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Side Hustle School

Ep. 3221 - Weekend Workshop: The Premium Pricing Paradox

Side Hustle School

Chris Guillebeau / Onward Project

Business, Entrepreneurship, Careers

4.83.3K Ratings

🗓️ 26 October 2025

⏱️ 9 minutes

🧾️ Download transcript

Summary

This new segment is all about helping you learn the key steps to a new side hustle in 2025, one step or concept per week. It includes activities, examples, and more—and of course it’s all free. Today’s topic: the $100 Alaska coupon book that sells over and over.

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

Connect on Instagram: @193countries

Visit Chris's main site: ChrisGuillebeau.com

Read A Year of Mental Health: yearofmentalhealth.com

If you're enjoying the show, please pass it along! It's free and has been published every single day since January 1, 2017. We're also very grateful for your five-star ratings—it shows that people are listening and looking forward to new episodes. 😎 🙏🏼 



See omnystudio.com/listener for privacy information.

Transcript

Click on a timestamp to play from that location

0:00.0

You know that customer reviews can have an enormous impact on your business. And you probably know this as a customer as well. When you go shopping for something, don't you look at the reviews? You might even filter them by star rating. You might see what people like, what they don't like. So if you want to have good reviews, if you want to have great reviews, it really helps to automate your process. And that's something our longtime partner, ShipStation, can help with.

0:21.5

They can grow with you.

0:22.6

They can help you deliver five-star customer experience with industry-leading scalable

0:26.7

features.

0:27.7

Wow your customers and get rave reviews with cheaper, faster, and better shipping.

0:31.8

Upgrade to ShipStation today to get a 60-day free trial at Shipstation.com.

0:35.8

Just use Code Hustle.

0:36.8

There's no credit card or contract required.

0:39.4

You can cancel any time. Shipstation.com code hustle.

0:46.0

Lemonada.

0:50.7

What if you could sell a coupon book for $100 when everyone else, all your competitors are charging $25?

1:02.2

And customers would actually thank you for it.

1:05.6

I love this story.

1:06.8

I love it so much.

1:07.6

The premium pricing paradox.

1:10.2

That's exactly what Scott McMurran and his partner, Gary,

1:13.0

accomplished with their Alaska Tour Saber books proving that premium pricing, in fact, can work even in the

1:18.7

discount business. It just kind of proves a lot of things wrong. These guys built a whole business out of this

1:24.5

concept. I first wrote about it long ago in the $100 startup. And Scott has been a friend of mine for many years. The guy I'm going to tell you about, I think the business is still going strong. So I'll mention that a little bit at the end as well. But first, let's talk about how this actually came to be. In this segment, it's all about helping you learn the key steps to a new side hustle, one step, or concept per week. It includes activities, examples. And of course, it's all free, just like everything that we do. We are using the book side hustle from idea to income in 27 days as our text. All right. So for the first half of the year, we went through the 27 steps in that book. Now in the second half, we're looking at these detailed case studies, so you can understand how people apply the framework. And the starting

2:05.2

point is Scott McMurran, this guy in Anchorage, Alaska. He's working in media sales at a TV

2:10.4

station, and his friend, Gary, keeps pushing this business idea. Alaska, the state, attracts over

2:16.8

one million visitors annually, many of whom plan

...

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