What we can learn from Guy Kawasaki's "Web 2.0, User-Generated Content, Citizen Journalism, Long-Tail Social Media Site" venture

I have been watching the development of Guy Kawasaki’s new venture, Truemors, from the sidelines for the last couple of weeks, fascinated by both the business idea and the reaction in the blogosphere.

He took a subtle approach to the launch at first, hinting at the kinds of input he wanted from his blog readers.  This garnered some strong reactions, among them:

• “Did you hear that Guy is the new Perez Hilton? He must be out of his mind! Please tell me this post is a joke.”
• “Did you hear that Guy has sunk to a new low? Come on Guy… gossip is one step away from pornography.”
• “All the pitch’s (sic) you hear, and this is the kind of thing you want to attach your name and valuable reputation to…another hurtful, hateful gossip site/company?”
• “stick to tech, guy, that’s what you are. don’t cover hollywood gossip bs.”

His response was interesting, and as always contained a general lesson about entrepreneurship in addition to responding to the criticism.  An excerpt:

“Truemors, and your idea, might not succeed, but if you listen to the naysayers, you won’t even try. Then, for sure you won’t succeed. The first lesson is:

If you believe in something, go for it. This is the only way to really find out. Mathematically, the naysayers are right 95% of the time, but believing you’re in the 5% is what makes entrepreneurs entrepreneurs.”

Subsequent coverage has been really interesting, from some virulent detractors (mixed with a few supporters) at TechCrunch to an unimpressed Seth Godin (although a recent post Pundits are (nearly) always wrong is an interesting follow up) to a very revealing interview on Red Herring.  Some of my favorite quotes from the Red Herring interview:

RH: You said something in your blog about you have to believe in something. You have to push it and see what happens.

Mr. Kawasaki: Granted, it may not work. The odds are 90 percent it won’t work. But how do you know when you have the 10 percent unless you try. That’s the whole point, right? Now, to say that a few years ago, you’d have to say, ‘Well, how do I know if I have the 10 percent chance of succeeding, but I need $2 million to do that.’ Now, you can say, ‘I have a one in 10 chance of succeeding, and I need $12,000 to know that.’

RH: Presumably you feel you’ve been successful.

Mr. Kawasaki:  As a person you tend to pick a definition of success that makes you successful. So at the end of the day, if I were to meet my maker, the question is, was I a good father, was I a good husband, and in my professional career, did I make the world a better place. And if you use that test, I think I was successful. And have I made the world a better place by evangelizing Macintosh? Yes. Have I made the world a better place by evangelizing, or writing these books and giving these speeches? Yes. I think I’ve helped many an entrepreneur be more successful. But do I have a yacht that can only go underneath the Golden Gate Bridge at low tide? No. Do I own a Ferrari? No. Do I have a G3? No. So, maybe I’m a failure. I don’t lay awake at night about this. But I would like to drive more than a Toyota Sienna.

RH: How do you deal with the criticism that shows up on your site.

Mr. Kawasaki: Well, I assume that all one thousand people in the world who hate me have now expressed themselves. It’s cathartic. You cannot take it personally. I bet you the day that Vista shipped, Bill Gates got a few emails and a few rants. And the day Steve Jobs announces the next iPod or whatever. It comes with the territory. It would be somewhat hypocritical for me to say, “But, hey, you can only say good things about me.” But don’t get me wrong. You know, the purpose of Truemors is to either inform or entertain. And if you just put something up there that says, “This site sucks,” I see no redeeming value of keeping that. I delete that. I don’t even hesitate.

Then there are perspectives like Bob Sutton who didn’t comment a lot on the business, but rather analyzed the way in which it was launched in  The Prototyping Process:  How it has Evolved on the Web.

I cannot profess objectivity when it comes to Guy, as I have had extremely positive and constructive interactions with him on multiple occasions.  But despite my respect for and friendship with him, I know he is a tell-it-like-it-is kind of person and abhors mindless “attaboys” as much as he does reactive criticism.  So here are some thoughts and questions about the venture:

• Is a lot of the criticism coming because people find an endeavor like this does not jive with Guy’s philosophy to “change the world,” or is it because we hate it when people we respect do unexpected things? How does this relate to each of us as we experiment with things that our parents, colleagues or target market may consider “out of bounds?”
• Is there anything inherently wrong with creating a venture to exploit popular social and technological trends, and try to make a lot of money, all in the name of experimentation? As long as no one gets physically hurt and air pollution is not increased, do we need to have every business we engage in have deep social impacts?
• What was it about this idea, out of the hundreds that he probably considers on a monthly basis, that lit a spark and seemed exciting enough to implement? I don’t see Guy being at a point in his life where he needs a lot more money or exposure, so there must be something about the benefits of starting this business that outweighed the risk of doing it.  Perhaps it was the challenge, or the financial opportunity or the simple urge to rankle his stuffy VC peers, or to tickle a funny bone.
• Does the nature of the site lean more towards citizen journalism and social networking, gossip or entertaining factoids like a modern Farmer’s Almanac on steroids?  Or might it spawn abuse and smear campaigns, like some fear?  Random samples from the page of Truemors:

• “Did you hear that Greenpeace is building a replica of Noah’s Ark to publicize the dangers of global warming?”
• “Lindsay Lohan’s back in rehab? Talk about unflattering photos!”
• “Google and Jeopardy are partnering. I think this is a good thing.”
• “Did you hear some guy in New Hampshire wouldn’t shake Mit Romney’s hand because Romney is a Mormon?”
• “Did you know that it costs $600,000 to get a NY taxi medallion?”
• And what John Dodds found amusing, “Mike Meyers got kicked out of yoga class for farting”

I will never be able to take the “morally superior” position on the content, as I am as likely to devour a People Magazine, watch American Idol, scan the headlines of newspapers and gasp at political scandals as anyone else.  Will I spend all my time perusing factoids at the expense of completing meaningful work?  Probably not, but I will enjoy taking breaks to entertain and distract myself from real life challenges.

One thing I look forward to is learning about the experiment every step of the way through Guy’s blog.  I am notoriously wimpy when it comes to sharing business challenges and failures with the blogging world, probably out of fear of criticism and ridicule.  Guy, on the other hand, seems to embrace it, and believes, as he once told me as I was whimpering due to attacks on my choice of Che to illustrate a blog post, “Controversy is good.”  That has stuck with me, and it somehow seems fitting behavior for entrepreneurs whose job it is to rock the boat and challenge widely held assumptions.

Guy is telling the behind the scenes story of Truemors at Launch:  Silicon Valley 2007, with a talk from which I stole the title of this blog post:  “How I Launched a Web 2.0, User-Generated Content, Citizen Journalism, Long-Tail, Social Media Site for only $10,918.09” Given the juicy reactions so far, it promises to be a lively session.

What is your reaction to the Truemors launch?  What can you learn from it to apply to your own startup venture?