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Pediatric airway surgeon Dr. Michael Rutter and I discuss risk-taking and effective market analysis in entrepreneurship. In the operating room, Dr. Rutter cultivates a congenial OR environment and often seeks ideas from other team members with different areas of expertise. These problem solving-driven conversations often result in pioneering new airway surgery techniques. In the medical device sphere, he outlines his journey of creating a tracheal balloon dilation device, explaining how he obtained intellectual property rights, cleared FDA regulations, and marketed the product.