(I write this post with the utmost of love. I am, and probably always will be, a hipster. I'm just built that way.)
I'm guilty of it.
I liked Kings of Leon before they got famous.
Aha Shake Heartbreak and Youth and Young Manhood blew my mind. I found em by accident too. I stole what I thought was a Black Rebel Motorcycle Club CD from my sister (these albums didn't have any text on the disc). And I spun those two albums for two months straight, memorizing every world. I even went out of my way to evangelize them. I use my car like a preacher uses a pulpit; anyone unlucky enough to get a ride from me would be subjected to me espousing the benefits of these super-awesome, under-appreciated Tennessee brothers.
Some years passed.
I heard Kings of Leon as muzak at my grocery store right as I was picking up my deodorant (extra-strength).
I felt a pit in my stomach. I couldn't like them anymore.
I'm a part of it. This is what's known as The Hipster Problem: the same people who will initially lift you up will hate you when you get "too big" (a arbitrary classification).
Right. Wrong. Doesn't matter. It happens. It's the way they're (I'm) built.
So what do we do? Cater to them? Give up on going big? Ignore em? Hire a hitman to personally punch everyone who dislikes the direction your art is moving?
Since the last option is too expensive, lets look to business and psychology for the answer.
New music is essentially the same as the creation of a new technology. Using the tools of the past, a brand new form is created. Whether it gets adopted or not depends on millions of factors: quality of product, marketing, market environment, salesforce, reliability, bad weather shutting down supply lines, etc... Same for music. The best band in the world doesn't necessarily win, if their live show is lame they might not get a chance that they so deserve.
Everett Rogers Technology Adoption Lifecycle model from wikipedia's Technology Lifecycle article.
Where do y'all think Hipsters are?
In the tech world they're the people who wait 8 hours in the show to buy the newest phone for $600 even when they know it'll be $400 within 3 months. In the music world, the hipsters brag about seeing/hearing this totally unknown three piece polka-core band out of a suburb of Nowhere, Texas. What's important is the newness, not necessarily the product.
The story you tell yourself about your life is a huge influence on how you act on and react to the world. We consciously and unconsciously write and rewrite our histories to suit the main character of our autobiography.
So if we want to connect with someone, all we need to figure out is the story they tell themselves.
Let's think. Imagine you're an actor given the role of playing someone who considers themselves an innovator. What kind of story would an innovator/hipster tell themself?
-"I'm a taste maker."
-"I can see quality long before anyone else."
-"I'm more sophisticated than the later-adopters."
-"These skinny jeans look rad."
When a new find (tech, band, fashion) is discovered, the most important step is showing off the find to those around them. The subtext of this is something along the line s of "Once again I, the tastemaker, have found what is fantastic and next. Now tell me you're impressed." (I do this one all the time. I wasn't kidding about using driving my car all the time to force people to listen to music I think is fantastic and next). This is how they (I) reinforce the story.
Groovy! People who live to evangelize our music! But should we focus everything we do on the Hipsters?
Remember, the stories revolve around the "searching" and the "identifying oneself as a tastemaker through identification of new bands". Once you become ubiquitous, that emotional connection might fizzle.
Some fans are more connected to the idea of your band then your band.
Soooo where does this leave us?
Hipsters are useful early on. Listen to them then. As you get bigger, they get less important as more commited fans begin to spread the word of your band not the idea of your band.
You're not selling out if your band gets bigger. It means your not appealing to the 100% Hipsters.
That can be a good thing.