Why The Founder of a $4BN Company Tracks Every Minute of His Life...

I'm Alexa from the Moneywise team with Sam Parr, and we’re trying something new here by taking our transparent approach and applying it to how companies get built. Today we sit down with Mario Schlosser, Oscar Health’s cofounder who has logged every minute since 2012, to unpack how time, problem solving, and conflict shaped a business now worth over four billion dollars.

Why track every minute, and what problem were you solving?

I started in 2012 to keep myself from drifting, and writing start and stop times forced focus. Hitting at least thirty minutes on a task felt like a measurable win.

What do you capture, and how does it guide decisions?

I log the start and end, what I did, who I was with, and a one to ten mood score with seven as expected, then a small script turns it into personal stats.

It helped when the IPO went sideways; therapy and antidepressants raised my baseline mood, and the data showed it. Later I saw external advising was crowding out creative work, so I turned that dial down.

Did you go all in on Oscar right away?

No; for months I spent about twenty percent, let it breathe, and only ramped as the idea proved itself, because a new thing can grow before you commit fully.

With no insurance background, how did you actually build a health plan?

I used what I call radical decomposition from my Bridgewater days, breaking the impossible into parts. Public filings and reports revealed the components like claims, network, underwriting, and utilization management, so we began with vendors and methodically brought each piece in house from 2014 through 2017.

Why did that matter in a crowded market?

Owning the core systems let us adapt through policy swings while others tied to vendors could not.

What hard lesson carried over from your gaming startup?

At Bostu, a Zynga suit was noisy but manageable, the real damage came from founder infighting during platform shifts and we were pushed out. External fights can rally a team, internal doubt drains it.

How do you prevent that kind of internal damage at Oscar?

Close the gaps fast, run into the fire, and never leave daylight between founders, and remember the world rarely ends. Living through crises gives you judgment you cannot get from a book.

What does radical transparency look like day to day?

In investor meetings I would flag risks so bluntly that Josh would kick me under the table to keep me from scaring people, so honesty needs calibration. Inside the company I asked the board, Joel Cutler in our case, to interview the org during a stall and the feedback was to stay the course, which steadied the team and set up a later raise from Google.

How do you rally the group when bad news hits?

We frame it as a shared opponent; when the government’s risk adjustment report arrived, leaders gathered, poured a quick whiskey, and opened it together, because the point was to face the hit openly with a story everyone can hold.

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