Much of the history is simply embedded within the nodes that make up the website. Try this, for example: Go to Super Search, click on the "PerlMonks Discussion" checkbox, and click on the "Oldest First" radio button. Then simply click "Search" (don't input any search text). This will yield a list of some of the earliest PerlMonks Discussions, from the days when the Monastery was in its infancy and most formative times.
The same can be done with Seekers of Perl Wisdom. By searching for the oldest such nodes you'll see some of the early questions, and who answered them.
If you do a Super Search without selecting a section check-box, and do select the "Oldest First" radio button, you'll get a chance to see the very first few posts to the Monastery. You'll find that for a long time the gods themselves were busy adding POD documents to the sites, back when they tried to maintain the Perl POD here.
One day in Oct. 1999 paco came along and posted How do I recursively process files through directories. He's never been heard from since. That's not all that unusual nowadays; we have lots of people ask questions and then disappear. But back "in the day", he was such an early poster that the few eyes that were here were all watching, and *poof*, he vanished as quickly as he came. He and the node gained such celebrity status that the node's reputation shot up to a record high.
The rest is all there for you to find as you search through the site.
I don't know much about the details of how vroom and (I think) nate came up with the idea for the site, developed the Everything engine, etc. Perhaps someone else could fill in those gaps.