by Tom Kaneshige

Silicon Valley Tech Execs Behaving Badly

May 28, 20146 mins
IT Leadership

Move over Donald Sterling. The exploits of these misbehaving technology executives give the now-infamous billionaire L.A. Clippers owner a run for his money when it comes to moronic acts.

Credit: Thinkstock

Acts of arrogance are a time-honored tradition among the Silicon Valley digerati. Tech billionaires and power-crazed chief executives live in their own worlds in which codes of social conduct — even some laws – don’t apply. Or, at least, these execs don’t think they do. It seems almost every day some news breaks about a tech titan acting in a way that leave us shaking our heads. Here is a list of a dozen doozies.

(Want more? Check out “10 Dumbest Things Tech CEOs Have Said and Done,” and see where Steve Jobs, Larry Ellison, Meg Whitman, Mark Zuckerberg and others have slipped up.)

Surfers? Not On My Beach!

Vinod Khosla

Image by Reuters/Stephen Lam

Billionaire Sun Microsystems co-founder Vinod Khosla bought prime California beachfront property for $37.5 million and closed the only road to the popular Martins Beach. Surfers and beachgoers filed a lawsuit claiming Khosla was violating the California Coastal Act. In what can only be called hubris, Khosla defiantly evaded questions on the stand while his lawyers argued he has a right to keep trespassers away. Then Khosla’s property manager said it was his decision alone to block access. The case is pending.

Out of Touch With History

Tom Perkins

Image by Wikipedia/Max Morse

Pity poor billionaires, especially old ones who say stupid things. Legendary venture capitalist Tom Perkins, 82, wrote an ill-advised letter in The Wall Street Journal (behind the paywall) in January comparing the treatment of the wealthy to the treatment of Jews in Nazi Germany. Amid the ensuing outcry, the firm he co-founded, Kleiner Perkins, quickly distanced itself. Perkins followed up with a classic non-apology to anyone who mistook his reference.

Egomaniac Alert!

Gurbaksh Chahal

Image by Wikipedia

RadiumOne CEO Gurbaksh Chahal has been charged with domestic violence — 117 violent acts during a 30-minute assault on his girlfriend. In a blog post, Chahal denied the charges, compared himself to celebrities who are the targets of false accusations, and wrote some very unkind things about his girlfriend: “The situation that resulted in my legal case began when I discovered that my girlfriend was having unprotected sex for money with other people.” RadiumOne’s board promptly fired him.

All Jazzed Up on Twitter

Rakesh Agrawal

Image by Carl V. Lewis/Google

Some people simply shouldn’t be allowed near a keyboard, let alone a Facebook or Twitter account. In May, PayPal’s new director of strategy Rakesh “Rocky” Agrawal was reportedly at Jazz Fest in New Orleans when he decided to take to Twitter and bash co-workers. He was promptly fired, although Agrawal claims he quit before sending the tweets. Here are some of Rocky’s best (or worst) shots: “Duck you Smedley you useless middle manager” and “Christina Smedley is useless piece of [expletive.].”

Class Warfare on Facebook

Greg Gopman

Image by Google Images

The great gentrification war of San Francisco, pitting techies against the lower class, has raged for nearly a year. In December, Greg Gopman, founder of AngelHack, infamously fanned the flames with a Facebook rant about his thoughts of the less fortunate. He wrote: “In downtown SF the degenerates gather like hyenas, spit, urinate, taunt you, sell drugs, get rowdy, they act like they own the center of the city… there is an area of town for degenerates and an area of town for the working class. There is nothing positive gained from having them so close to us.” Though some commenters supported him, Gopman later apologized.

Road Rage, Alleged Bicyclist Beat Down

Jeffrey Smock

Image by Google Images

In the quaint town of Mill Valley, north of the Golden Gate Bridge, Jeffrey Smock, founder and former chief executive of Iron Data, was riding his bike when he got into a physical altercation with a motorist, reports SFGate. Witnesses say Smock, 40, who was apparently the aggressor, beat up the 55-year-old motorist and hit him when he was down. The driver of the vehicle was transported to the hospital with “serious injuries” and has since been released; Smock was arrested for assault. He later declined to enter a plea and requested more time for his attorney to review evidence.

Panic on Highway 101

Nirav Tolia

Image by Reuters/Robert Galbraith

Last August, Nextdoor CEO Nirav Tolia allegedly caused a crash on Highway 101, which resulted in injuries to a woman, and then fled the scene, reports SFGate. Witnesses took down his license plate number, and the police arrived at his home. He faced felony hit-and-run charges (which were later reduced to a misdemeanor) and a civil lawsuit. Tolia told police he fled because he was “shaken” and hadn’t called 911 because he was in shock, according to the complaint. Ironically, Nextdoor is a social network designed to improve communication between residents and police.

Bitcoins on the Black Market

Charles Shrem

Image by Wikipedia

At just 24, Charles Shrem has already racked up a lifetime of accomplishments: He’s co-founder and CEO of BitInstant, a founding member of Bitcoin Foundation, a self-styled tech revolutionary, and now an accused money launderer under house arrest at his parents’ Brooklyn home. Shrem allegedly sold Bitcoins to a man in Florida, who then sold them on the black market for drugs and other contraband, according to Forbes.

McAfee On the Run

John McAfee

Image by Reuters/Joe Skipper

No list of misbehaving tech CEOs would be complete without a mention of John McAfee, founder of McAfee Associates. After losing millions of dollars in the market crash, McAfee relocated to South America where he quickly ended up on the wrong side of the law. He evaded police in Belize, spent time in a Guatemalan jail and now lives in Canada. His story has all the makings of a Hollywood movie.

Intolerance Will Not Be Tolerated

Brenden Eich

Image by Wikipedia

San Francisco/Silicon Valley denizens typically don’t take kindly to discriminatory practices — most refuse to work for people who do. In 2008, Brendan Eich contributed $1,000 to the campaign for Prop. 8, which was created to prohibit gay couples from marrying. The decision came back to bite him when Eich later became CEO of Mozilla. Employees angrily criticized Eich for his personal views, and after only 10 days on the job, he stepped down.

‘Abel, You’re Fired!’

Tim Armstrong

Image by Wikipedia

AOL CEO Tim Armstrong epitomizes the arrogant tech executive. Last year, he fired Creative Director Abel Lenz on the spot during a company conference call for taking pictures. A few months later, on another conference call, Armstrong cited a couple of employees’ “distressed babies” as reasons for reducing retirement benefits. One of the mothers, Deanna Fei, wrote a searing rebuttal, and Armstrong eventually apologized. 

Dishonorable Mention

Donald Sterling

Image by Reuters/Danny Moloshok

Los Angeles Clippers owner Donald Sterling isn’t a tech titan, nor does he live in Silicon Valley. But, in a way, Sterling inspired this list, so he deserves a dishonorable mention. Sterling’s privately recorded racist views, tinged with feelings of wealth-fed superiority and entitlement, brought the image of the arrogant mogul back into the national spotlight. His unapologetic apology bashing basketball star Magic Johnson is classic egotism.