Broken Pedestals: The Dark Sides of 10 Popular CEOs

The dark sides of popular CEOs

The following 10 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. 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 served as CEO of Alphabet until 2019 — deserves much of the credit. But at what cost?

Although 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 Those who worked closely with Page have described him as very withdrawn, often to the point of rudeness.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, suggesting that 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’s 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 percent approval rating — which says something about his leadership style.

How can a man so beloved by his underlings have a dark side? Consider the following: 

• 2010: In 2010, the U.S. Securities and Exchange Commission (SEC) officially charged Goldman Sachs with fraud in the structuring and marketing of collateralized debt obligations tied to subprime mortgages. With Blankfein at the helm, the company illegally profited from 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. 
• 2011: The following year, a United States 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. 
• 2012: Blankfein’s reputation took another hit when a departing executive ripped him in a 2012 op-ed piece in The New York Times.
• 2022: 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 involved in a money-laundering scandal. Shareholders specifically named Blankfein 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 raises the question of whether his image can ever be tarnished entirely.

3. Carly Fiorina

Improving employee engagement is crucial in business because unhappy workers are typically less productive. And where there’s a disgruntled employee, you can bet there’s a lousy 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. Consider the following: 

• Foreign controversy: 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.
• Domestic struggles: Back on the home front, 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). 
• Murky ethics: 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 percent. It seems that 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 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. After all, Aaron Sorkin made a movie, The Social Network, based on the premise that Zuckerberg straight-up stole the idea of Facebook from several of his friends. But business is often 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 been sued multiple times, criticized for his filings and, in recent years, served with subpoenas over the Cambridge Analytica scandal.
• He was 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. [Related article: Facebook Marketing Strategies for Businesses] 

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 X (formerly Twitter).

Instead of being best known for his game-changing innovations, Musk is most closely associated with questionable behavior. Consider the following: 

• Questionable claims: He has a well-documented history of making controversial statements and was accused of spreading misinformation and unscientific claims during the COVID-19 pandemic. 
• Tesla missteps: In 2018, the SEC sued him for a misleading tweet about taking Tesla private, which forced him to step down as chairman while remaining CEO. Musk’s claims about Tesla’s capabilities have also been called into question. At one point, 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. Autopilot issues, slowing demand, price cuts and cybertruck recalls are just a few of the issues Tesla faces today.
• Twitter to X: Musk’s Twitter takeover and transition to X have been eventful. After some waffling, Musk completed the deal to acquire Twitter in October 2022. He caused controversy immediately by firing executives and unceremoniously laying off nearly half the workforce. He launched an unpopular paid verification service (Twitter Blue), immediately dealt with a slew of impostor accounts, got rid of content-moderation rules and launched an abrupt rebrand as X that caused global confusion. 

Musk’s complicated personal life, arrogant public persona, suspect labor practices and other factors continue to make him a controversial public figure and businessperson. Even though he stepped down at X in 2023, he continues to wreak havoc (see below). 

6. Linda Yaccarino

Linda Yaccarino was the chairman of NBCUniversal’s global advertising and partnerships before being tapped to succeed Elon Musk as CEO of X. Over 11 years with NBCUniversal, she unified the company’s disparate global networks, business units and properties through strategic and operational initiatives. Yaccarino is credited with generating over $100 billion in advertising sales. So, it’s no wonder she caught the eye of Musk, who was looking to step down as CEO and find “someone foolish enough to take the job.”

This public comment from Musk perhaps should have been a red flag for Yaccarino. Although Musk ostensibly stepped down as CEO of X and handed the reins to Yaccarino in May 2023, his toxic and chaotic presence has continued to ensnare the company in controversy and internal discontent. Consider the following:

• Public attacks: While one of Yaccarino’s primary objectives as CEO was to increase advertising on the platform, Musk publicly attacked and threatened to sue organizations such as Media Matters and the Anti-Defamation League for pointing out the sharp increase in racist and anti-Jewish content on X. 
• Advertiser exodus: When advertisers expressed their dismay when their ads were posted next to Nazi content, Musk told them to leave the platform in a vulgar way. Advertisers, such as Disney, Apple and NBCU, left in droves. 

First and foremost, the CEO position is a leadership position and the person who holds it must act as a leader — and here is where Yaccarino has encountered trouble. She’s presented only a muted lack of response to controversies or weak justifications for Musk’s outrageous behavior. In retrospect, it appears she was installed at X to be a figurehead, while the real power remained Elon Musk. Yaccarino’s reputation is at stake as she tries to hang on to her job amid the chaos.  

7. 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. His missteps included the following: 

• Problems at Uber: During Kalanick’s time as CEO of Uber, the company was plagued by allegations of sexism, sexual harassment, overwork and knowingly misleading authorities. Kalanick was even recorded yelling at one of Uber’s drivers. He ran the business like a startup and never adapted his management style to align with Uber’s rapid growth. Kalanick didn’t adequately handle the company’s growing pains. 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.
• CloudKitchens toxic culture: 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. Additionally, in 2022, the company was sued for “deceptive business practices,” and some operators filed Federal Trade Commission complaints. 

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.

8. 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 run 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. However, 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.

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.

9. Sam Bankman-Fried

Sam Bankman-Fried was the celebrated CEO and founder of the FTX cryptocurrency exchange and one of the wealthiest people in the cryptocurrency space until his downfall. He launched FTX in 2019 and grew it into one of the biggest platforms for trading crypto derivatives. By early 2022, the company was valued at $40 billion. 

However, in November 2022, the company filed for bankruptcy following a report from CoinDesk that pointed out possible leverage and solvency issues. FTX’s failure shook the entire cryptocurrency industry, causing a landslide of losses in the billions. Bankman-Fried was arrested the next month and accused of stealing more than $10 billion from investors, manipulating the price of his exchange’s FTT token and front-running customers (a form of insider trading). About a year later, he was convicted of fraud and conspiracy to commit fraud and subsequently sentenced to 25 years in prison plus an $11 billion fine.

One of a CEO’s primary responsibilities is conducting business within legal guidelines and an ethical business culture. The bigger the company, the more people who can be hurt potentially by fraudulent, illegal and shifty CEO behavior — and the consequences of this behavior are severe. No situation justifies acting this way. Even if your company fails, you can file bankruptcy, reorganize, learn from your business failure and start again. Be aware of the laws and regulations that apply to your company and industry and stay compliant with them.

10. Dave Calhoun

Dave Calhoun has been the president and CEO of the global aerospace company Boeing Company since January 2020. However, due to a host of problems at the company, Calhoun recently announced his plans to step down at the end of 2024. Consider the following situations: 

• COVID-19 layoffs: The first of Calhoun’s travails was simply poor timing; he took office just as COVID-19 hit and planes were grounded industry-wide. As a result, he laid off around 16,000 workers and moved one of its manufacturing facilities to a nonunion plant. When the pandemic largely ran its course and travel ramped up again, Boeing struggled to rehire workers and dealt with union conflicts.
• Inherited tragedy: Under the previous CEO, two of Boeing’s Max planes crashed, killing almost 350 people. The planes were grounded at a cost of $20 billion and the fallout continued under Calhoun’s tenure. While the Federal Aviation Administration (FAA) cleared the Max plans to fly in 2020, it settled with Boeing to pay $2.5 billion to avoid prosecution for its unsafe design and lack of additional procedural safeguards. 
• More grounded planes and safety issues: As part of the FAA deal, Boeing’s safety procedures were supposed to be strengthened. However, Max planes were grounded in 2021 after electrical problems were discovered. In 2024, Boeing was again in the news regarding serious safety concerns after an Alaska Air plane’s door flew off while in the air and door bolts on another Boeing plane were found to be loose. 
• Quality control repercussions: The FAA is taking a strong stance, barring the company from expanding its Max plane production until it can address and fix its product quality issues. However, quality control problems continue to plague the company. According to a 2024 FAA audit viewed and reported on by The New York Times, Boeing failed 33 of 89 safety audits and the supplier of its 737 Max body failed seven of 13 safety audits. 

Just because the company’s problems began on someone else’s watch doesn’t entitle a CEO to place all the blame on their predecessor. Once a person becomes CEO, 100 percent of the responsibility falls to them and it is incumbent upon that individual to fix the problem. 

CEO dos and don’ts

Being the head of a company isn’t a walk in the park. You’re expected to raise profits, improve manager-employee relations, keep shareholders happy, maintain an excellent reputation and more. The gig requires long hours and forces you to face moral and financial challenges continually. It’s no wonder that some end up facing executive-level employee burnout. 

Fortunately, you can glean lessons from the mistakes of those who’ve come before you. We’ve compiled tips for business executives willing to take on this sought-after leadership role.

What should a good CEO do?

• Give employees freedom: Good CEOs empower their staff to become self-sufficient. You don’t have the time to answer everyone’s questions. Let employees find solutions themselves. Good CEOs also allow team members to speak up and try 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 hide in your office or make yourself unavailable to managers and employees. Learn how to be an inspirational leader who considers multiple viewpoints and perspectives.
• Maintain a network of mentors: You may assume a CEO should always have all the answers, but sometimes, 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.

What should a good CEO not do?

• Handle everything yourself: 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 instead of doing everything yourself.
• Cut benefits: Your workforce is the lifeblood of the company. Before eliminating employee benefits and perks, consider how to cut business costs in other areas, such as business trips and unnecessary inventory. Prioritize keeping employees satisfied.
• Keep poor managers: It’s not uncommon to put someone in a leadership position and quickly find out they’re not qualified for the job, toxic to company culture or a bad fit. Don’t leave the wrong leaders in place too long or you risk hampered productivity and increased turnover.

Jennifer Dublino contributed to this article.