Ep. 3107 - Q&A: “How do I turn digital nostalgia into a creative business?”
Side Hustle School
Chris Guillebeau
4.7 • 3.3K 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
Email: team@sidehustleschool.com
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. 😎 🙏🏼
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: team@sidehustleschool.com
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. 😎 🙏🏼
Hosted on Acast. See acast.com/privacy for more information.
Transcript
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| 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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