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Broken Pedestals: The Dark Sides of 7 Popular CEOs

Julie Thompson
Julie Thompson

It's easy to idolize certain CEOs and admire their drive to innovate. But some have gone way off course.

A CEO is constantly under immense stress and pressure to adjust to society’s demands, eliminate competitors and generate massive profits. The best CEOs demonstrate strong values from the start, allowing for consistent leadership, dynamism and long-term growth. However, not all CEOs can manage the countless hours, criticism and ethical issues with grace.

Behind some of the world’s most famous companies, you’ll often find a dark side to their CEOs. Corner-cutting, a toxic work culture and arrogance can lead to a lack of transparency and a blatant disregard for regulatory procedures, the consequences of which can be costly. Some well-known leaders have managed to survive their scandals, while others have found their careers in tatters.

These once-revered CEOs enjoyed immense popularity and success – until they didn’t. See how they fell off their pedestals and which ones survived the rough landings.

1. Larry Page

From Google Ads to Google Pay, Google’s services have become indispensable to businesses and consumers alike. Google and its parent company, Alphabet, are determined to move beyond search engines and find their way into every facet of our lives. There’s no doubt that Larry Page – who co-founded Google, was its CEO for years, and then served as CEO of Alphabet until 2019 – deserves a lot of the credit. But at what cost?

Though Google is often praised as one of the most employee-friendly businesses in the industry, it’s hard to fight your own nature. Those who have worked closely with Page have described him as very withdrawn, often to the point of rudeness. During important meetings, it’s said he would disengage and refuse to pay attention to those around him. Some describe him as “kind of a jerk” and “an egomaniacal asshole.” 

While Page was respected among his subordinates, many felt he’d prefer as little human contact as possible. Today, he remains on Alphabet’s board of directors and is a member of its executive committee. That suggests he still retains a fair amount of power, even if his personality isn’t as fun as a Google Doodle.

2. Lloyd Blankfein

When it comes to being respected and popular with the “troops,” for a long time it was hard to beat Lloyd Blankfein, who has been the senior chairman of Goldman Sachs since 2019 and previously served as CEO, COO, and president. At one point in his tenure, he had a 97% approval rating. That says something about his leadership style.

How can a man so beloved by his underlings have a dark side? Well, in 2010, Goldman Sachs was officially charged by the U.S. Securities and Exchange Commission (SEC) for fraud in the structuring and marketing of collateralized debt obligations tied to subprime mortgages. The company, with Blankfein at the helm, was illegally making money off the recession. Yet, when Congress officially interviewed the executive about his company’s actions, Blankfein claimed (under oath) that his company had never intentionally shorted mortgage-backed securities to increase profits. 

The following year, a U.S. Senate panel announced that Blankfein and Goldman Sachs misled both Congress and its clients. Sen. Carl Levin even wanted the U.S. Department of Justice (DOJ) and SEC to investigate the company for possible charges, including perjury claims against Blankfein. Ultimately, no charges were ever filed, but there’s no doubt Blankfein’s shiny veneer was cracked. His reputation further took a hit when a departing executive ripped him in a 2012 New York Times op-ed.

More recently, in the spring of 2022, Goldman Sachs reached a $79.5 million settlement with shareholders over claims of poor oversight tied to the controversial 1Malaysia Development Berhad wealth fund, which was tied up in a money-laundering scandal. Blankfein was specifically named by shareholders in the complaint, which was related to the DOJ’s 2020 foreign bribery charges against Goldman Sachs and the company’s $2.9 billion settlement. Blankfein has weathered several other scandals during his reign, which makes you wonder whether his image can ever be fully tarnished.

3. Carly Fiorina

Unhappy and disengaged employees usually aren’t the most productive workers. And where there’s a disgruntled employee, you can bet there’s a crappy boss not far off. Such was the case with Carly Fiorina. 

Fiorina was brought on as CEO of Hewlett-Packard (HP) in 1999, becoming the first female head of a Fortune 100 company in the process. For a while, it seemed she would be a good fit. In actuality, her tenure was plagued with problems from day one, and they just seemed to stack up as time went on. For example, she exploited loopholes in export sanctions by using foreign subsidiaries to sell millions of dollars’ worth of computer equipment to Iran, a controversy that came back to haunt her during her bid for the 2016 Republican presidential nomination.

Did You Know?

In 2021, about 8% of CEOs at Fortune 500 companies were women, according to the Women Business Collaborative. Did you know these 10 successful businesses were run by women?

Back on the homefront, Fiorina’s leadership was landing her own company in some serious hot water. Some 30,000 workers lost their jobs, and about 80,000 others agreed to either take pay cuts or give up accrued vacation time (many of whom were laid off regardless). Fiorina also came under fire for increasing her salary threefold and purchasing a private jet while her employees languished in near-poverty. [Related article: How Keeping Employees Happy Benefits Business]

Still, her stint as HP’s CEO wasn’t a total failure: When she was forced to resign in 2005, the company’s stock jumped 6.9%. Apparently, getting fired was the best thing Fiorina could have done for HP. As for her career, well, that’s been considerably damaged, due in part to her failed attempts to move into politics.

4. Mark Zuckerberg

“You can be unethical and still be legal; that’s the way I live my life.”

This eyebrow-raising statement is allegedly a remark made by Facebook’s Mark Zuckerberg, according to a former Harvard classmate. While its authenticity hasn’t been proven, it might give you a bit of a glimpse into how the founder of the world’s most popular social media site views the concept of morality.

Now, it’s no secret that Zuckerberg has a dark side – Aaron Sorkin made a movie, The Social Network, based on the premise that he straight-up stole the idea of Facebook from several of his friends – but the fact of the matter is that sometimes you need to play a little rough to get ahead in business. After all, it’s a dog-eat-dog world, right? Maybe, but some serious allegations regarding Zuckerberg’s behavior have emerged over the years.

The CEO has been accused of using Facebook login details to break into and read private emails. On at least one occasion, he hacked a rival social network site to vandalize social profiles and make it difficult for users to locate one another. He has faced multiple lawsuits, been criticized for lawsuits he himself has filed and, in recent years, been served with subpoenas over the Cambridge Analytica scandal and been widely blamed for letting misinformation run rampant on Facebook during the 2016 and 2020 elections. In 2021, he was even asked to testify about Facebook’s role in the Jan. 6 attack on the Capitol.

Petitions for Zuckerberg to resign seem to crop up almost every year, and his own employees have staged virtual protests against the company. Whistleblower Frances Haugen even said in June 2022 that Facebook can’t repair its reputation until Zuckerberg steps down, which he seems to have no intention of doing. [See which Facebook tools your business should be using.]

5. Elon Musk

Elon Musk has attained celebrity status with his boasts of science-fiction successes and seductive forward-thinking image. Unfortunately, the man that car enthusiasts put on a pedestal often gets in the way of his own achievements, which include varying degrees of success with Tesla, SpaceX and PayPal.

Instead of being best known for his game-changing innovations, Musk today is most closely associated with questionable behavior. He has a well-documented history of making controversial statements and was accused of spreading misinformation and unscientific claims during the COVID-19 pandemic. In 2018, he was sued by the SEC for a misleading tweet about taking Tesla private, which forced him to step down as Tesla’s chairman while remaining CEO. And he recently created a backlash with his attempt to take over Twitter and his insistence that employees give up remote work and come back to the office.

Among his inventions, Musk’s claims about Tesla’s capabilities have been called into question, and customers were asked to sign nondisclosure agreements to receive free defect repairs. That was a shady way to keep problems off the public’s radar so Tesla could continue to boost its stock price, take on new investors and hide safety concerns from auto regulators. Additional stories of environmental violations and countless employee accounts of mistreatment have often overshadowed the few successful products Tesla has been able to produce.

Musk has become a tabloid fixture both personally and politically, but he has a hold on millions of followers (though he needs preclearance from the SEC to tweet about certain topics). And with his billions in wealth, it’s unlikely he’ll be disappearing from the business world anytime soon.

6. Travis Kalanick

Whatever your career or industry, soft skills can make or break you. Travis Kalanick lacked a significant one: self-awareness. Self-delusion can cause you to make bad business decisions, take relationships for granted, and fail to drive growth and profits. Kalanick was driven by ruthless competitiveness, wasted money and fostered a “bro culture” that favored toxic masculinity and bullying.

During Kalanick’s time as CEO of Uber, the company was plagued by allegations of sexism, sexual harassment, overwork and knowingly misleading authorities. Kalanick himself was even recorded yelling at one of Uber’s drivers. He ran the business like a startup and never adapted his management style to be in line with Uber’s rapid growth. Kalanick didn’t adequately handle the company’s growing pains, and, due to pressure from Uber’s board and investors, he stepped down in 2017. Controversy continued to swirl as he remained on the organization’s board until resigning his seat in 2019.

After leaving Uber, Kalanick started CloudKitchens, restaurant rental spaces that provide delivery-only services. Although he’s proclaimed the business to be a massive success, it is said to have the same toxic culture he brought to Uber. More than 300 employees left in 2021 alone. Kalanick’s stature was further diminished by the 2022 Showtime series Super Pumped, which brutally depicted his rise and fall. It’s telling that the show’s second season is expected to center on Zuckerberg and Facebook.

7. Adam Neumann

Overconfidence is a trait few people have, and it often results in failure. Adam Neumann is a prime example. As CEO of WeWork, he was so confident in his skills that he once declared that his descendants would be running the company in 300 years. To his credit, Neumann was a charismatic fundraiser. He scaled quickly with an indulgent mixture of $12 billion in venture capital and debt.

Working nonstop, Neumann added 12,500 employees and half a million users in 111 cities and 29 countries in less than a decade. By 2018, however, the company had lost $2 billion. But because WeWork’s valuation continued to rise, Neumann didn’t rein in expenses. Instead, he purchased a $60 million private jet, spent $90 million on six homes and employed many nannies, chefs, and personal assistants. Investors saw the lavish lifestyle and bought in.


SpencerStuart, which guides companies in leadership decisions, found that rookie CEOs actually perform better than seasoned veterans. The turning point, according to its data, comes in the first-time CEO’s fourth year.

However, it wasn’t long before Neumann’s over-the-top lifestyle caught up with him. With the company bleeding money before going public and accusations of wildly inappropriate workplace behavior, the executive faced growing pressure to give up his post. Amid allegations of questionable business practices, including using the company to unethically benefit himself, Neumann resigned from WeWork in 2019. Similar to Kalanick and Super Pumped, Neumann was unflatteringly portrayed in the Apple TV+ series WeCrashed in 2022. Together, the programs serve as a warning to CEOs: Never get too big for your britches.

CEO dos and dont’s

Looking at the above CEOs, it’s easy to covet their successes and want none of their failures. Being the head of a company isn’t a walk in the park. You’re expected to raise profits and improve relations between managers and employees. The gig requires long hours and forces you to continually face moral and financial challenges. It’s no wonder that some end up burning out.

Fortunately, you can glean lessons from the mistakes of those who’ve come before you. We’ve also compiled our own top tips for business executives taking on this sought-after leadership role.

What should a good CEO do?

  • Give employees freedom and empower your staff to become self-sufficient. You don’t have the time to answer everyone’s questions. Let employees find solutions themselves. A good CEO gives others the opportunity to speak up and try out new ideas.
  • Keep an open mind. While a CEO should focus on the big picture, that doesn’t mean ignoring smaller puzzle pieces. Don’t always hide in your office or make yourself unavailable to your managers and employees. Learn how to be an inspirational leader.
  • Maintain a network of mentors. You may assume a CEO should always have all the answers, but it’s normal to feel isolated and underqualified. Seek out a trusted individual as a confidant, and take time to talk with business professionals who have been there and done that.

Keep in touch with those in your LinkedIn network and wider professional circle to gain valuable industry knowledge and be the first to learn when an opportunity arises.

What should a good CEO not do?

  • Forget to delegate. Being a CEO means you wear multiple hats within the company, but your team is only as strong as its weakest link. Concentrate on hiring qualified departmental leadership so you can delegate and check in instead of doing everything yourself.
  • Cut benefits. Your workforce is the lifeblood of the company. Before taking benefits and equipment away, think about how you can cut costs in other areas such as business trips and unnecessary inventory. Prioritize keeping employees satisfied.
  • Be afraid to change up leadership. It’s not uncommon to put someone in a leadership position and quickly find out that they are not qualified for the job, toxic to company culture or aren’t a good fit. Don’t leave the wrong leaders in place for too long, or you will risk hampered productivity and increased turnover.

Kade Call contributed to the writing and reporting in this article.

Image Credit: Nattakorn Maneerat/Shutterstock
Julie Thompson
Julie Thompson
Contributing Writer
Julie Thompson is a professional content writer who has worked with a diverse group of professional clients, including online agencies, tech startups and global entrepreneurs. Julie has also written articles covering current business trends, compliance, and finance.