This is Mario Schlosser. Since 2012, he's tracked every single minute of his life in a spreadsheet. Most people would call that insane, and maybe it is, but in that same time frame, Mario co-founded Oscar Health with Josh Kushner, a tech-powered health insurance company that's now worth over $4 billion. We sat down with Mario last week, and he walked us through the three things that made Oscar possible. Things anyone can use to take stock of your time, deconstruct complex problems, and handle conflict before it kills your company. It starts with a 56,000-cell spreadsheet.
I've been tracking my time on a minute-by-minute basis every minute since 2012 when I started researching new company ideas. I said to myself, I'm way too undisciplined. I start reading an article about health insurance and after four minutes I'm like, that's enough for today. I'm going to go watch Game of Thrones now. And so I thought a good forcing mechanism would be if I write down when I start doing something, I write down when I stop doing it, and then I can see, oh, this was at least 30 minutes. Great. I can feel good about this amount of work I've put into this task, and now I can go and, you know, get a beer or something.
Mario didn't just use his time tracker to reclaim his focus. He used it to make data-driven decisions.
So I track when I start doing something, when I end doing it, what I did, who I did it with. Sometimes I add a tracker on a scale of 1 to 10, how I feel about it, with seven being the expectation, like how people measure objectives and key results. Now I can put it into Claude Code and it can give me all kinds of cool statistics about myself.
But it mattered most when his instincts pointed one way and the time tracker pointed the other. The best example of this is when they took the company public.
I struggled with mental health after the IPO process actually went sideways. We really went public and the stock price was down right away. And it's the first time in my life I talked to a therapist, and then I went on antidepressants actually for a while. I think that was great to see for me because I think my mind fights the effect of drugs because it wants to rationally understand why something's happening. And in this case, actually seeing this drug just push up the floor of my moods and peg it to a certain point, to a certain level, was very helpful. And I think it created a self-perpetuating cycle of, all right, this is how it's going to be.
More recently, since taking the CTO role and stepping down from the CEO role, one thing that I noticed happen, and then I saw it in the data as well, is I started spending too much time with external work. There's all kinds of people who start calling you for advice, and in the past we have said, look, I just don't have any time. I would love to give you advice. And before long, your entire day fills up with you just giving advice to other people. And that is a great thing, and I love the fact that people think I have anything worthwhile to share, but it can completely just consume all the energy you have that you could put into something more creative that would be even more worth asking later on for your advice about. So when I saw that in the data, I realized I have to really start turning that dialogue in a different direction.
But in the early days, he wasn't spending nearly 100% of his time on Oscar, and he believes he didn't have to.
I looked at how much time did I spend on Oscar and when in 2012, and how that ramped up. And that was also very interesting to see because for months I didn't spend more than 20% on it. Sort of like researching a bit, but not doing that much other work on it. And I think that gives me some orientation today when I do something new. That the new thing you're doing doesn't have to start right away. You can play with it for a while. You can stare at it for a while, and it sort of will develop a life of its own if it is a real thing potentially. You have to also give it that life, but still you don't have to overthink that it's got to be amazing right from the get-go.
In the beginning, Mario was only giving Oscar 20% of his time. And as the idea proved itself, that percentage continued to grow. But how did he actually build a health insurance company with zero experience in insurance? Well, he leaned on something that he learned from Ray Dalio while he was working at Bridgewater, an idea called radical decomposition. And it's how you take an impossibly complex problem and break it down into parts that you can actually solve.
So I was at Bridgewater for a couple of years, big global macro hedge fund. And the best idea underpinning all of Bridgewater, in my view, is this idea of — I'm not sure they call it that way, I call it that way — radical decomposition. You say, I want to know what inflation will be next year. How do you do that? Well, the government tells you how they report inflation. And you can just look up on the websites of the governments of the BLS, whatever, how they report inflation and the 200 categories that go into the inflation basket in the US. And you can then go through the 200 categories and you can have an estimate for each one of the categories. And you add those up and you get probably some estimate of inflation going forwards. And so you take some complex piece, you break it down to its constituents, and then you go one by one basically.
And for building Oscar as an insurance company, that list of constituents was the list of components that we had to go and operate — claims system, network, all these things. Over the summer, I found a couple of documents, filings from insurance companies, public filings that you can download from regulatory offices across the country, or certain think tanks writing about the state of health insurance in New York State, whatever, stuff like that. And those reports showed me the components of what an insurance company has to have — claims system, network of physicians, underwriting, utilization management, all these things. And so I made a list of these components, I made a list of the possible vendors. I realized again I can look at these filings of insurance companies and see who they pay, and so that way I could see which vendors they were paying for certain components, and then we kind of knew what we had to go and do. That was one blueprint. And I had a chart early on that showed these components as bubbles.
And then the chart was, you know, like a fifth filled with liquids, with gray. I always like — I'm colorblind, so I like black and white presentations with thick black lines, you know, and maybe some gray in it. And over three years, 2014, 2015, 2016, this vessel of health insurance component bubbles would be filling up with liquids. Meaning we would take all these components in-house. We would start with an outsourced claims system, take it in-house. We would start with an outsourced customer service team, take that in-house. And that is what we did. Up until 2017, we insourced pretty much all the important components of what Oscar did, what Oscar does, what an insurance company does. And to this day, I think we're the only insurer that has really every one of these components in-house, in most cases built on our own technology infrastructure as well.
Over 30 other companies tried to enter the market at the same time as Oscar, but almost all of them failed. Oscar was able to survive because of radical decomposition. They broke down the components of insurance, brought them all in-house, and were able to survive market volatility that way. But there's a third thing that made Oscar possible, and it's something Mario learned the hard way. You see, right before Oscar, Mario was running a gaming company called Vostu. He and all the other co-founders scaled it to 700 employees and over 50 million in revenue, but they all got fired due to internal conflict.
