How I first began playing Pokemon:
I think I was in the fifth grade when the trading card game became popular at my school, and although I could never come across any worthwhile cards, I got into the anime somewhat and my interest was piqued in regards to the Game Boy games at about that time. For my birthday, I received a Game Boy Colour and Pokemon Yellow, which I played to death. My friends and I got into Pokemon Stadium for N64 when it came out, and transferred our hard-won Pokemon to duke it out. At that time, it was about the fun of battling (our most competitive battler used a Venusaur with Razor Leaf / Solar Beam / Vine Whip / Sleep Powder, go figure).
While the majority of them grew tired of playing in the coming months and years, I never really did, and so when Gold and Silver came out, I (secretly) got hours of enjoyment by playing through the storyline and raising up a team of my very own. This soon passed, but with the release of Ruby and Sapphire, old interests were once again sparked as I stumbled across a "competitive battling" guide on GameFAQs, and started training my Pokemon accordingly. I was surprised to discover that my Sceptile didn't have to use Solar Beam / Sunny Day / Leaf Blade / Bullet Seed to be effective, but could utilise other ingame moves like Dragon Claw!
How I got into online battling and found Smogon:
Ruby and Sapphire eventually got old, I didn't really have anyone to battle with outside of my nextdoor neighbour, who succeeded in getting a team of Level 100s before I did, while I got bored raising my team when they were only about Level 80. I decided to search for an online Pokemon experience; lo and behold, I found ... TPPC RPG! Ugh. The novelty was pretty cool for a while, but places like that can really only hold you for so long (or not at all, either one really!).
Still reeling from the possibility of "competitive battling", and hoping the humble Internet could provide me with the ability to play with people around the world, I came across a program called Netbattle, to which I immediately downloaded and informed my neighbour of. We hung out and battled at "the server with the most people", which coincidentally was Smogon. Like many Netbattlers (or maybe not so many, but whatever), I went through a period of anti-Smogon sentiment. You know the concept of "sticking it to the man", right? Well, Smogon was "the man", and gosh darn it I was going to stick it to him! I created my own clan server with my neighbour, which was awesome for a while, but then we were cruelly botted down by the likes of kaiba (who we now refer to as Shiv). It was this experience that forced me to learn how to script, so I could stop these spambots from spamming BOAH down my beautiful clan server!
As time progressed, I did become a better scripter, and abandoned the concept of clans. Still wishing to be independent of the community I now find myself posting in more frequently, I started and ran several more successful servers (by comparison to my first effort), such as Epsilon Battle Arena and the more recently successful Kirby's Casino, under which my ability to battle increased to a small degree. You may wonder why I even bothered mentioned previous servers, but it was through Kirby's Casino that I was reintroduced to the Smogon site, as you'll soon see.
When Diamond / Pearl came out, things proceeded as normal for me - I'd run my server on a daily basis. However, when I got a copy, I couldn't stop playing, and I still can't. I pretty much rushed through the storyline and immediately began breeding for my newfound favourite Pokemon, Bronzong. At about that time, I was alerted to the fact that Smogon would be releasing a new site soon (lol) and came to see things for myself. While the site wasn't up yet, the forums I had previously been oblivious to were, and I quickly set up a trade thread with my new Bronzor, and was pleased that I was able to get a few trades (and still do) out of it. Initially restricted to the WiFi subforum in Stark Mountain, it quickly became apparent that Smogon wasn't just that server with a lot of people that needed to be brought down, but rather quite a cool community!
... Well, that turned out a lot longer than expected, but there you have it; the story of how I first started playing Pokemon and how I first became interested in online battling, and consequently (eventually) the Smogon community.