Thanks to a new wave of AI tooling in the programming space (replit + cursor), projects that would otherwise be far to daunting with respect to time and effort can suddenly come to fruition in extremely compressed time horizons. Within the ether of the Zeitgeist you’ll often hear “You can literally just build stuff” echo’d.
Its in this vein that I made the decision to build a new personal website with functional CMS in the style and feel of Windows 98. I’m obviously a millennial, and as I’ve detailed elsewhere, was a PC kid growing up, even going to the launch of Windows 98 at the age of 12, which at the time was done via satellite in movie theaters around the world. To add, I actually feel a mock operating system is a great UX for a personal website and offers a ton of flexibility. In the future, I’ll likely add a photos folder, a retro video player that natively plays embedded YouTube videos I’ve created, and maybe even a Doom emulation (to compliment SkiFree of course).
Want to check it out? Follow the link here.

Here is a smattering of the features:
- CMS: I built a lightweight content management system to allow me to create/edit/delete posts, projects and categories. This is obviously core to any personal website where writing is a big part of it.
- Blog Post Reader UI: I needed a way to organize all my posts in an intuitive way (within the “blog” folder of course) without being too clunky and old school while still retaining the “Windows 98 Charm”.
- WordPress Importer: I built a little tool that imports from any wordpress site into my custom site and the formatting more or less carries over. Yeah, I could keep iterating on this, but I’m happy with the way it works, plus my writing tool works well with markdown.
- Substack RSS Parser: I will be using substack as my “point of truth” for my writing going forward because nobody really uses the blogosphere and hasn’t for a decade (ooph). Hence, my goal was to have posts flow from Substack TO my personal website when I publish (again, on substack) without any manual effort. I built this using an RSS feed parser that looks for new posts, parses them appropriately and saves them to my database with zero effort.
- Fun Stuff: The theme is fully functional with a game (SkiFree), a WinAmp inspired MP3 player that plays my AI album Tucker and the Robots, the ability to manipulate settings (like background) just like an old Win98 OS and my social links are set in the toolbar. I’m trying hard to showcase the little things that made the 90s fun while keeping the UX somewhat good.
Those really wanting to dive into the stack and how I built this, you can click the “about” button in the start menu (or just follow this link).
As you can all tell, I am still sticking with my “old” blog being its a lot friendly on the eyes while and being a bit more professional. Plus, I’m getting enough traffic to this site I don’t want to totally disturb the SEO that is driving traffic (and eyeballs) my way. I could be convinced otherwise those, so feel free to reach out if you feel I should take more risk and ditch this boring site in lieu of the retro-themed windows98 variant.
Jumping into this project did give me the much needed push to get this site (the one you are reading right now) off wordpress.com and onto a self hosted solution (bluehost) that gives me a lot more agility with less lock in at a lower price. I know, its still a wordpress site in that the CMS is wordpress, but I’m done with the awfulness that is wordpress.com. On that note, WTF are you guys over at wordpress.com doing anymore? I remember Sam Harris had the CEO on to talk about distributed work during the pandemic and I know he’s a sharp guy but what gives? Has the team more or less given up? Its insane how poor the service felt and how embarrassed I was sticking around as a customer for as long as I did. Yikes.
In any event, if anyone has any thoughts or feedback, feel free to hit me up at jeff.brines@gmail.com
Cheers!
*I ditched wordpress.com, not wordpress the cms, at least on this blog. The new new (old?) blog runs a custom CMS. But I digress…