Archives: Podcast

TBT: How ‘Pinspiration’ Became a Full-Time Hustle

What It’s About

Once again we meet the world’s most underrated social network: Pinterest.

Notes from Chris

Episode 3078

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 maker who turned a small Etsy shop selling custom pet memorials into a thriving business. Since their last appearance, they’ve expanded their product line and found new ways to help grieving pet owners honor their companions.

Today, in our latest feature, find out how one former lifestyle blogger ditched her old site and scaled up her Pinterest affiliate marketing into a reliable full-time income. Learn how seasonal boards, diversified merchants, and a dash of creative strategy helped her surpass her old ad-based blogging revenue.

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

Four Friends Create Conversations, Earn $400,000 in 8 Months

What It’s About

A conversational parlor game designed to get people talking.

Notes from Chris

Episode 3077

In today’s story…

…A group of Dutch friends creates a popular card game.

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 add a live chat feature to my website?”

What It’s About

Does every website need live chat?

Notes from Chris

Episode 3076
Have you ever visited a website and been greeted by a little chat box asking if you need help? Live chat has become a common feature for online businesses, but is it actually worth it? That’s what today’s question is about. A business owner is considering adding live chat but isn’t sure if it will boost sales and engagement—or just add unnecessary work. Let’s break down when live chat is a great addition, when it’s a distraction, and what to consider before implementing it.

“I run an online store selling specialty coffee equipment, and I’ve been thinking about adding a live chat feature to my website. I’ve read that it can help increase sales and improve customer experience, but I’m also worried it might create extra work for me. I don’t have a big team, and I can’t be available to answer questions 24/7. I’ve seen AI-powered chatbots advertised as a solution, but I don’t know if they actually work or if they’ll just annoy customers. Is live chat worth it for a small business like mine?”

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: Marketing Pro Builds GPT Bots—No Code Needed

What It’s About

In the future, will our only conversations be with bots?

Notes from Chris

Episode 3075

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: Measure What Matters

What It’s About

Today’s episode comes from Day 23, which is all about … choosing the right metrics!

Notes from Chris

Episode 3074

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: “What’s the purpose of more than one business bank account?”

What It’s About

Is one business bank account enough?

Notes from Chris

Episode 3073
Most business owners start with a single bank account, but as your business grows, that setup can get messy. Between taxes, reinvesting in the business, and actually paying yourself, money tends to blur together.

That’s what today’s question is about—do you really need more than one business bank account? Or is that just overcomplicating things? Let’s talk about how having multiple accounts can actually help you run a more profitable and stress-free business.

“Hi, this is Jordan calling. I’ve been running my side hustle for a little over a year, and I’m starting to take my finances more seriously. Up until now, I’ve just had one business bank account where all my income goes in and expenses come out, but I recently heard some business owners talk about using multiple accounts to manage their money. I don’t totally understand the purpose of doing this—wouldn’t it just make things more complicated? What’s the benefit of having more than one account?”

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: “Why do struggling businesses keep their doors open?”

What It’s About

What’s up with that struggling store that never closes?

Notes from Chris

Episode 3072
Ever walked past a shop that never seems busy and wondered how it’s still in business? You’re not alone. Today’s question comes from Adam in Minneapolis, who’s curious about how some retail stores—especially those in prime locations—manage to stay open despite low foot traffic or even reported financial losses.

Are they surviving on outside funding, tax advantages, or something else? Let’s break down the surprising reasons why some businesses keep their doors open even when they aren’t making money.

“Hey Chris, this is Adam from Minneapolis. I walk by a lot of small retail stores in my city, and sometimes I wonder—how are they still in business? Some of these places are in prime locations, don’t seem very busy, and I’ve even heard of businesses that operate at a loss for years. How is that possible? Are they getting outside funding, using some kind of tax loophole, or is there another reason why a store can stay open even if it’s not making money?”

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: From DIY Pet Tributes to Six-Figure Etsy Shop

What It’s About

A meaningful product-based business expands into services.

Notes from Chris

Episode 3071

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 3D printing enthusiast who scaled from making small gifts to crafting high-end home décor for designers and boutique stores.

Today, in our latest feature, we’ll hear from a maker who turned a small Etsy shop selling custom pet memorials into a thriving business. Since their last appearance, they’ve expanded their product line and found new ways to help grieving pet owners honor their companions.

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

High School Student Earns $20,000 Making Wooden Bow Ties

What It’s About

These bow ties are fashionable and hefty.

Notes from Chris

Episode 3070

In today’s story…

…High school students and young people, here’s a great story for you.

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: “I’m ready to sell my side hustle—how do I do it?”

What It’s About

This hustle has been great, but it’s time to move to something else.

Notes from Chris

Episode 3069
Turning a side hustle into something valuable is an amazing accomplishment—but what happens when you’re ready to move on?

That’s the position Natalie from Orlando is in. She built a side hustle that grew bigger than expected, and now she’s looking for the best way to sell it.

The challenge? She’s not sure how to find a buyer, determine its worth, or make sure she gets a fair deal. Let’s break down how to successfully sell a side hustle, step by step.

“Hey all, this is Natalie from Orlando. I started my side hustle a few years ago, and it’s grown into something bigger than I ever expected. The thing is, I’m feeling ready to move on. I don’t necessarily want to shut it down—I’d love to sell it to someone who could take it further. But I have no idea how to find a buyer or even figure out what my business is worth. What’s the best way to sell a side hustle, and what should I look out for to make sure I get a fair deal?”

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