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.