I think Spolsky does this best, even though I can't quite pin down how.
His company doesn't have a trendy name, he doesn't really have a gimmick (other than being a clear and prolific and useful writer, which is not a gimmick), but he's reasonably celebrated.
In the context of this "don't just be useful, have personality" idea, what's his personality? It must exist, because the following that he's built points to it, but I can't identify it directly, sort of like a marketer who you've heard great things about but don't know where. (Obligatory xkcd comic link to be posted by someone else.)
Note: I'm not saying he has no personality, just that I can't point out what makes it come to the forefront, because it's subtle. I love the guy, but don't know why I love his site so much more than, say, jwz's. Maybe it's the implied profitability of his software business, versus the "I sell beer because I hate computers" message?
Joel is funny. not comically funny, but enjoyably funny, such that you can almost always get through a post or interview or whatever without feeling labored.
Joel always brings in metaphors or stories from worlds outside development (only sometimes funny). Many stories still go back to the Army, or his first job at the bread factory, but the recurring stories make you feel like you know him, you know his past, his experience at Microsoft. You know his whole personality through his vast writing, and it's all masked in "clear and prolific and useful" writing.
You feel like he's an expert, because you didn't notice that he's always injecting personality, where, an example from AVC's comments is Mailchimp, who makes their entire brand about a single chimp.
It will be hard for Fog Creek to keep their brand after Joel leaves, but it won't be hard for Mailchimp
Yes, Joel is very funny, but not in an overbearing, obvious way.
In an old essay on software specs [1] he states: one of the easiest ways to be funny is to be specific when it's not called for
I've noticed that he does this a lot. All the time. Sometimes too much, like in hginit.com, which I did not find that amusing. But most of the time he is spot on.
"I like developers, and letting PHBs put devs in a dungeon is bad"? More to it, but that seems to be a recurring theme in Joel's writing.
He makes things that explicitly help developers, whether its a bug tracking system, or a Q&A board for devs. In one column he says that a small software company or startup manager's job is to provide the illusion that developing software is all there is to do (all that matters).
His company doesn't have a trendy name, he doesn't really have a gimmick (other than being a clear and prolific and useful writer, which is not a gimmick), but he's reasonably celebrated.
In the context of this "don't just be useful, have personality" idea, what's his personality? It must exist, because the following that he's built points to it, but I can't identify it directly, sort of like a marketer who you've heard great things about but don't know where. (Obligatory xkcd comic link to be posted by someone else.)
Note: I'm not saying he has no personality, just that I can't point out what makes it come to the forefront, because it's subtle. I love the guy, but don't know why I love his site so much more than, say, jwz's. Maybe it's the implied profitability of his software business, versus the "I sell beer because I hate computers" message?