Side Hustle School

By Chris Guillebeau

Side Hustle School episodes

June 17, 2025Q&A: “Can renting your car on Turo actually make money?”
What It’s About
If you’re not driving your car all the time, should you put it up on Turo?

Notes from Chris
Episode 3090
These days, you don’t need to own a whole fleet of rental cars to make money in the car-sharing space. Platforms like Turo allow regular people to rent out their personal vehicles, turning an everyday expense into a potential income stream. But how easy is it really? Can you actually make a decent profit, or do the costs—wear and tear, insurance, unexpected repairs—outweigh the earnings?
That’s exactly what Jordan from Atlanta wants to know. Jordan is considering listing his car on Turo but is unsure if it’s worth the effort, especially since he only has one vehicle. He’s wondering how much money he can realistically make, what the hidden risks are, and whether this is a smart side hustle or more trouble than it’s worth.
Let’s dive into the numbers, the risks, and the best strategies to make car-sharing work as a profitable side hustle. Whether you’ve thought about renting your car or just want to know how this business model plays out in real life, this episode will help you decide if it’s a worthwhile opportunity—or just another gig that sounds good on paper but falls apart in practice.
“I’ve been looking into the idea of renting out my car as a side hustle, using platforms like Turo. It seems like a great way to make passive income, but I have some concerns. How profitable is it really with just one vehicle? What kind of risks should I be aware of, and how do I make sure I’m actually making money instead of just covering wear and tear? I’d love to hear your take on whether this is a smart side hustle or if I should look for something else.”
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
7 min
June 16, 2025First $1,000: Custom Trekking Gear from a Home Printer
What It’s About
Pole grips and other hiking gear, made directly from a home 3D printer.

Notes from Chris
Episode 3089
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
8 min
June 15, 2025Weekend 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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
9 min
June 14, 2025Q&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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
8 min
June 13, 2025Q&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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
8 min
June 12, 2025TBT: 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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
7 min
June 11, 2025Kiwi 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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
7 min
June 10, 2025Q&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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
7 min
June 09, 2025First $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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
8 min
June 08, 2025Weekend 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:
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,
<img class="alignnone wp-image-1825" src="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png" alt="cg-sig-newsletter" width="176" height="82" srcset="https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter-300x140.png 300w, https://sidehustleschool.com/wp-content/uploads/2017/04/CG-Sig-Newsletter.png 450w" sizes="(max-width: 176px) 100vw, 176px">

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
<img class="aligncenter wp-image-1272 size-full" src="https://sidehustleschool.com/wp-content/uploads/2017/03/ChrisGuillebeauSideHustleSchoolFull-1.jpg" width="1076" height="251">
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
Facebook,Instagram,Twitter

Email
[email protected]

Say Hi
From your favorite airport

To infinity and beyond,
Chris Guillebeau
8 min

About Side Hustle School

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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…

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