workshop, and it’s new!

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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: “Should I create a free course before launching a paid one?”

What It’s About

Is it best to go straight to a paid model?

Notes from Chris

Episode 3087
Giving something away for free can be a great way to build trust and attract customers—but when does it actually help, and when is it just a waste of time? That’s the question Jake from Minneapolis is wrestling with. He’s developing a productivity course for freelancers and is wondering whether launching a free mini-course will help grow his audience—or if he’s just delaying revenue.

Let’s break down when a free course works as a sales tool, when it backfires, and what to consider before offering one.

“Hey Chris, this is Jake from Minneapolis. I’m in the process of creating an online course about productivity for freelancers, and I’ve been debating whether to launch a free mini-course first to attract an audience. I see a lot of people doing this, but I’m not sure if it actually leads to more sales or just attracts people who never intend to buy anything. Would offering a free course help me build trust and generate more customers, or am I just giving away value without getting anything in return?”

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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: “Should I monetize my free Facebook group?”

What It’s About

This Facebook group has been a public service—should the owner charge for access?

Notes from Chris

Episode 3086
Running an online community is exciting, but at some point, it can start to feel like a full-time job—without the paycheck. That’s the challenge Danielle from Raleigh is facing. She started a Facebook group about sustainable fashion that’s grown to 15,000 members, and now she’s wondering if there’s a way to monetize it without hurting the sense of community.

Let’s talk about when—and how—to introduce revenue streams in a way that adds value rather than turning people away.

“Hey Chris, this is Danielle from Raleigh. A few years ago, I started a Facebook group for people interested in sustainable fashion. It started as a fun side project, but it’s grown to over 15,000 members, and managing it takes a lot of my time. I love the community, but I’m starting to wonder if I should be making money from it—especially since other businesses are benefiting by promoting their products in the group. I don’t want to ruin the vibe or drive people away, but is there a way to monetize the group that feels natural and fair?”

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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

TBT: Print-on-Demand Store Crushes It Without Ads

What It’s About

This POD designer scales up, but without giving money to Meta.

Notes from Chris

Episode 3085

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 former lifestyle blogger who ditched her old site and scaled up her Pinterest affiliate marketing into a reliable full-time income.

Today, in our latest feature, we’ll hear from a side hustler who builds a thriving print-on-demand business by tapping into ultra-specific niches—like “retired paramedic” mugs—without ever spending on ads.

Listen to today’s episode to hear more…

 

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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

Kiwi Coder Makes Extra $50,000/Year from Digital Paintbrushes

What It’s About

Digital paintbrushes—a very popular thing!

Notes from Chris

Episode 3084

In today’s story…

…What happens when a software engineer discovers digital calligraphy? For Karin Newport, the answer was a creative explosion that evolved into a thriving side hustle.

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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: “Is a high-ticket offer the right move for my business?”

What It’s About

Should every business introduce a premium offer?

Notes from Chris

Episode 3083
Raising your prices can be scary, but what about launching a high-ticket offer—something significantly more expensive than your current services? That’s what Amanda from Denver is considering. She runs a branding and web design business and wants to introduce a premium offer, but she’s worried that it might scare off her existing audience.

Let’s talk about whether high-ticket offers make sense, how to position them, and what to consider before making the leap.

“I run a branding and web design business that primarily serves small businesses and solo entrepreneurs. My services are mid-priced—typically in the $2,000 to $5,000 range—but I’ve been considering introducing a high-ticket offer, like a premium VIP experience or an all-inclusive branding package for $15,000 or more. My concern is that it might scare off my existing audience, who are used to my current pricing. Is it worth testing a high-ticket offer, and if so, how do I position it in a way that doesn’t alienate my current customers?”

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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

First $1,000: Partners Turn Neglected Washers into Solid Profit

What It’s About

A refurbished laundromat returns to life!

Notes from Chris

Episode 3082

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:

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

Yours in the revolution,

cg-sig-newsletter

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.

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

Weekend Workshop: Grow What Works, Let Go of What Doesn’t

What It’s About

Today’s episode comes from Day 24, which is all about … grow what works, let go of what doesn’t!

Notes from Chris

Episode 3081

It’s Weekend Workshop, and it’s new!

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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: “Should you fight unfair refund requests or just move on?”

What It’s About

What’s the best strategy when faced when an annoying refund request?

Notes from Chris

Episode 3080
Refunds are part of running a business, but what happens when a customer wants their money back for a reason you don’t agree with? That’s what Michael from San Diego is dealing with. He runs an online store and gets the occasional refund request that doesn’t follow his policy—like a customer trying to return a well-used item.

He doesn’t want to encourage bad behavior, but he also doesn’t want to damage his brand’s reputation. So, how do you handle tricky refund requests the right way? Let’s break down the best strategies for standing your ground while keeping things professional—and when it’s best to just give the refund and move on.

“Hey Chris, this is Michael from Anaheim. I run an online store selling premium home office accessories, and I’ve been getting more refund requests lately. Most of them are fine, but every now and then, I get one that doesn’t follow my refund policy—like someone wanting a full refund on a product they clearly used for months. I don’t want to damage my reputation by refusing refunds, but I also don’t want to encourage people to take advantage of me. What’s the best way to handle refund requests when I don’t agree with them?”

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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: “How do I get featured in holiday gift guides?”

What It’s About

Holiday gift guides can bring in a ton of customers—how can you get listed?

Notes from Chris

Episode 3079
It might only be May, but if you’re hoping to get your product into holiday gift guides, now is the time to start. Many big media outlets work months in advance, which means waiting until November is way too late.

Today’s question comes from Rachel in Philadelphia, who wants to know how to get her home goods business featured in gift guides or holiday shopping lists. Should she pitch magazines? Bloggers? Websites like BuzzFeed? Let’s go over the best ways to increase your chances of getting featured—and when you need to start preparing.

“I run a small business selling unique handcrafted home goods, and I’ve heard that getting featured in holiday gift guides can be a great way to boost sales. But I have no idea how to actually get my products included in one of those lists. Do I pitch magazines, bloggers, or big websites like BuzzFeed? And when should I start? I don’t want to miss out on the holiday rush, but I also don’t want to waste time if my chances are slim. What’s the best way to get my products featured in gift guides?”

Listen to today’s episode to learn more…

 

 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

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