20 CEOs Who DESTROYED Their Own Companies

20 CEOs Who Destroyed Their Own Companies

Welcome to WatchMojo, and today we’re discussing the corporate execs who drove their companies straight into disaster.

#20: George Shaheen

Webvan

Imagine inventing Instacart more than 10 years before the real Instacart actually came to be. Webvan could have been a billion-dollar idea if its own leadership hadn’t screwed things up so badly. The company began operating in 1999, taking grocery orders online and delivering them super-fast. Unlike today’s grocery delivery services, Webvan had its own warehouses full of food instead of shopping orders from Walmart or Target. The problem is that Shaheen and other execs had no experience running a supermarket, and had no idea that they ran on such small margins. Webvan quickly racked up plenty of sales, but its costs were way too high, and it never turned a profit. The company folded in 2001.

#19: Trevor Milton

Nikola Corporation

If you think this company sounds like a rip-off of Tesla, you’re not far off. Milton founded Nikola in 2014 and pitched a concept for a semi-truck powered by natural gas, though the design was later changed to use hydrogen fuel cells. In December 2016, Nikola demoed a supposedly “fully functional” model, but the presentation was a lie. The truck didn’t actually work. Milton started taking orders for the vehicle anyway, but by 2020, journalists and financiers started digging into Nikola Corp. It turned out that nearly everything Milton had claimed about Nikola’s trucks was a lie. He was later found guilty of fraud and sentenced to four years in prison, but was pardoned by President Trump after donating almost $2 million to Trump’s campaign.

#18: Al Dunlap

Sunbeam

This scandal should be a lesson in doing your diligence before hiring a CEO. Dunlap loved closing factories and laying people off so much, he was nicknamed “Chainsaw Al.” He became CEO of Sunbeam – which made small household appliances – in 1996. Sales shot up in 1997, as did the company’s stock price. But it was all a scam. Dunlap had been cooking the books, overreporting Sunbeam’s losses in ‘96 to make its turnaround seem more impressive. He’d also engaged in illegal sales tactics with merchandisers and other shenanigans to conceal Sunbeam’s financial problems. Dunlap was fired in 1998, and Sunbeam went bankrupt in 2001. It later came out that he’d also committed accounting fraud in the 70s while president of a New York paper mill.

#17: Archie McCardell

International Harvester

Don’t mess with labor unions. This farm equipment manufacturer made record profits in 1977 thanks to McCardell’s aggressive cost-cutting. But while he was scaling back production and laying off workers, he was taking home one of the highest salaries in the country for a CEO at the time. Employees weren’t impressed. In 1979, after McCardell’s $1.8 million bonus was announced, the United Auto Workers called a strike. McCardell couldn’t have handled it worse. He refused to compromise, figuring they’d be forced to cave eventually. He was wrong. The strike lasted 172 days, and the union ultimately came out on top. The company, meanwhile, lost more than $600 million. McCardell was fired and International Harvester sold off most of its assets, becoming defunct by 1985.

#16: Dennis Kozlowski

Tyco

He made $100 million a year and still decided to defraud his own company. Kozlowski became CEO of this security systems business in 1992, and under his leadership, Tyco thrived. However, during his 10 years in the role, Kozlowski was secretly funneling tens of millions of dollars into his own accounts. He illegally used company money to pay for all kinds of over-the-top purchases, like his $30 million house with a $6,000 shower curtain that the media couldn’t stop talking about. Along with Tyco CFO Mark Swartz, Kozlowski was accused of stealing more than $150 million. And unlike most ultra-wealthy people, he actually paid the price. He served over six years in prison and had to pay back every penny he earned from Tyco.

#15: John Rigas

Adelphia Communications

Rigas did what Dennis Kozlowski did, but he brought the whole family in on the fraud. Rigas and his brother Gus founded cable TV provider Adelphia in 1952. Over the next half-century, they grew it into one of the largest providers in the country. But in 2002, investigators discovered that the Rigas family had been bleeding the company dry. They’d been moving money back and forth between Adelphia and their other companies to hide the fact that they had stolen $100 million. They used it to buy cars, land, and other personal assets. Adelphia filed for bankruptcy, and Rigas and his son Timothy went to prison. Rigas was released due to health problems after serving eight years, and died in 2021.

#14: Martin Shkreli

Turing Pharmaceuticals & KaloBios

You remember Pharma Bro. He became the most hated man in the country after his company bought a medication that treats pneumonia associated with HIV and hiked the price 5,500%. Under America’s broken healthcare system, that was totally legal, but his other slimy behavior was not. It turned out Shkreli was running a gigantic Ponzi scheme, starting new companies and using investor capital to pay off investors in his other companies. His behavior during the trial didn’t win him any favors with the judge, but his conviction gave everyone watching a huge dose of schadenfreude. He served four years in prison and his companies, of course, went bankrupt.

#13: Sam Bankman-Fried

Alameda Research & FTX

He’s not as unlikable as Shkreli, but he committed an even bigger fraud. In 2017, at just 25 years old, Bankman-Fried cofounded crypto trading firm Alameda Research. Two years later, he cofounded the crypto exchange FTX to raise capital for Alameda, but it did a lot more than that. Over the next three years, Bankman-Fried illegally took customers’ deposits from FTX to pay Alameda’s debts and fund its research. Even before the fraud was revealed, critics raised alarm bells about the close relationship between the two companies, arguing that it would never be permitted outside the unregulated crypto space. Bankman-Fried was eventually convicted of fraud and money laundering and sentenced to 25 years.

#12: Richard Fuld

Lehman Brothers

He didn’t cause the housing market crash that led to Lehman’s collapse, but he’s a major reason the 158-year-old bank never recovered. Fuld poured Lehman’s money into subprime mortgages – those loans that created the bubble that popped in 2008. A senior trader at the company later reported that Fuld ignored advisors’ warnings that the market was unstable, and even banished Lehman’s chief risk officer from meetings. Immediately after the crash, Lehman lost billions, and Fuld desperately tried to find a buyer for the firm to prevent it from going bankrupt. Yet he declined offers that could have saved it because he felt they weren’t good enough. Lehman did go bankrupt, but Fuld had already been paid more than $400 million over the previous seven years.

#11: Gerald Ratner

Ratner Group

It’s one thing to sell cheaply made products – it’s another to admit in public that your products are junk. Ratner inherited a group of family-run jewelry stores, which he successfully grew into a massive chain by offering major discounts. But while giving a speech to an entrepreneurs’ association in 1991, he made a fatal mistake that killed the company. Ratner joked about his jewelry’s quality, calling it “total crap” and implying that it would fall apart quickly. His remarks made headlines the next day, and Ratner Group lost £500 million in a matter of days. Ratner was fired the following year and the company later changed its name to Signet Group.

#10: Carly Fiorina

Hewlett-Packard

Fiorina’s aggressive pursuit of a bold vision arguably eroded the very foundations of a tech giant. Her tenure at IT behemoth Hewlett-Packard, from 1999 to 2005, was defined by her controversial acquisition of Compaq, a move she championed as essential for HP’s future relevance. Despite fierce internal and external opposition, the deal went through, but the promised synergies and market dominance largely failed to materialize. Instead, the merger proved deeply unpopular, led to widespread layoffs, and created significant cultural friction, ultimately diluting HP’s competitive edge and resulting in a period of underperformance that culminated in her forced resignation.

#9: Fred Goodwin

Royal Bank of Scotland

Across the pond, in the world of high finance, Fred Goodwin took the Royal Bank of Scotland on what could only be described as a ride off a cliff. Goodwin’s aggressive expansion spree, especially his disastrous acquisition of ABN AMRO at the peak of the 2008 bubble, left RBS reeling with debt and overexposure right as the global financial crisis hit. The fallout was so devastating, it required a government bailout and saw RBS post the largest loss in UK corporate history. He was even stripped of his knighthood – a rare and public shaming for a failed banking boss.

#8: Marissa Mayer

Yahoo!

When it comes to tech icons, Yahoo! was once a titan – until Marissa Mayer hopped into the driver’s seat. Hired as a turnaround CEO, Mayer’s tenure was marked by expensive acquisitions, like the $1.1 billion purchase of Tumblr, which failed to deliver anything close to the expected returns. She also invested heavily in redesigns and new features that failed to recapture the magic of Yahoo!’s glory days. The company struggled to innovate, couldn’t adapt quickly enough to the mobile revolution, and continued to see its core advertising business erode, eventually leading to the sale of its core internet operations to Verizon for a fraction of its former valuation.

#7: Eddie Lampert

Sears Holdings

Sears was once America’s go-to department store, so its slow-motion collapse is nothing short of tragic – largely thanks to the leadership philosophy of Eddie Lampert. Lampert’s control of Sears and Kmart from 2005 onward saw him prioritize cost-cutting and asset sales over investment in the stores themselves. Instead of modernizing aging infrastructure or adapting to the rise of e-commerce, Lampert treated the companies as a portfolio of assets to be stripped, selling off valuable real estate and brands like Craftsman. This systematic underinvestment alienated customers, demoralized employees, and left the stores increasingly irrelevant, leading to decades of decline and ultimately the bankruptcy and near-total disappearance of both once-beloved brands.

#6: Bernard Ebbers

WorldCom

Ebbers presided over one of the most jaw-dropping downfalls in corporate history. The charismatic CEO of WorldCom spearheaded the rapid expansion of the telecommunications giant through aggressive acquisitions throughout the 1990s. However, when the tech bubble burst and growth stalled, Ebbers and his executives resorted to a massive scheme to falsely inflate company assets by nearly $11 billion. This elaborate deception masked the company's financial struggles, artificially boosting its stock price and deceiving investors. When the fraud was uncovered in 2002, WorldCom promptly collapsed into bankruptcy, costing shareholders billions and thousands of employees their jobs and pensions. The scandal cemented Ebbers’ legacy as a CEO who played fast and loose with the truth.

#5: John Sculley

Apple Inc.

Sculley’s case is perhaps one of the most infamous examples of a CEO leading a company astray immediately after its visionary founder's departure. Sculley, brought in from PepsiCo by Steve Jobs himself, famously ousted Jobs from Apple in 1985. What followed was a decade where Apple, despite some innovative products, lost its way. The company suffered from bloated product lines, high prices, a confusing brand identity, and a failure to license its operating system effectively, allowing Microsoft to dominate the burgeoning PC market. By the mid-1990s, Apple was teetering on the brink of bankruptcy, bleeding market share and relevance, until Jobs’ triumphant return in 1997 pulled it back from the abyss.

#4: Martin Winterkorn

Volkswagen

Few corporate scandals have shifted global conversations quite like the Volkswagen emissions scandal – and much of the fallout falls at the feet of Martin Winterkorn. Winterkorn, the long-serving chairman of Volkswagen, was at the helm when the "Dieselgate" scandal erupted in 2015. It was revealed that VW had deliberately installed "defeat devices" in millions of its diesel vehicles to cheat on emissions tests, making them appear far cleaner than they actually were. This systemic deception, driven by a corporate culture that prioritized market dominance above all else, led to Winterkorn's resignation, massive fines exceeding tens of billions of dollars, and a profound erosion of trust in the brand that continues to reverberate across the automotive industry.

#3: Adam Neumann

WeWork

A flamboyant founder whose unchecked ambition and chaotic leadership style nearly imploded a multi-billion-dollar startup, Neumann co-founded WeWork with a vision to revolutionize office spaces. However, his tenure became synonymous with extravagant spending, questionable self-dealings, and a cult-like corporate culture. From lavish parties to personal use of company jets and selling trademark rights to WeWork itself, Neumann's financial impropriety and erratic management were legendary. The culmination was a disastrous attempt at an IPO in 2019, which exposed the company's massive losses and unsustainable business model, sending its valuation plummeting from $47 billion to under $10 billion in weeks and nearly bankrupting the entire enterprise.

#2: Jeffrey Skilling

Enron

While Skilling was the CEO in charge, the most infamous corporate scandal of the early 21st century was engineered by two men at the pinnacle of power. Skilling and Kenneth Lay, the founder and chairman, spearheaded Enron's transformation into a massive energy trading and services company. However, beneath the veneer of innovation lay a complex web of elaborate accounting fraud, including the use of special purpose entities to hide massive debts and inflate earnings. Their deceptive practices created a false perception of profitability, attracting vast investments. When the house of cards inevitably collapsed in late 2001, Enron filed for bankruptcy, erasing billions in shareholder value, destroying thousands of jobs, and sparking a national crisis of corporate governance.

#1: Elizabeth Holmes

Theranos

The story of this health-tech corporation is one of audacious fraud built on the promise of revolutionary technology that never existed. Elizabeth Holmes, the company’s charismatic founder, captivated investors and the public with claims that her company could perform hundreds of medical tests from just a few drops of blood using a proprietary device called the Edison. She amassed billions in funding, built a powerful board, and was hailed as a Silicon Valley prodigy. Her elaborate deception unraveled spectacularly, leading to the complete dissolution of Theranos, and her subsequent conviction for criminal fraud, marking one of the most stunning corporate downfalls in modern history.

Which of these CEOs do you think made the dumbest decisions? Let us know in the comments.