I remember watching a talk by Joel before he'd even brought Leo on board in Nottingham, UK (Joel was starting up in Birmingham, UK if I remember correctly), about his previous products/failures and how he'd just built Buffer and the problems it solved. I think I saw a post about Leo joining 3 to 6 months later, at the time a recent uni grad compared to Joel's more experienced dev + freelance dev background.
I've always been pleased to see Joel succeed, as he's a great guy, but I have to admit some of the posts they came out with have ultimately proved to be utter b%!!$hit. I remember calling them out on a post about how the UK was a bad place to startup, I've seen a couple of $100+ million buyouts of startups here since then just in Nottingham. Then they claimed bootstrapping was best, then raised. Claimed a flat structure was best, then go a traditional management structure, etc., etc.
I sometimes felt they were just echoing back to the startup community what the community wanted to hear, and to be fair, it really worked, they got lots of upvotes on HN, etc., so great marketing out of it, and good traction. There was a time when like clockwork they'd have a high-rated post here every Sunday (or Monday, can't remember).