Leading Into The Unknown with Clair Stoddard

Leading Into The Unknown with Clair Stoddard

April 23, 2026 · 50 min

About this episode

Matt Landau and Clair Stoddard discuss the importance of stepping into the unknown for personal and professional growth.

A conversation between Matt Landau and Clair Stoddard , co-owner of Cascade Vacation Rentals , on the power of stepping into the unknown—where growth, leadership, and authenticity truly begin. From career-defining leaps of faith to redefining "failure" as a pathway to opportunity, Clair shares how embracing uncertainty shaped her journey from hospitality operator to co-owner. Together, they explore how nature, human connection, and curiosity can ground us in an increasingly automated world—and why the most powerful leadership skill today may be the willingness to not have all the answers. This episode dives into building businesses that scale without losing their soul, the importance of real human relationships in the age of AI, and how small, courageous decisions can unlock entirely new paths.

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