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Side Hustle School

Ep. 3184 - Q&A: “How can a coast-to-coast road trip pay for itself?”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Entrepreneurship, Careers

4.83.3K Ratings

🗓️ 19 September 2025

⏱️ 7 minutes

🧾️ Download transcript

Summary

A coast-to-coast road trip sounds expensive—unless you turn the highway into a revenue stream. Today we map out five travel-friendly hustles that can cover gas, motels, and maybe even a little profit.

Side Hustle School features a new episode EVERY DAY, featuring detailed case studies of people who earn extra money without quitting their job. This year, the show includes free guided lessons and listener Q&A several days each week.

Show notes: SideHustleSchool.com

Email: [email protected]

Be on the show: SideHustleSchool.com/questions

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Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

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Transcript

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0:00.0

business owners are built differently and there's nothing more satisfying than your business keeping up with you.

0:05.8

But of course, sometimes your growth outpaces what you can handle, especially when it comes to shipping.

0:11.1

That's why I'm so grateful to our longtime partner, ShipStation, been helping us out for many years,

0:15.3

been helping out many of our listeners as well. With ShipStation, you can make all your packages

0:19.9

count and save up to 90% off rates on all

0:22.7

major carriers. Basically, if you ship out product, you're going to save money with ShipStation.

0:27.4

I've heard it over and over from our listeners, and that's why I'm happy to partner with them.

0:32.3

Upgrade to shipping software that does more than keep up with your business. Shipstation propels it

0:36.2

forward. Start your 60 day free trial at Shipstation.com code hustle. Once again, shipstation.com code hustle.

0:46.6

Lemonada.

0:51.3

Have you ever been on a coast-to-coast cross-country road trip?

0:59.5

Have you ever gone out west or I guess gone out east?

1:03.3

Coast-to-coast road trip is fun.

1:05.5

It's adventurous.

1:06.4

It can also be expensive.

1:08.5

Unless, of course, you turn the highway into a revenue stream. That's what we're

1:12.7

going to talk about today, an idea from a caller. We're going to map out five travel-friendly side hustles

1:17.8

that can cover your gas, your hotels, your food, maybe even a little profit along the way.

1:23.3

This route from a listener is going to go from Rhode Island to Los Angeles, 3,000 miles.

1:28.2

And she wants to know, how can I get some road-specific income?

1:31.3

How can I capitalize on the fact that I'm passing through dozens of cities and small towns?

1:35.8

Well, as I said, let me give you a couple of ideas.

...

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