NICK DOUGLAS — Look, I can dig old people. Just because I'm young, energetic and oversexed doesn't mean I'm not aware that some day I'll reach the doddering age of 25. But I know there's a way to keep my inner child, or at least my inner arrogant college junior, by watching the example of still-cool graybeards like Steve Jobs. Guys like Yahoo's awkward CEO Terry Semel, though, show that you can't earn cool just by trying hard. While some of the following lords of tech have kept their cool past age 50, some have turned into embarrassing old men.
Name: Vint Cerf
Schtick: Cerf invented the TCP/IP protocol in the 70s, making the Internet possible. He now chairs ICANN, the organization that decides, for instance, when to release a new top-level domain like .biz or .xxx. He's also a VP and "chief internet evangelist" at Google. And the dude knows how to dress, often wearing a well-cut three-piece.
Verdict: All that power makes Cerf seem like a Tolkein-style wizard or the Matrix's Architect. He's badass.
Name: Steve Jobs
Schtick: Apple's founder has always been cooler than the nerdier Bill Gates, but he still had a dorky hairdo and outfit. But how has he held up? Well, in the past decade, he's recaptured his own company, released the slickest looking personal computers and mp3 players, and adopted a casual uniform that copycat nerds try (and fail) to pull off.
Verdict: Okay, he does have an embarrassing love for U2. But that can't stop Steve from earning an overall rating of cool.
Name: Craig Newmark
Schtick: Newmark (who, by the way, looks 45 tops) has gone from being famous for starting Craigslist.org to being famous for not turning it into a billion-dollar business. He and his CEO Jim Buckmaster land in several news stories a year just for not gouging their millions of users for money; Craigslist only collects fees for employer postings and certain real estate ads. Craig represents the live-and-let-live half of San Francisco liberalism without the annoying babysitter-state part.
Verdict: Dig Craig's man-of-the-people flair; he works in Craigslist's unassuming office in SF's remote Sunset District, and he lives in the city's Cole Valley neighborhood where he holds court at the Reverie Cafe among the yuppies and their kids. But most importantly, Craig is the ultimate self-effacer; he likes to compare himself to George Costanza. Craig is subtly cool.
Name: Terry Semel
Schtick: Yahoo's always wanted to go Hollywood, and so has its CEO. Semel tries harder than any other tech exec to look cool, even arm-wrestling with Tom Cruise in front of an audience of his employees. Dude, look how tense Semel is in this admittedly pasted-out-of-context shot! Facebook founder Mark Zuckerberg, whom I've heard is awkward enough himself, reportedly called Semel an embarrassing uncle.
Verdict: Sorry Terry, you've been rejected from the frat. Maybe you can star as the clueless uncle in an Apple Jacks commercial.
Name: Larry Ellison
Schtick: Oracle's founder is married to the lovely and witty (at least at this party I snuck into at the Ellisons' guest house last summer) romance novelist Melanie Craft. (People also allege that he fools around on the side, but we get the feeling Melanie doesn't mind.) The dude looks like the lost brother of Chuck Norris and George "You're gonna like the way you look" Zimmer from Men's Wearhouse. He recently joined his own yachting team; he owns more of Malibu than Mel Gibson. His son's a Hollywood actor. Steve Jobs took the photos at his wedding.
Verdict: As the kids say, dude is peeeyamp!
Schtick: Peter Oakley doesn't live in the Valley or run a tech company; he's the most famous elderly person on YouTube. He's posted seventy videos, mostly stories from his long life.
Verdict: Wikipedia says he's been called "the coolest old dude alive." I've no idea who said that, but they were right.
Photos courtesy of Getty Images; photo of Geriatric1927 from Wikipedia. Nick Douglas writes for Valleywag and Look Shiny. Editor Nick Denton pitched this story to Douglas with, "Your best items are written from the perspective of callow youth."