The Deal That Almost Died: Perseverance Turns a "No" into a Big Win

In the high-stakes world of hospitality, closing a multi-million-dollar deal is rarely a straight path—it's a test of resilience, perseverance, strategy, and mental endurance. In this episode, we dive into the real story behind a deal that nearly fell apart multiple times, and what it took to bring it across the finish line. From financing roadblocks and tense negotiations to moments of doubt, Berkadia's Jennifer Dakin and Webb Wilson of Kemmons Wilson Hospitality Partners join Ernie to pull back the curtain on the unseen challenges behind major hospitality transactions. More importantly, it explores the difference between blind persistence and strategic perseverance—knowing when to push harder, when to pivot, and how to maintain momentum.