Evolving Insurance Together: Legia & Lukas Oswald on Their Mother-Son Partnership

In this episode, I had the chance to do something a little different, and really special, by hosting my first-ever mother-son conversation with Legia and Lukas Oswald. Legia, founder and CEO of Out of Pocket EXP, has spent years in the insurance and temporary housing space, and together with her son Lukas, they’ve built a business focused on improving how additional living expense claims are handled. Hearing how Legia was introduced to the industry and ultimately co-founded a company with her son was such a full-circle story rooted in real frustrations, real experiences, and a genuine desire to make things better for adjusters and the families they serve. What I loved most about this conversation was the mutual respect for one another’s strengths. Legia brings deep industry experience and a strong customer-first mindset, while Lukas adds a fresh perspective shaped by technology, product thinking, and a younger voice in the industry. Together, they challenge each other, learn from each other, and lead in a way that’s grounded in trust, respect, and open communication. We talked about what it’s like to build a business as a family, the leadership lessons they’ve learned along the way, and why the future of insurance depends on bringing together experience and new perspectives.