Many Tech CEOs see themselves as revolutionaries - skilled at the kind of blue sky thinking necessary to imagine a better world. But many find themselves gracing gossip sites for different, entirely less noble reasons.

In contrast to the pioneering but publicly sedate tech CEOs of yore - think Bill Gates - today's crop of techpreneurs are a different breed. Growing up during the dot-com boom, and fed on a diet of tech evangelism and Soylent, some on this list soared to billionaire status before brushing their thirties.

Whether through their colourful Twitter feeds, penchant for celebrity girlfriends or simply the unorthodox ways they run their businesses, here is a definitive list of the most controversial tech CEOs grabbing headlines around the world.

Larry Ellison

Former Oracle CEO Larry Ellison courted public attention throughout his career at the software vendor, famously making not so subtle statements at or about the competition.

But he moved surreptitiously in one instance paying private detectives to search around in the rubbish of a business suspected to be working with rival Microsoft, at the time under an antitrust investigation.

He paid a cool $500 million for his own private island in 2012 - Lanai, a former pineapple plantation.

There have been many rumours about Ellison's personal life, some more rooted in reality than others. One story went that Ellison paid $40 million for a Pacific Heights house that was next to his because the trees had been blocking his view, which Ellison denies.

He also livened up the sometimes ultra-corporate enterprise market with surprise statements, and once joked that, while attempting to take over PeopleSoft in 2013, he would shoot its CEO.

In an analyst meeting he reportedly said: "If Mr. Conway and the dog were standing next to each other, [and] I had one bullet, trust me, it wouldn't be for the dog."


Sean Rad, Tinder founder and former CEO

Perhaps it's unsurprising that the founding father of swipe-fuelled modern day hookup culture would appear on this list, and perhaps even less surprising that the controversy in question centres on a sexual harassment case. The 2014 case involved him and co-founder, Justin Mateen being accused by another co-founder, Whitney Wolfe, alleging sexual harassment and discrimination. Although eventually settled without any ‘admission of wrongdoing’ (with the complainant leaving the company to found female-friendly dating app, Bumble) it led to Rad stepping down as CEO for a period, before being reinstated.

However, when the company was taken over by IAC, parent company of online dating conglomerate Match Group, which oversees, OkCupid and Tinder to name a few - Rad was again pushed out and replaced by former CEO of OkCupid, Elie Seidman.

Now, serial 29-year-old entrepreneur Rad is back in the spotlight in a $2 billion lawsuit levelled at IAC, accusing the organisation of inappropriately valuing stock leading to the undervaluing of stock held by the founders and early investors.


Jeff Bezos, Amazon

Jeff Bezos makes this list not for his revolving door of celebrity girlfriends or taste for the occult (keep reading) but for his political entanglements. The richest human to ever live on earth, he has been repeatedly pilloried for his treatment of his staff - who have been known to be paid poverty wages and endure poor working conditions in warehouses - and his lack of humanitarian efforts. Amazon famously does not recognise the right to unionise.

Only recently did he pledge $2 billion (still a relative pittance for someone worth around $160 billion) to a fund - the Bezos Day One fund - to help homelessness and schools. And although he committed to a well-publicised pay rise for Amazon workers, it was a case of 'robbing Peter to pay Paul' - with funds moved around rather than a raise in real terms.

He has also come under fire recently for the high-profile bidding war he orchestrated to decide on where Amazon’s new headquarters would be based, pitting states and cities against one another and accepting billions in American taxpayer money in the form of government subsidies from the chosen locations, New York and Washington DC. But scrutiny is growing and eyeballs are increasingly on the movements of Bezos and his trillion dollar ecommerce empire.


Jack Dorsey, Twitter

Controversy has swirled around Dorsey in different guises - whether it's his longtime advisor and Twitter board member, Peter Fenton, shacking up with his longtime on and off girlfriend, Kate Greer; his love of 10-day silent retreats sans internet, or clumsy displays of cultural insensitivity.

But frankly, nothing compares to the showstopping revelation in late 2018 that he once sent rapper and general hellraiser Azealia Banks clippings of his beard for her to create an amulet that would protect him against ISIS (who once personally named him in one of their propaganda videos).  

To back up for a second, the events actually transpired in 2016, after Banks and Dorsey allegedly met for a meal where it was decided that in exchange for Dorsey tweeting out his support of Banks' new mixtape, Slay-Z, Banks would work her hairy witchcraft, and ensure Dorsey's everlasting safety from Islamic State. What smacks as a hugely lopsided bargain was clearly not appreciated by Dorsey, who ended up reneging on his side of the deal and leaving Banks without the supportive Tweet but not, apparently, before dispatching the required hair.

At the time, Banks reportedly tweeted: “i have 3 Strands of a billionaire’s hair. i should steal his luck.”

After recently being contacted for comment on the tale by Business Insider, Banks again confirmed its veracity and the fact that she is still in possession of one of the strands of hair. Of course, this begets the all-important question of what fate exactly, befell the other two strands.

Right now, Dorsey's credibility is hanging by a thread as slender as the dainty nose ring he intermittently dons.


Travis Kalanick, Uber, former CEO

The Uber founder and former CEO was famously caught up in a string of controversies not just about the way the ride-sharing app company conducted itself but his own personal conduct too.

This long read at Bloomberg goes into great detail about the many controversies that surrounded him during his time at Uber, which began to rev up following Kalanick's joining the Trump business advisory council.

Allegations of a culture of sexual harassment within the company emerged when engineer Susan Fowler wrote a post on her blog titled 'Reflecting on One Very, Very Strange Year at Uber'. There was, Fowler said, discrimination and sexual harassment from managers - which was raised to human resources but disregarded. The culture was "stoked and even fostered" by those at the top of the company, writes the New York Times in reference to the blog post.

Then details of the secretive Greyball project emerged - a custom-built tool that could be used to deceive law officials and inspectors who had the power to shut down the service.

Incumbent CEO Dara Khosrowshahi, who took the post in 2017, was widely viewed to be a mediating force installed to steady the ship and reverse some of the damage done by Kalanick and the company's previously gung-ho operations.


Mark Zuckerberg, Facebook

Founder of the world's most-used social network Facebook, Mark Zuckerberg, has been controversial from the very beginning - so much so that a film about the company's rags-to-riches story, the Social Network, proved a blockbuster hit.

In the early days when the founder was just 19 he allegedly offered a college friend information about "anyone at Harvard" and said that the site's early users were "dumb fucks" to "trust" him.

Recently, of course, was the Cambridge Analytica scandal - which unfurled when questions were raised about that company's surreptitious use of Facebook user data for political ends - with associates of the company claiming that they had the power to topple governments and swing elections.

He was also the star of bizzare hearings at the US Senate and the European Parliament about the Cambridge Analytica scandal, but refused requests to appear at a Parliamentary committee in Britain.

The famously awkward character has been mocked since he has been in the public eye, with users commenting on his odd mannerisms and joking that he is an android or possibly an extraterrestrial.

More seriously, Zuckerberg caught flak when he treated holocaust deniers with kid-gloves in an interview with Recode, saying that these people were not "intentionally" getting their facts wrong. 

He said in 2018 that although he was Jewish and found it "deeply offensive", he didn't think these beliefs should be censured from the platform. Strangely, this was occurring at the same time that the company seemed to be deleting legitimate political pages from Facebook (officially because they are 'divisive') and deleting alternative news sources, including those reporting a pro-Venezuela position such as TeleSur English.

Activists in Myanmar, meanwhile, levelled claims at Facebook that it had not done enough to prevent anti-Rohingya sentiments spreading throughout the social network - ultimately convincing to the ongoing ethnic cleansing of Rohingya people in Burma.

And there was that time he filed lawsuits against native Hawaiians who were living on their own plots of land within the 700 acres of Kauai that the founder bought in 2014, although these were later dropped.


Elon Musk, Tesla, SpaceX

Of course Musk was the only one who was ever going to seize the top spot on this list. His at-times spicy Twitter feed, his run-ins with various celebrities, and his core beliefs all render him 'outlandish' to say the least. In fact, his sometimes childish-seeming demeanor and inflammatory tweets have unsurprisingly prompted comparisons between the Tesla founder and the cheeto-dusted president of the USA.

Like Trump, his most ardent fans respond fervently to his candour, deeming him more ‘authentic’, open and relatable than other tech execs.

In the past, he has dated celebrities such as Amber Heard and married, divorced, remarried then re-divorced actor, Talulah Riley, but 2018 really was a vintage Musk year.

In just 365 days, he managed to get a new, at first glance very ill-suited girlfriend - the music artist and countercultural icon, Grimes, who is 17 years his junior. If you missed this, remember pictures of what may have appeared to be a businessman accompanying his daughter to a Halloween party circulating a few months back? That's them. 

What else? When a group of Thai schoolboys were stuck in a cave, Musk tried to torpedo to the rescue. But when his prototype mini-submarine-rescue-mobile was roundly mocked as completely bonkers, he retaliated in the most Trumpian way possible, by denouncing the literal hero who saved the boys, Vernon Unsworth, as a ‘pedo’. He later called Unsworth a 'child rapist' in an email to a reporter.

Musk had yet more in store for us. In August, he tweeted that he was planning to take Tesla private with shares priced at $420 and had ‘funding secured'. But it seems that Musk simply disregarded the health of his company and his own credibility in favour of desperately trying to earn some ‘street cred’ in the eyes of his new girlfriend. Pricing his stocks at £420 was a nod to the stoner holiday 4/20 and barely disguised desperate plea for acceptance (‘Get it kids?! I’m one of you!’)

This was revealed in a text from Grimes to none other than ever trustworthy fount of knowledge, Azealia Banks: "he just got into weed cuz of me and he's super entertained by 420 so when he decided to take the stock private he calculated it was worth 419$ so he rounded up to 420 for a laugh and now the sec is investigating him for fraud".

Banks also alleged that Musk sent the initial tweet while on acid. How does she know this? A weekend round his mansion on the invite of Grimes which she compared to the horror film, Get Out.

However, Musk later denied this and told the New York Times that he had rounded up from $419 to $420 for karmic purposes and was not in fact 'on weed'. 'On weed'? That’s the sound of the collective snort of teenage stoners everywhere. So close, Musk, so close.

The events following that fateful tweet culminated in Musk being forced to step down as the chairman of Tesla and pay a $40 million fine to the SEC. But the incident has done little to dampen Musk's exuberance. He's currently tunnelling beneath LA like some mad giant mole. We closely await what 2019 has in store.