Stax was around before HeadRoom, and they did make electrostatic headphone amps. Geaorge Bishoff who started Melos built the SHA1 also prior to HeadRoom, but George really wasn't interested in headphone amps very musch. He built the SHA1 as a pre-amp, but many people told him it worked so well as a headphone amp that he change the name to a headphone amp---but it wasn't very interesting to him. His real interest was big, BIG tube power amps. About the time HeadRoom started, Corey Greenberg had a 1991 artical in Stereophile called "Aunt Corey's Homemade Buffered Passive Preamplifier" that would act as a headphone amp, and went on to review the Grado SR60s with such enthusiasm that audiophiles began to pay attention.
HeadRoom incorporated in 1992, and our first amps were portables similar to todays Desktop Portable. Our first home amps were a couple of years later. Shortly thereafter, Audible Illusions built a pre-amp that had a great headphone jack on it, Sonic Fronteers built a pre-amp with our crossfeed in it, and Audio Alchemy followed suite with a headphone amp that also had our crossfeed in it. Also early on, the EarMax came out and was probably our strongest competitor for quite a while.
Once Head-Wize appeared things started rolling a little faster, mostly on the DIY side, but certainly marked the beginning of small DIY operations becomming a market force. Meta42 and Gilmore amps started popping up all over the place. Jan was the first powerhouse player to come along, he predates Head-Fi and was a strong contributor to HeadWize activity. By the time the community had largely shifted over to Head-Fi (due to the inconsistant bandwidth at HeadWize and the ever growing community's voracious posting appitite) the DIY market had significantly gelled into a virtual power house of small amp manufacturing ability. It was the age of the mint tin amps. Ray, Mikhail, JMT, and Justin at Headamp had also gathered steam and they started really comming on strong with quality offerings.
I think it's fair to say the HeadRoom was the center of the headphone enthusiasm world early on, of course that world was about 7 people at first. I had the first headphone meet at Lonnie Brownells house, it was organized on "The Audiophile Network" a dial-up bulliten board in the days before the internet. But that event didn't lead to any meet momentum; it was a pretty isolated event and doen't really count. The first meets really started as I prepaired for the "World of Headphones Tour". I did a dry run to the Northwest about 6 months befor the tour, and the folks in Texas couldn't wait so they self-organized their own meet. That was the first real meet.
I'm sure there were some other worthy benchmarks that don't come to mind, but that's pretty much how I remember it.