How running websites has changed in the last two decades (for an Ars IT guru)

The Pit, a BBS door game. In this shot, Lee Hutchinson was attacking these guys. Or, maybe they're attacking him. (credit: Lee Hutchinson)
I was a true nerd growing up in the 1980s-not in the hipster way but in the 10-pound-issue-of-Computer-Shopper-under-my-arm way (these things were seriously huge). I was thoroughly addicted to BBSes (Bulletin Board Systems) by the time I was 10. Maybe it's no surprise I ended up as a technical director for a science and tech site.
In fact, I'd actually draw a direct line between the job of managing your own BBS (aka SysOping) to managing a modern Web infrastructure. And with everyone around Ars looking back given the site's 20th anniversary, let's make that line a bit clearer. It won't be an exhaustive history of websites, but here's how my own experiences with managing websites have evolved in the past two decades-plus how the tools and thinking have changed over time, too.
LOAD "*", 8, 1My first SysOp experience was powered by a Commodore 128 (in 64 mode, of course) running Greg Pfountz's Color 64 software. I sent Greg my check-well, my mom's check-and received back a single 5.25-inch floppy diskette along with a hand-bound dotmatrix-printed manual. It was on.
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