In this special feature, EO Portland fathers and founders reflect on the ways fatherhood has transformed how they lead, define success, take risks, and build community. Their stories are honest, thoughtful, and deeply personal, filled with lessons on resilience, boundaries, ambition, presence, and purpose.

EO Portland Board Member and CEO of Casework, Casey Keasler, sat down with Tim Bergler to discuss the realities of building a business while raising a family.

What has been one of the hardest moments of trying to show up fully for both your family and your business?

Some of the hardest moments of being both a father and an entrepreneur occurred early in the growth of the company and when my kids were very young. I started the company the same year that my daughter was born. I was in my early 30s and had to manage long hours where I was spread very thin within the company. I had not yet joined EO and by necessity I was wearing a lot of hats. My solution to everything at the company was just work harder. It was hard to balance my commitment as a father and my leadership of the company. It took a good partnership and understanding from my wife to recognize that we were working on balancing parenting and building a foundation for growth. Honestly, looking back I had a different level of energy and emotional reserves to do both. Hustle paid off but it wasn’t easy early on.

What's a decision you made that honored both your ambitions and your commitment to your family?

I feel like being a father made me focus on stability within the company. I always viewed the financial health of the company as a foundation for providing a stable and safe home for my kids and to enable them to have opportunities and options. This extended to how I viewed my relationship with the company itself. I viewed my team as an extension of my family and I ultimately felt responsible for helping them "feed" their family.  This motivated me to manage the company responsibly. This approach may have limited some of our growth but I focused on financial stability over growth so my team believed they worked at a stable company.

What legacy are you hoping to leave—for your children, your employees, and your community?

I think a legacy I will leave for my kids is their belief in their ability to chart their own path. Our kids were by our side the entire entrepreneurial journey. They absorbed many conversations about the challenges and joys of entrepreneurship. I think they truly believe in their ability to create their future. They understand some combination of grit, hard work, and risk-taking will open up options for them. I think they understand there are so many opportunities available to them. This can be scary and unsettling; it can also be extremely rewarding. They don’t have to be boxed in and are free to chart their own path.

In what ways has connection with other entrepreneurs made you a better parent?

My connections within EO have given me perspective on everything in life including being a parent. There are few places where you can be fully honest with your peers about your challenges and victories. The culture and values of EO encourage openness and vulnerability. As a result, I had exposure to the challenges and journeys of so many people as they were navigating parenthood. No one has a playbook for parenting; we are all just trying to do our best. I was able to walk through so many real-world situations with close friends within EO and learned from their experience. I have also been able to share wins and joyous moments with my peers. It is so encouraging to be surrounded by people that are rooting for you and your family.