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When someone has a question, give an honest answer, the one that is dying to come off your tongue, because if it doesn't come from your tongue, it will come from someone else. And Gen-Y will find out and make decisions about your brand, or even worse, make no decisions about your brand like you do not exist.
Everyone is trying to market to Gen-Y. Why? Because contrary to this whole we're in a recession thing, Gen-Y is still spending money, buying new cars, securing jobs, starting companies, getting promotions, drinking at bars and buying new clothes/shiny things.
We all know that the problem most companies are having is being authentic to Gen-Y. Having a voice that is actually a part of this generation, that lives and breathes mainstream, urban and underground culture. Someone like Joel from Pancheros. They are going all in and it is working. He is engaging, he is informative and he brings a character and face to Pancheros that resonates with Gen-Y, and yet, even reaches X'ers and Boomers.
Yet, even in reading a Gen-Y marketing book by a team I really respect, they tend to generalize Gen-Y too much. In fact we all do. And that is tough when you are looking for a "spokesperson" to speak to Gen-Y.
Reality
The reality is that we grew up on MTV. Doesn't matter if you are a prep or a jock or a nerd, you knew about MTV and what was going on. What MTV did was a complete mash-up of youth culture. TRL, the only music staple that was left at MTV (and even though I'm old and haven't watched in years, I'm sad to see it go), mashed up the best in pop, rock and hip-hop and even got country to go pop (Taylor Swift anyone?).
The reality is that at my high school (in suburban South Florida), I played football, baseball, volleyball and surfed on the weekends, dated a girl Student Government, rapped in a group called the Burglazz (don't deny that the boy got skills), worked 20 hours, partied with everyone from every race and age and got good grades. The thing is, so did most everyone at my school.
The reality is that we grew up where race is not an issue. There was no segregation for Gen-Y growing up. I am not saying that racial tension is a non-issue, just that it is now more of a choice and in underground culture. If anything there is a cultural difference as more and more people from more and more backgrounds start to get interested in the same topics. Our country is the biggest mash-up of cultures in the world, where anyone from any background, culture, color or schooling can get ahead and make a difference for their own lives and that of the people around them.
The reality is that the same kids that listen to hip-hop in the burbs are watching political videos on YouTube and the same girl that just moved here from India is buying Rock & Republic Jeans from Nordstrom.
So who is a Gen-Y Spokesperson?
I read a post from the Social Citizens blog about this same topic titled, "Is Kanye our Kurt?" The writer got the title from a Twitter question asking, "Who is Gen-Y's Kurt Cobain?" The author doesn't suggest that Kanye is our Kurt, but does suggest that our voice may be crowd sourced.
With information available so freely and the ability to put thoughts out everywhere, at any time - is the Gen-Y voice cluttered and drown out? Do sites like Brazen Careerist go back and generalize our voice - or speak for only a portion of our Generation, that of the overachiever, career oriented, go-getter? Are we too young to define a voice?
If we keep generalizing, how then, do companies find the authenticity that will break through to this generation and make them buy, click, react, talk and feel?
By being yourself.
By inviting Gen-Y in to see what your company is really like, not the perception that your overpaid PR agency told you to look like.
That is hard to say coming from the guy running the agency, but its the truth. When things suck, you need to talk about it. When things are great, you need to talk about it. When someone has a question, give an honest answer, the one that is dying to come off your tongue, because if it doesn't come from your tongue, it will come from someone else's. And Gen-Y will find out and make decisions about your brand, or even worse, make no decisions about your brand like you do not exist.
Get back on track, Greg
So then, if brands are looking to target Gen-Y, who should talk for them? Hiring a musician or an actor, celebrity or community figure may help you sell a product today, but a long term strategy for winning Gen-Y is to be true to your brand, true to your beliefs and not being shy about who you are.
Remember...
You can be a surfer, musician, nerd or whatever else you want to be as long as it is you. That is the spokesperson that is going to win over Gen-Y.
Who do you think is doing a good job of being a Gen-Y spokesperson?
I think it's a complete waste of time to go looking for Gen Y's answer to Kurt Cobain. It's a waste because of the things you mentioned: the mashup of cultures,and being "colorblind" specifically. Because there is so much diversity in our generation and because we are such a large group, no one person or figure can represent Gen Y as a whole. Not to mention the fact that we are a very team oriented generation (yes, I'm generalzing) who probably wouldn't want one person to represent us.
All that said, you're right. The only way to appeal to Gen Y is to be open and honest. Most importantly, be yourself.
As I type this, I can't help but think that if we were FORCED to choose one person to represent Gen Y, it may just be Barack Obama. Funny, because he's in his forties and clearly a Gen Xer. But that's the thing about our generation, we don't have boundaries and we don't really know about discrimination.

There should not, now or ever, be a single voice or representative of Generation Y. We all speak equally. So I'm pledging eternal hostility to anyone who tries to anoint a spokesperson for a generation that doesn't need one.

@Ryan - luckily, i don't think that we are forced to pick anyone. Companies do need to pick someone to speak to us and that is the problem. And also, Kurt wasn't a voice to an entire generation, he was a rock star in a time when the rock and urban worlds were not as connected, when there was no Internet, etc. So he's not even the best model for that time.
@Brandon - Do we all speak equally? Is there sometimes too much clutter and at some point a few voices NEED to stand out to make change happen. Barack gave us a voice, he is the one person that many people chose to speak for the country. (disclaimer - not saying he is the voice of our Gen) In all good innovations and times of change, voices of individuals do collectively get more attention than others.
I am also curious, why doesn't Gen-Y need a voice?

We don't need a voice because we all have the opportunity to speak. No previous generation has had access to a global audience like we do.*
*Unless, of course, you want to talk about the wireless radio revolution prior to WW1 before the airwaves were controlled by corporations. Our generation doesn't have to worry about a monopolized media.
One or two voices can emerge, but I don't think there will ever be a Kurt Cobain*or a Bob Dylan for us. It's just not needed, or even desired.

Kurt Cobain's music was hugely popular, but he didn't speak for Generation X as a whole either.

@KateNonymous - agreed

Is Kurt Conbain still dead?
Looking for a voice for Gen Y is as frustrating as trying to nail a chocolate pudding pie to a wall. It looks like you should just be able to hold it up there, drive a nail in the middle and it will stay, but the reality is it will fall right away.
The issue is mainly that members of Generation Y have been addressed as individuals. Johnny is special; Susie is gifted; everyone here wins a trophy. This is not good or bad and please don't attack this as negative, because you will miss the point in doing so.
GenY has been nurtured to believe that every person matters, every self-esteem needs attention. Everyone has their own Facebook profile, their own personal MySpace, Twitter, etc. Even newspaper web sites can be customized to only contain stories that interest the individual. You have Hulu.
Boomer generations were schooled as groups, as members of communities. We had four channels on the TV and only one TV. Personalized TV watching wasn't an option and so we either did without or sucked it up during the Lawrence Welk Show and The Beverly Hillbillies (Google them.)
We learned in large groups of people reciting multiplication tables. Teachers counted on peer pressure and public humiliation to motivate us to read and learn cursive. There was no tutoring. You learned as a group or you got left behind.
In short, we were conditioned to think about the needs of the COMMUNITY and be doing that, everyone benefits. GenY is conditioned to think about the needs of the INDIVIDUAL and then everyone benefits.
So, there is no voice for GenY because GenY can't sing in unison, teaching the world to sing in perfect harmony (sorry Coke, sue me) The perfect harmony of GenY isn't everyone singing the same tune, but the symphony of individual voices combined.

@Rufus - great points, something to think about as brand marketers begin to heavily hit the younger generation this coming year. I think the more businesses that open up and allow for individual voices will have a greater chance of succeeding than the companies who tell it their way or the highway.
The difficulty I see is in filtering the voices to get to a point where you can move forward to benefit the greater good of whatever it is you are promoting/pushing.

For anyone paying attention, I know it is Kurt Cobain.. that was just a typo. I violated lesson one of the Boomer Rule of Publishing. There is no delete key on a typewriter :-)
(Typewriters are those things with keyboards, but no screen. They go klackety-klack-klack-ding and you have to roll paper in them. ..... Paper is stuff that is like a computer screen except it isn't backlit and.. never mind... I wonder if this what a conversation between someone from 1800 and a GenY would be like?
In reference to Cobain, I think about a song lyric from a Vandals song: "Excuse me, Seattle junkies don't speak for my generation".
I don't think there is, or needs to be, a single 'voice' of a generation. As Rufus makes reference to, previous generations were taught and brought up in groups, with similar ideas and motivations. Right or wrong, Gen-Y was brought up as individuals, encouraged and provided avenues for self-expression. While I agree that the 'everyone gets a trophy' mentality was bullshit (they're all in a box in my attic), they was done by the Boomer parents themselves.
But back to the main point. I don't need someone speaking for me, because I can do it myself. Unlike the past, where the availability was few and far between, it's harder now NOT to have a voice. If I see someone looking for a "voice" for them, then I wonder if they really have anything to say at all.

@Andrew. Unwittingly, again, GenY has made my argument for me.
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