Started Phobia Consulting
The Web was becoming a thing, and I had learned much more than needed to build sites. So I started a side business: $75 for a three-page site, then $30/month for hosting. This included receive-only email, using my little FreeBSD server which ran a script every night that disconnected from dial-up and used the modem to send faxes.
It was named Phobia Consulting, simply because my personal domain was phobia.com. When DNS was being rolled out, I had reserved a dozen domain names on a whim, and I thought arachne.phobia.com was a funny hostname for a web server.
The email-to-fax gateway was a nice feature and for a while I had enough clients to pay our rent. Until a bad one decided to stop paying in 1998, then sued me when I replaced their site with a notice about that. Their case was that I had hijacked their domain name, when in truth I never controlled it and they weren’t savvy enough to point it away from my web server. Nevertheless, my efforts to explain the internet to a small claims judge failed; they won and I had to pay their legal fees. It didn’t bankrupt me, per se, but it scared me away from growing the business.