In this special feature, EO Portland mothers and founders reflect on the ways motherhood 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, asked Anna Madill two questions about her experience as a mother and entrepreneur.

If you had to sum up entrepreneurial motherhood in a single word, what would it be?

Prioritization. I didn’t realize how much space I actually had in my life to do the things I wanted to do until I had my son. And I realized I could still have that space if I prioritized properly. For me, motherhood hasn’t taken things away. It’s added new dimensions to my life while also reshaping how I think about joy, purpose and what really matters. Some things that once felt important naturally fell away after becoming a mom, creating more room for the things that matter most to me now, both in business and in life.

What are you building now that matters most?

In my business, I’m building more capable, confident and successful humans. As an agency and professional services company, our product is our people. Motherhood has really deepened the way I think about investing in and developing them. I’m less focused on chasing only the numbers or impact, and more focused on building the people who create those outcomes. It’s the long game. Growth and development don’t happen overnight. But by investing in people, I’m helping build and develop the humans who will deliver more effectively for Avenue while also becoming more confident and successful outside of Avenue’s walls. That’s where I find the most joy and meaning these days.