The Exchanges

Every argument clarity score on this site is built from rows on this page. Each question and answer was assessed with names hidden, the host's own answers included, on four things from 1 to 5: directness (does it answer the question asked), coherence (do the ideas follow), precision (concrete details and clear references), compression (says a lot per word). The weighted mix (30/30/25/15) is the exchange score. A person's published score averages their exchange scores on raw tape only, at least 8 of them, shrunk toward the cohort mean. Full method →

Billy Hult argument clarity score 3.8/5 from 32 exchanges on raw tape · average scores: directness 4.2 · coherence 3.9 · precision 3.2 · compression 3 record → ← everyone

Every exchange below was scored with names hidden, four dimensions each from 1 to 5. An exchange's score is 0.30·directness + 0.30·coherence + 0.25·precision + 0.15·compression. The published score averages the raw tape exchange scores and shrinks small samples toward the cohort mean, so five great answers can't beat twenty good ones. Produced feed rows count only toward coarse estimates, never toward a full score.

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Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Do you feel, do you feel like you've been there for your kids like you would like to have been? It's really hard when you're CEO of a public company.

A I miss, you know, the, the, the broad answer and it's a, it's a really, it's a genuine question. Um, the broad answer is definitely yes. The, the, the, the, the truthful and the more, more recent answer is no. So like this year, my, my, my, I have, um, I have three kids in my, my, um, my middle, my younger daughter, um, She's a senior, you know, senior in high school, and she's got, like, all these, like, big basketball games. You know, it's her last basketball games of her, probably, like, of her life, and I missed a bunch of them, you know, because I was working. And I, and I felt like the work was really important, and I relied on my relationship with her that she would be understanding of it, and of course she was, but I feel the loss of, of missing those moments the most, I think.

AI assessment note: “The truthful and the more recent answer is no.”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Did you have a hard first job? Uh, someone said to me the other day, uh, it's very transformative to have a really hard first job, be it, like, Doing lawn mowing when you were seven all day, or like, doing paper rounds. Did you have that?

A I did. I mean, I, you know, I grew up in Manhattan, like, like, you know, so there were no lawns to mow. Um, but I'm gonna make you laugh with this, because, because, um, sometimes, like, the, the, it's a good question, sometimes, like, the most true stories are kind of, like, entertaining. My first job, and it was like, um, You know, for sure, um, either end of high school or kind of early college, kind of one of those summer jobs, was working Harry at a place they called, like, OTBs. It was, it was, uh, off-track betting, um, a place where people would go in back in the eighties and nineties in Manhattan and place bets on horses, and I was a, a betting clerk Um, in, in the South Bronx, um, which was, um, it still is a, it was, it's a, it's a tough neighborhood, and it was a tough job, and you had to learn very quickly to think on your feet, Um, you met all different types of people. Um, it wasn't, um, it wasn't like an internship at, um, you know, Brown Brothers or Morgan Stanley. It was the school of, the school of, a little bit of the school of hard knocks.

AI assessment note: “I did. I mean, I, you know, I grew up in Manhattan”

Answered raw tape D 5 · C 5 · P 5 · Cm 4 4.85

Q Do you feel, do you feel like you've been there for your kids like you would like to have been? It's really hard when you're CEO of a public company.

A I miss, you know, the, the, the broad answer and it's a, it's a really, it's a genuine question. Um, the broad answer is definitely yes. The, the, the, the, the truthful and the more, more recent answer is no. So like this year, my, my, my, I have, um, I have three kids in my, my, um, my middle, my younger daughter, um, She's a senior, you know, senior in high school, and she's got, like, all these, like, big basketball games. You know, it's her last basketball games of her, probably, like, of her life, and I missed a bunch of them, you know, because I was working. And I, and I felt like the work was really important, and I relied on my relationship with her that she would be understanding of it, and of course she was, but I feel the loss of, of missing those moments the most, I think.

AI assessment note: “The broad answer is definitely yes. The, the, the truthful and the more, more recent answer is no.”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q But does this feel better than it did then in 2008 in 2000 with the dot com?

A The markets feel better and more resilient and in sort of like in an obvious way in better shape. There's a playbook in place around sort of preserving the structure and the, and the, And the high functioning-ness of the market in a way that should, people should feel sort of, I think, in a good way, um, confident in. The world feels like shakier than ever. I mean, you tell me if I'm wrong about that, but I see not a ton of good things out there. If you start with, like, American politics, and then get into the Middle East, and then get into kind of Russia, and then we have, you know, I'm not a, I'm not a political expert, but everything even around China feels pretty fragile. So that's, we're pretty volatile. So that, that's like, that has to keep us all, all up at night.

AI assessment note: “The markets feel better and more resilient and in sort of like in an obvious way”

Answered raw tape D 5 · C 5 · P 4 · Cm 4 4.60

Q You said about kind of earlier that you're kind of really leaned into things that you were good at or passionate about and discarded or didn't like the things that you didn't. Do you think people should lean into their strengths and discard their weaknesses?

A I think that there's a way maybe to, like, Overdo all of that. And maybe there was a time when I was a, you know, when I was a kid where I was definitely overdoing it. There's something about like, you know, the three C minuses and the, and the two A's that doesn't always please the parents. Plus it can cause some alarm bells in the school. So I wouldn't necessarily pattern all of that. That, that being said, I think, especially as you get older, I think there are, you know, inherent strengths That you want to kind of lean into. Um, there are things that like you're good at, the things that you gravitate to, but most importantly, I think there is an aspect of, you know, what, what are you really ultimately emotionally engaged in? Like, what do you really truly care about? And then my instinct is you tend to do the best with things that you really care about.

AI assessment note: “I think, especially as you get older, I think there are, you know, inherent strengths”

Answered raw tape D 5 · C 4 · P 4 · Cm 4 4.30

Q What do you, what do you think makes a good CEO? Like, what are the core checklist of my job as CEO is this?

A I'm not gonna make you laugh with this, but I, I do think there's something which is interesting, which is like, you're the CEO of a company, and what is a company? It's like people. So I, I do constantly kind of remind myself that I'm dealing with people, and people have egos, they have opinions, they have personalities. There are ways to sort of motivate people the right way, and then you can demotivate people. So, I do think there's a concept of like, remind yourself what a company is. Um, I think high level, you have to be the external face of the company and you have to really be the person that at the end of the day represents the company at the highest level. I think you have to set strategy. And I, and I say that like in a, in a very straightforward way, I think it's the CEO's responsibility to set the strategic direction of a company. And then the company executes behind that. I try to. I think in a good way, I try to get my kind of sleeves rolled up and my hands around execution, because I do think that's where companies kind of ultimately make their bones around like, how good are you at really ultimately executing on a game plan? And if you get yourself like too removed from the actual kind of like the execution piece of it, I sometimes think that there can be a little bit of a, Passivity.

AI assessment note: “I think it's the CEO's responsibility to set the strategic direction of a company.”

Answered raw tape D 5 · C 4 · P 4 · Cm 3 4.15

Q Did you have a hard first job? Uh, someone said to me the other day, uh, it's very transformative to have a really hard first job, be it, like, Doing lawn mowing when you were seven all day, or like, doing paper rounds. Did you have that?

A I did. I mean, I, you know, I grew up in Manhattan, like, like, you know, so there were no lawns to mow. Um, but I'm gonna make you laugh with this, because, because, um, sometimes, like, the, the, it's a good question, sometimes, like, the most true stories are kind of, like, entertaining. My first job, and it was like, um, You know, for sure, um, either end of high school or kind of early college, kind of one of those summer jobs, was working Harry at a place they called, like, OTBs. It was, it was, uh, off-track betting, um, a place where people would go in back in the eighties and nineties in Manhattan and place bets on horses, and I was a, a betting clerk Um, in, in the South Bronx, um, which was, um, it still is a, it was, it's a, it's a tough neighborhood, and it was a tough job, and you had to learn very quickly to think on your feet, Um, you met all different types of people. Um, it wasn't, um, it wasn't like an internship at, um, you know, Brown Brothers or Morgan Stanley. It was the school of, the school of, a little bit of the school of hard knocks.

AI assessment note: “it was a tough job, and you had to learn very quickly”

Answered raw tape D 5 · C 4 · P 3 · Cm 4 4.05

Q Okay. That's a, that's a great lead on to the final one, which is like 10 years time. Where do you think, You will be as a company, and as an addendum to that, what is the one reason why you would not achieve that?

A The company is going to continue to be this, like, high-powered, kind of, global marketplace that's going to continue to march in all of these, um, new directions, some of which will, we, you and I could plot out right now, and some of which we haven't thought of, but when you think about the concept of this company's ability to partner with the most important Market participants. There's nothing stopping sort of a forward march for us. So we're going to be bigger, stronger, and a better company. Complacency is the, is the killer of the whole thing. You know, dude, like, um, getting, getting the things that matter wrong. Is the killer. You stop placing, like, you know, idea generation at the top. You start putting, like, you know, office politics ahead of that. Like, hmm, you lose sight of, like, who the customer is. Bad traits. You know, I'm, I'm, I'm very determined, and, and I'm gonna work my best to make sure, like, those things don't kind of enter our world, but those are the killers.

AI assessment note: “Complacency is the, is the killer of the whole thing.”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q No, listen, I'm totally with you. I'm terrible at it, bluntly. So, but in the 50% that don't, are there commonalities in why it doesn't work out?

A Maybe chemistry. You know, maybe I saw something in them that they didn't quite have, or I pushed them in a direction That maybe they didn't quite want to go to, and then maybe in, like, the human nature of the whole thing that the chemistry broke down, and you, sometimes you get stuck, and then it's kind of like, you know, can you, can you sort of get unstuck? You know, can you find another kind of Run at this whole thing. Um, you know, and I've had to sort of like assess like a little bit of, of, of, of the very first kind of things that you and I were talking about, and this is turning into like an amazing, um, therapist session, which is, you know, have I been clear enough? Have I been direct enough? Have I given enough kind of feedback along the way? Most of the time, the answer is yes, and I don't, like, put a lot of blame for myself when something doesn't work out, but as you know really well, like, there's always, like, a sort of, like, a co-created dynamic. And, and when you're CEO and you, and you place a bet on someone and it doesn't work, you know, you're bummed.

AI assessment note: “Maybe chemistry. You know, maybe I saw something in them that they didn't quite have”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q How was it when you became Freddie Mercury or Chris Martin?

A It was comfortable. And normal. And it felt, um, it felt, um, sort of like a, like, um, a process that had kind of worked. And for me, it felt like a moment in time, maybe, maybe like in my life and career where I was for sure, like ready to do it, which is like a big part of, I think, like when succession works the right way and a big part of the process of, of ultimately running a public company, but it did not feel honestly Um, and, and I think you know very well that I would kind of tell you if it was true. It did not feel like laden with like anxiety. It felt like, let's go, let's go do this. Um, I've done a lot in my career and I'm ready for like this next chapter.

AI assessment note: “It was comfortable. And normal. And it felt, um, it felt”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q What do you, what do you think makes a good CEO? Like, what are the core checklist of my job as CEO is this?

A I'm not gonna make you laugh with this, but I, I do think there's something which is interesting, which is like, you're the CEO of a company, and what is a company? It's like people. So I, I do constantly kind of remind myself that I'm dealing with people, and people have egos, they have opinions, they have personalities. There are ways to sort of motivate people the right way, and then you can demotivate people. So, I do think there's a concept of like, remind yourself what a company is. Um, I think high level, you have to be the external face of the company and you have to really be the person that at the end of the day represents the company at the highest level. I think you have to set strategy. And I, and I say that like in a, in a very straightforward way, I think it's the CEO's responsibility to set the strategic direction of a company. And then the company executes behind that. I try to. I think in a good way, I try to get my kind of sleeves rolled up and my hands around execution, because I do think that's where companies kind of ultimately make their bones around like, how good are you at really ultimately executing on a game plan? And if you get yourself like too removed from the actual kind of like the execution piece of it, I sometimes think that there can be a little bit of a, Passivity.

AI assessment note: “you have to be the external face of the company... set strategy”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q Has your style of parenting changed over the years, Billy?

A No. I mean, I think I was like, um, you know, I, I think I was always, um, probably a little bit of like, uh, I don't wanna say like the, the, the, the, the, yes, dad, but, but maybe I was, I was, um, I struggled saying no. I love my kids. So it was easy to kind of, um, you know, sort of, uh, um, you know, surround them with, with, with love and to try to be the person that did a lot of fun things with them. And I find myself doing, you know, different, obviously versions of that, but being kind of similar along those things, you know, 15 years later or 20 years later that, that sort of dynamic Is kind of still in place.

AI assessment note: “No. I mean, I think I was always”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q How was it when you became Freddie Mercury or Chris Martin?

A It was comfortable. And normal. And it felt, um, it felt, um, sort of like a, like, um, a process that had kind of worked. And for me, it felt like a moment in time, maybe, maybe like in my life and career where I was for sure, like ready to do it, which is like a big part of, I think, like when succession works the right way and a big part of the process of, of ultimately running a public company, but it did not feel honestly Um, and, and I think you know very well that I would kind of tell you if it was true. It did not feel like laden with like anxiety. It felt like, let's go, let's go do this. Um, I've done a lot in my career and I'm ready for like this next chapter.

AI assessment note: “It was comfortable. And normal. And it felt... like ready to do it”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q Has your style of parenting changed over the years, Billy?

A No. I mean, I think I was like, um, you know, I, I think I was always, um, probably a little bit of like, uh, I don't wanna say like the, the, the, the, the, yes, dad, but, but maybe I was, I was, um, I struggled saying no. I love my kids. So it was easy to kind of, um, you know, sort of, uh, um, you know, surround them with, with, with love and to try to be the person that did a lot of fun things with them. And I find myself doing, you know, different, obviously versions of that, but being kind of similar along those things, you know, 15 years later or 20 years later that, that sort of dynamic Is kind of still in place.

AI assessment note: “No. I mean, I think I was always... that sort of dynamic Is kind of still in place.”

Answered raw tape D 5 · C 4 · P 3 · Cm 3 3.90

Q No, listen, I'm totally with you. I'm terrible at it, bluntly. So, but in the 50% that don't, are there commonalities in why it doesn't work out?

A Maybe chemistry. You know, maybe I saw something in them that they didn't quite have, or I pushed them in a direction That maybe they didn't quite want to go to, and then maybe in, like, the human nature of the whole thing that the chemistry broke down, and you, sometimes you get stuck, and then it's kind of like, you know, can you, can you sort of get unstuck? You know, can you find another kind of Run at this whole thing. Um, you know, and I've had to sort of like assess like a little bit of, of, of, of the very first kind of things that you and I were talking about, and this is turning into like an amazing, um, therapist session, which is, you know, have I been clear enough? Have I been direct enough? Have I given enough kind of feedback along the way? Most of the time, the answer is yes, and I don't, like, put a lot of blame for myself when something doesn't work out, but as you know really well, like, there's always, like, a sort of, like, a co-created dynamic. And, and when you're CEO and you, and you place a bet on someone and it doesn't work, you know, you're bummed.

AI assessment note: “Maybe chemistry. You know, maybe I saw something in them that they didn't quite have”

Answered raw tape D 4 · C 4 · P 4 · Cm 3 3.85

Q But my question to you is, you said there about kind of, you don't want to be too far removed. We often hear the statement, hire great people and get out the way. How do you think about that? And then micromanagement and the balance between the two?

A It's, um, it goes back a little bit to sort of like, how do you lean into what you do really well? And so I think that there are aspects of a sort of ecosystem or a complicated company where you hire great people. And it's not that you get out of their way, but maybe you support them in a way where they feel empowered to do their job really well. And then there's the concept I think of, You know, what is my responsibility, Harry, to, like, make a difference? You know, how do I become a difference maker player for my team? You know, and so how I try to do it is, you know, high level, like, engage with, you know, the biggest, most important investors and engage with the biggest, most important clients. I think I'm really good at that. Um, and so I try to make a difference for my company by putting myself in those, you know, in those situations. Um, early on when I became CEO, I was invited nicely. I don't think they regret it now, but, but I was, it was a very nice invite from them to, um, be a part of the sort of JP Morgan like CEO conference in Napa. Um, quite a nice conference, and it was a nice invite. Um, you know, these CEOs from like all over the, all over the world were there, and I got to watch, and this won't surprise you at all, I got to watch like Jamie in action. You know, as the CEO of, of JP Morgan, he's there, but like JP's hosting, you know, this event for their …

AI assessment note: “it's not that you get out of their way, but maybe you support them”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q Do you worry about that? Yeah, because you are informal and human and it's wonderful for me.

A Yeah, I do. Yeah, I do because like, like I said to you, I'm more driven now than I was when I was building my career, but I don't always show it. Right? So for me, my, my, I, um, I wouldn't say it's like a technique, because it's like, it's my personality, and it's who I am. Um, I'm comfortable in my own skin, and I, I, um, I come across that way. I'm also, again, let's throw this other thing back in the mix, like, I think, like, firmly aware of, like, this totem pole thing. I don't know, like, when someone takes themselves, like, so seriously, it's like, come on, guys, like, let's remember, Um, you know, there are bigger problems in the world. There are bigger problems in the, in the, you know, in the financial service industry. Like, you know, we don't have to all, what was the thing with, um, I'm gonna make you laugh when, um, The famous line when, you know, the financial crisis was kind of roaring and the story was, was that like Lloyd was, you know, in a, in a town car headed down to see the fed and kind of one of the bankers in the car said to him, like, I don't, you know, I don't know how much more I can kind of take of this because they were stressed. They were working really hard. Like everyone was going like, you know, a hundred miles an hour. And I think the guy was like, you know, I don't know how much more I can take all this. It's like the pressure is like, you k…

AI assessment note: “Yeah, I do. Yeah, I do because like, like I said to you”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q You said about kind of earlier that you're kind of really leaned into things that you were good at or passionate about and discarded or didn't like the things that you didn't. Do you think people should lean into their strengths and discard their weaknesses?

A I think that there's a way maybe to, like, Overdo all of that. And maybe there was a time when I was a, you know, when I was a kid where I was definitely overdoing it. There's something about like, you know, the three C minuses and the, and the two A's that doesn't always please the parents. Plus it can cause some alarm bells in the school. So I wouldn't necessarily pattern all of that. That, that being said, I think, especially as you get older, I think there are, you know, inherent strengths That you want to kind of lean into. Um, there are things that like you're good at, the things that you gravitate to, but most importantly, I think there is an aspect of, you know, what, what are you really ultimately emotionally engaged in? Like, what do you really truly care about? And then my instinct is you tend to do the best with things that you really care about.

AI assessment note: “especially as you get older, I think there are, you know, inherent strengths”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q Kind of harder for me because there's no ticker, um, but I'm down when my company's down. How do you not get depressed when your ticker's down, and how do you detach from the performance of the company?

A I think it's, it's sort of like, um, it's hard, and it's sort of like, um, is it, you know, Is it, is it down because the market's getting repriced around, you know, an extra genius event, and like, it's not personal? Or is it down because there's been some sort of like subpar performance in your business and the market's reacting to subpar performance? So I do think you can kind of kilter your reaction differently. I think when it's like, you know, it's not that, you know, we've been lucky because we've performed like really, really well. Um, but it's not like we've performed perfectly. So you wear those moments where maybe, you know, you feel like there's been a reaction, uh, you know, a negative reaction to your business. Um, and you're human.

AI assessment note: “So I do think you can kind of kilter your reaction differently.”

Answered raw tape D 5 · C 3 · P 3 · Cm 3 3.60

Q Do you worry about that? Yeah, because you are informal and human and it's wonderful for me.

A Yeah, I do. Yeah, I do because like, like I said to you, I'm more driven now than I was when I was building my career, but I don't always show it. Right? So for me, my, my, I, um, I wouldn't say it's like a technique, because it's like, it's my personality, and it's who I am. Um, I'm comfortable in my own skin, and I, I, um, I come across that way. I'm also, again, let's throw this other thing back in the mix, like, I think, like, firmly aware of, like, this totem pole thing. I don't know, like, when someone takes themselves, like, so seriously, it's like, come on, guys, like, let's remember, Um, you know, there are bigger problems in the world. There are bigger problems in the, in the, you know, in the financial service industry. Like, you know, we don't have to all, what was the thing with, um, I'm gonna make you laugh when, um, The famous line when, you know, the financial crisis was kind of roaring and the story was, was that like Lloyd was, you know, in a, in a town car headed down to see the fed and kind of one of the bankers in the car said to him, like, I don't, you know, I don't know how much more I can kind of take of this because they were stressed. They were working really hard. Like everyone was going like, you know, a hundred miles an hour. And I think the guy was like, you know, I don't know how much more I can take all this. It's like the pressure is like, you k…

AI assessment note: “Yeah, I do. Yeah, I do because like, like I said to you”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q Like, they don't need to. Right. How do you encourage them to be really ambitious?

A Super hard. I would say that, like, from a parenting perspective, you know, that's like the number one thing on my mind. Um, I think I think there's a difference between sort of having, I don't know, what are we talking about, like privilege? Like having access to privilege or maybe being privileged, and I think that's like a, it's like an interesting word these days, and being like, um, spoiled, you know, and being, um, unmotivated. You know, and, and, and so I learned a long time ago, sort of a little bit of a lesson, which is like other people's successes, like aren't your success. And I've also kind of learned a lot around the concept of like, I'll make you laugh with this one. It's sort of, um, you know, the beer's not as cold when it's like not yours. You know, so there's a really nice feeling to go into, like, your house, you know, with your cold beer in your house and having a sip of that and knowing, like, hey, like, I, I kind of earned that, you know, and so I really, you know, I, I, I go out of my way and, you know, in the best possible way as a father just to kind of reiterate You know, those kinds of things with my kids. Um, but yeah, they live a different life than I did.

AI assessment note: “I go out of my way... just to kind of reiterate You know, those kinds of things”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q I get you. In venture, consensus often leads to, leads to a bit of a challenge. Uh, I, I do, that's when it comes to decisions, and on decisions before, you've said about the importance of CEOs making, kind of, big bets, so to speak. Can you talk to me, why is it so important that CEOs make big bets, and how do you think about them?

A You're not, it's like funny, I'm gonna make you laugh, but that you're, you're by no means the first person that's like taken a phrase of mine and then like put it in like ink. So, so let me, let me, let me describe a few this way for a second. So my company TradeWeb has, you know, largely gotten to where we are today through a lot of like really good sort of, you know, organic investments and organic growth. Right. So we are not some company that's arrived here through lots of like M&A. Right. Um, but as you know well, and you talked about like for yourself, like the sort of like the personal kind of evolution, the personal growth things, sometimes like companies need to grow through, I think, change. You know, and so one of the things I've been doing a little bit, um, is like using the language of change, right? Which is like, we've gotten here and we've, we've arrived through all of this like organic kind of investment and growth and continuing to kind of move ourselves forward in this very one specific way. Let's start talking about like putting more bets on the table. Let's start talking about like doing more deals. And since we're going to talk about that and we're going to look in that direction, let's talk about it like in big ways. Let's talk about it in like transformative ways. Let's not be afraid to sort of start using the language of like real ambition. Like why no…

AI assessment note: “Let's start talking about like putting more bets on the table.”

Answered raw tape D 4 · C 4 · P 3 · Cm 3 3.60

Q Kind of harder for me because there's no ticker, um, but I'm down when my company's down. How do you not get depressed when your ticker's down, and how do you detach from the performance of the company?

A I think it's, it's sort of like, um, it's hard, and it's sort of like, um, is it, you know, Is it, is it down because the market's getting repriced around, you know, an extra genius event, and like, it's not personal? Or is it down because there's been some sort of like subpar performance in your business and the market's reacting to subpar performance? So I do think you can kind of kilter your reaction differently. I think when it's like, you know, it's not that, you know, we've been lucky because we've performed like really, really well. Um, but it's not like we've performed perfectly. So you wear those moments where maybe, you know, you feel like there's been a reaction, uh, you know, a negative reaction to your business. Um, and you're human.

AI assessment note: “So I do think you can kind of kilter your reaction differently.”

Answered raw tape D 3 · C 4 · P 3 · Cm 3 3.30

Q I get you. In venture, consensus often leads to, leads to a bit of a challenge. Uh, I, I do, that's when it comes to decisions, and on decisions before, you've said about the importance of CEOs making, kind of, big bets, so to speak. Can you talk to me, why is it so important that CEOs make big bets, and how do you think about them?

A You're not, it's like funny, I'm gonna make you laugh, but that you're, you're by no means the first person that's like taken a phrase of mine and then like put it in like ink. So, so let me, let me, let me describe a few this way for a second. So my company TradeWeb has, you know, largely gotten to where we are today through a lot of like really good sort of, you know, organic investments and organic growth. Right. So we are not some company that's arrived here through lots of like M&A. Right. Um, but as you know well, and you talked about like for yourself, like the sort of like the personal kind of evolution, the personal growth things, sometimes like companies need to grow through, I think, change. You know, and so one of the things I've been doing a little bit, um, is like using the language of change, right? Which is like, we've gotten here and we've, we've arrived through all of this like organic kind of investment and growth and continuing to kind of move ourselves forward in this very one specific way. Let's start talking about like putting more bets on the table. Let's start talking about like doing more deals. And since we're going to talk about that and we're going to look in that direction, let's talk about it like in big ways. Let's talk about it in like transformative ways. Let's not be afraid to sort of start using the language of like real ambition. Like why no…

AI assessment note: “using the language of change... Let's start talking about like putting more bets on the table.”

Answered raw tape D 3 · C 4 · P 3 · Cm 3 3.30

Q Like, they don't need to. Right. How do you encourage them to be really ambitious?

A Super hard. I would say that, like, from a parenting perspective, you know, that's like the number one thing on my mind. Um, I think I think there's a difference between sort of having, I don't know, what are we talking about, like privilege? Like having access to privilege or maybe being privileged, and I think that's like a, it's like an interesting word these days, and being like, um, spoiled, you know, and being, um, unmotivated. You know, and, and, and so I learned a long time ago, sort of a little bit of a lesson, which is like other people's successes, like aren't your success. And I've also kind of learned a lot around the concept of like, I'll make you laugh with this one. It's sort of, um, you know, the beer's not as cold when it's like not yours. You know, so there's a really nice feeling to go into, like, your house, you know, with your cold beer in your house and having a sip of that and knowing, like, hey, like, I, I kind of earned that, you know, and so I really, you know, I, I, I go out of my way and, you know, in the best possible way as a father just to kind of reiterate You know, those kinds of things with my kids. Um, but yeah, they live a different life than I did.

AI assessment note: “go out of my way and... as a father just to kind of reiterate”

Redirected raw tape D 3 · C 4 · P 3 · Cm 2 3.15

Q But my question to you is, you said there about kind of, you don't want to be too far removed. We often hear the statement, hire great people and get out the way. How do you think about that? And then micromanagement and the balance between the two?

A It's, um, it goes back a little bit to sort of like, how do you lean into what you do really well? And so I think that there are aspects of a sort of ecosystem or a complicated company where you hire great people. And it's not that you get out of their way, but maybe you support them in a way where they feel empowered to do their job really well. And then there's the concept I think of, You know, what is my responsibility, Harry, to, like, make a difference? You know, how do I become a difference maker player for my team? You know, and so how I try to do it is, you know, high level, like, engage with, you know, the biggest, most important investors and engage with the biggest, most important clients. I think I'm really good at that. Um, and so I try to make a difference for my company by putting myself in those, you know, in those situations. Um, early on when I became CEO, I was invited nicely. I don't think they regret it now, but, but I was, it was a very nice invite from them to, um, be a part of the sort of JP Morgan like CEO conference in Napa. Um, quite a nice conference, and it was a nice invite. Um, you know, these CEOs from like all over the, all over the world were there, and I got to watch, and this won't surprise you at all, I got to watch like Jamie in action. You know, as the CEO of, of JP Morgan, he's there, but like JP's hosting, you know, this event for their …

AI assessment note: “it's not that you get out of their way, but maybe you support them”

Partly raw tape D 3 · C 3 · P 3 · Cm 2 2.85

Q Money, fame, power. How do you rank the three in what's important to you?

A Fame, distant third. Um, It would be really easy to say like, you know, like money first, power second, but I think, um, I think power is like pretty interesting. So I think if you dismiss power, so, so obviously maybe you're not quite being, being super, super true or super assessing like how you really feel. Um, I kind of, I've always sort of thought like a little bit of like prospering kind of below the radar is not a terrible place to be. You know, you're going to blow up my Instagram account with this one. Um, so I'm going to become less, less below the radar at some point, but, but like, I think like, you know, prospering below the radar is kind of cool.

AI assessment note: “Fame, distant third. Um, It would be really easy to say like”

Partly raw tape D 3 · C 3 · P 3 · Cm 2 2.85

Q Money, fame, power. How do you rank the three in what's important to you?

A Fame, distant third. Um, It would be really easy to say like, you know, like money first, power second, but I think, um, I think power is like pretty interesting. So I think if you dismiss power, so, so obviously maybe you're not quite being, being super, super true or super assessing like how you really feel. Um, I kind of, I've always sort of thought like a little bit of like prospering kind of below the radar is not a terrible place to be. You know, you're going to blow up my Instagram account with this one. Um, so I'm going to become less, less below the radar at some point, but, but like, I think like, you know, prospering below the radar is kind of cool.

AI assessment note: “Fame, distant third. Um, It would be really easy to say like”

Answered raw tape D 3 · C 3 · P 2 · Cm 2 2.60

Q What does that mean? You bet on people who don't have the qualifications and the experience, but you believe you, what is placing a big bet on a person?

A I've brought people into my world who I took, took a bet on. I sort of like, I want it to work out, and I've, I've, I've invested, and I've, um, you know, co-created relationships that have worked. And by the way, that can be people I've hired, that can be board members that have entered my world. It can come from kind of like different directions, but I have taken sort of What, what, what I would describe to you as like, honestly, like risks in sort of relationships, um, that I felt like were sort of beneficial to both me and the company, you know, and some people kind of like, when we talk about like a bet, you can talk about it or think about it in a couple of different ways. Some people are like, oh no, like, like we're just gonna like stick to knitting. We're not gonna bring people in. I'm not gonna be sort of open to sort of different voices in a boardroom and all of that stuff. And I've, I think benefited From having very strong intuition about people, and ultimately putting a bet on the, the, the, you know, The partnership that exists in, in a, in a business relationship.

AI assessment note: “risks in sort of relationships, um, that I felt like were sort of beneficial”

Partly raw tape D 3 · C 3 · P 2 · Cm 2 2.60

Q All long processes. How quickly do you know if a bet on a person is a bad bet?

A It can really depend, and then there are these moments where, you know, truthfully, like, someone clearly kind of turns it around, and that initial instinct can be wrong. As someone was telling me recently, you know, the first time a CEO feels like, you know, something hasn't worked out, they should act on it. Because, like, if they have that impulse with, like, you know, all of the sort of importance on the line, Um, there's a reason why they're having that impulse, and, um, it's gonna be tough to kind of ultimately resurrect the relationship. I don't, I have not found that to be the case. As we're kind of talking about this, like, and I don't feel like this is a defect. I feel like this is a, um, an absolute strength. I'm an optimist, and I really see qualities in people. And, and sometimes it's a struggle of like, hey, I see this in you. You can do better here. I'm going to keep pushing you because I know you have it in you. But I'm demanding of it, by the way, like, this isn't like for a forever chance, but it's there.

AI assessment note: “It can really depend, and then there are these moments where”

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