In the heart of Silicon Valley, a place synonymous with innovation and groundbreaking success, "The Monk and the Riddle" offers a refreshing perspective on the essence of entrepreneurship and the quest for meaningful work. Randy Komisar, a Silicon Valley insider with an unconventional career path, brings to life his journey from a "Virtual CEO" to a mentor and visionary, challenging the traditional paradigms of professional achievement. Through engaging narrative and insightful dialogue, Komisar shares not just the mechanics of startups and venture capitalism but, more importantly, the philosophical underpinnings of what it means to truly live and work with purpose. This book unfolds through captivating dialogues between Komisar and aspiring entrepreneurs, revealing the core question that drives Komisar's ethos: Why do you work? Beyond the simple narratives of success and failure, "The Monk and the Riddle" delves deep into the significance of passion, leadership, and personal fulfillment. It's a story that transcends the conventional business book, offering readers a profound look at how to embrace the journey of life and work. With humor, wisdom, and an unyielding sense of curiosity, Komisar invites us to reconsider our definitions of success, urging us to find joy and meaning not in the destination, but in the journey itself.