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.
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My 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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