My over blown sense of drama would have me saying that when I did my first triathlon you rode a penny farthing on the bike. 
Truth is that even for a young sport I am still second generation. Seeing as the first triathlon was in 1974 and the first Ironman was in 1978. For me I started into the sport on a whim. Back in 1993 I was talking with a group of surfers in Santa Cruz, while we all waited out in the water for waves to make a guest appearance. One of the guys was talking about how his training for a triathlon down in San Luis Obispo next month was really helping his surfing. I have no idea why I thought that doing a sprint course triathlon would be a good idea. At that point in time I had not run in over two years and did trail rides on a mountain bike a couple times a month. The only thing I had going for me was surfing 2-3 times a week. Sadly, this would be my training regimen for most of my triathlon career.
Deciding to do it was easy, signing up to do it was more of a trick. The internet was in its infancy and wasn’t something I would even try to use for another year or so. Since it was the old days, I handled it the old-fashioned way. I called a friend in San Luis Obispo and asked if he knew anything about a triathlon next month. Turned out that he was going to be a volunteer lifeguard for event and he gave me a phone number for the production company who was organizing the race. I called them up and got the details on the race and they said they would mail me an entrance form since they didn’t do phone registrations. A month later I was headed south for my very first sprint course: ½ mile swim, 15-mile bike ride and 3.1 mile run.
My troubles started almost as soon as I hit town. The hotel was not bicycle friendly and so the assistant manager (small man + a little authority = large attitude) decided I couldn’t keep my bike in the room. He was afraid it would get grease everywhere. We eventually worked out that they would store it in the maintenance shop overnight and I could get it before I left at 6am. Not ideal but it worked. At this point I had no idea about transition areas or what gear I needed beyond a bathing suit, bike and a helmet. The thing that helped me most was something that is VERY rare for triathlons – it was a pool swim. No wave start, you simply waited for your number to be called and then you got into a lane in the pool to start swimming. So, my first ever swim to bike transition was done in the locker room at the YMCA pool. I had no idea that I was supposed run out to the parking lot and jump on my bike wearing what I swam in. I simply changed into sweats and a t-shirt at a nice casual pace and then went and found my bike. I must admit that it was a lot less stressful that way.
The bike course would see me start a tradition of using the wrong equipment that would last until only very recently. I did use a road bike but it was a touring bike that still had the racks and bags on it – took me a few races to figure out why people looked at me so oddly. Of course, it could also have been the baggy sweat pants or the Styrofoam helmet (yup it was race legal in 1993). It was a slow ride but the course was beautiful, winding through vineyards and farm land just outside of SLO. I have only just recently remembered to enjoy the scenery while I am on a course, a habit I lost when I tried to “get serious” about racing and yes THAT will be discussed at some point.
The run also would start a lifelong trend for me – it was horrific and barely even counted as a run. I ran maybe 1/3 of it. Mostly running ¼ mile and then walking for ½ a mile. Not terribly surprising when you consider I never even tried to do any run training. The official time is lost to the mists of time or the Rubbermaid storage tubs under the stairs (back then you race results were mailed to you along with race entry forms for other races). I do remember it being over 2 hours though.
While it was going on all I could think was “what the F### was I thinking” but by that night I was wondering which one I would do next, That is a feeling that would hold true for almost every race I have ever done. Only the really good and the really bad don’t follow that rule.