20VC: Oscar Health: How to Deal with a 94% Decline in Market Cap, "Why I Stood Aside as CEO" and The Rebound Journey to $5.8BN in Revenue with Mario Schlosser, Co-Founder @ Oscar Health

22:54The stock exchange provided us back for a three anniversary literally two weeks ago. I told everybody I'm not going until the prices back at the IPO price or the IP1X company just because I have almost only bad memories associated with this day. And I see this just from the bottom of my heart and you really go into a depression. I mean, I had a period afterwards where I had to get prescribed antidepressants from a psychologist, which then by the way, worked wonders to just get out of that complete basement of what do I do next. And the other thing you then sort of realize as well, and this is a very unique public company issue, is you have this price every day and you know it can it can just keep falling every day.

23:31My favorite joke from that time then was what do you call a company that's down 95%. The answer is a company that was down 90 % and fell by half. which is just so crazy to imagine, right? The step from 1995 doesn't seem that big, but it's another 50 % down. Getting used to the fact that just there is no bottom, is incredibly, incredibly difficult. So the way to get through it is to take drugs. I mean, I say this only half jokingly. At that point, you have to step in with professional help and get yourself pulled out of it because you do have people depending on you or at least being functioning.

24:03Did you talk to someone? And I never had a psychologist before a psychiatrist, But then I was able to get somebody. I had an executive coach who's a fantastic IJF Hunter from Bridgewater and he referred me to somebody. You know, he said at the time They were other founders in the York. He was also coaching and you know We sort of had a almost a community of those folks who all were beaten up at various points in time But Oscar was down before everybody else was down that period of 2021 when crypto was still riding high when companies Was to go in public like do it as came after us for example They were all still going up and doubling on the first day So there's a time when it was very very lonely stopped down and that's psychiatrist was helpful but frankly the chemistry helped I took a thing called surgery and that was a unique way to do this thing.

24:45It was very I do this thing where I track my my my moods so I do this thing I start doing this in 2012 and I started Oscar actually I write down if it a when I start doing something when I stopped doing it so like I would now say 11 o 'clock you know from whatever 1230 like Harry and Mario talk and I put the name of the person who I talked to with that back in there so I have a full record of everything I do. And I categorized it by, was this thing for me, was this thing for the company, whatever else. I think my joke is now that I can trade my I replacements on this data very easily. I haven't tried that, but it'll happen at some points.

25:16I start putting mood into that too. It's Caleb 1 to 10. And it's like OKRs, which I think he results, 7 is the expected, so 7 is like where you want to get to. With the drug, it's interesting, you really are just always at 7. He's fastening to see when I look back at that charts. And without it, you go down a lot, and then you stay down a lot as well, at least in those days and you climb back up again, you crash down again. And that is an incredibly interesting to me in a qualitative data sets that helps me even look at, do I need to go back on this thing or whatever when certain things happen.

25:45Did you mind that? Like, I've been around to this presence too. I find it not everything has been easy too. I hated the level all the time. I didn't ever feel happy either. I really happy. I asked this my psychiatrist, you don't have a good answer. My concern is that what is the real world. Are you perceiving the real world when you're on the drug or you're perceiving it when you're off the drug? And I just don't know there's a good answer. Like you talked earlier about, once the universe has something great early on that you can sort of see, right? The flip set, as I mentioned, is yes, but also the things that you don't see won't come in on Twitter.

26:18Now there's this video of the young of the condition AI guy who won this math competition when he's like nine years old or whatever else like four years old. I don't even know. Yeah, he looks pretty young in the video. Oh, I don't have that ability. That means there are certain things I should not try to do in life. I should not try to build a company for example that relies entirely on a scientific breakthrough. For example, it's just a silly thing for me to try to do. That insights, being on the drug, might not come to you and you might end up actually doing the wrong thing because a drug sort of cuts out some of these deeper insights that you shut that shut flood into your consciousness and I don't have a good answer there.

26:51I don't want to, yeah, need to see beyond it either. What I find hard in those really hard times is I feel that I drop the ball on many other important aspects of my life being good son, being good brother, being good friend, and because of this shit storm here, all the other plates drop as well. Yeah. How did you manage being a husband, being a father? Well, your stock's down 94 % and you're like, oh my god. Yeah, I mean I do think the the the old trope of a family life that is not in itself unstable right ideally you have a stable family life does help in these situations it is definitely a thing that if you come home and you I don't know you can lie down next to your kids and they will ask you whatever what's going on stuff like that and you say oh it's shitty day stopprices down or whatever I mean I honestly I did not even look at the stock price that was one way which I dealt with it didn't look at it the other day I got very mad because chrome doesn't keep your full history apparently it like deletes it after two years of levels because I wanted to show on Twitter how often I looked at the stock price in the last few years.

27:49And I look at it when it goes up, I don't look at it when it goes down anymore, which makes me a bad financial trader for sure. Like I couldn't be that. But going to your kids and just doing nothing with them is a good sort of safety blanket for the soul. It just is. Then not making the mistake, by the way, of projecting your frustrations with your own life into your kids. I had that quite a bit as well. I'm like, well, I'm shitty CEO apparently and I don't know how to do math because otherwise the stock price would be better so now I'm mad at my son for being not the worst -best mathematician either next time.

28:22That's another thing I think that actually the drugs help with that a little bit and to not have that extrapolation of stuff you think about yourself into many other situations but a family life of people who support you love you is a great thing. And I have a great relationship with my, I think my wife and kids and my parents also or just going back to drum, a child of home, for example, was one of these places where you really felt like, you know what, Facket, these are the same, Donald Duck comics that were back in the days. I lost investors a lot of money, but I could still read that comic book.

28:51That was a weird way stabilizing. I find that actually it sounds so hippie -like, but like actually being in nature stabilizing, because it's like the tree that's been there for 200 years will be there for another 100, and it doesn't care about your stock price. And it's unimpacted by the rain, the wind, and whatever, and it's like the permanence of life goes on. Yeah, yeah. Josh, my co -founder likes to say this. The world doesn't end that often. That is actually one of the things you do realize that you don't get from reading books, that experience, the more you go through this stuff, it does get easier.

29:24You sort of pattern matching, you say, well, I did survive this before, that at least gives me the opportunity of surviving again. And Lama of Oscar, I had dinner with a couple of days ago. One of the great things when people leave your company and they start companies themselves, right? and they get bigger even then than Oscar I hope certainly and that guy asked me oh I have somebody leaving who was with me from the very beginning what should I do? I said what you should do is not just like say fuck yeah, it's great that you're leaving it's great I love it like best of luck for you for your next steps and then mean this on the bottom of your hearts so many people will leave your company the first time you will freak the fuck out like what did I do wrong?

29:57how can I do people don't like me anymore or whatever I'm too stupid to do this? it just is not the case people have all kinds of other reasons but you can't do anything about those reasons so whatever, just be okay with it so the repetitions do matter. So that goes to the gents of Wang's thing. If you can at a low stake situation survive getting shot at a couple of times, it does get easier than really go on the battlefield. And by the way the other thing I would say is, now they are real wars in the world, right? And none of us is fighting any of those real wars. So sometimes the rhetoric is so convalued like oh my god, laughing death whatever is also just fucking stupid.

30:29Like none of us is gonna get shot at in the trenches of Ukraine if a sunrise goes down. Oh, this night I agree, I kind of months but end all the founders that's me the other day when I was moaning to him like you're trying to do something Very very hard. It was never meant to be easy if it was easy. I let lots more would do it You are in this position because it is hard. You have to be punched and get back up again Can I ask you a weird one? You just said hey, I feel like a shitty CEO. Do you think you're a shitty CEO now out of the seat? I mean, I'm certainly about it. Some things that's I think professional CEO should be good at For the bad at delegation and for the bad at operation managing people like saying hey I told you to do these three things did you do those three things next week?

31:08You know, but do you think that's what see your ship is about? That's a huge question. There's a lot of stock advice VCs give you and books give you whatever and I used to wonder if I'm like a purely scientific view How is that we could get dietary advice or wrong over so many years right? We took people for a while you should not eat fats and we're like oh boops never mind You should eat fats, but don't eat carbs or whatever and then oops never mind like do another thing whatever Well, now's the drugs, so now we're all fine anyway. The only explanation scientifically is not people as stupid or like cheat on their scientific papers.

31:37I think this generation is, it depends. It depends on the person and the metabolism and the genetic makeup, whatever the people who take the advice. And I think that very thing is true for CEO ship as well. I actually remember a conversation with my with with an executive coach as well. And I'm sure every founder has had the question of What would Elon Musk do? It should be like a bumper sticker, you know? What would Elon Musk do with my company? And I so many times thought when they watch another fucking rocket launch him like what the fuck am I doing? You know trying to configure this database when Elon Musk is just doing all these things all the time I asked my coach should I try to like fire more people or whatever like more executive should I be just like You're not good enough you get out the door now or whatever He's like well, it's not what you do do So if you do it's you can't play acts So you have to do it all the way and every time and with everybody and throughout all of your life.

32:29You can't be inconsistent about these kind of things. And I thought that simple thing was very good. For better or worse, you are what you are. You might as well stick to the understand that better and stick to that and try to design organization around those things. That introspection is good. But to then say, good CEO advice is to have more to do lists. That's your genetic makeup and the makeup of your brain, the embedding space that you live in or whatever else. It's not necessarily with the things that ever you should be pulling. I think the secret to unhappyness is comparing yourself to other people.

32:59I often ask like, you know, what would he do, what would Mr. Beast do in my case here? Oh yeah, content business. But I really don't try and assess myself according to anyone else. Like, you know, Alex Wang at scale is my age. Jesus Christ, this guy's made a $7 billion company. And I do podcast and funds. Like, I look like a complete chump compared to him. But as she, I'm fine, I'm happy I'm doing well, in other cases I'm doing much better. Like literally when I said I'm gonna be on Harry's podcast, I got like tons of people in the company saying, oh my god, you're on 20 minutes we see, that's amazing, fucking love it.

33:36And the lesson here is, I'm sure in your life and when we first met in 2017, you did not think that that's the level you would get to. I would imagine you didn't, and the bar consistently shifted upwards for you. You would not, and back in the days you were looking for your own, yeah, obviously I'm not Elon Musk, you know, that's like an obvious comparison. Why would I compare myself to that silly whatever just like you wouldn't commit yourself to messy, right? Like playing soccer looks easy like there's a guy running past the ball to the fucking guy, right? So you're British, so you've had your share of soccer pain And the bar just shifts up as long as you understand that part I think it's actually not a bad thing.

34:09I mean the mere honor of being at a point where you can even Think for the sake of the start of well, maybe I could do more than you know the next guy whatever is a great place to even get to a life I think and it's also a good place to not stop there. I mean that's something I think about a lot today as well that's I admire the people who put their, we have an ability of putting their chips back on the table when they get to a certain place and I mean that's one of the great people that eat a musk certainly right that he's like screw this and just gonna take my hundred million and buy Russian rockets.

34:38So I think visions are one of the most dangerous things that people can have and that sounds very strange but visions often underestimate to make your true ability. Well, going back, when I started this, I wanted to be an associate at a fund in London. That was like the dream end goal. You know, now we manage over half a billion dollars and we have millions of listeners. If I had stuck to the vision, I would have accepted the jobs that were offered to me and just done that, I think visions can limit you. Do you agree or not? Absolutely, yeah, totally. What is it, I think Jeff Bezos saying is, I reserve the right to change my opinion even without new facts.

35:14The days totally true, I think you just should constantly try to rethink what should I do with my life Whatever and what should the company do and stuff like that. You don't need to tell people all the time about it But if you have this one thing you cling to that's limiting I agree Okay, so if you preserve the right -singer opinion and change the way that one lives You made a decision to step aside as CEO take on the CTO role and then obviously bringing in an amazing CEO Why and what did that decision making process look like Mario? It was for me a couple of different things. I remember watching the 2018 World Cup, which was in Russia and Germany a kickdown in the first round, after winning the World Cup in 2014.

35:54And the coach was Yogi Lufth, the same coach who had coached him to be in World Champion in 2014. And you and I, I don't know about you, but I certainly measure my life in Germany's performance at World Cups. I'm like, oh, that's when they last won, that's when they were next to the referee. And now it's like such a marker that you just remember. So they win the thing and then they go back to Russia. The guy stays on and they just get kicked out in the first round in a embarrassing fashion. And then he didn't leave again still even after that. And of course they get kicked out of the next tournament as well.

36:22It was such a great example of the guy just lost his, his like hat was empty of magic of rabbits to pull out. So you just lost his ability to talk to the team, motivate them, whatever. And I was very concerned about that. At that time, at the beginning of last year, Mark came in in April, I think we announced him. At that time, it was relatively clear that the company would not need to raise money again. It would be profitable within a foreseeable future. It would have a profit and a short business in 23. Because the way insurance companies work is we get all membership at the end of the year before.

36:51It's all locked into a price that we can't change. And we do all these things in such a way that we have very good visibility into the annual numbers. I mean, stuff can always happen, but it's exactly what ended up happening. I mean, our 23 numbers were the same if not better than what I thought they would be in January 2023. Okay, so I knew we were essentially out of the woods. I had a very very strong feeling about that And I think the board thought that too and whatever else with quit the ride markets with quit the ride sort of other deals I didn't work out and whatever that was all behind us I had made those decisions and we were done But I was concerned that if we would ever turn down again and if stuff ever happened again It would be my last crisis.

37:26I would not be able to go and do the same stuff that I said before and people would still believe me And I didn't want to risk that I think greater leaders and greater CEOs would have risked that for sure And maybe there's a survivorship bias of people who didn't do that and then become great and others to don't and just faith Moxuri obscurity, but I thought it's a better thing for the company and it's I think it probably a better thing for me if I then do the right things with That's later on there's a code out of this to just hand that over and have somebody come in who if there was a crisis again Would have a different bag of tricks and could do different things with a company and to me that was Mark the other thing there was, I had spent two years talking to him.

38:03We made him in the IPO process. We asked him to join up with words. He's like, I'm on enough boards. I don't want to do that, but I talked to you once a week. And so I talked him once a week for an hour and hour and an half. And I got to know him. I thought really well. And he told us stories about, you know, when he had crises and, you know, just really deep private stuff that we shared with each other. I read his biography. I read the biography. I underline stuff. I shared the underlying quotes with my chairman of the board and with Josh Schner. Like, okay, What kind of guy is he basing the book?

38:29Ha ha ha. So try to do the research there. I never showed him that. I should show him that. He was a unique guy to bring in. They wouldn't have been any other person. I think I wouldn't have wanted to run a CEO search, whatever. I wouldn't have run the, try to look for other people. It's a unique moment in time. Did you feel like you were out of tricks? You mentioned kind of the German manager pulling tricks out of the hand. I thought I was out of tricks, certainly against the next crisis. I mean, Oscar needs a bunch of more tricks. That's for sure. I think we, there's a huge opportunity for us to, to shift more towards software as a service, to what's this, some of the stuff that's happening the US healthcare market around individualization of care, those are big of a two -on -least.

39:06I didn't think there's only my bag of tricks was the way they'd gone and looked at these. In the CEO's seats. I think a really unfair thing that happens with the idolization of Elon Musk, Jeff Bezos, Mark Zuckerberg is this idea that founders should be the CEO forever. And it's like, as you said, it needs a different bag of tricks and you need to find product market fit in each stage as a CEO and as a founder. And I think so few actually do respectfully. Yeah. And there's nothing wrong with that. No, some founders should, by the way, right? Like, I mean, you know, it must probably show us. That guy has a, seems to have a capacity to do things that is just not the same as what we have.

39:41By the way, I always, I read the biography so carefully for all the stuff that others then say that he does. And it does seem to me, he's not always the engineering ability he has. It seems to be some of these other things, like fire people quickly, or like spending three hours on a topic whatever that have maybe even more to do with the success, but that's a different topic. But yeah, I agree with you. I think people need to not always clung to these things. Marry, what are your biggest lessons from moving out of the role of CEO demoting yourself as you've put it before? What are your biggest lessons from doing that?

40:11If you do what you have to do it wholeheartedly, what blow startups up is, if you say, I'm going to 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, maybe Mark has a different idea. You can do this. You have to say, that's a decision for the CEO. You've got to go talk to Mark. Sometimes I hate seeing that. I'll tell you honestly. Sometimes I love seeing that. I'm like, I'm so glad. I don't know. I don't have the side. I want anymore. It's an annoying decision. So fuck yeah, Mark, go take it on. So that's definitely one important piece of advice.

40:39What one do you hate to delegate on which one do you love to delegate just as an example. I think there's certain ways in which I would go about brainstorming strategy or even management tooling in the company. Like who meets at what point in time, what data do we look at or whatever. I've always thought about that in a certain way. I could never quite get there, but this is like a system in my mind. I would like to see that system be the thing, but Mark is now doing it in a different way. That one I don't like giving away. I don't like it. I mean, look, it is difficult not be the person with the top authority anymore.

41:10It's just this. I mean, anybody doesn't tell you that isn't fucking idiots. You know, like if if you're the guy who can tell everybody what to do and they all have always respect for it, that's a sweet gig. If you don't have that anymore, you feel like a chump. You know, you have dreams at night of like literally not getting the bite of the party anymore. Like that's how it translates almost. You know, that part's more difficult. The part that's easier is things along the lines of you got to deliver a tough message to a person. You gotta tell this person to shut up and do this now. That was always more difficult for me and one of the reputation's Mark had was to be more of a hard ass I always thought the company needs more of a hard ass and Mark is not I would say showing up that way as much in at the moments of just like a guy So he's probably also mature mellow and whatever and but he's got that more than I have it One of my biggest weaknesses is I shy away from hard conversations because I hate discomfort and I care about being light I use the same and what do you do because that's not how it's a really bad trait I think I don't know anybody who's good at that.

42:10That's one of these other things. Like, when you would, this is why I'm glad you're doing these kind of podcasts. And if you think that the people who are famous in this world somehow are good at these things, it's a complete nonsensical thing. In fact, they're better at avoiding these conversations than we are. You and I are good at maybe avoiding commission because we don't like want to have it. They are good at manipulating you in such a way that you didn't realize they avoid the conversation. You know, it's so that is a the whole different scale. They're very few people who are schizophrenic or psychologically hampered enough that they don't feel difficulty telling you something you don't want to hear.

42:45In fact, to the point where you need to get you need to get it out of people. This is something I always disliked that's when I talk to my board for example, or even a Josh, and like you don't be polite to me. Like it's just not helpful. Don't tell me oh this wasn't really nice thing you did, Ma 'am. Like okay, but then why are you not happy? Clearly you are uneverybody, the other three things I did, that were not good. I get you'd be, you've got to be willing to accept that. And I mean, I had a time probably about a year or two years ago where literally just another bit of bad news just broke me even more and it just didn't feel like I could take another hit in the face.

43:20And so when Mario's that to Harry, do you really want the hard feedback? My heart screamed no because I just could not take another hit. Did you ever have that? Oh, oh my god. I used to have this issue of when there's an email and I know it's bad Most likely where there's an excel tape and know it's bad you don't want to open it and I just find ways not to open it By the way a good trick is to open it in the presence of other people It's a grad -ass like how I got over it eventually So we used to have this thing is actually an Oscar thing I don't want to go towards the weeds But the federal government redistributes revenue of insurance companies in the market We are in depending on the risk of the membership -assured attracted.

43:58So if Oscar has a younger membership base than another insurer in the same states, we have to send money to the other insurance company because members of Oscar went to the doctorate this, in this called risk adjustments. It's an incredibly clever way to actually get insurance companies neutral in who they want to sign up as members. You want to get every member and then manage a member well. It's actually a very well -working system now. It didn't work so well early on. Now it works well. But the way it works is that in late March, we get the first report from the federal governments as to wear our risk correlates and it moves the numbers by a staggering amount like it used to move the Oscar numbers by a billion revenues this thing would move by like a hundred million up and down.

44:38It's insane like it's completely crazy and big public companies have failed and sometimes estimating that thing well. We now know how to do this. We now know how to have a really good system that lands within like $10 ,000 or so whatever you know of the estimate because we get so much to of the year or whatever. But that was one of these things where I could not bear to be the openly email or whatever or hear the phone call or whatever and we would then go and sit down as usually comes in the fire nights. We have whiskey out with the actuaries and we would sit there and wait for this thing to come.

45:06That is the way to deal with bad news, to just deal with other people for who is equally bad but at least you share the badness in some way. So yes I had this to it's totally normal. There may be some schizophrenic head for managers who don't have it, but I'm glad you have it because it makes you a real human and that's a great thing. Maybe you and I were not builds fusion power or a fly to Mars. I've accepted that limits to my abilities. It's okay. But if you didn't have that, I think you did many other things you would not be able to do. I did not know about this mechanic in readjustments. I do want to go a little bit below you and your leadership.

45:40We mentioned the bag of tricks earlier for the team. I'm being able to lead then, you said to me before, you might as well build organisations the way you like it, not the way that a book or advise a teller see you. I just want to throw that one out there and be like, what did you mean by that? Where does that come from? There's a state every founder goes to where the board tells them now you have to bring in professional people, and then you go in higher and they go recording for them and you find the first CFO and COO and whatever else, and I wouldn't miss any other people we hadn't those wrong words.

46:11They were all, they still great friends, every and so do one of them and so great relationships. But what then happens inevitably is that those people will bring in management systems that have worked for them. They will make you as the founder and CEO feel that it's time to grow up to it. You know, like, just don't be in every meeting and let us handle this one and let's, and you do that and so on. That can be a good thing. I mean, you should certainly always learn from other people as to how they do things. For example, I am so surprised that these podcasts, for example, don't ask me where the very simple question of what is your weekly meeting?

46:42How do you meet with the management team? I remember asking the CEO of Airbnb that and she was telling me oh we changed it all the time which was very relieving to hear because they had also come through the same different iterations of men we too mentioned reading compositions. In the same way we have and I always thought there must be some kind of way to do it and you eventually get there. No there isn't so different stuff works with different periods and different people and all that kind of stuff and so listen and ask people what they do That's great. Don't just do what the professional managers will tell you to do for sure.

47:09And so, for example, I've always thought there is no way around spending hours and hours and hours in a room to just go through all priorities of your company with people in detail once a month or whatever else. And we just never really did that because people are always like, oh, that's, this is you necessary or that's not, whatever. That is one thing where I today know that's suited my style. I'd like the ideas I get when I do that. I can make more connections. I do think it has an ability of keeping more piece of information in my mind at the same time than most others. So design around that as opposed to just sort of reading the book.

47:42What are the biggest things to breaking company scaling? I fundamentally don't believe that you can have how many people are at Oscar now? Employee what? About three thousand? Okay, three thousand. Whereas I'll hire a plus talent. There's not three thousand a plus talent. A plus by definition is top one percent in my mind. It's just too hard. Yeah. And that for me is where it breaks. You see degradation and quality. Why do you think companies break and do you agree with my assessment now? Well, I think one thing I certainly observed is if you try to professionalize management at the top level, everyone below you will try to do the same thing.

48:13And that's how you end up with nine layers. If you as a CEO say, look, I have a great idea. I want to have a meeting now. We meet and go through these things. And that's where we're going to get our ideas. I want to delegate more and whatever. You are people are going to do the same thing. And the people that they that reported them will do the same thing. That's how you end up with lots of meetings, lots of spans of control and fewer people doing the actual work. The other thing I would say is, and this is actually a problem I have, if things remain unspoken about how stuff should run. It's a weird story at Oscar actually, where I think it's 2014 -2015, and so we're around like two years or so.

48:46We didn't have values written down, and at that time it was actually a little bit more rare that companies had values. Now it's a very common thing, right, and the episode of that real stuff. And I also you're making a very funny face the funny face might mean Oh, it's like if you have to say I'm an if the company you probably don't know through the company that whole thing Company values you should I'm sorry. I'm gonna jump in it You should be four or against them. You know we were fairness and honesty if you're not in for these Then obviously you're an immoral person respectfully. What are you doing for unfairness and immorality?

49:16I my values are this will be the place where you work harder than you will ever work in your life You will also make more money here than anywhere else and that's cool to be about money. That's fine. We are very hard. Don't have feelings in this business because you'll get roasted. People can be four against those. Their values. Okay, but there are certain things I think that you, if you go one level down from these, you expect certain behaviors that flow for you from these values where you're obviously. They make money, for example, it means that you don't have to share all of them from, I don't know, maybe it's okay to be competitive from like steal a deal from the other guy I don't know, you know, it might be too far, but there's certain things you implicitly expect as behaviors and other people I don't understand that's and so that is a problem I think we had people don't know when when I want a brainstorm They don't know when I want to get work done or whatever else and that you have to codify for people Otherwise you get locked that's the other thing three thousand person companies don't do they don't know Why are you in this meeting with me?

50:13Are you in the meeting with me because you don't trust me? Or are you in the meeting with me because yeah, you do trust me and I think my work's getting done well but you want to brainstorm, you want to have ideas, you want to be in the juices, you know? That stuff you have to explain to people, and Cuppies don't do that enough. I didn't even have values, I think that's a personal preference. Cuppie, that's the desire for creativity, for innovation, for collaborative thinking. That's the way that you like to do it, which is great and that's fantastic, but it's not like a company -wide value. To me that's a value.

50:42I tell you the story of Cuppie in 2014 -15, we said we should write down our values. What we did is we gave the old company an afternoon office, but a hundred people at the time Let's do a values bizarre people were able to write values that they thought I should have on the screen And they were older than my opinion people would congregate and gather and we would pick values that way And then I got all the data back and they were the most boring fucking values ever It was like excellence and integrity and like all totally vanilla because you took an average of extremes And that is just gonna be somewhere in the boring middle you just need a lean into something as a company You need to say, we are a company that is gonna generate ideas, and we're gonna do it unabashedly.

51:19It means we all do all these things, but it means I wanna understand what else is in your minds. And it's not every company that way. No, I agree, and I totally agree with you in terms of taking the average, and actually the binaries of those is probably what you should be or where most telling signs are. We mentioned money there. I do find it interesting, and a telling point, actually, which I think we demonize unfairly. How do you reflect on your own relationship to money, Mario? Go in public making money your public company CEO for a long time. Yeah, public company founder How do you think about your own relationship to money?

51:50Okay, I actually do have an opinion on that Yeah, and this is a bit my observation from navigating the woods of Silicon Valley as well And this might be a bit of a European thing and have a fairly strong feeling that others should judge my value in my worth And I trust the system doesn't agree so I say shouldn't be on me to decide And what equity I get were you know how much money I have or other kind of stuff if some there is enough systems in place that allocate value based on whether I did something that was useful for society at large or not. I certainly by the way think money is the best way we have to measure societal impacts.

52:22I get it's not perfect by any means and I don't like it necessarily, but I absolutely think that it's not that the wrong It's always the wrong people who are ritual every else that that's stupid as well. Like it's a good metric to sort of assist us How can you say about trusting systems to align values efficiently when health care is the most inefficient alignment of values. Sure, it might not be true, but certainly in the world I live in, I think, you know, the venture, investing, whatever, that, like, put it from myself. I did not try to somehow go to the board of everyone, say, I need more money, this and that and whatever else.

52:54And so, and that actually is not, that's not a good piece of advice. And I'm a white mayor, so probably it's easier for me comparatively to get paid the right amount than other people who probably, I actually do believe these inequities are in the system. And we gotta do something about the fact that, you know, women, a few particular people, and people of color and everything else, and we try to really pay attention to that, unabashedly, and none of the black men, bush, or whatever, change their mind anyway on that. But I do think that the people who make the real amounts of money, the people who become the moguls, they have an incredibly strong sense of what they are oaths by society and by the system of other people.

53:29That I don't have. And I think it's almost a brain defect. If you become a billionaire, you don't just become randomly your brain tells you I am all this I will get it for me I will demand it for me and I don't do that and that is actually not a good thing if you want to be one of the absolute top people you have to have that as well and some a certain amount of self delusion about it as well. This is always the favorite famous thing in in AI now right like there's a fairly this IQ's on normal distribution and not a they're not a power lot of distribution so by definition we know that you know the whatever top IQ there's like you know there's 1 % of them is not that there's like three people of them whatever so they're not as extreme of a distribution and yet the outcomes that they need to are extreme.

54:09The distribution of wealth and influence in the world is a power law and so a normal distribution somehow worked their way through the system into power law outcomes that has to mean that the mechanism is not perfect for going from one to the other. There's some weird non -linearities that are random in that thing. When did you first become a millionaire? I mean, it's questions paper versus versus not on paper I think was when the 2015 fundraising rounds there about we did a catch, a paper's one thing, but cash is another, like looking at the bank and seeing that. We did a secondary rounds, I think in that 2015 fundraising round I might say, and we tried to at that time make it so that we took everybody above a certain tenure and level at that time.

54:52They were all able to sell just about the same amounts and we thought that that was important because otherwise you'd have that sort of inequity of like why did the you know I can the founder says something, whatever, how did you feel? You know, people will say, oh, money doesn't make you happy money. 2015, you do actually have a million in cash. How did you feel? And that's something wasn't a million yet, by the way, but it was approaching that level, I think, but it was close enough. Like 900 ,000 something like that. I have a screenshot of the bank account still of my checking accounts and that that was in.

55:19It really gives you a feeling of fushua of accomplishments. There's no question about it. You're very relieved that that is the case. There's relief as well that if chip goes to hell now, not everything will be taken from you but the third thing is you have an instant feeling of holy shit now it's on and the level of fall just goes up like you're like okay now if you fuck it up it's really painful. Now I have the excuses go away I admire people who have an ability of going through that and then pushing the t - I'd say before the pushing the t -tips back and chips are back on the table. This is one reason why I think you know mathematicians do their best work before the age of 25 of whatever right, Nobel Prize laureates tend to be 35 or something like that because you just don't want to venture out into the woods anymore.

56:01In some sense, I know how improbable the journey of oscar was because I was there for the whole thing. I was there for all the times when it almost blew up in fellow parts and it is that sense of improbability that I will now forever project into everything else I will do for me or now. And that's a terrible thing because you start measuring it's that improbability as opposed to instant naivety you had I had in 2012 is like I'm smart, I can figure this out, no problem at all. And if there's one thing I want to do in my life, from his many things, I would try to get over that sense of improbability again and say, you know, if I do something again, I try to build a computer based on ant hills, then I want to go and do it.

56:37And if it doesn't work out of the ants, eat me, that is a completely fine outcome. You know, and it is the case with that money you can do more of that, for sure. What thing that money buys or brings to you most value? I think it is that sense that I do not have to go do what others tell me to do I love and it is unbelievably ineffective to just do something that I find Intellectually somewhat interesting like I learned Mandarin in the last two years for example for no reason whatsoever Now I'm trying to learn how to read Arabic I think there might be something coming out of it at some point But it's not useful right now for sure I built this game over this week this weekend I'm open a publisher next week or so that's Takes like words and puts them into some kind of riddle thing else.

57:15It's heart -explain but I just programmed this myself and it's very ineffective I should hire some needed words or whatever but I love doing those things and I like the idea of being able to move over those things and I also think those things have sometimes randomly gotten me somewhere and you have to put yourself into these like male storms of randomness. Final one for you to a quick fire but you go to many events with the biggest CEOs exacts in the world now, you sit at all the tables with the most powerful people, I luckily now sit at them too. And a little bit of me is like, you've got that house and you've got that thing.

57:48And I always laughed at people who were like, oh, a bigger boat. Do you ever have that bigger boat di -lamer? For me, it's not the boat at all when we fly with the kids or whatever. Or even when I fly somewhere myself, I probably just do economy or something like that when people are flying with planes nowadays. And there's a very nice like putting that backpack on in the pillow or whatever. It reminds me of when I still thought everything was possible. In this whole discounting imperabilities in some sense and look I mean I again this is not a big hardship right? It's the flyer to the west coast on an economy it's not like that somehow in the trenches of Ukraine that's very clear again here as well.

58:20The thing where exactly the way you just said is in the influence sides and I forgot who said this to me as well probably I don't know Charlie Munger or whatever but there's always a there's always a room you're not in and I'm sure that's still the case even for Zuckerberg like if Zuckerberg isn't getting invited to I don't know the royal wedding whatever else he's like damn it I wish I was at the royal wedding. There is It's just always a thing that you don't get invited to when you don't, and somebody who doesn't call you back. And by the way, I learned plenty of those things. And that attention economy, once you get to the level of, I don't know, Silicon Valley, whatever, where money is less of the issue, that is much more important, I think.

58:54Way more important than money. Everybody can sort of get some NBA tickets or something like that. I couldn't care less as who's a super bowl or something like that. I just really didn't give a shit. Like a Taylor Swift concert, who gives the shits. I really don't care. It's the influence. a you getting a phone call when people want to know something about AI and language models and by the way not just from the big guys but from the even former engineers and the company whatever else that actually does that I love it when them somebody like calls me about oh this I have this I saw this model do you think it's a useful model whatever as I like that way more and I actually do think that that is a relatively efficient market as well I used to think why do actors hang out with actors it's so stupid that's like a sign of you know they're stupid whatever it's not the case like I actually think actors and writers of every, they are incredibly creative people, they operate at this level of performance that few others can get to and they just don't want to be bored in conversations and so not being boring in conversations is maybe the one of the biggest goods you can have which is great, maybe I hope this was not boring.

59:53I'm still laughing at Zach coming a little Hissy fit that he wasn't invited through or wedding. I can't quite see that happening, I think it'd be a relief for him probably not to be, but I want to move into a quick fight. I've so enjoyed this so I say a short statement you give me your immediate thoughts does that sound okay? Go ahead. So what if you change your mind on most in the last 12 months? How much time I have left I used to I used to not care about it at all and I'm like ask her to 12 years How many things of that nature could I try to do and try to bite off? Is Oscar your life's work?

1:00:24I think it is something I'm incredibly proud of it very likely is the most useful and interesting thing I've done Well, that overvalued you too much right it has a lot of challenges to the edge of it and whatever That's very possible. It doesn't mean I shouldn't try to do some other things It has to be another company right and not saying I want to go and do something else tomorrow But even just like oh a game some people will play that I could build my free time or at peace of advice I can give somewhere how many more of those can I give out that that's not that many anymore It just takes time and so therefore it gave me more of an appreciation for whatever I do in an hour of a day It doesn't mean I don't waste a ton of time every single day and like I don't know reading the internet or whatever else or even Twitter But it does compress the amount of things you can do in the day in just shorter trunks That's that was a big one the other thing is you cannot imagine going back before you had kids anymore when you had them They will always be there you hope they will always be the last thing in your life You can go and I think feel good about if you let yourself do it You can also just be ambitious about them and being a fucking unhappy person because they didn't go do this do that whatever else.

1:01:28But it's like the last thing you did in your life is probably that. And that is comforting. How did having kids change your mind? So positive, it gives you a lot to talk about. I really love when we get a dinner with my F and I and just like saying, oh no, I did this today. And I did that today or whatever. Oh, that's that. By the way, that's them in the back here. So you have a lot to talk about, which is great. Like it's a real, in marriages, I think the worst thing is to run out of stuff to talk about. So that's great. It makes it awesome to go to them, to go on vacation with them. Like we went to Egypt last year.

1:01:55I actually love going with my wife because we have a very similar streak of like, oh let's do some adventures, something adventures, whatever else. But to do it with the kids, it's just really like, oh that's a hieroglyphic. And it is cool, it's been around for 5 ,000 years. And Jesus Christ was here and all that stuff. Like it's just cool stuff. Or do you think it's secret is to happy marriage? I think it is that attention piece. It is if you are bored, if you don't have anything to talk about anymore, that's probably the biggest thing. Because everything else, I think, you know, I don't know, attraction levels.

1:02:21That comes and goes in waves, I think. It just does. But that's sort of whether you can stand each other like this will there be ways we don't and then they would be ways We like oh this is what it used to be like great awesome. I'm happy again But that's something to talk about is if you run out of that So I think that's a problem weird one, but it says a lot about a mindset You can be in a cage with a tiger or in a swimming pool with a shark Which one do you choose and why I think cage and a tiger is like a much more pleasant death? No drowning seems like a very bad way to die So that's the one that's the one I would I would think.

1:02:54I mean, I love that you're so European that you went straight to just losing. Most people would like fight. They're like, oh, I do a shot because I could punch it in the nose. You're like, fuck it, I'm gonna die. And you can also scream louder in the tiger's cage. How do you scream under water? What do you know now that you wish you'd known when you started Oscar? I would go with a Jensenquan thing, which is the pain is deep and the lows alone and all that stuff. They would be there. And so you just need to basically say, step outside of yourself almost and observe yourself and say, you've done this before, it is gonna be fine, and if not, then you can't change it anyway.

1:03:28So, be okay with that. You have a finite amount of time to do this. Ten years sounds like a long time, it's not that long. And so, it does matter a lot what you do. Like, I remember there were times when it's weird and I don't get enough emails today. Should I feel good about this or bad about this? And, you know, that's okay, maybe I can do anything. It is your job to bring the intensity back in. It just is. And, you know, there's obviously family, this rest of your life and so on as well, but if you let the intensity go out, I think the intensity goes out of the disappears from the company. You don't have that much time.

1:03:59It's the other thing I would actually say to myself. I love that. But ultimately one, I love Josh. You mentioned Josh a couple of times. What's your biggest takeaway from working with Josh now for 12 years? Josh and I started our first company together in 2006, so it goes way back before Oscar. That was a thing that would later become a gaming company, but it wasn't a gaming company at that time. It was It was a social network and none of us was doing it full time and between the years 2007 and 2010 I think he and I didn't talk we hated each other because I Wanted to say that strongly, but we just had like we had fight over equity and and I thought he's young kid He's doing and he was arrogant about it and whatever and like by the fact I'm doing the programming.

1:04:40What is he doing as pointless and all that stuff and we needed to get that out of the way And I think my takeaway there therefore is Josh is an incredibly good person very loyal very smart obviously an Incredible guy that's knowing what to ask of the right person, but he's also the other things He also has those you know, he's also a guy you can fight with and at some point if they get out of the way If you think he's a saint if you think he doesn't have those things you will awaken to it at some points And so you might as well get the fighting out of the way at the very beginning maybe that's a that's one learning there I think the other learning is that this is thing is still a business.

1:05:17Don't just think that everything in life If you've been with one person it is up to people like Josh to connect to many many others who could do interesting different things You should do the same thing. That is a much better kind of working together of equals if you both have value You can bring it to this relationship. That's I think the other marriage advice people give right if the relationship becomes too asymmetric in terms of value generation I really want to define that in a marriage, you know It becomes difficult as well Don't worry, mate, you said a trash and comes and goes over time, so that probably is not the most offensive thing So it's okay final one for you my friend.

1:05:49Where will you be in 10 years? 2034 scary thing is it's not that far away from when we last spoke Terrifying me. I mean I mean I hope I'm at the equivalence of what Oscar was in 2012 Some area that people don't have on the radar screen that as you said has the bad talent brands And it's just not interesting for most people but it has so much more impacts on big part of the world or something That is just not on people's radar screen at all. I hope I still have a notebook with the last interesting notes I took with the day before I look at my notebook and I look at when it was the last taken notes on something interesting And that is a big part of whether I still think I do something interesting, you know, and I still feel engaged on something And so I still I hope I have that wherever I am at this notebook Mario, I've so loved doing this.

1:06:34Thank you for being such a great guest. I hope I've improved as an interviewer. You've definitely improved as an interviewer, so I can't thank you enough. I love doing it to Erie. We're really glad to see you. Honestly, I so enjoyed doing that show with Mario. For me, the joy is when you feel like you really got to know someone and interview when they reveal... maybe a part of themselves that they wouldn't normally have revealed publicly. I can't thank Mario enough for being so open -minded about some of the challenges that he faced, how he dealt with them. I hope it was okay for me to also open up about how I've dealt with some of mine.

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1:09:32Now stay tuned for an incredible episode this This coming Monday with the one and only Bastie layman, founder of Postmates, to reveal that incredible journey ultimately selling to Uber.