Editor's Note: Two years after Michael Arrington sat to talk with Lloyd Grove, he sold TechCrunch to AOL while he continued on as editor of the influential blog. On September 1, 2011, AOL announced that Arrington was leaving the site to start a venture capital fund. What follows is the interview from 2008.

Nobody is more obsessed with the doings of Silicon Valley than Michael Arrington, whose 2½-year-old website, TechCrunch.com, has become an international clearinghouse for gossip, rumor, and inside information about the internet business.

Arrington, 37, who left a lucrative career as a mergers and acquisitions lawyer to become a cyberspace entrepreneur, runs TechCrunch from his rented house in Atherton, California, presiding over a tiny staff of bloggers and reporters who regularly reveal the secrets of life and death in an industry that produced Google, Microsoft, Facebook, and thousands of other startups that you've never heard of, because they crashed and burned into oblivion and lost billions of dollars for adrenaline-seeking venture capitalists.

"I look at entrepreneurs as, in a sense, modern-day pirates," Arrington told Portfolio.com this week in an exclusive interview.

The outspoken Arrington also gave his views on Microsoft's attempt to acquire Yahoo, Barry Diller's recent troubles, and how he has managed to generate millions of dollars in advertising revenue for himself and his partners by never taking a vacation.

Lloyd Grove: You must keep crazy hours. I see that you're posting stuff all the time in the wee hours, aren't you?

Michael Arrington: Yeah, I try to get on normal hours and it just never seems to work.

L.G.: Really? Tell me what the rhythm of your day is like.

M.A.: Just a lot of news breaks at 9 at night and 11, 12, and so I'm usually up and kind of just try to wind down after that, and it's hard. Then I end up writing a couple more posts and suddenly it's 2 o'clock or 3 o'clock in the morning. But even when I don't have to write, I have some trouble falling asleep. It's not a healthy lifestyle.

L.G.: One of the things that sort of charmed me was that at some point when you were practicing as an attorney, you were so nervous about meeting Steve Jobs that you spilled coffee all over yourself. What was going on there? Are you starstruck?

M.A.: I was a very junior associate, I was a second- or third-year practicing attorney and I was working on a deal when Apple bought Next and brought Steve Jobs back into Apple, and the deal itself was crazy. It's just like one day, the partner said it's happening, let's do it. And usually we have a little prep time, but we didn't. We just started working, and we actually didn't even leave the law firm for six days. We showered there, we went home and grabbed some quick clothes and came back, and I actually got pneumonia because I hadn't slept and people were sick. But they got the deal done. It was nuts, and then a few weeks later when everything was closing, a partner, needed to get everything signed by Steve, who lives in Palo Alto, and I lived there at the time, and he brought me along with all the documents. And I was able to meet him, and shook his hand and all that. I was nervous and didn't say much, but he was very nice. I mean at that point it's just that I was a 26-year-old attorney and he was Steve Jobs! Then the closing happened probably a couple months later, and I remember I was at Apple with another associate, and we just had all the documents laid out and the other attorneys were coming in, and the general counsel of Apple was coming in, and Steve was going to come in and sign a couple of last things. And laying everything out, I had gotten a Styrofoam cup of coffee and I was just so nervous about the deal going right and Steve coming in and the general counsel coming in, my hands started shaking. And it literally just shook the coffee all over my shirt. It was hilarious. It was luckily near a shopping mall. I had a dark suit on so it didn't affect my pants. I drove to the mall, bought a new shirt, lost the tie, put it on and went back to the closing, and I actually got there before anyone else got there.

L.G.: You had lunch with Bill Gates as well, more recently.

M.A.: Yeah, in '06, I had lunch with Bill Gates, it was a surprise, that was fun.... There were only five or six of us. I got a chance to hang out with him a little bit beforehand.

L.G.: Now that you're older and wiser and have a reputation of your own in this world, do you approach these folks more as an equal?

M.A.: No, no. I look at entrepreneurs as, in a sense, modern-day pirates. They tend to be bright individuals, although sometimes they're uneducated and they become stars based purely on will and intelligence. But they tend to walk away from high-paying jobs that help them support their family and they're not in a position where there's a lot of risk. And something drives them to walk away from that to start a company, just to see if they can. They're so passionate about the idea, they just have to see if they can do it. But they actually do something that economists would call insane, which is that they attach utility to risk instead of the other way around. So the more risk that's there, the better. And pirates used to do that. I really think entrepreneurs are a little bit crazy and really cool, but they also drive the economy. If you look at the economy, particularly in Silicon Valley, how much of it is driven by startups that were once just an idea of a person or two, you know, it's pretty awesome. And if you look at the Googles and the Yahoos and the Microsofts and the Oracles—I could list 200 other companies—and how many people they employ and how their products are so much more productive, that's pretty awesome too. No, I'm still in awe of the entrepreneur. And it's not just the Bill Gateses and the Steve Jobses. Last night I was at a small dinner party, and I met an entrepreneur who moved here from Philadelphia recently. He's doing a small startup, he hasn't raised money yet, but it seems to be doing well. And I talked to him for, I don't know, 45 minutes to an hour, just wanted to hear everything about his life, why he did it and why he left the consulting firm that he was at, and what he wants to do. To me it's just fascinating.

L.G.: There's been some suggestion in recent weeks that, with the recession looming, allegedly, people in Silicon Valley are getting a little cautious and perhaps even nervous, and people are tightening their belts and hunkering down. Do you get any sense of that?

M.A.: There's definitely a sense that maybe the economy is turning. The key there, though, is to watch venture capital and how it's flowing, and what we're tracking right now is almost $1.3 billion in new V.C. dollars just in February. That's way up from January and up from December, and more than November. So V.C.'s are sort of still spending as far as I can tell, and as long as that keeps going, generally speaking, things stay good.... If we're in a recession...people might be cutting back a little bit on spending. But we're not there yet. Now if it does happen, though, having a recession every few years isn't necessarily bad. It tends to separate the wheat from the chaff, and it gets rid of all the startups that aren't going to make it, and lets those who leave go on to other things and be more productive.