Why Imagining Your Startup's Death Sets You Free

When founder and CEO Casey Kelly died suddenly in a car accident, Jesse Pujji was texting her the day before. She had no time to say goodbye. That kind of loss has a way of forcing the question that most of us spend our whole careers avoiding: how do you actually want to show up with the time you have?In this episode of Heart of Entrepreneurship, Dave Kashen and Jesse Pujji go somewhere most startup podcasts won't: a direct, honest conversation about death, grief, and what it means to build a company as a human being. Dave had just returned from a meditation retreat where he recognized how much he had been quietly searching for something, even after years of practice. That recognition opened into a wide-ranging conversation about spirituality, the fear of startup failure, and why truly facing the cost of how you're living is often the only thing that changes behavior.What they explore together: why grief is one of the most honest responses to love, how the "via negativa" reframes spiritual growth as seeing through false beliefs rather than achieving a new state, and what a founder's relationship with startup death reveals about how present they're actually able to be. They also challenge the widespread belief that trade-offs between success and a full life are simply required, and offer a concrete practice for working with the fear of failure rather than being driven by it underground.