In this episode, I interview Layna Thompson, Founding Head of Customer Success and Growth at PowerBroker.ai, to talk about how insurance can modernize without losing its humanity. With nearly two decades of industry experience, Layna brings a refreshingly grounded perspective on AI and automation, emphasizing that talent has never been the issue, it’s the amount of time insurance professionals spend stuck in administrative work. We discuss how thoughtfully applied technology can clear space for better thinking, stronger advising, and more meaningful human connections.

What I loved most about this conversation is Layna’s unwavering belief that curiosity, trust, and real human connection are still the foundation of our industry, and always should be. We talked about why trust isn’t built through forms and e-signatures alone, but through moments that people remember. Layna shared how thoughtful automation can move busy work into the background so insurance professionals can spend less time typing and more time thinking, interpreting, and showing up when it matters most.

In this episode, I interview Kaiza Molina, Co-Founder and Chief Operating Officer at StretchDollar. Kaiza discusses how we think about health insurance and why it so often feels overwhelming, emotional, and inaccessible. She shares how many people equate choice with risk, questioning whether coverage is “good” or even legitimate, and how much of her work is rooted in myth-busting and helping people move through the fear and uncertainty tied to healthcare decisions. We discussed how health insurance is rarely a rational, spreadsheet-based decision and is often a household-level choice shaped by trust, past experiences, family needs, and risk tolerance.

We also dug into her “why” behind StretchDollar and her mission to empower small business owners to offer meaningful health benefits without carrying impossible pressure. Kaiza reframed the problem in a way that feels immediately approachable: the job isn’t picking the perfect plan for everyone, it’s setting the right budget. Kaiza emphasized that there is no longer an “average employee,” and that solutions must account for real life, from unplanned medical needs to caregiving, fertility, and mental health. Ultimately, Kaiza believes that accessible health insurance starts with simplicity, empathy, and designing systems that respect how people actually make decisions.

In this episode, I interview Angelina Vereshchagina, a sophomore student at St. John’s University. Angelina shares what initially drew her into insurance, the sheer scope of what can be insured, and the realization that this industry touches nearly every part of the world around us. We talk about that moment of curiosity when you start to see insurance not as rigid or boring, but as endlessly complex, creative, and full of opportunity.

Angelina also discusses what it takes to attract and engage the next generation of insurance professionals, and why young voices need to be at the forefront of that effort. Through her work with Gamma Iota Sigma and as a university ambassador, she’s on the front lines of introducing students to the industry. We discuss how early exposure, honest conversations, and visible role models can significantly impact the way students perceive insurance as a career filled with purpose and growth.