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Entrepreneurship stories usually focus on the wins. This conversation focuses on the part that rarely gets discussed.

In this episode, Chase Murdock of Durable sits down with three operators who have lived through some of the hardest moments a business owner can face: Caroline Chapdelaine (CEO of North Star Photonics), Andrew Heer (former CEO of Summit Mountain Cleaning), and Damon Chlarson (former owner of Pacific Installation Supply).

Together, they share candid stories about what it's like when a business begins to unravel — losing key customers, navigating crushing financial pressure, managing employees through uncertainty, and confronting the emotional toll that comes with it. The conversation explores the isolation many owners feel during difficult times and why those struggles often go unspoken in entrepreneurial circles.

The group also reflects on where they are today: rebuilding, closing chapters, and finding perspective after the dust settles.

For anyone building a company — or considering buying one — this episode offers an honest look at the realities of ownership and the lessons that only come from going through the hard parts.