Mario Schlosser on Oscar Health, Public Markets and Leadership

Oscar Health co-founder Mario Schlosser describes the emotional impact of a sharp stock decline and the value of recognizing that difficult periods can pass. He joins Harry Stebbings to discuss healthcare, public markets, leadership and stepping aside as CEO.

Schlosser recalls growing up in a middle-class German family, teaching himself to use an early computer and spending a summer trying to draw lines on screen. He identifies intrinsic motivation and persistence as important traits, while resisting the idea that a single early test can determine someone’s destiny.

He says low expectations helped him appreciate later opportunities, but exposure to talented peers also raised his sense of what was possible. A youth research competition and time at Stanford and McKinsey showed him skills and ambitions he had not previously encountered.

Stebbings contrasts ambitious frontier technology investments with seemingly mundane business software. Schlosser says healthcare contains valuable but unglamorous workflows; replacing outdated systems can matter even without a dramatic claim to reinvent the whole industry.

He argues healthcare startups often misunderstand incentives: better quality does not automatically receive higher payment, and buyers may have difficulty assessing value. He wants founders either to understand the system or bring in people who do. This is his industry assessment as an insurer and technology executive.

Asked whether he would start in healthcare again, Schlosser says the 2012 opportunity appealed because few technology founders were building insurers. Today he would seek another neglected field with low competition, old infrastructure and difficulty attracting technical talent; his examples are speculative.

On Oscar’s stock decline, he believes investors feared the company would run out of money and require dilutive financing. He also thinks they questioned whether its technology could actually improve insurance economics. These are his interpretations, not independently established causes of the share-price movement.

Schlosser acknowledges that he could have communicated more simply. He says the underlying data changed less dramatically than the stock price and describes a medical loss ratio moving from about 86 to 82; that company-specific measure is his example, not a complete account of financial performance.

He cautions against dismissing Wall Street analysts: although price targets can lag markets, some analysts possess detailed knowledge of business drivers. In his view, a smaller company still competes for limited investor attention, making clear communication important.

He does not regret the IPO. He says Oscar raised about $1.5 billion and needed the capital to avoid raising later under worse conditions. His belief that going public helped the company survive is a counterfactual judgment, not proof of the alternative outcome.

He recalls the stock falling immediately after the opening and feeling embarrassed during a television interview. He says the day became associated with painful memories and describes how a daily public price made it difficult to feel that there was a bottom.

Schlosser says he sought professional mental-health care and was prescribed an antidepressant after that period. He describes it as helpful for his own functioning and mood; this is an individual experience, not medical advice or evidence that the same treatment works for others.

He had tracked his activities and later added a daily mood score. He observed a flatter pattern while taking medication and discusses uncertainty about what that meant for insight and emotion. Stebbings shares a different experience; neither establishes a general effect of medication.

He says time with his family and not checking the share price during declines helped him manage stress. He also reflects on trying not to direct frustration with himself toward his children. Supportive relationships were important to him, though people’s circumstances differ.

Schlosser says repeated experience with setbacks helped him recognize that a crisis need not end everything. He advises a founder facing an early employee’s departure to treat it as a normal transition rather than automatically interpreting it as personal failure.

Asked whether he was a good CEO, he identifies delegation and routine operational follow-up as weaknesses. He questions generic CEO advice: different people and organizations need different management styles, and a leader must understand their own strengths rather than copy another personality.

He and Stebbings discuss comparing themselves with more famous entrepreneurs. Schlosser notes that ambition tends to reset as people achieve more; he values the ability to keep trying new things without treating someone else’s path as a mandatory template.

They also question whether a fixed vision can limit ambition. Schlosser favors revisiting assumptions about both life and the company rather than clinging to a plan simply because it was once announced.

He explains his decision to leave the CEO role and become CTO. By early 2023, he believed Oscar’s insurance business was on a path to profitability, but worried that after a prolonged crisis he might lack the credibility and energy to lead through another one. This was his assessment at the time.

He had spent two years getting to know Mark Bertolini, including regular conversations about past crises, and believed he could bring different experience to the company. Schlosser says this was a specific succession decision, rather than a broad CEO search.

A transition must be wholehearted, he says: a former CEO cannot keep quietly overruling the new leader. He admits giving up authority and preferred approaches to strategy is difficult, even as he appreciates no longer having to make every hard personnel decision.

Both discuss discomfort with difficult conversations. Schlosser says he wants colleagues and board members to give him honest feedback instead of polite praise that conceals a problem. His broader comments about other leaders’ behavior are personal impressions.

He recalls avoiding emails or spreadsheets he expected to contain bad news. One coping practice was opening them alongside colleagues: Oscar’s insurance risk-adjustment estimates could move financial results substantially, and reviewing the information together made the uncertainty easier to face.

When organizations hire experienced managers, he says, they bring useful practices but may also create unnecessary layers and meetings. He encourages founders to learn from others while retaining ways of working that fit their own strengths and the company’s stage.

He argues leaders should explain the behaviors they expect and why they attend a meeting: to brainstorm, monitor a problem or make a decision. Otherwise employees may interpret involvement as mistrust. He recalls a company-wide values exercise that produced generic language rather than clear choices.

On money, Schlosser says he once trusted systems to judge his contribution and did not push strongly for compensation. He acknowledges inequities in access and pay and that his position as a white man can affect his experience. His suggestion that money measures social impact is a personal view, which Stebbings challenges by citing healthcare’s misaligned incentives.

He reflects that exceptionally wealthy people may have a stronger sense of entitlement to rewards, and considers how unequal outcomes can emerge from less extreme differences in ability. These are his interpretations, not a demonstrated explanation of individual wealth.

Schlosser distinguishes paper wealth from cash, recalling a 2015 secondary sale that allowed eligible employees as well as founders to sell. He says his own cash was then close to, but not yet, $1 million; he remembers both relief and a heightened sense of what could be lost.

He admires people willing to take another major risk after success. Having seen how many times Oscar nearly failed, he finds that experience can make new ambitions feel improbable, and wants to recover some of the openness he had at the start.

Financial freedom, he says, gives him time to pursue curiosity: studying languages, coding a game and following interests without an immediate business purpose. He values opportunities for unexpected discoveries even when the activities appear inefficient.

Schlosser says he cares less about luxury than about influence and interesting conversations. He recognizes that there is always another room one may not be invited into and reflects on the temptation to compare access with others.

In quick fire, he says he has become more aware that time is finite. Oscar is likely his life’s work, he says, but he still wants to make other contributions. Parenthood has made him value limited time and the lasting relationships in his family.

He says shared curiosity and having things to discuss matter to his marriage. Looking back at starting Oscar, he would remind himself that difficult periods are inevitable, that perspective helps and that sustaining intensity requires deliberate effort.

He recounts a long partnership with co-founder Josh Kushner, including an earlier disagreement over equity. He values Kushner’s loyalty and ability to connect with people, while saying partners should recognize each other’s imperfections and maintain independent sources of contribution.

Looking ten years ahead, Schlosser hopes to work on a consequential problem others overlook and to keep a notebook full of ideas that engage him. He and Stebbings close the conversation with thanks.