You know how they have the Society for Creative Anachronism? They're the geeks who get dressed up like knights and hit eachother with padded Claymore replicas, revitalizing traditions of yore. Then there's also the Civil War Re-enactment nut-jobs, but unelss you live below the Mason-Dixon line you probably aren't familiar with them.
What about starting a Society for Creative Capitalism? Everyone pretends it's 1999. We could rent out Moscone Center in San Francisco, make up some imaginary (or real, but since mothballed) company to work for (as a Technology Evangelist!) and have a high old time. Instead of jousting or shooting cannons at eachother, we could see who can draft the most powerful Non-Binding Letter of Intent. Instead of selling antiquated hand-bound books at your booth, you could sell old copies of ATG Dynamo or Oracle 8i.