For me, the first player I'd heard of that was good, was Malcolm(although by the time I heard of him, he had already dropped Sonic). It wasn't until the beginning of 2010 that I had got my disc. I started out playing basic brawls, since I didn't realize SWF or AIB existed lol, and around March I joined SWF, didn't actually use it til like late April, eventually I heard of Malcolm, checked out vids, was amazed, heard about Espy from my friend JRUGS (who now lives in Maryland), I checked out some vids was amazed and was pretty hyped that he lived in our same city :D eventually ended up seeing other Sonics eventually, and found a fondness for Kojin's gameplay/combo vids especially :3
Around August of last year I went to my first smashfest, got ***** by pretty much everybody lol.
While I kept on trying my best to improve, Espy did too, no matter how hard I tried, he always seemed ridiculously good, to the point where at times I almost doubted that I could ever get even near his level XD, eventually grew out of that, accepted that he's good because he'd put in work just like anyone else. When MLG Dallas happened I was about as happy as every other Sonic here, maybe a bit more, because he's been one of the Sonics I looked up to and wanted to succeed (also city pride). At the same time I was envious because he'd accomplished something pretty amazing while I didn't feel like I'd been making much progress.
Now, here we are in 2011, I feel like I've improved quite a bit since then, the game may have changed some too with more rules being applied and what not, MK maybe being banned. New playstyles, new players, and new skill levels. Espy's still much better though, hoping to catch him soon, guess I'm still too slow haha. Hopefully, (for me) Espy doesn't pull a Malcolm on us and do a character switch (it'd suck because then I'd never get the chance to really surpass him), though with as much as Espy likes Sonic, I can't say I'd see him drop Sonic before I'd see him drop brawl.
I guess for me though, I can't exactly 100% relate because I haven't been around as long, but, I'd say brawl's been pretty fun for me through and through, cool people to hang with just as Espy mentioned, and I guess I haven't gotten bored yet simply because unlike Espy, I haven't exactly accomplished the goals I've set for myself yet.
Edit:
TL;DR
Brawl Career's story+ I learned from Malcolm, Espy, Kojin, and some other Sonics :D