The Tech Industry's C-Suite Convicts, Ranked

Well, Sam Bankman-Fried is headed up the river. Once a powerful crypto power broker, SBF’s glittering Web3 kingdom came crashing down on his head after a multi-billion dollar scandal. It’s a good reminder that not only does Silicon Valley produce a lot of software products, but it also produces a whole lot of criminals! Those criminals may be smart, well-dressed, and charismatic but, at the end of the day, they are still, ultimately, crooks. As we bid farewell to Sam, here’s a quick look back at some of the tech industry’s other most notorious C-suite gangstas.

1. Pharma Bro

You’d be hard-pressed to find a more ridiculous individual than Martin “Pharma Bro” Shkreli. A perfect epitome of the douchebag ethic of tech capitalism, Shkreli shocked the world by saying the quiet part out loud in 2015, when his pharma-tech company Turin bought an anti-parasitic drug and parasitically raised its price by over 5,000 percent. When criticized for this price hike, Shkreli said: “This drug was doing $5 million in revenue...And I don’t think you can find a drug company on this planet that can make money on $5 million in revenue. Most costs are much higher than that.” In 2017, the smuggest smile in the world was briefly wiped off his face when he was charged and convicted of securities fraud. He subsequently cried and was sent to prison. He later convinced a Bloomberg journalist to leave her husband for his slimy embraces, only to dump her after he got out of prison. Now he loves crypto, which makes a lot of sense. Shkreli wins the tech industry convict competition purely because he has one of the most punchable faces in the world.

2. Elizabeth Holmes

She’s blonde, she’s ruthless, and she’s baritone (well, allegedly). She’s the unforgettable Elizabeth Holmes. You probably know her story well: she convinced much of the world that she had pioneered some sort of paradigm-shifting blood testing technology and managed to amass a megaton of investment and gushing publicity...only for us all to discover that her company was built upon a heap of lies and that the world-changing technology she’d been hawking was actually a useless hunk of junk that executives kept well hidden in its basement. Holmes, who was found guilty of fraud in January of 2022, was sentenced to 11 years in prison.

3. SBF

He’s currently the man of the hour, but there are a lot of reasons that we’ll be talking about SBF for a long, long time. What a ridiculous executive. What a ridiculous company. If subsequent investigations are to be believed, FTX was run like a drunken pirate ship or a frat house in a skyscraper. The company, which briefly enjoyed world renown and massive financial inflows, imploded in a spectacular explosion of corruption and fraud in 2022. So long, Sam, and thanks for all the crime.

4. Razzlekahn

Razzle dazzle. Who could forget “Razzlekahn,” the endlessly rapping, cringingly awkward, deeply unconventional (read: weird) social media influencer who is accused of helping her husband steal $4.5 billion in cryptocurrency? Khan’s real name is Heather Morgan and, in 2021, she and her husband, Ilya Lichtenstein, were arrested by the FBI and accused of a massive hacking and theft scheme. Previous to her arrest, Morgan headed her own marketing startup and dabbled in other entrepreneurial efforts. The duo later pleaded guilty to many of the crimes they were accused of, which related to the hacking of crypto exchange Bitfinex in 2016 and subsequent money laundering. Morgan was released on bail in 2022. Predictably, there are murmurs that a “Razzlekahn” movie may be in the works. Keep your eyes peeled for what is sure to be a mediocre adaptation, coming to a streaming service near you.

5. CZ

Changpeng Zhao, also known by his initials, CZ, was swept up in the wave of crypto crackdowns that have taken place over the last few years. His downfall was sorta buried beneath the news related to FTX and SBF, whose crimes were admittedly much larger and more ridiculous. Last summer, the SEC sued Zhao and Binance, accusing it of securities violations. He subsequently entered a plea deal and pleaded guilty to a single count of money laundering and stepped down as the top executive at Binance. He was also ordered to pay $50 million in fines.

6. Trevor Milton

When you think about corporate corruption, you don’t typically think of the EV industry, but then you might remember the terrible mess that is Nikola. The scandal-ridden electric vehicles company has been having problems since at least 2020 when the Securities and Exchange Commission and the Justice Department opened an investigation into the company over allegations of securities fraud. The government ultimately concluded that Nikola’s CEO, Trevor Milton, was responsible for securities and wire fraud. Milton was ultimately sentenced to four years in prison.

7. Bernard Ebbers

An oldie but a goodie: Bernard “Bernie” Ebbers helped cook a whole lot of books during his stint as the top executive at Worldcom. Never heard of Worldcom? In the 1990s, it was one of the largest telecommunications companies in the world. Investigation revealed an $11 billion accounting fraud, designed to manipulate the company’s image of profitability, which was primarily blamed on Ebbers. In 2005, Ebbers was convicted of securities fraud and sentenced to 25 years in prison. Worldcom later filed for bankruptcy, emerging from the scandal with billions in debt. It later changed its name to MCI and was bought by Microsoft.

8. Kobi Alexander

Israeli-American businessman Kobi Alexander previously founded telecom tech firm Comverse Technology and served as its CEO. Comverse began as a big player in the voicemail services industry during the early days of cell phones, and Comverse eventually began generating serious money. However, Alexander’s luck ran out in 2006 when he and other executives were charged with involvement in a backdating scheme. He was subsequently sentenced to 30 months in prison for securities fraud.

9. Michael Kail

Streaming is a dirty business. Or, that’s what you’d be led to believe by the likes of Michael Kail, the former Vice President of IT Operations at Netflix. Kail was caught doing a lot of bad financial stuff, including taking bribes from clients/other tech companies in relation to contracts with the streaming giant. Prosecutors said Kail accepted as much as half a million dollars in kickbacks. He was ultimately sentenced to 20 months in prison. After his stint behind bars, he predictably decided to get into crypto, which seems like it’s been a smooth transition for him.

Chris Kirchner

Chris Kirchner is the founder and former CEO of Slync, a logistics company. The company did alright for a while, but Kirchner fired a bunch of its top executives, reportedly after they raised questions about the company’s finances. Kirchner was ultimately arrested and accused of fraudulently sucking $25 million out of investors. This past January, he was found guilty of money laundering and fraud. Slync was liquidated last October.

For the latest news, Facebook, Twitter and Instagram.