Side Hustle School

By Chris Guillebeau

Side Hustle School episodes

May 07, 2025Internet Trolls Eat Their Words In This Comedic Cake Hustle
What It’s About
Troll Cakes!

Notes from Chris
Episode 3049
In today’s story…
…When a woman reads a mean comment on Dolly Parton’s Facebook page, she then realizes the absurdity of internet trolling and bakes up a hilarious and ironic 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
8 min
May 06, 2025Q&A: “Best practices for Meta ads?”
What It’s About
Before you spend money on ads, listen to this.

Notes from Chris
Episode 3048
Running ads on Meta platforms like Facebook and Instagram can be a powerful way to grow your business—when done right. But without a clear strategy, it’s easy to feel like you’re throwing money into the void.
Today’s question comes from James in Round Rock, Texas, who’s had mixed results with Meta ads and wants to know how to make his campaigns more consistent and profitable. Let’s dive into some best practices for 2025 to help James and others get the most from their ad budgets.
“Hi, I’m James from Round Rock, Texas. I’ve been operating a small online shop selling fitness gear, and I’m trying to figure out how to use Meta ads (Facebook and Instagram) effectively. I’ve experimented a little, but the results have been all over the place. Sometimes I get great sales, and other times it feels like I’m just burning through money. What are the best practices for running Meta ads these days, and how can I make sure my campaigns are profitable without wasting my budget?”
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
May 05, 2025First $1,000: Pop-Up Cosplay Salon Takes Con-Goers by Surprise
What It’s About
A creative approach to trade show representation.

Notes from Chris
Episode 3047
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
7 min
May 03, 2025Weekend Workshop: Ask 10 People for Help
What It’s About
Today’s episode comes from Day 19, which is all about building your support network.

Notes from Chris
Episode 3046
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
May 02, 2025Q&A: “Should I switch my business to a subscription model?”
What It’s About
If you’ve been selling one-off products, should you change to sell them as part of a subscription?

Notes from Chris
Episode 3045
Subscriptions have become a popular business model for everything from digital products to physical goods, offering consistent income and the potential for long-term customer loyalty. But is it the right move for every business?
Today’s question comes from Megan in Denver, who’s considering transitioning her digital template shop to a subscription model. Let’s explore how to evaluate this change, minimize risks, and ensure the shift adds value for both Megan and her customers.
“Hi Chris, this is Megan! I’ve been running a small business selling digital templates for entrepreneurs, and it’s been going pretty well. Lately, I’ve been thinking about switching to a subscription model where customers pay monthly for access to my entire library instead of buying individual items. While the idea of consistent income is really appealing, I’m worried about alienating existing customers who prefer one-off purchases—or worse, losing money if subscriptions don’t take off. How do I know if a subscription model is right for my business, and how can I transition without risking what I’ve already built?”
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
6 min
May 02, 2025Q&A: “Why do authors offer pre-order bonuses?”
What It’s About
If you have a book coming out, should you offer readers an incentive to pre-order?

Notes from Chris
Episode 3044
Pre-order bonuses have become a go-to strategy for book launches, especially in nonfiction, with authors offering everything from downloadable resources to exclusive webinars. But do they really work?
Today’s question comes from Dylan in Nashville, who’s planning to release a book next year and wants to know if pre-order bonuses are worth the effort. Let’s break down why authors use them, whether they move the needle on sales, and how to decide if this strategy fits your launch.
“Hi Chris, this is Dylan from Nashville. I’ve noticed that a lot of authors, especially in nonfiction, offer pre-order bonuses for their books, like exclusive downloads or live webinars. Why is this such a popular strategy? Does it actually move the needle in terms of sales, or is it just a way to get people excited? I’m planning to release my own book next year and wonder if this is something I should try—or if it’s more work than it’s worth.”
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
May 01, 2025TBT: From Cracked Screens to Tech Buyback Business
What It’s About
It starts with fixing phones, but now he earns $20,000/month.

Notes from Chris
Episode 3043
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 pro videographer who ditches travel hassles by mailing filming kits worldwide and directing online course shoots entirely from afar.
Today, in our latest feature, we’ll hear from a college student who scaled from fixing cracked screens to creating a buyback platform that turns over $20,000 in inventory each month.
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
April 30, 2025Fashion Buyer Creates Quirky Comfort Craze
What It’s About
Swoveralls!

Notes from Chris
Episode 3042
In today’s story…
… Kyle Bergman has always had a unique and edgy taste in fashion. Then, thanks to one viral Buzzfeed article, he was able to create a brand that appeals to other people like him.
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! ✅
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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!

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From your favorite airport

To infinity and beyond,
Chris Guillebeau
8 min
April 29, 2025Q&A: “Should I expand the services I offer?”
What It’s About
Is it time to grow, or stay focused on what’s working?

Notes from Chris
Episode 3041
As your side hustle or business grows, clients often ask for more—more services, more expertise, more of your time. It’s exciting, but it can also lead to overwhelm.
Today’s question comes from Gabriel in Madrid, who’s juggling multiple client requests and trying to decide which new services to offer without spreading himself too thin. Let’s explore how to evaluate these opportunities and create a focused, scalable business model.
“I started off doing video editing for small businesses, and things took off so quickly that my clients began asking me for extra services—like managing their social media, writing promotional copy, and even coaching them on presentation skills. Each new request feels like a golden opportunity, but I’m overwhelmed by how many directions this could go. If I say yes to everything, I might spread myself too thin. But if I say no, I could miss out on bigger revenue streams. How should I figure out which add-ons to offer and which ones to skip?”
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
April 28, 2025First $1,000: Flipping Phones and Tablets for Fun and Profit
What It’s About
This guy built a phone-flip business, not a flip-phone business.

Notes from Chris
Episode 3040
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
7 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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