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  • Writer: Matt Heelan
    Matt Heelan
  • Mar 27, 2023
  • 3 min read

Updated: Mar 28, 2023

"Ignorance more frequently begets confidence than does knowledge." - Charles Darwin



I have worked with leaders and managers who exhibited both ignorance and arrogance. While I find both traits to be incompatible with my own leadership style, I believe that the combination of the two can be extremely detrimental to the organization. This is especially true when the founder of the company is also the leader who is plagued by these weaknesses. In such cases, the overconfidence and reluctance to adapt to changing market demands can pose a significant threat to the company's success and even its survival.

Throughout my career, I have had the privilege of working for seven Founder-led CEOs. These were privately held companies that offered a wide range of professional services and technology solutions to clients across various industries. From global law firms and Fortune 500 in-house counsel, healthcare systems, innovation teams, technology companies, physicians, attorneys, researchers, and computer and data science engineers, these companies catered to a diverse clientele. They ranged in size, with revenues varying from $1 million to $20 million and teams ranging from 20 to 250 members.

Although I have worked with these entrepreneurs, I have never founded a company or been a CEO. Therefore, I cannot fully comprehend what it takes to transition from a founder's mindset to a CEO's mindset. Nevertheless, over the years, I have witnessed some of the challenges, frustrations, and crises that arise when founders undergo this transition.

"In technology, failure is often a precondition to future successes, while prosperity can be the beginning of the end." - Jacquie McNish, author of Losing the Signal: The Untold Story Behind the Extraordinary Rise and Spectacular Fall of BlackBerry.

Take the case of Mike Lazaridis, the Co-founder, Electrical Engineer, and CEO of Blackberry. Despite being a highly respected figure in the industry (even today, lawyers reminisce about their Blackberries), Blackberry ultimately failed due to a variety of reasons, one of which was Mike's inability to acknowledge his own limitations. As the company's founder, it was natural for him to feel a sense of ownership and expertise over every aspect of the business. However, when consumers began demanding new features like touchscreens and internet browsers, Mike's inability to listen to his team and reluctance to acknowledge his own knowledge gaps prevented Blackberry from keeping up with the competition. This is in stark contrast to someone like Steve Jobs, who actively sought out new ideas and input from his team while building the first iPhone. *(See note below) Ultimately, Mike's lack of humility and adaptability would be his downfall. During my time working with founder-led CEOs this is what I have learned:

  1. Vision: Since they are the ones who founded the company, they may have a strong attachment to their original vision and may struggle to pivot or adjust as the market changes.

  2. Delegating: Founders may have a hard time letting go of certain responsibilities and delegating tasks to others, which can lead to burnout and a lack of scalability.

  3. Change: Founders may resist change or new ideas, as they have a deep attachment to the company's original culture and values.

  4. Experience: Many founders are not experienced in managing teams, scaling businesses, or handling complex financial matters, which can lead to challenges in these areas.

  5. Networking: Founders may have a limited network of contacts or industry connections, which can make it more difficult to secure partnerships, funding, or other resources.

  6. Emotional attachment: As the company is often seen as an extension of him or her, founders may struggle to separate their emotions from business decisions, which can lead to poor choices.

  7. Succession planning: Founders may struggle with planning for their eventual departure from the company, as they may feel that no one can replace them or continue their vision. This can lead to challenges in grooming and retaining talent for leadership roles.

The majority of CEOs who have hired me in the past to run their companies have recognized the need for help in these seven areas, along with some coaching, counseling, and advising. The successful ones understand the importance of acknowledging what they don't know and seeking out the skills, expertise, and experience they lack in order to grow their business. By recognizing their limitations and actively seeking support, these CEOs demonstrate a commitment to their company's success and a willingness to learn and grow as leaders. *Note: In 2004 Apple team members pitched the idea of turning the iPod into a phone to which Jobs responded with, "Why the f@*& would we do that? That is the dumbest idea I've ever heard."

"The only thing more dangerous than ignorance is arrogance." - Albert Einstein



Updated: May 22, 2023



My mother wanted to be a teacher from a very young age and she was the first one in her family to graduate from college. When I was 8 years old my mother quit her job as a teacher and she never taught again. Whether you're an entrepreneur starting a new company, a CEO leading an organization, or a teacher instructing students, we all hold a set of ethics, values, and principles that guide how we operate our businesses, teach our children and lead our lives. If we're fortunate, we learn these principles from our parents, families, and friends at a young age and continue to develop and refine them as we grow older. Building on that idea, I would like to explore how we can identify whether an organization shares similar values, ethics, and principles before deciding to join them. Throughout our careers, we're bound to make poor decisions when choosing companies to work for. One of my most significant mistakes has been joining organizations that didn't align with my values, ethics, and principles. This became apparent in various ways, from how they handled employee crises to their decision-making processes for promotions and transparency regarding the company's stability.


Back in 2018, I had a conversation with a CEO about joining his firm as an executive. I had gotten to know the CEO well over the previous couple of years and believed that I understood their values, ethics, and principles. He was eager to grow the organization rapidly, and I was thrilled to be a part of that journey. However, I was mistaken. The CEO wasn't necessarily a terrible person or difficult to work with, but he didn't live up to my expectations for transparency. Ultimately, he was less than forthcoming about the extent of the company's issues, his willingness to address them, his own maturity level as a leader, and the overall direction of the organization. During our 3-4 hour-long conversations, I posed difficult questions to the CEO about the leadership team's performance, the company's strategic direction, growth plans, and any employee issues. Additionally, I conducted due diligence by speaking with people in my network who were familiar with the CEO's executive reputation and standing in the business community. Here are some lessons learned from this experience: 1) Do detailed research. Conduct thorough research on the company, its products or services, competitors, and industry trends. This can provide insight into the market, the company's position, and growth potential. Additionally, it's essential to gauge the organization's values, ethics, and principles as a part of this research." 2) Consider talking to people who have left the organization. Talking to people who have left the organization can be valuable, but it's essential to weigh their perspectives appropriately since you'll only hear one side of the story. Nonetheless, this can still provide insight into the company's culture and any potential issues.

In my case, I spoke with someone who had left the organization a year earlier through a mutual connection. While their perspective didn't necessarily change my decision, it provided valuable context regarding what it was like to work in the organization. It's worth noting that talking to former employees can offer useful insight, despite the limitation of only hearing one side of the story.


3) Identifying one of the company's customers and connecting with them can provide valuable insight into their experience working with the organization. In my case, I spoke with people who had done business with them and most reported a positive experience with the leadership and team members. In one instance, a customer explained how the company handled a dispute related to invoices, which offered insight into their organizational ethics.

4) Requesting to review the company's financial statements can provide valuable insights into their financial performance and potential red flags. Look for trends in revenue, profitability, and liquidity. Keep in mind that the CEO and leadership team may reject your request, which is understandable but also insightful in itself.

5) Ask smart, challenging questions. When speaking with the CEO, ask smart, challenging questions that cover a broad range of topics and issues. Ask "why" questions to understand the reasoning behind their decisions, and ask about mistakes they've made and what they learned from them. Direct questions about the company's values, social responsibilities, ethics, and principles as a leader can also provide valuable insight.

6) Case studies and hypothetical situations. Creating case studies or sample situations can be helpful in understanding how the company operates in different scenarios. It can also give you insight into the decision-making process and the company's approach to problem-solving. This can be especially useful if you are considering joining a startup or a company in a new industry where there may not be as much information available. By creating hypothetical scenarios, you can gauge how the company might respond to real-life situations that could arise in the future.

7) Examine their actions. Examining the actions of an organization can be a good way to gauge whether their values and principles align with yours. Look for examples of how they've acted on their stated values and principles in the past, such as charitable donations, volunteering, or sustainable practices. You can also research how they treat their employees, including benefits, pay, and work-life balance, to get a sense of how they prioritize their people. Additionally, look for any public statements or policies that the organization has released on topics such as diversity, equity, inclusion, environmental responsibility, or ethical business practices.



8) Ask for access to the leadership team and board members. Again, not all organizations may allow you to talk directly to the leadership team or board members but it is worth asking. It can be very insightful to have conversations with the leadership team and board members to get a sense of their values, leadership style, and overall direction for the company. It can also help you understand how decisions are made and how different viewpoints are represented in the organization.


9) You may never know. No matter how much research and due diligence you do, there will always be some uncertainty and risk involved in joining a new organization. However, by taking the time to conduct thorough research, asking tough questions, and examining the actions of the organization and its leaders, you can increase your chances of making an informed decision and joining an organization that aligns with your values, ethics, and principles.


In the end, my mother quit her job as a teacher because she had a set of values, ethics, and principles that were non-negotiable. I learned from her the value of integrity, honesty, and transparency at a very young age. I learned that especially during difficult times and situations it is even more crucial that you evaluate your decisions against this set of personal criteria. Finally, I learned that if over time you understand that the organization does not align with your values then it should make your decision to leave even easier.

  • Writer: Matt Heelan
    Matt Heelan
  • Feb 1, 2023
  • 4 min read

Updated: May 22, 2023



What is confidence? Have you ever lost your confidence? Where did it go? How did you get it back? I lost my self-confidence in 2008. In that same year, my wife gave me a compass to help me find it again. On the compass was an inscription that said,

“What lies behind us and what lies before us are small matters compared to what lies within us. - Emerson.”

I used this compass to find my way back to the self-confident person that I was before 2008. Unfortunately, there are several factors that don’t allow some of us to recover from this loss. So what is this mysterious thing that some of us have, many more want and some never seem to be able to get it? What is confidence? We oftentimes believe that confidence is something that everyone either has or doesn’t but that’s not true because confidence is not a fixed attribute. Confidence for me has traveled on this sort of spectrum throughout my lifetime.

The definition of confidence for me is the attitude or belief that I have in myself to be able to do something. I also, over time, have learned to trust in myself that I have the knowledge, skills, and abilities to do something. It also means I can learn new subjects and concepts, rise to new challenges and hold myself accountable if something doesn’t go as planned.

There is also an important link between self-confidence and self-esteem. Self-esteem is the value that I put on myself. The mistake that I made for many years was allowing other people to assign me my own value vs. defining my value for myself. The day that I shifted to caring less about what other people thought of me was also the beginning of my becoming a more confident person. I say to people all the time that the only people whose opinions I truly care about are my wife, my kid, and my parents.

"You wouldn't worry so much about what others think of you if you realized how seldom they do." - Eleanor Roosevelt

Additionally, I could not have pursued a path to leadership and management roles without high self-esteem and self-confidence balanced with a healthy amount of humility and gratitude. I believe that because of the valleys that I experienced with low self-esteem and lack of confidence really prepared me for all sorts of challenges I faced as a leader. In one example, I was able to rely on my own confidence when I had to lead an organization through a crisis that could have caused the company to go out of business.


Also, a number of the entrepreneurs, founders, and CEOs I have worked with have also struggled with self-esteem and self-confidence issues. I don’t know why I always found it interesting that these individuals that had such great wealth, built great organizations, and impacted so many people also struggled to assign their own value and believe in themselves. The lack of self-esteem and self-confidence are not only reserved for certain zip codes or income brackets.


"If you hear a voice within you say 'you cannot paint,' then by all means paint, and that voice will be silenced." - Vincent Van Gogh

I don’t pretend to have some magical advice for you but here is what has helped me:

  1. Understand Neural plasticity. When a person has a stroke the brain begins to restructure or reorganize itself, create new connections, and create new neurons. Keep that in mind when you lack the confidence to learn something new - your brain can do amazing things it just needs you to believe in yourself.

  2. Create a trusted network or personal advisory board. As I mentioned earlier, I rely heavily on my family when I need help boosting my self-esteem or self-confidence. Over my career, I have also built a trusted network. This network consists of people who have gotten to know me over the years. These people have witnessed me as a success and as a failure. We have earned one another’s trust by giving each other sound personal and professional advice. I also make sure that this personal advisory board encompasses many different people with a broad array of skills, knowledge, and experience.

  3. Stop listening to your inner critical voice and remember your greatness. When our confidence is low we may have a tendency to listen to this inner critical voice. I am generally a positive-thinking person but when I hear this critical voice I make a conscious effort to reject it. How? Listen to the words in your head. If you truly examine what this critical or negative voice is telling you about yourself it is typically not based on actual facts. As a former college athlete, one of the proudest things I can say is that my father never missed a single game. After each game, my father would then get the local newspaper and cut out the box scores that would detail my performance. He would then send me the box scores. He always told me that sometimes you need to look at your old box scores to remind yourself of how great you were and can be in the future.

  4. Exercise regularly. I have always understood the value of exercise as an ex-athlete but as I have gotten older the value that it has on my own confidence and mindset is undeniable. There is also a relationship related to (1) in that exercise prevents neuron loss in the hippocampus and increases new neuron formation. I need all the help I can get.


If your confidence is low reach out to me and I would be happy to help in any way that I can. We can start with your box scores. matt.heelan@thaystack.com

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