Fortune Article

Dan Benjamin’s 5by5 podcasts are the place to go to hear Mac gurus free associate

In the middle of a live broadcast discussing Twitter’s new president, Google’s (GOOG) Android market share and why Microsoft’s (MSFT) Windows Phone 7 is a terrible name for an operating system, the guest pauses to ask his co-host: “Speaking of well-hung Wookies, does this show have a sponsor?”

The guest is Daring Fireball‘s John Gruber, dean of the Apple (AAPL) bloggers. The co-host is Dan Benjamin, a Linux programmer turned talkshow impresario whose 5by5 Internet Broadcast network has become destination listening for hundreds of thousands of Mac and iPhone devotees.

That Gruber, who does a weekly 5by5 podcast called
The Talk Show
, felt free to leap from a discussion of the latest Nielsen smartphone survey to why Chewbacca was permitted to wander through the George Lucas’ Star Wars series without any pants is one of the things that makes Benjamin’s talk shows so appealing.

In stark contrast to the rapid-fire, deadline-driven pace of most cable news and drive-time radio, Benjamin gives the impression that his guests have all the time in the world — which in a sense they do. Any subject that he and his co-hosts can’t dispose of in 60 to 90 minutes is simply pushed forward to next week’s show.

And what co-hosts they are!

In addition to Gruber, one of the smartest and quirkiest writers covering Apple, there’s …

Hypercritical with Ars Technica‘s John Siracusa, whose motto is that there’s no technology so perfect that he can’t find something to complain about. My favorite episode was the one in which he makes the case — in an SAT-type analogy — that Apple’s Lion is to OS X as the original Mac OS was to MS DOS. See Episode #3 The mouse is not a finger.
Build & Analyze with Marco Arment, co-founder of Tumblr and creator of Instapaper, who brings a razor-sharp software engineer’s mind to bear on everything from iOS app design to brewing a perfect cup of coffee. He did a show right after Rupert Murdoch and his team launched The Daily in a live webcast — his first glimpse of the men who run mainstream media. His on-air reaction: “What a bunch of dicks!” See Episode #11 The Mustache Guy.
Back to Work with Merlin Mann, a brilliant, eccentric Mac enthusiast who urges listeners to follow Buddha’s path to work-place enlightenment. His third broadcast was a roller coaster ride with a brain fired up on ADHD meds — and 5by5’s most-downloaded episode of all time. See Episode #3 The Second Arrow.
The Talk Show with John Gruber is the longest-running of Benjamin’s Apple-oriented one-on-one shows. Chewbacca’s pants are discussed in Episode #11 Hans Solo’s Dog.

“I’m fascinated by these guys — the pundits, the experts — who think about the stuff I care about every day. And I’m lucky enough to talk to each of them for an hour every week,” says Benjamin. “For me, it’s a dream come true.”

Literally. Benjamin’s parents tell stories about little Dan at age 3 carrying around a tape recorder and interviewing his Superman toys. He grew up listening to talk-radio hosts, first in Philadelphia and then in central Florida, and he told his parents and his girlfriend — now his wife — that that’s what he wanted to be when he grew up.

But he switched from broadcasting — his major in college — to English and computers after a couple of veteran talk show hosts warned him off. “‘Don’t do this,’ they told me. ‘It’s a terrible career. You’ll spend decades spinning vinyl in no-name towns before you get your own show and, if you’re very lucky, get to talk about things that matter to you.'”

All that changed in June 2005 when Apple announced that iTunes would include built-in support for podcasts.

“When podcasting came around I said, this is great. I can do my own interview show.” He started a weekly called The Conversation, which he ran on the side while working as chief technology officer for a Silicon Valley start-up. “The show was mired in geek space,” says Benjamin, “but I loved it.”

Meanwhile, Leo Laporte, the host of TWiT (This Week in Tech), had shown that a well-run ad-supported tech-related netcast network could generate real revenue.

So in 2009, at age 37, with a two-year-old son and a supportive wife but no visible means of financial support, Benjamin decided to take the plunge. “I bet I could pay the rent,” he recalls. “I bet there was business here.”

He built his own broadcast facilities, coding the website by hand and putting together the Linux network that runs it. 5by5 — an old NATO radio term meaning “loud and clear” — was launched in January 2010.

Today Benjamin hosts nine shows himself — all with audio, some with video — and produces shows for a half dozen outside hosts. And he’s more than just paying the rent.

“I feel like there is the potential to make this much bigger,” he says. “My goal is not to be on every show. My goal is to build a platform for people who are creative and insightful, and to remove the obstacles for them to show up for 30 minutes every week and be awesome.

“This is the next form of media. It’s like radio. It’s like TV. But it’s different, this platform of independent content creation. This really really is the future.”

For a weekly schedule of 5by5 showtimes, click here. Past episodes are available for free on iTunes here.

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[Follow Philip Elmer-DeWitt on Twitter @philiped]