I’m : a programmer, writer, podcaster, geek, and coffee enthusiast.

Live with Phil

John Gruber’s live performance of The Talk Show at WWDC was unusually special this year.

It was announced and sold out without John specifying any guests. He didn’t hype it up or drop any enticing hints. Nobody knew who would be on stage until they walked through the curtains, but we all assumed it would be some of the developers, journalists, and friends who usually join John to give The Talk Show its great personality.

But after a brief introduction from Merlin Mann and Adam Lisagor, John introduced, “and I shit you not,” Apple’s senior vice president of marketing, Phil Schiller.

Being familiar with John’s dry humor, I’m not sure most of the audience believed him. Many cheered. Some hesitated. For a few seconds, nobody walked out, and people started laughing, thinking they got the joke.

And then Phil Schiller really walked on stage.

Apple doesn’t do this.

Apple executives rarely speak publicly outside of Apple events, especially for live interviews. One of the highest-ranking executives of the world’s highest-profile company being subjected to questions, unprepared and unedited, in front of a live audience full of recording devices, is rarely worth the PR risk: the potential downside is much larger than the likely upside. Do well, and a bunch of existing fans will like you a bit more; do poorly, and it’s front-page news worldwide.

Both Apple and Phil Schiller himself took a huge risk in doing this. That they agreed at all is a noteworthy gift to this community of long-time enthusiasts, many of whom have felt under-appreciated as the company has grown.

With the wrong interviewer, this could’ve been a recitation of PR-friendly softball questions with perfectly designed, talking-point responses that would’ve gone nowhere and benefitted no one. But Apple PR doesn’t want that any more than the audience does.

Or it could’ve been boring questions about hardware rumors that no Apple executive would ever answer. I’ve never seen another interviewer that didn’t waste time on these dead-ends that, in their wildest dreams, might answer questions relevant only for a few short months or years.

But John Gruber is better than that, and we all know it, including Apple.

John asked real questions on challenging subjects, including gender diversity, my alleged software-quality decline, discoveryd problems, thinness trade-offs with battery life, the new MacBook, continuing to sell 16 GB iOS devices, and whether the Apple Watch should have shipped without WatchKit 1.0 apps since the native SDK was so imminent.

And Phil gave real answers to each one. Apple iterates, argues, and evaluates trade-offs. Sometimes they don’t get it right. Sometimes they’re more aggressive pushing the tech forward than power users like us think they should be. Sometimes there are trade-offs in product design that we don’t consider, or that we prioritize differently than they do.

Phil made quick, smart, informed references to Apple-related podcasts and sites, including mine, that made it clear that he personally reads and listens to our community.

I’ve heard that this was the case for Phil and many other Apple higher-ups for a long time, but I’m not sure it has ever been made so clear publicly.

Apple is listening.

Between the serious and technical discussions, Phil and John lightly joked about typography and sports teams with each other and the audience.

They had the great rapport of professional acquaintances who’ve known each other for a while and clearly respect each other.

I’d listen to their podcast.

Apple is just people. Their usual communication style makes that hard to see and easy to forget.

Phil’s appearance on the show was warm, genuine, informative, and entertaining.

It was human.

And humanizing the company and its decisions, especially to developers — remember, developer relations is all under Phil — might be worth the PR risk.

Or maybe he just thought it would be cool. He’s a pretty cool guy. I’m glad we got to see that, and we got to see that because of the career, personality, and perspective that John Gruber has been building for over a decade.

John has always seemed to want The Talk Show’s annual live show at WWDC to resemble his fond childhood memories of the Johnny Carson late-night TV talk show. Past years have been closer to that format and pacing, but this was nothing like it at all.

John isn’t Johnny — John is better. And I’d much rather watch this show than anything on TV. Talk shows on TV must be liked by everyone; podcasts sell out live venues by being loved by a niche.

This meant a lot for both John and podcasting. Apple sent an executive to be interviewed on a podcast, and one of the highlights of John Gruber’s career as a writer didn’t involve writing at all.

I’m just hoping he can get Moltz for next year’s show, because I sure as hell wouldn’t want to follow this.

Special thanks to the App Documentary guys for lending me the camera to shoot these photos at the event.