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CEOs can be polarising figures and such power can take a toll at times — at work and in the media. Here are insights from top CEOs who ventured to the dark side this year

Chief executives are interesting creatures — most are believed to be born with a ridiculously good skill set comprising resilience, “play with fire” attitude, brilliance and… arrogance.

Many CEOs are considered polarising figures and not to be trifled with — Apple’s Steve Jobs, Amazon’s Jeff Bezos, Uber’s Travis Kalanick, the list could go on.

Apparently it is considered all right to be arrogant in the entrepreneurial game. Jobs, the highly-venerated Apple chief executive, had two sides to him — “Good Steve” and “Bad Steve”, according to his biographer Walter Isaacson. Jobs was known to make people cry when they weren’t able to meet his expectations, but then those people later agreed that Jobs was actually right in the first place.

Another story suggests that Bezos used to wreak havoc in his organisation with his single character email responses – “?”.

With so many bad CEO episodes taking place, I thought it’d be a great idea to have a story around the subject: Are arrogance and greatness mutually exclusive?

Think of it like a parade of badass chief executives, instead of top celebrities, in the video of Taylor Swift’s number one single Bad Blood, a pretty convincing inspiration behind this story.

 1. Martin Shkreli aka Pharma Bro and ‘The Most Hated Man in America’

Earlier this year, Martin Shkreli, CEO of Turing Pharmaceuticals, did something to earn the title of ‘The Most Hated Man in America.’ The young chief’s firm acquired patent rights to a drug used to treat malaria, cancer and AIDS, and hiked its retail price from US$13.50 to US$750 per tablet (5,455 per cent).

Also Read: GIZTIX named winner of Echelon Thailand Startup LaunchPad

To make matters worse, Shkreli gave many TV interviews and got involved in a series of heated Twitter exchanges in which he seemed to suggest others were too stupid to understand how pharmaceutical research works.

Shkreli attracted ridicule from almost everybody with both US Presidential candidates Hillary Clinton and Donald Trump finall agreeing on something.

Takeaway – Respect public sentiments and be circumspect of social media.

 2. Sean Rad aka ‘Tinder addict’

Not exactly a hot blood case, but Sean Rad, CEO and Co-founder of casual dating app service Tinder, reaped in some serious trouble over his casual remarks confusing the term ‘sodomy’.

Recently, in an interview with London’s Evening Standard, Sean made an interesting comment about his company’s spectacular vision and that it has solved “the biggest problem in humanity: that you’re put on this planet to meet people.“

But the evening didn’t end right there for the Tinder CEO, for Sean is a living embodiment of the service user. He describes his addiction with Tinder in this excerpt from the Standard’s Charlotte Edwardes below.

 “She’s one of the most beautiful women I’ve ever seen, but it doesn’t mean that I want to rip her clothes off and have sex with her. Attraction is nuanced. I’ve been attracted to women who are … well, who my friends might think are ugly. I don’t care if someone is a model. Really. It sounds cliched and almost totally unbelievable for a guy to say this, but it’s true. I need an intellectual challenge.

“Apparently there’s a term for someone who gets turned on by intellectual stuff. You know, just talking. What’s the word?” His face creases [with] the effort of trying to remember. “I want to say ‘sodomy’?”

Rosette [Pambakian, Vice President, Communications and Branding] shrieks: “That’s it! We’re going to be fired” and Rad looks confused. “What? Why?”

I tell him it means something else and he thumbs his phone for a definition. “What? No, not that. That’s definitely not me. Oh, my God.”

Tsk tsk, Sean.

No offense to Sean because it seemed like an honest mistake. But as the face of a billion dollar dating business, come on, you’ve got to know the right terms!

Takeaway – The media can be a bully at times, but as the CEO one should control the outcome of your actions.

 3. Deepinder Goyal: More punishment, less reward

The Zomato CEO notoriously shot a lengthy email to the entire sales team (which was later leaked to the public by an internal employee) educating them on the hard reality of the company’s growth and future sales projections.

Reportedly, the email emphatically titled with the subject line, “Perspective for our sales team” was later sent to all Zomato employees within a couple of weeks of the mass-firing of 10 per cent (250-300 people) of its workforce.

What was supposed to be a damage-control gesture turned out to be a PR nightmare for the company with the public, business journalists, stakeholders and possibly investors questioning the blooming sense of insecurity under the Zomato roof.

Some people ridiculed Deepinder’s actions while others cited it to be a case of the bigger problem at hand — a bursting of the startup bubble in the country.

Takeaway – If your sales stack isn’t performing the way it should, may be talking and encouraging them would work better than sending stern tone emails.

 4. Rahul Yadav aka the Bad Boy of Indian startups

Rahul isn’t CEO of Housing.com anymore. Having been ousted from his own venture, Rahul did little to stay away from the limelight. What started with a bunch of angry statements against the who’s who of industry stalwarts, including Zomato’s Goyal, Sequoia Capital MD Shailendra Singh and more, followed a controversial resignation which ultimately led to him being let go of the company he co-founded.

Here’s the rundown of his tryst with the spotlight.

• A widely-covered social media spat with Shailendra Singh, MD of leading Indian venture capitalist firm Sequoia Capital.
• A controversy involving Times Group, Rahul accused the company of maligning Housing.
• Submitted his resignation and accused board members and investors of not being “intellectually capable of any discussion”.
• Another social media brawl involving Ola’s head in command Bhavish Aggarwal and Zomato CEO Deepinder Goyal provoking them to also give away half of their shares to employees, just like him.

Also Read: Is the term ‘woman entrepreneur’ sexist?

Widely considered a polarising figure, many fellow entrepreneurs viewed his raw attitude, brashness and arrogance as “a recipe for disaster.” Many even saw a “hint of Steve Jobs” in him.

Rahul’s popularity grew by leaps and bounds and he’s reportedly working on his new project — data visualisation and data analytics. A few of his old Housing buddies have joined him and it remains to be seen if he will be able to revisit his path to success.

Takeaway – Voicing out individual opinions is no crime, but as a CEO one should be calm and not sensationalise them to further one’s own agenda. 

The views expressed here are of the author’s, and e27 may not necessarily subscribe to them. e27 invites members from Asia’s tech industry and startup community to share their honest opinions and expert knowledge with our readers. If you are interested in sharing your point of view, please send us an email at writers[at]e27[dot]co

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