To build an insurance company with no experience, founder Mario Schlosser used a method from Bridgewater he calls 'radical decomposition'. He used public regulatory filings to identify every operational component of an insurer, then created a multi-year roadmap to systematically build or insource each piece.
To cope with a recurring, high-stakes government report that often delivered bad financial news, the Oscar Health leadership team created a ritual. They would gather, pour whiskey shots, and open the report together, transforming a moment of potential dread into a shared, resilience-building experience.
After a previous company failed due to infighting, Mario Schlosser learned that unresolved internal conflict is the most destructive stress—worse than lawsuits or market threats. At Oscar, his primary rule for co-founder relationships is to 'run straight into the fire' and address brewing issues immediately before they can fester.
Facing a senior leadership exodus and slowing growth, Mario Schlosser took the counter-intuitive step of asking his board to interview his team and assess his performance. This act of extreme transparency validated his strategy, re-energized his team, and stopped most of the key leaders from leaving.
Contrary to the 'all-in' startup mantra, Mario Schlosser initially dedicated only 20% of his time to Oscar Health. This approach allowed him to explore the idea without immense pressure, letting it develop organically before he fully committed, demonstrating that a venture doesn't need 100% focus from day one to succeed.