I didn't plan to pick a fight with Steve Jobs last night. It just sort of happened: An iPad advertisement ticked me off; I sent the Apple CEO an angry email; he told me about "freedom from porn."

The electronic debate proceeded from there.

Of course, there was a bit more to it than that. There's the context: Jobs' legal fight with my employer Gawker Media, over the handling of an iPhone prototype; my long-simmering worries about Apple's growing power to limit self expression through its lockdown on iPad apps; and the fact that my wife, who might normally (and quite sensibly) veto the idea of spending Friday night sending email flames, was out of town.

So in retrospect I was primed to lash out. But there was some serendipity too: Watching a new episode of 30 Rock on my digital video recorder, I somehow failed to skip over an Apple ad I'd never seen before, one that billed the iPad as nothing less than "a revolution." You can see an excerpt of the ad at the bottom of this post.

With a Stinger cocktail at my side, I dashed off a short, pointed question to Jobs' well-known email address.

A few hours later—after midnight here in California—he got back to me. And I got back to him. And so on.

I didn't identify myself as a writer for Gawker in my initial email, sent from my ryantate.com email address. But, as you'll see in the exchange below, I eventually made my affiliation clear, and Jobs didn't seem bothered. Between that and the fact that Jobs regularly uses emails to disclose new information to the public, knowing full well recipients now regularly make the exchanges public, I feel fine reproducing the thread below.

It's a feisty discussion, as you'll see. And heated, especially on my part.

Rare is the CEO who will spar one-on-one with customers and bloggers like this. Jobs deserves big credit for breaking the mold of the typical American executive, and not just because his company makes such hugely superior products: Jobs not only built and then rebuilt his company around some very strong opinions about digital life, but he's willing to defend them in public. Vigorously. Bluntly. At two in the morning on a weekend.

As much as Jobs and his actions anger me, and as harsh as I was to him, I came away from the exchange impressed with his willingness to engage.

Some notes on the actual content follow after the emails. Click any message to enlarge:

A few notes on the emails:

  • There's something absurdly Orwellian about Jobs' line that the iPad provides "freedom from porn." It's a statement I suspect will haunt him.
  • My line about Flash and my MacBook Pro is silly; Flash as a Web plugin is, as I myself have written, a resource hog, no matter how well the miraculous battery in my Apple laptop handles that hoggery. There's no telling how Flash might hobble my iPad''s A4 processor. But cross-compiled Flash apps are an entirely different matter: They run as native Objective C code, and Apple has a chance to review them for performance. Apple has never tried to argue that cross-compiled Flash wears batteries down any more quickly than other Objective C code, and in fact approved more than two dozen such apps before changing its policies.
  • Speaking of regrettable lines: Why the heck did I bring up my wife in connection with "freedom from porn?" I was trying to say it's a canard that porn somehow harms families, or something terrible and shameful, so I mentioned the other half of my family.
  • I was a little unfair summarizing my contact with Time Inc.; the company has not "crowed" about its iPad bridge software, and in fact has plans to iteratively improve its iPad product. That line was based on email exchange that I had with a Time Inc. executive who was speaking off the record and not on behalf of the company. As such, I've blurred a name that I had no business dropping. But I do think, as I said, that a native Objective C app that merely contains magazine content, like Time's, is a lot less exciting than an app that has some real interactivity, even if it's been cross compiled from Flash.

And here is the end of the iPad commercial that set me off:

Related: Steve Jobs Is Opening Up Apple One Email at a Time