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, sat down with Jodi Levy to discuss the realities of building a business while raising a family

How do you define success?

I joined my mom in her company when I was 23 years old – so I was the daughter and SHE was the mother. Back then, success was all about growth – revenue, scale, hitting milestones. Today, my mom is retired and I co-lead Destira with my sister. Between the two of us, we have 6 kids, age 10 – 16. Success is about alignment. It’s about building a business I’m proud of while being present for my kids. It’s naming our first core value Relationships Matter. It’s showing up so my team feels supported, our customers and vendors feel seen, and my kids feel loved and prioritized. If I’m living this core value at home and at work – that’s success.

What legacy do you want to leave for your children?  

I want my kids to see that you can dream big and still do the right thing. That you can lead with heart and build something meaningful without sacrificing who you are and what you stand for. More than anything, I want them to remember how I showed up, not just what I built.

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

Integrated. There’s no clean separation – just a constant weaving of both worlds.

What advice would you give your younger self about balancing business growth with raising a family?

Working motherhood comes with its own set of guilt. Some of the best advice I ever got was only volunteer when your kids can see you. Let someone else do the behind the scenes work. This one has let me release a LOT – between the PTA, sports, etc, there are a lot of asks. 

Also, you won’t get it right – and that’s okay. Progress happens in a spiral. Be where you are in this moment.

What lesson(s) has motherhood taught you about leadership?

Listening matters more than having the answer. Ask more questions. Slow down before reacting. Kids don’t need you to fix everything – they just want to be understood. The same can be true in leadership.

What skill have you developed as a parent that benefits your business today? 

The power of a time out! Give yourself and your team time to think, come to a calm place, get grounded. Tough conversations at work or meltdowns at home take nearly the same de-escalation skills.

What do your children teach you about leadership?

When they were little, they were present, curious, and celebrated every step of the way. Now, with 3 teenagers, they’re direct, they don’t overcomplicate things, and they tell me when I’m carrying the weight of work. These are all powerful leadership lessons.

Business Glimmer: We’re a business rooted in empowerment and purpose. We share the good, create community, and support girls in sport and confidence. Our impact goes beyond the product with partnerships (Women’s Sports Foundation and Wendy Hilliard Foundation).

What are you building now that matters most?

Right now, it’s about strengthening our foundation – our people, our processes, and our systems. Sustainable growth that allows us to keep dreaming big without losing who we are.