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Side Hustle School

Ep. 3107 - Q&A: “How do I turn digital nostalgia into a creative business?”

Side Hustle School

Chris Guillebeau / Onward Project

Business, Entrepreneurship, Careers

4.83.3K Ratings

🗓️ 4 July 2025

⏱️ 7 minutes

🧾️ Download transcript

Summary

Is late-90s internet culture more than just a vibe? In this episode, we explore whether digital nostalgia can become a sustainable business—or if it’s better left as a passion project.

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

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Visit Chris's main site: ChrisGuillebeau.com

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Transcript

Click on a timestamp to play from that location

0:00.0

Lemonada.

0:02.7

What's up, everybody? I'd like to wish you a happy Independence Day.

0:14.1

This is, of course, an American holiday that occurs every 4th of July.

0:18.0

We've got a worldwide audience, so if you are not in the United States,

0:21.2

I can still wish you a happy Independence Day. Independence, of course, is a wonderful value.

0:26.6

Independence, autonomy, ownership. You can always ask yourself at any point in life,

0:30.8

what am I doing to create more independence for myself so that then I can do more of what is

0:35.0

important to me, including service to others. It's not all about yourself, but independence is good. So happy independence day.

0:41.8

Today's question, loosely related, how do I turn digital nostalgia into a creative business?

0:47.8

Is late 90s internet culture more than just a vibe? We're going to explore whether digital

0:53.2

nostalgia can become a sustainable

0:55.0

business or if perhaps it's better left as a passion project. Now, this was kind of a throwback.

1:00.5

I was thinking about some things in the 90s or from the 90s, AOL away messages. Some people

1:06.2

might remember that. Other people are like, I have no idea what that is. Blurry webcam, selfies,

1:10.4

lime wire

1:10.8

playlists for a whole generation. These were kind of tech milestones and also emotional

1:16.0

touchstones. So we're going to hear from a listener, Logan. He is a self-proclaimed internet

1:20.7

history nerd. He wants to turn digital nostalgia into a creative business. The question is,

1:25.9

are people actually willing to pay for this, or is it just fun to look at? It's kind of like selling memes. I had a creative business. The question is, are people actually willing to pay for this,

1:27.7

or is it just fun to look at? It's kind of like selling memes. I had a question once.

1:31.7

I don't think we ever ran it as an episode because somebody was like, hey, I want to sell

1:35.3

memes. Well, people like to look at memes. They like to share them, but do they want to go and

...

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