My first computer related job was as a systems operator in the CS dept at the University of Lowell (since renamed UMass-Lowell) while I was a student there in 1987. It was also my first exposure to the Internet. No Web back then, though.
For 3 years, I helped manage DEC VAXes, DG MVs, a Sequent Balance, some LISP machines and various other minicomputers and workstations. I also set up the department's PC lab. Just DOS, no Windows. I didn't understand why they were so popular.
In 1991, I went to work at MIT's Dept of Economics as a systems administrator where I was responsible for various PCs, Athena workstations, an AT&T 3B2, and an IBM RS/6000.
In 1992, I was responsible for servers running SunOS and A/UX which handled email and USENET at Apple's R&D lab in Cambridge, MA. I also set up Majordomo mailing lists and USENET gateways for various Apple products.
After working at Apple, I was pegged as a "desktop" guy. From 1993-95, I set up and supported hundreds of seats at 3COM, Kodak, and BBN along with Netware and Lotus Notes servers.
In 1995, I went to work for NewMarket Ventures in Boston which was creating the website for the Car Talk radio show. At this point, I started working with Linux servers running Apache, Mini SQL, and various Perl scripts- the LAMP platform.