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  • 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
  • Jan 5, 2023
  • 3 min read

Updated: May 22, 2023

Since I began my career in 1995, I have worked for 6 different entrepreneurs/founders. All of these individuals started these companies and have since either sold the company, closed the company or they still exist. I have kept a journal of all my observations of the organizations and the Entrepreneurs/Founders I have worked with. The majority of these notes were for me to be able to learn from the strategies that worked and to be able to learn from their failures or challenges. I recently went back through these notes to understand what some of the common themes were around their challenges. Here are my notes:



  • The technical founder failed to acknowledge how his/her role needed to change for the long-term success of the company based on where he/she was at in the company maturity process. Over the course of time companies, leaders and team members go through a maturity process. Note: I created a maturity assessment checklist and matrix to understand a common way to understand where each company is within that maturity timeline.

  • Entrepreneurs/Founders failed to acknowledge their lack of business acumen and waited too long to hire the necessary people or team. A relatively old book but still some relevant content around this topic can be found in the EMyth by Michael Gerber.

  • Entrepreneurs/Founders failed to pay attention and respond to trends in the marketplace for their product or service and then lost their competitive advantage. Think of Polaroid not responding quickly enough to digital transformation. Note: Although there has been a resurgence as the old is now new again.

  • Entrepreneurs/Founders lack the ability to leverage or learn from their network/community. When the business is struggling, his/her unwillingness to rely on their network or community for help. I think if you are willing you can find your community of executives who have already lived through some of the challenges you are facing. I always find it surprising when I still talk to CEOs who think they are the only ones that can solve their issues or problems. The organization and maybe your board may not tolerate this approach or attitude.

  • Entrepreneurs/Founder's inability to think strategically about innovative ways to grow the business beyond traditional methods. (new markets or new applications of a product or service). I worked for this company that built software for the fintech world. They had one product that they kept iterating around but the idea of building anything else for a different industry or selling services around that product was just foreign to the leadership team.

  • Entrepreneur/Founder failure to hire competent executives and leadership team members. Also, inability or unwillingness to fire incompetent executives or leadership team members. The old term is “hire slow, fire fast.” I have witnessed more damage done by CEOs to their own organization because they were unwilling to fire underperforming leaders. Conversely, I have observed senior leaders unwilling to pay top dollar to executives that could take their company to another level.


  • Entrepreneurs/Founders ignored or did not understand how to build a culture of excellence. Yankees vs. Brewers. The Yankees have won 27 World Series titles. The Rangers, Padres, Brewers, Mariners, Rockies, and Rays have never won a world series. I have worked for companies that were considered the Yankees of their industry and the culture was so distinctly different, expectations were high from each other, and being really good was always a lot of fun.




As a Mentor in Residence at UMKC Regnier Institute, I will occasionally get asked to speak to different classes. I recently spoke to a class on “Corporate Entrepreneurship” with Eric Anderson, Director of Technology Commercialization, and Ben Williams, Assistant Teaching Professor, Entrepreneurship and Innovation. A part of Ben’s presentation was distinguishing the four types of innovation. They are:

  1. Invention – the creation of a new product, service, or process

  2. Extension – expansion of a product, service, or process already in existence

  3. Duplication – replication of an already existing product, service, or process

  4. Synthesis – a combination of existing concepts and factors into a new formulation

These types of innovation are what most of the entrepreneurs that I have worked with over my career were doing on some level. I think back to these individuals and none of them were labeled “visionary geniuses.”


The entrepreneurs that I have worked with were successful because:


(1) Their innovation (no matter what type) worked and was successful in its ability to solve a problem which generated significant revenues and profitability.

(2) They created an organization that became a part of the community that symbolized greatness through the quality of their products and services.

(3) They created new opportunities for their employees and substantially invested in their professional development in order to grow their careers within the organization.

(4) They created lifelong organizational wealth for their employees. Some of those employees took that new wealth and went on to become entrepreneurs and innovators themselves.

(5) They created new wealth for their families which enabled them to give their time to different foundations, initiatives, and causes.



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