I'm gonna take some time to ramble about my own history with Pokemon communities, so sit back and get comfortable.
PS: I RAMBLED TOO MUCH. The first two parts are about how I found my way to online Pokemon in general. I talk about communities later.
Early Days
We'll say it was 2007, but I don't really remember, it could have been earlier or later. When I wanted to look for info on games, I would find all sorts of guides on IGN and GameFAQs. I remember an IGN board about the first Mystery Dungeon game pretty fondly - it had a guide for clearing Purity Forest, recruiting that damned Kelceon, etc. I wanted to find those threads right now, but I think the board is lost in time or something. Uhh, nevermind,
I just googled the title and got it.[1] That should show you how well I remember those times.
The other thing I'd do is follow Serebii's main site for news. I don't remember how I found it, but it was the other source I had for all sorts of gameplay info and tips. I didn't know they had a forum at all.
At some point I also started watching YouTube videos. Like, in general. Not long passed until I searched for Pokemon videos and found out there were people uploading Wi-Fi battles. From that point I'd just constantly search for "Pokemon wifi battles" all the time - it was pretty amazing seeing competitive videos for the game series you liked so much and knew so much about. I mean, in retrospect they were pretty horrible videos, but when you've never seen a competitive battle before, you get impressed by anything. This was just the time Marriland, MTGxerxes and others were uploading videos, so I wasn't the only one being impressed.
Then something led me to Serebii's forums. Maybe some of the links from the main page's headlines. I was super impressed they too had a forum like IGN, and it took me only a few minutes to find posts that mentioned Smogon. Hilarious in hindsight, this made me check out this site and I never signed up for Serebii, despite lurking on the main site for years.
Relatively Old Smogon
This was around the beginning of 2009. I hadn't signed up for the forums yet, because the first thing I noticed was the damned Pokemon battling simulator that you could use to play against people all over the world. I was dumbstruck. I had my old man set up the port for Shoddy Battle and started battling. It didn't take long for me to feel the need to make an account on the forums, maybe because of tournament signups or something. I wasn't original with names. There were plenty of people called Blue something, it sat at the back of my mind and I just went with it.
I was a big fan of team showcases (Rate My Team) and battle showcases (warstories). I'm not sure these things even exist nowadays. They had the archive for good RMTs and warstories, which made me post some of my own. I also joined some small tournaments, but I didn't really have any friends from the forums. Funny that the opening post praised Smogon for its hospitality, because between Trou du Cul, Firebot, the shunned Wi-Fi subforum and the general elitism culture left by the oldies, those were some pretty different times!
I rediscovered one of the old Garchomp videos a few weeks ago and I had a great time watching it again.[2]
Anyway, it took me a stroke of luck to branch out a bit. One day the main Shoddy server was down, so I tried one of the smaller ones...
Splinter Communities
I checked out some of the smaller servers, and they were ordered by the number of people present on the servers, like you'd expect. I think I went through some foreign language servers first, though, which wasn't a great time. I eventually went to some server called Pokecentral101 which had around a dozen people on it. The ladder was working fine, though, and I battled the same few newbies until I almost topped their leaderboard. I mean, with a small community, that's not really a problem. Then the guy on the top of the ladder showed up, we traded a few losses, and he invited me over to their forum. This was my first time interacting with other communities, let alone a really small one, but I quickly figured that I could have a lot of influence on a smaller board, so I started executing all the things I wanted to do on the Smogon forums - type out Pokemon analyses, make a new tier between OU and UU, host tournaments, all sorts of things in the competitive sphere.
I'd never been on an online chat aside from Shoddy, which never felt very personal, so the possibility of a community chat didn't cross my mind. One day the site admin hollered me over to a webchat that all the frequents hanged out in. I had to do a little sleuthing (all of these sites are dead now, christ[3][4]) to remember what the site was called, but the site was called "xat", and it was some flimsy webchat that allowed avatars and link embedding and some more, along with auth and kickbans and other things you'd expect. This was a little while before I was introduced to IRC, and xats seemed pretty cool at the time, not to mention I wanted to hang out with the people from the community, so I stuck around for a while.
Hanging out in small communities was a pretty big deal. It introduced me to a lot of Internet Drama, people getting mad over nothing, some anxiety, but also a lot of in-jokes and good times. I had Wi-Fi battles with friends over the chat and participated in all sorts of streams and competitions we organized. I still remember a lot of the things we did back then, and I also remember a lot of the people I hung out with. It's a constant source of nostalgia whenever I catch someone I remember from those days, and we can reminisce.
Wrapping Up
Around the time my old communities broke up, I already had other hobbies and I started to branch off from Pokemon. I couldn't ever really reproduce the sense of community I had back then, but maybe that's just me looking back fondly at my teenage years. Still, to this day I think having a small, close-knit community to share your hobby with is pretty top. Kinda like in life, if you float around and not really get into a community and talk to people, you will not have done much by the time you move on.
I mean, Smogon has all sorts of subforums and tiny IRC channels you can hang out in, but it's a little different when it's all interconnected under the same site. Having your own independent group of friends doing your own thing is what I'm talking about, and that's why I'm a pretty big fan of spread-out, tiny communities. There's problems with small communities like toxicity and stuff, but you just gotta make sure not to focus on bashing other people as your pastime and you guys should be fine.
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Footnotes
[1]
lapton32s guide to Purity Forest, or indeed any other Level 1 Dungeon / IGN game boards
[2]
Smogon's Truth: The Real Garchomp Story / YouTube
[3]
http://www.pokecentral101.com/
[4]
http://regileague.forumup.com/