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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



  • Writer: Matt Heelan
    Matt Heelan
  • Feb 10, 2023
  • 4 min read

Updated: May 22, 2023



The first job I had out of college I worked for an entrepreneur. I worked for him for 11 years. It wasn’t until I had been there 7 years that he finally felt comfortable allowing me to run a part of the business. I vividly remember that day. We had just sat down to review the monthly financials which usually turned into an intense exercise or interrogation. I recall the session went really well and I left his office feeling pretty pleased with myself. Later that night when he was leaving for the day he stopped by my office. He said that he felt very comfortable with me and that he trusted me with running the department but it wasn’t because I had answered all of his questions successfully earlier in the day. He said, “Matt I trust you because you are finally starting to think like me about the business.” From that point forward in my career I challenged people to, “Think like the owner.” Thinking like the owner is different than thinking like an employee. The ability to be able to see the entire interconnected organization vs. just the individual parts where you play a role. Once you begin to see the organization as a system then your whole mindset will begin to change as you see it from an entirely different vantage point.

In order for people to think like owners we have to create the right environment. Here are some characteristics of those environments: 1) Empowerment+Autonomy+Trust. In order for people to act and think like the owner they have to be empowered. What does that truly mean? It means that as the owner and leaders within the company, we need to give people projects which expose them to all areas of the organization in order to gain new and different skills, experience, and knowledge. In my own experience, I worked in the professional services group and was able to work on joint projects with marketing, sales, finance, and HR. It is also the responsibility of the organization to empower people in the “right way” and then give them the autonomy to execute individually or as a team. Also, a part of thinking and acting like the owner requires us to understand when something doesn’t go as planned and we fail. It is imperative that we have created a culture in which team members understand how we deal with failure both individually and organizationally. We need to have created a culture that emphasizes and makes them feel confident that they will be supported. If team members feel safe to make mistakes and fail at certain projects we can create a sense of trust. The trust that is created as a part of that process also motivates team members to want to do better. Team accountability can be more powerful.


2) Accountability and Servant Leadership. Several years before I joined the business the owner had to file bankruptcy and faced potentially having to shut down the business. During the bankruptcy, the owner promised the entire team that he would not miss payroll. He never did. As the owner and someone that wants to act like the owner, you have to be accountable to yourself and of equal importance be accountable to your team. This means that you are accountable to all of your team members even those that may be outside of your group, division, or department. The owner is accountable for everyone from the boardroom to the bathroom and so should you. If you look up “Servant leadership” this approach puts the needs of the organization, employees, and community above themselves. Servant leaders create a culture of trust, have an unselfish mindset, and promote others into leadership roles. What is the connection between “Servant leadership” and thinking like an owner? I believe that the Servant leader often has the same mindset as a person who thinks like the owner. The majority of the entrepreneurs that I have worked with built organizations that understood the critical nature of trust, autonomy, and empowerment.



3) Incentivize and celebrate. In order to increase this behavior organizations need to determine ways to incentivize and reward people who demonstrate the think like an owner attitude and mentality. Some companies actually formalize this through equity or ESOP programs. In other companies, they incentivize this through bonus programs or salary reviews. In one example, as a leader, I created a cross-functional team in order to review ways for us to reduce companywide expenses. Utilizing a systems thinking framework we outlined the outcomes, criteria for success, and gaps where we need more data and created a plan. I assigned two leads to manage the project and after 3 months they had created a set of recommendations that would have reduced our monthly expenses by 20%. We ended up implementing a portion of their recommendations and each member of the team was recognized at the company quarterly meeting, received a quarterly bonus and a few of the members were eventually promoted. A few of the members asked that we forego a bonus and wanted us to pay for some leadership and professional development.


In the end, the organizations that incorporated the“think like the owner approach or who are able to get their team members to “take ownership of the work” or had “high levels of engagement” all had the following things in common:

  • Hired smart people and empowered them to do good work.

  • Paid them really well and provided great benefits.

  • Created and maintained an environment with a high degree of trust, autonomy, and accountability.

  • Provided the systems, structures, frameworks, and tools in order to help their team be successful for the customer.

  • Incentivized, rewarded, and celebrated successful accomplishments and learned from their failures, and improved.

  • Invested in people’s personal and professional development.

  • Built a great product or provided a great service that the customer loved.


  • 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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