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.

One year ago today, the LA wildfires changed lives, neighborhoods, and the way many of us think about risk, resilience, and recovery.

In the first episode of season 3, I interview Shanna McIntyre, co-founder and Chief Data Officer at Delos. Shanna’s journey into the industry began far from it, with a background in physics, aerospace, and satellite data, before she and her co-founder recognized the urgent need to apply serious science to one of the most personal challenges facing homeowners today. We talk about why insurance is such a critical enabler of stability and recovery, how wildfires have exposed the limits of traditional risk models, and what the industry has learned in the year since communities were forced to rebuild.

Shanna shares how Delos’s wildfire hazard models performed during recent fires, and how better data, automation, and climate-aware science can actually expand insurability rather than restrict it. We discuss the role insurers played in recovery, the emotional weight these moments carry for homeowners, and why understanding the full insurance ecosystem is essential to creating equitable, sustainable solutions. What stayed with me most was Shanna’s belief that curiosity is a catalyst for progress: when we truly understand risk, we can price it more fairly, respond faster, and design coverage that meets people where they are, especially when they need it most.