Q&A: “Managing cash flow across PayPal, Stripe, Venmo, and Etsy…”

What It’s About

Too many payment apps? Here’s how to turn cash-flow chaos into a clear system.

Notes from Chris

Episode 3171

Collecting money from customers used to be simple: you’d accept cash or a single PayPal payment and call it a day. Now we’ve got Stripe for subscriptions, Gumroad payouts, Etsy deposits hitting on Wednesdays, Venmo tips on Fridays, and maybe a rogue Zelle payment from an old client. Reconciling these streams can devour an entire Sunday—and if you don’t keep up, tax season becomes an archaeological dig.

Today’s caller’s dilemma captures a pain point that many modern creators face: revenue is up, but visibility is down. Money lands in half a dozen silos, each with its own fee structure and payout schedule. Today we’ll stitch those silos together into one clear, auditable cash-flow pipeline.

“My side hustle brings in money from half a dozen places—PayPal for digital downloads, Stripe for course payments, Venmo for one-off consulting, and Etsy deposits for physical products. It’s turning into a bookkeeping nightmare. What’s the smartest way to keep track of cash flow when the money lands in so many different platforms? I need a streamlined system before tax season turns into a disaster.”

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: “Do followers still matter in the age of algorithms?”

What It’s About

If the algorithm rules everything, do followers still give you an edge?

Notes from Chris

Episode 3170

The old playbook for social media was clear: build followers, reach those followers, sell to those followers. Then came the For You Page, Reels, and endless algorithm tweaks.

Today, even huge accounts complain that only a fraction of their audience sees any given post. So are follower counts now vanity metrics? Or do they still give you leverage in this new world?

“Lately I’ve started to wonder if followers even matter anymore. Every time I post on Instagram or TikTok, it feels like the algorithm decides whether anyone sees it—regardless of how many subscribers I have. If that’s the case, why should I bother growing a follower base at all? Has social media shifted so much that every post is basically thrown into a giant lottery for attention? I’m trying to build a real audience for my side hustle, but I’m not sure if chasing subscribers is still worth the effort.”

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: Selling Ads for Medical Conferences on Commission

What It’s About

She sold ads for medical conferences—earning thousands without ever planning an event.

Notes from Chris

Episode 3169

Welcome to Throwback Thursday, where we take an in-depth look at someone who’s story has evolved considerably since we first featured them.

Last week, we heard how one side hustler launched an app that didn’t take off, but ended up turning that hard-won experience into a consulting service for other early-stage founders.

Today, in our latest feature, we’ll hear how a freelance marketer started selling ad placements and sponsorships for medical conferences—on commission only—and turned it into a surprisingly consistent side hustle.

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

IT Guy Earns Extra $50,000/Year Restoring Vintage Radios

What It’s About

This IT pro tunes up vintage radios—earning $50K a year on the side.

Notes from Chris

Episode 3168

In today’s story…

… you’ll learn about an IT professional who wants to start a side business and put his engineering degree to good use. When he stumbled across two 1950s radios, he finds an idea that is right on his wavelength. He goes on to create a business buying, repairing, and reselling them, working only 5-10 hours a week and earning an extra $50,000/year.

Listen to today’s episode to learn more…

 


 

SEE ALSO:

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

Yours in the revolution,

cg-sig-newsletter

Resources

GET $625 IN FREE TRAVEL

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

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

CREATE YOUR ONLINE STORE

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

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

Sponsors & Gratitude

Learn More With Skillshare!

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

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

Like the Show? Leave a Rating!

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

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


Here's How

Keep in Touch

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


To infinity and beyond,

Chris Guillebeau

Q&A: “How to handle customer service without burning out?”

What It’s About

Can you keep customers happy without answering emails at midnight?

Notes from Chris

Episode 3167
Growth is a double-edged chef’s knife: more orders, more revenue—and a flood of “Where’s my package?” pings at 11 p.m. Lucas’s e-commerce shop is a dream come true, except it’s devouring his weekends. The problem isn’t just volume; it’s the expectation of instant replies in the Amazon era.

The good news: you can deliver great service without being on call 24/7. Today we’ll build a lightweight customer-service stack that scales with one person and zero burnout.

“So my one-person e-commerce shop is doing well—but my inbox is out of control. I’m spending nights and weekends answering customer emails, handling returns, and chasing shipping issues. I don’t have the budget for a full-time support rep yet, but I also can’t keep sacrificing all my free time. How can a solopreneur manage customer service efficiently, set boundaries, and maybe automate some of it without hurting the business? I’d love to know any thoughts or tips you can share.”

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: Language Nerd Builds “Fake Language” Creation Kit

What It’s About

This linguistics grad sells kits to help writers and gamers invent their own languages.

Notes from Chris

Episode 3166

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: How Makeup Videos Built a Million-Dollar Brand

What It’s About

She turned bedroom makeup videos into a multimillion-dollar beauty empire—no glam squad required.

Notes from Chris

Episode 3165

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: “Is there a market for fancy cookware rentals?”

What It’s About

Could renting out your fancy cookware be a recipe for profit—or just a kitchen nightmare?

Notes from Chris

Episode 3164
Sometimes, the best business ideas come from looking at what you already have.

Today’s listener, Jenna from Minneapolis, has an enviable collection of high-end kitchen gear—designer knives, premium cookware, and top-tier gadgets. But instead of letting them gather dust, she’s wondering: could she rent these out to home chefs, food stylists, or influencers who want a taste of luxury without the price tag?

Let’s break down whether luxury cookware rentals are a promising niche—or a logistical headache waiting to happen.

“I’m a total kitchen gear nerd—I own some fancy cookware, designer knives, and high-end gadgets that I absolutely love, but honestly, they sit unused a lot of the time. Recently I wondered: is there a market for renting this kind of stuff out? Could home chefs, food stylists, influencers, or even small events need short-term access to fancy tools they don’t want to buy themselves? I’d love to know if this is a feasible side hustle—or if the logistics and risks make it too complicated.”

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: “Can MacBook arbitrage work as a side hustle?”

What It’s About

Could flipping MacBooks across borders be the ultimate tech side hustle?

Notes from Chris

Episode 3163
Arbitrage is a classic entrepreneurial play: buy low, sell high.

But what if you tried it internationally, using price differences between countries? Mateo from Sydney has been eyeing Apple products, noticing that MacBooks, iPhones, and iPads sometimes cost significantly more depending on the market. Could you really build a profitable side hustle buying new tech devices where they’re cheaper and reselling them where they’re expensive?

Let’s unpack the fantasy—and the friction.

“I’ve been reading about price differences in Apple products between countries, and it got me wondering: could you actually build a business doing MacBook arbitrage? Like, buying new Apple laptops or devices in one country where they’re cheaper and reselling them in another where they’re marked up? On paper it sounds clever, but I’m guessing there are legal, logistical, or tax hurdles that make it harder than it looks. What do you think—could international arbitrage work for premium electronics, or is it just a fantasy?”

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: Failed App Becomes Successful Consulting Business

What It’s About

After his app failed, this founder turned the lessons learned into a thriving consulting business.

Notes from Chris

Episode 3162

Welcome to Throwback Thursday, where we take an in-depth look at someone who’s story has evolved considerably since we first featured them.

Last week, we heard how a side hustler who once flipped storage unit finds gradually specialized in rare historical items, and now supplies props and artifacts to small museums and exhibits.

Today, in our latest feature, we’ll hear how one side hustler launched an app that didn’t take off, but ended up turning that hard-won experience into a consulting service for other early-stage founders.

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