Mark Bertolini, CEO of Oscar Health, shares his extraordinary life story of resilience and transformation. From surviving a catastrophic skiing accident that broke his neck and left him in chronic pain for 18 years, to saving his son's life, Bertolini reveals how suffering led to profound personal growth and business success. The conversation explores his vision for transforming American healthcare through personalized insurance, the power of servant leadership, and how ordinary people can achieve extraordinary things. A remarkable story of courage, compassion, and the pursuit of meaning through service. TIMESTAMPS: 0:00 Intro 1:04 A Near-Fatal Accident 4:04 Growing Up in Detroit 5:57 From Auto Worker to Business Leader 9:21 Building and Fixing Companies 15:50 The Evolution of US Health Insurance 22:28 Oscar Health: A New Approach 35:13 The Role of AI in Healthcare 37:55 Son’s Battle with Cancer 42:45 Eastern Beliefs & Personal Transformation 53:25 Yoga and Employee Wellness 58:33 Raising Employee Wages and Benefits 1:07:40 Balancing Success & Personal Struggles 1:10:56 Early Lessons in Work & Money 1:15:56 Bridgewater and Transition Challenges 1:20:25 Joining Oscar Health 1:23:54 The Importance of Curiosity and Courage 1:30:47 Reflections on Personal Growth 1:35:30 The Kindest Thing #MarkBertolini #OscarHealth #Healthcare #Leadership #Resilience #Transformation #ChronicPain #BusinessSuccess #EmployeeWellness #HealthInsurance #stocks #OSCR Presented by Ramp: https://ramp.com/business-cards?utm_s Sponsored by AlphaSense and Ridgeline: https://www.alpha-sense.com/invest/ https://www.ridgelineapps.com/ ****** Patrick O'Shaughnessy is the CEO of Positive Sum. All opinions expressed by Patrick and podcast guests are solely their own and do not reflect the opinion of Positive Sum. This podcast is for informational purposes only and should not be relied upon as a basis for investment decisions. Clients of Positive Sum may maintain positions in the securities discussed in this podcast. To learn more, visit psum.vc