When you storm out of a spat with your girlfriend, the perfect riposte comes to you only on the second flight of stairs. I’ve been standing on that stairway all week, thinking about what I should have asked TechCrunch editor Michael Arrington when interviewing him at Atlassian’s Starter-Day conference.
It was a big opportunity. In Silicon Valley, no one has asked more important questions than Mike, yet no one has ever really asked him anything. So why wasn’t I ready? I didn’t have time. My old friend Jay Simons asked me to interview Mike after my own talk, when I was on my way out of the conference.
Mike had agreed to give a speech about starting TechCrunch, but then he showed up without actually having prepared one. This was mostly on principle: he is against preparation, and he is definitely against being boring. Which most talks are.
But I also think Mike is incapable of summarizing what he has been through over the past five years, certainly not in a top-ten list or a how-to guide. The story of TechCrunch, like that of many startups, isn’t a recipe that you could follow by adding an egg and a half cup of oil.
Maybe Mike was hoping he could tell that story, but I didn’t quite ask him to, and he couldn’t have even if I did. Whenever someone asks me the simplest question about Plumtree or Redfin, I think of an exchange between two loners in a David Mamet play, and then I can hardly say a word:
-Let me tell you. It is so f***ing crazy. If it were a movie, no one would believe it. And do you know why?
-BECAUSE IT HAS NO PLOT.
This is probably why Mike hasn’t written anything to commemorate TechCrunch’s fifth anniversary.
Just before our interview, I found Mike slumped in a green room, diddling with his phone. I asked him what he wanted me to ask him. He held up his phone and said “Can you believe the battery life on this thing?” He often talks to me as if we share a love of mobile devices. A Tom-Cruise impersonator hired by Atlassian then walked in with his girlfriend, and our attention turned to getting him to take off his wig, which was made from human hair.
Without realizing that Mike has repeatedly called for an end to the friendly, ancient custom of shaking hands, the impersonator asked if he could “go Oprah” while on stage with Mike, with incessant physical contact; to my surprise, Mike agreed. Meanwhile, I drew up a list of my favorite San Francisco restaurants for the impersonator’s girlfriend.
And then, somewhere between “Shalimar” and “Gary Danko,” it was time to face the crowd. Even though Mike would complain more than once that I didn’t ask the agreed-upon questions, that was because we never actually agreed upon any questions. We had a nice chat. I smiled a lot, and he looked down at his paper a lot.
Afterwards, I walked out into the toothless San Francisco sun wondering why I hadn’t asked what was really on my mind:
- What is your all-time favorite TechCrunch post?
- Which posts do you regret?
- You’ve made much of the fact that the New York Times technology editor told you he enjoyed reading your blog every day. But don’t you read the New York Times every day? What else do you read?
- Why do you review sex toys? How do you find someone so intrepid, fun-loving and pleased with himself as self-appointed head tester John Biggs, who tackles both his and her equipment with equal gusto?
- You’ve argued that digital content such as music and books should be free, and that the most interesting technology services are free. Since the success of Zynga, iTunes, Groupon, Gilt — and the bankruptcy in 2009 of many free online services, not to mention many bands and authors — has the world shifted away from this model? Does free only work if you shoot the moon, and reach Yahoo’s scale? And I’ll be honest here, the answer I’m looking for is “Kelman, you were right all along.”
- TechCrunch loves saying newspapers have no future. What about the future of blogs? How many blogs will grow beyond their original authors to become sustainable, independent businesses? How many small-scale bloggers can post day after day, year after year, on relatively meager economics? How is a large-scale blog like TechCrunch going to be different from a newspaper? And given that the top-25 blogs are almost all five years old or older, is it fair to say that blogging has become an institution in its own right?
- Story problem! A startup is launching a major new online service at midnight, give or take three hours for glitches. It doesn’t want anyone else to notice the site until TechCrunch gets the scoop. But it can’t brief TechCrunch in advance. Should it call you at 1 a.m.?
- Why is TechCrunch so worried lately about the privacy of the world’s least-private person?
- Is TechCrunch becoming an events company that happens to have a blog?
- How many Chipotle burritos do you estimate you’ve eaten in your life?
- What relationship do you want to have with entrepreneurs? Are you one of us, or one of them (journalist)?
But really, if I only had one question, I’d ask Mike a variant of this one.