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.


  • http://www.zillow.com Spencer Rascoff

    Glenn Kelman “boring”? Say it ain’t so!? Never.

  • http://wac6.com William Carleton

    Glenn, this is really thoughtful, and moving (and sobering). One thought, or hope, I have is that folks like you and Fred Wilson are really ahead of the curve. That is, having behaved and spoken in the public eye eye for so long and having blazed the trail of transparency for others to emulate, you guys are now feeling the implications that argue for reassessing the wisdom of limits. But you’ve earned that re-assessment. Others remain withdrawn for not-the-right-reasons. Some of us are still on a journey exploring what happens when transparency, not secrecy, becomes the default.

  • Bryan Waters

    “Good judgment comes from experience. Experience comes from bad judgment” from fortune cookie I received last week. I believe you, Fred, and the person who wrote that fortune cookie have it figured out! Very interesting, thanks.

  • http://blog.redfin.com/blog/author/glenn%20kelman Glenn Kelman

    Spencer, I’ll try to spice things up once and a while just for you…

    Bryan, how do fortune cookie companies hire such geniuses? I really like that line.

    And William, thanks very much for the kind words. A very thoughtful comment.

  • julie S. Jacobson

    GO Bears – don’t we usually just stick it to Stanford though, isn’t that what they’re there for?? BA 1994 me ;-)

    thank you for this piece. it is true, in this age of everything landing on the internet we do need to be mindful, yet stay genuine. a fine balance.

  • http://www.gmail.com Anonymous

    Glenn – I love almost everything you write. I wonder how partisan things actually are. We did have a Civil War at one point. That was pretty partisan. During the election between Adams and Jefferson, allegations of incest were bandied about. Alexander Hamilton was shot in a duel. William Jennings Bryan, as Secretary of State, resigned in protest at the start of World War I. We had McCarthy. Nixon-Kennedy in 1960 was almost as close as Bush-Gore. We had the Civil Rights Era. Politics is politics. Do you know what happens when people agree: You get things like the Gulf of Tonkin Resolution passing 416-0 under false pretenses authorizing use of military force in Vietnam under the President’s authority.

    Today seems downright boring. Both parties basically agree that Capitalism works. No one can argue about present American supremacy, especially militarily. Both parties have a similar foreign policy. There is no risk of overturning Roe v. Wade. Crime is the lowest it has been in decades. What exactly is the divisive issue of our day? Nothing, it seems.

  • http://blog.redfin.com/blog/author/glenn%20kelman Glenn Kelman

    Excellent points Anonymous. There is some nostalgia about the absence of partisanship among “statesmen” of a different era. And I agree that we have to less disagree about than in the past, which makes the disagreements all the more silly…

  • Ben

    My first job out of school was at a management consulting firm. I came in big-haired and untamed, a flyer in the recruiting process that didn’t fit the mold but presented as someone with potential, if he only had some grooming. I learned quickly: the hair soon cut, I shopped for khakis at the Gap, and even wore the requisite suit and tie til 6.30pm most Mondays through Thursdays. But along with the standout rawness of youth, my standout brutal honesty and even my creativity were tempered. Since they weren’t backed by years of business experience, that rawness was more likely to more often cause big problems with the client than to produce unexpected insights.

    Over the years, I admit it, I’ve gotten boring.

    The allure of avoiding making mistakes is that it spares the pain of the hot stove burner. But it doesn’t create success.

    Now I search deeper within myself to find the impulsive brash strength of self and let it out more often.

  • Pingback: About Last Night… | Redfin Corporate Blog