42:59

In this episode of the You Winning Life Podcast, host Jason Wasser, LMFT, interviews Dr. Bobby Grassi, a former dentist turned "Dentist CEO" and business coach. Grassi shares his personal back‑story—growing up in a single‑parent household, early dreams of music and sports, and a pivotal moment when his grandfather’s throat cancer and his future wife’s warning about a pager led him to dentistry. He describes the challenges of entering a profession with high debt and modest earnings, and how he shifted from a practitioner mindset to an entrepreneurial one by building systems, delegating, and creating multiple income streams (including a dental lab and franchise concepts). Central to the conversation are three "gatekeepers"—fear, judgment, and ego—that act as internal safety mechanisms but can also stall growth if given too much power. Grassi explains how recognizing these gatekeepers enables effective pivots: redefining processes, strategies, or even personal habits when a problem is identified. He emphasizes the importance of "relentlessly committed" targets (laser‑focused goals) over vague goals, and shares daily rituals such as gratitude/ prayer/ rage "stacks," movement, meditation, and affirmations to maintain mental and physical balance. The discussion also covers the loneliness of leadership, the need for clear boundaries, and the role of family and personal health in sustaining business performance. Grassi promotes his "Dentist CEO" platform as a coaching resource for dentists and any health‑oriented entrepreneur willing to adopt an entrepreneurial mindset, stressing that true growth requires personal accountability, disciplined habits, and alignment of mind‑body‑family.

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