Why CEOs Are So Boring

Henry James once wrote that a novelist has only one obligation, “to be interesting.”
I’ve sometimes approached being a CEO in the same way, straining when in public to compare Redfin to a penguin devoured by a leopard seal, a public-square streaker, a second-tier basketball player. I said what I really felt, but I also tried to be interesting, too.
When did that change? Two years ago, standing before a room full of computer-science students snoozing through a speech on how to get a primo job, I was relieved to hit upon the vein of emotion I felt as a Berkeley student competing against Harvard and Princeton graduates: sticking it to the rich kids.
Imagine my surprise when my child’s nanny told me last month that she saw the speech on UW TV. Hopefully class warfare doesn’t motivate her to stick it to anyone, especially not a pampered little kid.
Had I known how many people would see that speech, including many of the folks at private schools we’re now earnestly trying to recruit, I’d have been more measured. When I think about all the funny things I’ve said to the press, I worry. So now, as I walk off-stage from a speech, I tally up a damage report: who could possibly be offended by what I said?
I’m not the only one who worries. Fred Wilson yesterday recommended reviewing the footage of a talk before it’s published, but you don’t often get that opportunity, and it takes too long to review when you do. Others, like Jason Calacanis, go Jersey Shore, letting the fur fly and forgetting the consequences.
I’ve had to adopt a different solution: to become boring. This isn’t a simple matter of being less flamboyant. In my new, long straight phase, I just say less, period. As the Internet gets more interesting, reality gets less so; as communication technology improves, discourse deteriorates.
And as the Internet gives power to the people, less and less gets done.  We all talk about the sharp increase in political partisanship as if it were a curse visited on us from the sky, or largely the fault of only one side, when its actual origin is plain as day: the Internet. The government is at war with itself because every Congressperson is posting zingers to Twitter, Facebook and the blogs. We saw the same trend when newspapers first proliferated across cities like New York in the 19th century.
There’s a quieter way to talk to one another. Redfin will always be transparent about what we’re doing and why — it is one of our cherished values — but there are still words you whisper late at night, moods in falling snow, grievings in loneliness, gusty emotions on wet autumn roads that all of us want to be able to share in an intimate setting without worrying that it will become titillation fodder on the Web.

Glenn Kelman

Glenn Kelman

Glenn is the CEO of Redfin. Prior to joining Redfin, he was a co-founder of Plumtree Software, a Sequoia-backed, publicly traded company that created the enterprise portal software market. In his seven years at Plumtree, Glenn at different times led engineering, marketing, product management, and business development; he also was responsible for financing and general operations in Plumtree’s early days. Prior to starting Plumtree, Glenn worked as one of the first employees at Stanford Technology Group, a Sequoia-backed start-up acquired by IBM. Glenn was raised in Seattle and graduated from the University of California, Berkeley. He is a regular contributor to the Redfin blog and Twitter.

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