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5 Tech Leaders Who Are Not All That

Silicon Valley CEOs and successful startup founders are often elevated to lofty proportions. Think Steve Jobs, Bill Gates, Steve Wozniak, and Mark Zuckerberg–all have reached celebrity status.

With celebrity, comes notoriety. Jobs’ arrogant behavior and tendency to belittle others is well documented in Walter Isaacson’s biography of Apple’s founder, Steve Jobs. He once told a hardware designer at Xerox, “Everything you’ve ever done in your life is shit…”

Of course, he was Steve Jobs and often got a pass on downright nasty behavior because he was so incredible at leading Apple. In fact, many successful tech leaders get passes on obnoxiousness and sometimes are even rewarded for it:

1. Evan Speigel:

The co-founder and CEO of Snapchat is praised for launching the immensely popular messaging platform, as well as for his boyish good looks, which has landed him dates with supermodels. He’s also been taken to task for a series of juvenile, sexist, and homophobic emails written during his not-so-long-ago fraternity days.

In one unfortunate email, he invited frat brothers to a President’s Day party, celebrating “the legacy of our two-timing forefathers.” In the message, he made mention of Sally Hemmings, the slave and mistress of Thomas Jefferson, writing, “Get some, Jefferson!”

He also wrote a series of crude emails about sexual acts, shooting “lasers at fat girls,” and criticized a rival fraternity for “being gay.”

2. Marissa Mayer:

The CEO of Yahoo got her start in tech as one of the only female engineers during the beginning of Google. Touted early on as an example of women achieving in tech, she has since been besieged by criticism for running a floundering company that is now trying to sell off assets just to stay afloat.

Mayer has been further scrutinized for what many see as tone-deaf leadership and excessive spending on the unnecessary. She is reported to have spent $70,000 on a Wizard of Oz holiday theme party; installed a nursery in her office when she was

expecting while no longer allowing employees to telecommute; and reported a $4.4 billion revenue loss last quarter.

She remains an object of fascination for the media, appearing on the cover of Vogue. Recently, a controversial cartoon depiction of Mayer appeared on the cover of Variety, showing Mayer staggering under the weight of a cross on her shoulders.

Despite the problems, Mayer is set to receive $37 million if Yahoo is sold and she gets fired.

3. Carly Fiorina:

The failed Republican presidential c

andidate ran tech giant HP before her foray into politics. Her failures at HP are regarded by some as to why Fiorina may have failed at her shot for the presidency. Politico’s Jeffrey Sonnenfeld wrote that Fiorina, “Was one of the worst technology CEOs in history.”

During her tenure at HP, the company lost half its value. While other tech companies were moving away from hardware, Fiorina made the pricey misstep of purchasing a failing Compaq for $25 million.

HP’s stock dropped 55% and 30,000 employees were laid off due to Fiorina’s Compaq deal. Eventually, HP’s board fired her, as did the American voting constituency.

4. Dharmesh Shah:

Shah, the co-founder and CEO of HubSpot, a marketing software company, got really publicly defensive after a book revealed shenanigans going on with the company’s walls.

In his book Disrupted, author Dan Lyons, who spent time working for HubSpot after working for decades as a journalist, described some truly cringe-inducing scenarios. He wrote about the lack of diversity, ageism, and some really bizarre stuff, including shower rooms that the largely Millennial-aged staff use as “sex cabins” for workplace hookups.

Lyons was also brutal in his depiction of some of the laughable management practices. Before the book was released, HubSpot’s marketing head was fired for ethics violations for trying to obtain an early release of the book–no doubt, in order to plan damage control. The stunt only helped underscore Lyons’ observations about the buffoonery taking place at HubSpot.

Shah wrote a lengthy

tome on LinkedIn answering the accusations in the book and the criticisms of HubSpot. It was an overwrought, defensive blog post that gave further ammunition to HubSpot’s critics.

5. Travis Kalanick:

Uber is cool, convenient, and affordable. It also provides a solution for the problem so many people of color face; being unable to hail a taxi. While the company is loved by many, CEO and founder Kalanick has indulged in some really questionable behavior.

In an interview with GQ, Kalanick referred to his ability to attract women as a successful tech CEO.”Yeah, we call that boober,” was his statement.

Two years ago, the company was accused of trying to sabotage rival Lyft by having employees make 5,560 fake Lyft rides and then canceling them.

And Uber’s senior vice president, Emil Michael, suggested Uber hire a team of opposition researchers–equipped with a million-dollar budget–to dig into the personal lives of journalists who reported negatively about the company.

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