Oscar Health

“We would have not even gotten licensed as an insurance company had we not had in the early team about 70% experienced insurance hands. The early team was about 70% people who had run insurance companies, been in insurance companies.”

“We, I think, knew fairly early on that given that we were literally the first insurance company startup, health insurance company startup ever, I mean, we essentially defined the category of insure tech, if you want to think about it that way.”

“We had a grand plan from the very beginning, and it was actually about a five-year plan as it happens. And in that five-year plan, we basically mapped out that early on, we largely want to rely on outside vendors where we want to be the matchmaker. You know, w…”

“In five years from now, I think it means that we are able to look at data coming from your inhaler, let's say if you're an asthmatic, and are able to come in there with our nurses, with our doctors, much more proactively when we see something that might be tak…”

“The first year of Oscar was really mostly spent getting a license, and we ended up being the first newly licensed commercial health insurance company in New York State in about 20 years, and California later on about 25 years or so.”

“We know in real time when you're in the emergency room and make, can make sure that you get discharged from the ER with knowing what to do next and don't go back in there.”

“We file on a quarterly basis, regulatory reports with all of our revenues, all of our costs.”

“If you do it, you have to do it wholeheartedly. That, that what blows startups up is, is if you say, oh, I'm gonna take a different role now, and then you don't, and people still come to you when you tell them, oh, yeah, I would do this, you know, but whatever…”

“And frankly also Oscar wouldn't be around having not gone public.”

“I do think I have an ability of keeping more pieces of information in my mind at the same time than most others. And so design around that as opposed to just sort of reading the book, you know.”

“I'm, I am not going to go until the price is back at the IPO price or I pay my next company.”

“An efficient market is not efficient if you go down by 95% and then up by eight X. You know, that's not a hallmark of an efficient market.”

“If you let the intensity go out, I think the intensity goes out, it disappears from the company.”

“It's difficult to not be the person with the top authority anymore. It just is. I mean, anybody who doesn't tell you that isn't fucking idiots. You know, like, if you're the guy who can tell everybody what to do, and they all have always respect for it, that's…”

“I, at that time, it wasn't a million yet, by the way. It was, but it was approaching that level, I think. So then, but yeah, it was close enough, like 900,000, something like that.”

“I honestly, I did not even look at the stock price. That was one way in which I dealt with it. I didn't look at it.”

“We went public, right, I think it was March third or whatever, twenty-twenty-one. It was Josh and I ringing the bell. And we're like, fuck yeah, this is going to be great. And then we open and the thing falls. It opens low right away and it falls right away.”

“I'm certainly bad at some things that I think professional CEOs should be good at. I probably bad at delegation. I'm probably bad at you know, operationally managing people like saying, hey, I told you to do these three things. Did you do those three things ne…”

“We now know how to do this. We now know how to have a really good system that lands within, like, 10,000 dollars or whatever, you know, of the estimate, because we get so much throughout the year or whatever.”

“In late March, we get the first report from the federal government as to where our risk score landed, and it moves the numbers by a staggering amount, like it used to move the Oscar numbers by, like, you know on a, I don't know, half, on a billion revenues, th…”

“Public markets don't care about that. They just don't, they have limited attention spans, at least for companies like ours.”

“Oscar took 12 years. How many more of those, how many things of that nature could I try to do and try to bite off?”