Episode Details

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.