He presents himself somewhat as just some geek who happened to write about it - you know, one of us - I think as a marketing thing. So now it's biting him back. I think that's OK; the main thing is it worked.
But apart from his weird material, and although it's a matter of personal taste to some extent, he is really really good. He has a great voice; the melody and guitar are effective folk/pop; the bizarre lyrics at times are a vehicle for guerrilla poignancy. e.g. I Crush Everything http://www.youtube.com/watch?v=2RFEzpUsUBk
(starts at 0:30)
Just for the record: I know Jonathan a bit and he markets himself as himself. The story of programmer to musician is 100% true and both are things he's pretty much always done.
As for the money side of it...the difference between a programmer salary and where he's at now is that his current level of income is probably a spike -- the arc for most musicians is usually steep -- and he's working his butt off for that spike.
So maybe it's a marketing thing, but only if you count being yourself in public as marketing.
Yeah, the Things A Week series still blows my mind: writing and recording a song per week for a year? That's both dedication and productivity, especially since most of them don't even suck.
It's true. And the current push to record a record while in a busy touring cycle is crazy but apparently working. It's sometimes easy to forget that touring musicians are basically working 15+ hour days of long drives, load-ins, etc -- all away from home and family. I really admire his work ethic, and it's great to see someone enjoy their work so much.
But apart from his weird material, and although it's a matter of personal taste to some extent, he is really really good. He has a great voice; the melody and guitar are effective folk/pop; the bizarre lyrics at times are a vehicle for guerrilla poignancy. e.g. I Crush Everything http://www.youtube.com/watch?v=2RFEzpUsUBk (starts at 0:30)