Once upon a time, marketing music must have been so simple: in the ’50s you just bribed a local DJ and off you went. By the ’80s it was a little more complicated – in addition to cash you needed to bring coke and hookers, but still, it was a straightforward process and everybody understood the rules.

Maybe that’s understating the difficulty of getting discovered back in the Good Old Days^®, but there’s no arguing that things are a lot trickier here in the 21st Century, as nichification, genrefication, segmentation, fragmentation, the consolidation of major labels, the profusion of new media and the ascendancy of coolmongering has so dramatically complexified the challenge facing new bands that it’s a wonder anybody even tries anymore. (And if you’re naïve enough to think that hard work and talent will ultimately win out, well, welcome to math class.)

The problem is bad enough if you’re a young band targeting a young audience (like our boys Doco, for instance, who are insanely talented and had they come along in the ’70s they’d probably be doing arena tours by now). But imagine if you’re aiming for a slightly older audience with a sound that’s way too sophisticated and hip for commercial AC radio. I know a number of artists in this general boat and I really, seriously feel for them.

Last night I got an e-mail from Rich Flierl, the mastermind behind Dotsun Moon. To give you a sense for where they reside in the musical landscape, here’s part of what I said about them back in March:

Who do they remind me of (because since you haven’t heard them, we have to triangulate via bands you may know, right)? Well, I mentioned Portishead, and Flierl admits to a fondness for Massive Attack and Jah Wobble. “Who Do You Love?” suggests that he’s heard a bit of Love & Rockets, as well. There are places where Ognibene reminds me a lot of Girl Next Door’s Kat Green and the CD’s more animated numbers put me in mind of a sort of noir version of Supreme Beings of Leisure. Other places I swear I hear bits and pieces of The Church, U2, maybe a little Echo. Or maybe I’m projecting – hard to say. Sounds and influences sneak into a mix from all over the place.

There is no American Idol for bands like this, although if the networks put me in charge of an adult version of that show it would be the single best thing involving music and television since The Beatles played Ed Sullivan. There’s nothing terribly special about me, except that I’d pack the stage with so much real talent that you’d be embarrassed to admit that you’d even heard of  The X Factor.

Rich had a direct question. He knows I’m in marketing, so he wondered if I had any bright ideas about how they could reach a bigger audience, given who they are. My initial response, for all the good it does, was to note what we call “affinity marketing.” Basically, think about the people you want to reach. Now, where are they already united marketing-wise? What do they have in common? Are they members of a particular organization? Do they read the same magazines? Are they fans of a particular band? Where, in other words, are you likely to find them in one spot as it stands now?

Then partner with the thing they already pay attention to. If they read a particular mag or site, you need to score an interview or feature there. If there’s a band they all love, you need to be touring with/opening for/whatever that band.

Flierl has an important piece of the equation figured out. Here’s how he described the people the band is after:

Generally well educated. If not through college, probably read. Former lovers of punk rock that tired of its sonic limitations. People who wish Sting was more interesting. Want to go to shows but tired of festivals and standing around dives until midnight for a band, because they have jobs and/or kids. Probably listen to Pandora, Sirius or have an Internet radio. Probably like small-budget films.

Probably read Big Takeover. The women like Adele and Dido but wish they were a bit more like Massive Attack.

Generally consider themselves liberal. Listen to NPR. They are on Facebook but don’t want the hard sell. I just don’t know where they congregate. And the reaction to music isn’t as over-the-top like it is for a teen. The good news is they are more likely to pay for music than a teen.

I’ve been in marketing for a long time and have, on any number of occasions, dealt with start-ups (and even established companies) who cannot articulate their target market as well as Rich did in those three short paragraphs. So he knows who, but how is trickier. If he had lots of budget he could buy some awareness easily enough, but what indie band has budget?

The irony, of course, is that Dotsun Moon gets some airplay. A couple of times recently, in fact, Art and Tracey Jipson have played the band on their outstanding Tuesday afternoon School of Rock show on WUDR (University of Dayton). No indie band is going to be unhappy about that kind of exposure, but when push comes to shove they know they’re not going to make their bones on college kids. (True, Art and Tracey probably have a lot of older listeners, like myself.)

Flierl credits the band’s airplay successes to The Planetary Group, an artist development firm that helps bands with everything from radio placement to touring to Web design and digital marketing. (Dotsun Moon only uses them for radio.) “I don’t have the contacts and what they do in 10 weeks would take me two years. They’re a big reason we’re getting airplay. They’re a godsend.”

When an indie band does get big enough that you may have heard of them, Flierl emphasizes that “it just doesn’t happen by accident.” An artist like Bon Iver, for instance, has a serious management company. “We can’t afford that level of support and right now touring is the only way aside from commercials and movie or TV placement to make money. Most bands make the bulk of their money through t-shirts sales, etc.”

Touring is a bit of a problem, though, because the thing about bands seeking adult audiences is that they tend to be adults, too. Adults with jobs. Take Dotsun Moon. They have a lawyer, a physician’s assistant, a school teacher and college professor in the band, which makes extended touring, well, just about impossible. They’re hardly the exception, either – a significant percentage of the really exceptional bands I know are like this. Very few people are making enough cash off their art to live on. I don’t know all of the artists on last year’s Best CDs list, but my best guess is that at least five, and probably more than 10 have to work for a living to support their music habit.

It is what it is, but most artists, in any genre, really don’t hit their stride until they’re at an age when the teeny-obsessed music industry ceases to care about them. All too often, ugly economic realities keep our most talented artists away from the audiences who would love them most.

How about playing a festival, like SXSW or CMJ? Easy to say, hard to do. Flierl says the band’s rankings get reported to CMJ and they have been in the top 30 at 50 stations since April. “I’d say the chances of playing CMJ are nil.

“CMJ wants a band with extreme name recognition, extensive touring and constant blog coverage. We’re doing well, but we don’t have those requirements.” Listen to #4 (an actual mp3 interview recording) to hear it straight from the horse’s mouth.

Still, despite the obvious frustrations, Flierl says he feels lucky. “We have careers so this is a labor of love. But it would be nice to make enough to cover the cost of recording, mastering and (even though the format is almost dead) printing the CDs. Honestly the payment for downloads or CD purchases is less about the money. There’s no way we could sell enough music to make up what we put into equipment and recording, anyway.

“Really, it’s just about loving the music and wanting to play for audiences who will appreciate it. When somebody buys a CD, it’s gratifying to know that they respect what you do enough to pay for it.”

I don’t have a magic bullet for adult bands seeking adult audiences. Any radio you can get is good. Tour, tour, tour, if you can, and especially tour with bands that have similar audiences but who are known in areas where you aren’t. (Dotsun Moon plays shows with The Lost Patrol, for instance. But heck, TLP is in the same situation, although they’ll be featured on what we hope is a major movie soundtrack next year – fingers crossed). Pursue all the press you can get in pubs that cater to the slightly older reader. If you can somehow get yourself featured on NPR, then that’s worth its weight in gold. If you really get it rolling maybe you can score with CMJ or SXSW. Keep working on your craft, obviously. Use the hell out of social media. Etc.

And pray that I hit the Powerball so I can spend my money promoting you and other bands like you. Because that description of your target audience above? Yeah, that’s me and a lot of my friends, and as I told someone yesterday, I live to connect people with music.

So, as a public service, let me take a second to prop Dotsun Moon and some others that you might like if you heard yourself implicated in Rich’s description of his target audience.

Hope everybody is having a nice weekend.

Let’s see, who else might you like? Well, there’s The Blueflowers. Here’s something live.

And Baron Bane, for our European readers.

There’s no video yet, but I love the new CD from Able Archer.

Here’s a great solo acoustic performance from the new Ron Hawkins disc, which is one of the best of 2011 so far.

And you knew I was going to mention The Lost Patrol, right? Here’s a page with a couple of videos, some tracks from past records and one from the forthcoming CD, to boot.

One more, from the inimitable Jeffrey Dean Foster, who may (or may not, depending on funding) have a new disc for us this year.