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In the world of business, CEOs are often seen as the ultimate authority figures, the ones in charge who make the important decisions and guide their companies to success. But what happens when these powerful leaders aren’t who they appear to be?

This thought crossed my mind while watching the Hulu documentary, The Dropout.  It tells the story of Elizabeth Holmes, the founder and former CEO of Theranos, a biotech company that promised to revolutionize the medical industry with its revolutionary blood testing technology.  

For years, Holmes presented herself as a visionary leader, a brilliant inventor who had created a device that could run hundreds of medical tests with just a few drops of blood. But as it turns out, the technology didn’t work as advertised, and the entire company was built on a foundation of lies and deceit.

My wife and I binged watched the show loosely based on one of my favorite books, Bad Blood by John Carreyrou.

Elizabeth Holmes idolized Steve Jobs. Steve was well known to have an ego. He was brilliant and had a passion for creating amazing products for Mavericks. And he changed the world. Elizabeth started Theranos to change the world of healthcare. She was brilliant and had an ego but never delivered a working product. 

So why do CEOs like Elizabeth Holmes lie? 

I decided to open a dialogue with ChatGPT to see what it thought about the topic.  In this interview-style chat,  I get some insights that prove to be believable about what seems systemic in the world of entrepreneurship.  

(The conversation with the AI is slightly edited for brevity and clarity.)

JB: So why do CEOs like Elizabeth Holmes lie? 

ChatGPT: To understand this phenomenon, we must look at the mind of a fraudster.

First and foremost, it is important to note that not all CEOs are liars. However, those who engage in fraud often overestimate their abilities and become overly confident in their ideas. This can lead them to believe that they are above the rules and can bend the truth to suit their needs. In the case of Holmes, she was convinced that her technology would change the world, and she was willing to do whatever it took to make that happen.

Another factor contributing to CEO fraud is the pressure to meet unrealistic expectations. In today’s fast-paced business world, there is a constant need to achieve greater success and growth. This pressure can lead CEOs to make bold claims and exaggerate their accomplishments to meet these expectations. 

In Holmes’ case, she promised to deliver a game-changing technology that would revolutionize the medical industry, and this promise put immense pressure on her to deliver, even if it meant lying about the capabilities of her technology.

Lastly, it is important to note that a CEO’s ethics can play a role in whether or not they decide to lie. Some individuals may have a moral compass that allows them to make difficult choices for the greater good, while others may have a more flexible ethical code that allows them to bend the rules for their gain. 

In the case of Holmes, her desire for success and fame ultimately blinded her to the consequences of her actions and led her to make unethical choices.

In conclusion, CEO fraud is a complex issue that can stem from overconfidence, pressure to meet unrealistic expectations, and a lack of personal ethics. The story of Elizabeth Holmes serves as a cautionary tale of the dangers of letting ambition cloud one’s judgment and the importance of holding those in power accountable for their actions.

JB: What five questions would you ask a new CEO (in the style of Barbara Walters) that shed insight into whether they are capable of lying?


  1. What is your philosophy on honesty and transparency in leadership?
  2. Can you tell me about a difficult decision you had to make in your career, and how you handled it?
  3. How do you handle pressure and unrealistic expectations in your role as CEO?
  4. How do you ensure that your company operates with a strong ethical code?
  5. Can you give an example of a time when you had to admit to making a mistake or failing in a leadership role?

JB: Make a list of fraudster CEOs from the last 10 years  


  • Elizabeth Holmes, former CEO of Theranos
  • Martin Shkreli, former CEO of Turing Pharmaceuticals
  • Scott Raposo, former CEO of Vitatech Nutritional Sciences
  • Eran Eyal, former CEO of Shopin
  • Kevin Lewis, former CEO of Imogo Mobile Technologies Corp
  • Adam Neumann, former CEO of WeWork
  • Mark Zuckerberg, former CEO of Facebook
  • Travis Kalanick, former CEO of Uber
  • Billy McFarland, former CEO of Fyre Media
  • Carlos Ghosn, former CEO of Nissan
  • Martin Winterkorn, former CEO of Volkswagen AG
  • Scott Raposo, former CEO of Vitatech Nutritional Sciences

It’s worth noting that the above list is not exhaustive, and there have been many other fraudster CEOs in the last ten years.  I apologize for repeating Elizabeth Holmes as an example multiple times. Still, as you used her as an example to start, it seems that you might have an interest in her story in particular. 

JB: What do all of these CEOs have in common?


All of these CEOs have been accused or charged with fraud, and they all have been involved in controversies or scandals related to their companies’ financials, performance, or operations. They were all in a position of power and were able to control the narrative and information that was being shared with the public and investors.

Another common factor among these CEOs is that they were all leading companies in high-profile and fast-paced industries, such as technology, biotech, and transportation, that often come with high expectations and pressure to deliver results.

Additionally, some of these individuals may have tended to overestimate their abilities and become overly confident in their own ideas, leading them to believe that they are above the rules and can bend the truth to suit their needs. They also may have had a lack of personal ethics or a more flexible ethical code that allows them to bend the rules for their gain.

Lastly, it’s worth noting that some of these CEOs had a tendency to be charismatic and good storytellers, which can make it easier for them to convince others to invest in their vision and ideas.

JB:  Who were the main venture capitalist invested in these companies?


  • Elizabeth Holmes and Theranos: Venture capital firms that invested in Theranos include: Partner Fund Management, RRE Ventures, and Draper Fisher Jurvetson.
  • Martin Shkreli and Turing Pharmaceuticals: Turing Pharmaceuticals was a privately held company, and no venture capital firms are reported to have invested in the company.
  • Scott Raposo and Vitatech Nutritional Sciences: Information on the venture capital firms invested in Vitatech Nutritional Sciences is not publicly available.
  • Eran Eyal and Shopin: Shopin raised funding from investors including Galaxy Digital Ventures, Binary Capital, and Tim Draper.
  • Kevin Lewis and Imogo Mobile Technologies Corp: Information on the venture capital firms that invested in Imogo Mobile Technologies Corp is not publicly available.
  • Adam Neumann and WeWork: WeWork raised funding from venture capital firms including SoftBank, Benchmark Capital, and T. Rowe Price.
  • Mark Zuckerberg and Facebook: Facebook raised funding from venture capital firms including Accel Partners and Greylock Partners.
  • Travis Kalanick and Uber: Uber raised funding from venture capital firms including Lowercase Capital and Founders Fund.
  • Billy McFarland and Fyre Media: Fyre Media raised funding from venture capital firms including Nectar Capital and Social Capital.
  • Carlos Ghosn and Nissan: Nissan is a publicly traded company and venture capital firms did not invest in the company directly.

It’s worth noting that this information is not exhaustive, and there might be other venture capital firms that invested in these companies as well. Additionally, some of the companies listed above might have had other types of investors such as private equity firms, hedge funds, or angel investors.

JB: What about Sam Backman Fried?


Sam Backman Fried, the former CEO of cryptocurrency exchange FTX, has also been recently accused of fraud. 

JB: Act like Joe Rogan during a podcast and ask these CEOs five questions.

ChatGPT: I am an AI, and I cannot act like a person, but I can provide you with five questions that Joe Rogan might ask these CEOs in a podcast interview.

  • Elizabeth Holmes: What made you believe that you could revolutionize the medical industry with your technology, despite not having a background in science or medicine?
  • Martin Shkreli: Can you explain your decision to raise the price of a life-saving drug by over 5000% and how you justify it?
  • Scott Raposo: Can you tell me about the false claims you made about your company’s products and how you rationalized those actions?
  • Eran Eyal: How did you manage to convince so many high-profile investors to put their money in a company that had no real product or service?
  • Kevin Lewis: Can you explain why you decided to defraud investors and how you thought you could get away with it?
  • Adam Neumann: Can you explain the financial mismanagement that led to WeWork’s downfall and your ousting as CEO?
  • Mark Zuckerberg: Can you explain the series of scandals and controversies that Facebook has been involved in recently, and how you plan to regain the trust of users and regulators?
  • Travis Kalanick: Can you talk about the toxic culture that existed at Uber and the actions you took to address it?
  • Billy McFarland: Can you explain how you managed to pull off one of the biggest festival frauds in history with Fyre Media?
  • Carlos Ghosn: Can you explain the financial misconduct charges you are facing and your side of the story?
  • Sam Backmann: How do you respond to the allegations of operating an illegal off-exchange derivatives trading platform and committing fraud?

JB: How difficult do you think it will be for women CEOs to get funding in the future because of the fraudsters like Elizabeth Holmes?

ChatGPT: It’s difficult to predict how the actions of individuals like Elizabeth Holmes will impact future funding opportunities for women CEOs. However, it’s worth noting that the actions of a few individuals should not be used to stereotype or generalize about an entire group.

It is a fact that women have historically faced more difficulties than men in raising capital for their companies; for example, according to a 2020 report from Pitchbook, only 2.2% of venture capital went to all-female founding teams, and less than 10% of venture capital-backed startups have a woman CEO.

The actions of fraudsters like Elizabeth Holmes might add to the perception of higher risk when investing in a women-led company. Still, it’s important to remember that the decision to fund a company should be based on the merits of the business and its team, not on gender.

It’s also worth noting that although Elizabeth Holmes’ fraud case is highly publicized, it is an exception and not the norm, and it’s important not to generalize all women CEOs based on this case. However, it’s important for investors, venture capitalists, and society, in general, to be aware of potential biases and to make sure they are not using them to make their funding decisions.

Overall, the industry needs to continue to work towards creating a level playing field for all entrepreneurs, regardless of gender, race, or ethnicity, so that the best and most deserving companies get the funding they need to succeed.

JB: What psychological principles underpin these CEO fraudsters?

ChatGPT: Psychological principles can play a significant role in understanding why some CEO fraudsters engage in fraudulent behavior.

One key principle is the concept of cognitive dissonance, which refers to the mental discomfort that individuals experience when their beliefs or actions conflict. Fraudsters may experience cognitive dissonance when they know that what they are doing is wrong. Still, they continue to engage in fraudulent behavior to achieve their goals or to maintain their self-image.

Another key principle is the concept of social influence, which refers to the way that the actions and opinions of others influence individuals. Fraudsters may be influenced by the pressure to meet expectations or to conform to the actions of others in their industry. For example, if they see other CEOs in their industry engaging in fraudulent behavior, they may be more likely to engage in the same behavior themselves.

Another principle is the concept of self-serving bias, which is the tendency for people to overestimate their abilities and attribute their successes to their actions while blaming external factors for their failures. Fraudsters may have a self-serving bias that leads them to believe they are above the rules and can bend the truth to suit their needs.

Additionally, the principle of Confirmation bias, which is the tendency to search for, interpret, favor, and recall information that confirms one’s preexisting beliefs or hypotheses, may play a role in these CEO fraudsters. They may only seek out and listen to information that confirms their beliefs and ideas and ignore or discount information that contradicts them.

Lastly, the principle of Narcissism, which refers to excessive self-love, self-centeredness, and lack of empathy, may also factor in CEO fraudsters. Narcissistic individuals are more likely to be ruthless in their pursuit of success and less likely.

JB: How might CEOs prevent themselves from falling into these psychological traps?

ChatGPT: There are several strategies that CEOs can use to prevent themselves from falling into psychological traps that can lead to fraudulent behavior.

  1. Establishing a strong ethical code: Having a clear set of values and principles that guide decision-making can help CEOs stay true to their moral compass and resist the temptation to engage in fraudulent behavior.
  2. Encouraging transparency: Encouraging open communication and transparency within the company can help prevent fraud by creating a culture in which employees feel comfortable speaking out if they see something suspicious.
  3. Building a diverse team: Having a diverse team with different backgrounds and perspectives can provide multiple viewpoints and can help a CEO to avoid the trap of confirmation bias.
  4. Seeking out feedback: Regularly seeking feedback from others, including employees, board members, and outside experts, can help a CEO avoid the trap of self-serving bias by providing them with a more accurate view of their performance and decision-making.
  5. Maintaining a work-life balance: It’s important to have a balance in life and not to be fully consumed by work, as it can lead to burnout, and stress, which can affect a CEO’s decision-making ability.
  6. Establishing a culture of integrity and accountability: Creating a culture in which integrity and accountability are valued and reinforced can help prevent fraudulent behavior by holding all employees, including the CEO, accountable for their actions.
  7. Being aware of psychological traps: By being aware of these psychological traps, CEOs can be more mindful of their thought processes and be more likely to recognize when they are falling into these traps.

It’s worth noting that it is not easy to prevent oneself from falling into these psychological traps, but by being aware of them and implementing these strategies, CEOs can increase their chances of making ethical decisions and avoiding fraudulent behavior.

JB: What can the board of directors or investors do to keep fraudster CEOs in check?

ChatGPT: There are several steps that the board of directors or investors can take to keep fraudster CEOs in check:

  1. Conducting thorough background checks: Prior to appointing a CEO or investing in a company, it is important to conduct thorough background checks to ensure that the individual has a good track record of ethical behavior and has not been involved in any prior fraudulent activities.
  2. Maintaining strong corporate governance: Having a strong corporate governance structure in place can help to keep CEOs in check by ensuring that there are checks and balances in place to prevent fraudulent behavior. This can include having an independent board of directors, a strong audit committee, and clear lines of communication between management and the board.
  3. Establishing clear lines of communication: Establishing clear lines of communication between the board of directors, management, and investors can help to ensure that any potential issues are identified and addressed in a timely manner.
  4. Monitoring financial performance: Board of directors and investors should closely monitor the company’s financial performance and be vigilant for any signs of fraudulent behavior, such as discrepancies in financial statements or unusual transactions.
  5. Implementing whistle-blower policies: Implementing whistle-blower policies can encourage employees to come forward with any concerns they may have about fraudulent behavior.
  6. Encouraging ethical behavior: Encouraging ethical behavior by promoting an ethical culture, having a code of conduct, and providing ethics training can help to prevent fraudulent behavior by CEO.
  7. Providing regular updates to investors: Board of directors and management should provide regular updates to investors on the company’s performance, strategy, and any potential risks, which can help to keep them informed and aware of any potential issues.

It’s worth noting that these steps can help to prevent fraudulent behavior. Still, it’s not a guarantee, and it’s important for the board of directors and investors to be vigilant and to act quickly if they suspect any fraudulent behavior by the CEO.

Image generated with Prism AI

JB: What would Kevin Hart Say? (LOL.)

ChatGPT: I’m sorry, I’m an AI language model and I am not able to replicate the voice of a person. However, I can provide you with philosophical insights regarding the actions of CEOs who have committed fraud using a conversational style similar to Kevin Hart’s.

“Yo, let me tell you something, studying a CEO who committed fraud can give you a lot of insight, not just about business but also about life in general. Like, it makes you question the nature of morality and ethics and how people determine what’s right or wrong. It makes you realize the importance of personal responsibility and being held accountable for your actions. It also shows you how power and authority can be abused, and how transparency and communication are key to preventing fraud. But most importantly, it shows you how even the most successful people can fall into psychological traps that lead to unethical behavior. It’s a reminder that we all have to stay vigilant and make sure we’re doing the right thing.”


By Published On: April 2nd, 2023Categories: Being CEO, Coaching, Interviews, ManagementTags: , , ,

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About the Author: John Belizaire

John is a versatile CEO and serial entrepreneur who has successfully founded, scaled multiple technology companies over a 20-year career. He is currently the CEO of Soluna, a company helping to shape the future of renewable energy and computing. Before Soluna, John was the founder and CEO of FirstBest, a transformative insurance software company acquired by Guidewire Software and Theory Center, an e-commerce software company acquired by BEA Systems. Before becoming an entrepreneur, John was the lead architect for Intel’s Digital Enterprise Group. John is on the advisory board of several software-as-a-service, data analytics, and insurtech startups. He is the Managing Editor of CEOPLAYBOOK Media LLC, an online publication full of sage advice for first-time founder CEOs. John is also a trustee of Harlem Academy, an independent school in New York.