My biggest regret is not getting into domaining in the mid to late 90's.
The odd part is at the agency I was working for, we were registering domains for clients. The internet was still fairly new and I viewed domain names as a form of "vanity plates" - a form of personalized license plate.
All our work that dealt with internet marketing and design (website) was farmed out to one guy that could do computer graphics and site design. I remember this guy very well. Russell was showing me what he could do, literally creating his own type fonts, with his new computer - an Apple. He was totally freelancing, not working for any one agency, but was making so much money on his own. I also remember him trying to talk sway me going into business with him and starting our own agency.
That part of computing interested me most - the graphics capability, not domain names or websites. One agency I was working for was making several hundred million per year in late 80's to early 90's. Meanwhile, we were registering names for clients like there was no tomorrow. Most were furniture manufacturers and NASCAR and NASCAR teams and even some Las Vegas Casinos and I had no interest in them.