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[JimH]

Where would you start?  What group?  What genre?

Anyone heard of Pink Martini?

[KingSparta]

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[glynor]

So-called "Indie music".  They're the bands that are abandoning the traditional labels in droves already anyway, and their target audience (high-school through college aged kids) are the most tech savvy demographic (and likely to use pure-digital delivery services).

Artists like: Arcade Fire, Apples in Stereo, Arctic Monkeys, Belle and Sebastian, Bloc Party, Blonde Redhead, bright eyes, brand new, Fruit Bats, My Morning Jacket, the New Pornographers, Clap Your Hands Say Yeah, etc.

I'd also try to target lower-volume artists in non-mainstream Genres.  Things like Americana, Bluegrass, Classical, Reggae, and World-Music.  All of these Genres have significant followings and sales, but they're not mainstream enough to garner real support from the big labels.  Many of those artists are extremely frustrated with their labels' level of support and their levels of distribution and are "ripe for the picking".  I'm thinking Artists like: Avett Brothers, Be Good Tanyas, Beenie Man, Lambsbread, Old Crow Medicine Show, and Tony Rice (and Classical is a huge opportunity too).

Better deals for the Artists, with increased exposure, could be a potent combination for many of these artists, I suspect.

[jgreen]

If i was doing this, I would go as "niche" as possible.  Probably, I would start with Christian music (I'm an Aetheist), and then market the heck out of it the old-fashioned way.  If the first stab flew, I would keep expanding to other niches until I got my @$$ handed to me.

ALSO:  Be aware that many of the acts that us oldsters know and love (and some current acts that are no longer A-list) cannot get arrested these days.  A determined bit of phone tag may land some of these in your lap.  HOWEVER, I think "live" performance is the way to exploit yesterday's roses. 

$.02