Pod Insights The Twenty Minute VC (20VC): Venture Capital | Startup Funding | The Pitch 20VC: The Memo: The $23BN Company You Might Not Have Heard Of: Tradeweb, The Story of 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue and 50% EBITDA Margins About this episode Billy Hult is Chief Executive Officer of Tradeweb Markets (Nasdaq: TW), as Billy puts it, they are the "electronic interface that connects Citadel and Goldman". They are also one of the most under the radar but incredible businesses of the last 20 years. Through no glitz acquisitions or specific moments, TradeWeb has compounded organic growth for the last 27 years to today, with a market cap of $22BN. In Today's Episode with Billy Hult: 1. From Betting Shop Worker to Public Company CEO: How would Billy's teachers and parents have described the young Billy? Why does Billy think it is so important to have a hard first job when growing up? What does Billy know now that he wishes he had known when he started? 2. What it Takes to be a World-Leading CEO: How does Billy define the role of the CEO? What are the core tenets? What has been the single hardest element of CEOship to learn? Does Billy care about being liked? How does that impact his management style? Why does Billy think it is so important for CEOs to make "big bets"? What have been his biggest? 3. Hiring World-Class Teams in 2024: What have been some of Billy's biggest hiring mistakes? What did he learn from them? How does Billy weigh IQ vs EQ and hustle? Which wins? Why? Does Billy think this generation of millennials is too soft? What are the single biggest lessons Billy has on when to delegate vs when to retain control? 4. Money, Power and Family: How does Billy approach his relationship to money today? How has it changed over time? Fame, power or money, rank them from 1-3. How does Billy rank them? How does Billy describe his own style of parenting? How has it changed over time?
Transcript 10,247 words · 3 speakers
Speaker names marked ? are inferred from speaking time and the show’s known hosts — they are not voice-verified.
0:00 Speaker 00 It's not about pedigree, it's not about polishedness, it's not about what school you came from and who you know. It's about old fashioned grit and resiliency and street smarts. I have an ego, you have to have an ego. I'm a person that was, you know, president of my company, the number two person in my company, you know, for a long time. You know, when people show you who they are, like, believe them.
0:21 Harry Stebbings? This is 20 VC The Memo with me, Harry Stebbings. Now, 20 VC The Memo is our monthly show where we highlight an incredible company that you might not have heard of. Today, we highlight the story of a $23 billion juggernaut, Tradeweb, the electronic interface that connects the likes of Citadel to Goldman. Now, joining us in the hot seat today is their CEO, Billy Halt. This is an incredible discussion on CEOship, parenting, relationships to money, ego, and so much more. But before we dive into the show today, Merge is the leading product integration platform, offering a suite of unified APIs across key software categories, from HRIS to CRM. That allows organizations to offer hundreds of customer-facing integrations.
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2:59 Speaker 02 You have now arrived at your destination.
3:02 Harry Stebbings? Billy, I am so excited for this. I heard so many good things from Rana when I was walking with her in the park. I was like, I want to have Billy on the show. Please make the intro. So grateful to her for doing so and thank you for joining me today.
3:12 Speaker 00 Well, thank you for having me. Rana is amazing. I want to tell you, Harry, I think this is maybe like a bucket list thing for me to do with you. Cause I've been watching, you know, your growing kind of YouTube presence and I was hoping to get the invite. And sometimes you get lucky and actually get it.
3:25 Harry Stebbings? I remember when we started, I could actually get away with not doing video. And now I actually have to look presentable, Billy. I mean, this is a tiring life.
3:32 Speaker 00 More than presentable. I think you're ready for the biggest platform available.
3:38 Harry Stebbings? Well, you're very kind. Charm will get you a long way, but I want to go back way, way back, which is, I think we're shaped actually a lot in our childhood. And so if we go back to your early years, how would your parents and teachers have described the young Billy?
3:50 Speaker 00 I do agree with your premise that like, it's amazing how much of you gets formed from like the age of like zero to six or zero to eight. So I think I was like a much more quiet kid. And I think I've become a fairly, you know, boisterous. I'm not a young adult anymore. I think I'm like middle aged now, believe it or not, Harry. But I was a quiet kid. I tended to do very well in school at things that I was interested in and very poorly in things that I was not interested in. So I was like, almost like that prototypical kid that. Flourished when I was engaged on something and then really struggled like capital S struggled. When it was not interesting to me, there's like a story about, you know, the kid that took French
4:30 Speaker 00 from like zero to 11th grade and couldn't learn to speak like three sentences in French. And then he moves to Paris, meets a girl who only speaks French and learns the language in like two months. I was kind of like that. As soon as I was emotionally kind of engaged on a topic, then I would do okay. But I struggled with everything that was sort of like not straightforward to me. I was not like by any stretch, I was no Rana.
4:54 Harry Stebbings? Did you have a hard first job? Someone said to me the other day, 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.
5:06 Speaker 00 I did. I grew up in Manhattan, you know, so there were no lawns to mow. But I'm going to make you laugh with this. It's a good question. Sometimes like the most true stories are entertaining. My first job, and it was like either end of high school or early college, kind of one of those summer jobs, was working hairy at a place they called like OTBs. It was off track betting, a place where people would go in back in the eighties and nineties in Manhattan and place bets on horses. And I was a betting clerk in the South Bronx. 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. It wasn't like an internship at Brown Brothers or Morgan Stanley. A little bit of the school of hard knocks.
5:49 Harry Stebbings? You said about 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 did. Do you think people should lean into their strengths and discard their weaknesses?
6:00 Speaker 00 I think that there's a way maybe to like overdo all of that. And maybe there was a time when I was a kid where I was definitely overdoing it. There's something about like the three C minuses 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 being said, I think especially as you get older, I think there are inherent strengths that you want to kind of lean into. There are things that like you're good at, the things that you gravitate to, but most important. I think there is an aspect of 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.
6:42 Harry Stebbings? Someone said to me the other day, everyone says like, do what you love. I say that's bullshit. Do what you're good at, because what you're good at, you'll generally like. And if you don't, suck it up.
6:51 Speaker 00 I I think that's true. It's a little bit of you can be misleading when it's sort of just follow your passion, Harry. Just do what you love. You know, life can be a little more kind of exacting. And sometimes decisions you make early in your career, early in your life, have like longer term consequences. So you can be sometimes a little naive if you just go down that path. What's the that sort of Hemingway like? Isn't it pretty to think so? Like, wouldn't it be nice if we could all just do like things that we love?
7:18 Harry Stebbings? You're a PM way back, weren't you?
7:21 Speaker 00 I had a couple of jobs in the old kind of traditional world. I was a bond broker and then a sort of sell side bond trader, learning along the way. I was never like, never good at it. I think maybe that's because I didn't like it.
7:31 Harry Stebbings? Did you find being CEO very natural? It is a very different role. Every CEO ship is different.
7:36 Speaker 00 There are aspects of the job that I have found to be natural. And there are aspects of the job that I think I gravitate towards and I enjoy. And then there are kind of things about it that I think maybe aren't like in my perfect sweet spot and are harder.
7:50 Harry Stebbings? What do you think makes a good CEO? Like, what are the core checklist of my job as CEO is this?
7:56 Speaker 00 I'm like, not going to make you laugh with this, but 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. I do constantly remind myself that I'm dealing with people and people have egos. They have opinions, they have personalities. There are ways to 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. 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 say that like 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 think in a good way, I
8:40 Speaker 00 Try to get my kind of sleeves rolled up and my hands around execution. That's where companies ultimately make their bones around like, how good are you at really ultimately executing on a game plan? 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.
9:00 Harry Stebbings? But my, my question to you is, like you said there about 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.
9:13 Speaker 00 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 what is my responsibility, Harry, to like make a difference? You know, how do I become a difference maker player for my team? And so how I try to do it is 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. And so I try to make a difference for my company by putting myself in those situations.
9:57 Speaker 00 Early on, when I became CEO, I was invited nicely. I don't think they regret it now, but I was, it was a very nice invite from them to be a part of the sort of JP Morgan, like CEO conference in Napa. Quite a nice conference and it was a nice invite. These CEOs from like all over the world were there and this won't surprise you at all. I got to watch like Jamie in action as the CEO of JP Morgan. He's there, but like JP's hosting this event for their clients. He's amazing with clients. You talk about a guy that can flip the switch from he's the most well-regarded esteemed person in a lot of ways at that event. He makes it all about his engagement, you know, with JP Morgan's clients.
10:40 Speaker 00 His ego goes away and every single one of his interactions is about like, how are you doing? What's going on in your business? How can we help you better? That was kind of like an interesting. Visual that I got like I'm like if he can be still that good at that, then we all have to up our games a little bit because my goodness, like talk about like a difference maker. You know, that's like a big deal. You know, how many people like walked away from that conference like, yeah, the wine was great. But I got like 30 minutes with Jamie and he like really like understands my business now. Like, that's cool.
11:10 Harry Stebbings? Well, I think it goes back to the Maya Angelou quote. It's not what you say, it's not what you do, it's how you make someone feel.
11:15 Speaker 00 I think that is true. You know, the other thing she says, which I love, we're going to get into like a quote contest. Is like, you know, when people show you who they are, like believe them. And so I've always thought of that, which is like, you know, good and bad. When people reveal themselves to you, it's happening for a reason.
11:31 Harry Stebbings? Okay, help me understand that. Do people not change though? I look at myself, I'm not old, but I've grown up quite a lot in the last 10 years. I did stupid shit. I used to lie when I was nervous. I would be too arrogant because I believed that bullshit. And now I realize that I'm just another person figuring life out. And so I don't know if that's fair.
11:52 Speaker 00 Well, people grow for sure. And I think that's a very kind of intuitive comment that you're making. And I think as you grow, you show people your evolution. And so you don't just believe them once. I think maybe there's this concept of you're believing them all the time, but you're seeing who they are. And so maybe there was a moment where you showed someone one thing about yourself a long time ago. And now you have the ability to show someone something else about yourself. And if they're evolved the right way, they're seeing your growth along the way.
12:19 Harry Stebbings? There's this kind of recurring theme in my management, which is that I very much dictate. There is no voice but mine and people are scared of me. It's not great, actually. I mean, my response is you should be.
12:34 Harry Stebbings? What would you advise me? I don't want to have a culture of fear. How do I not, but also be very direct, set the direction and lead?
12:43 Speaker 00 You don't seem unbelievably scary, but I hear you. Sort of since we're like sharing notes a little bit. I do think the most important thing is like being direct. I think that's really important. Do you sugarcoat? You know, we all have things to work on. Either I sugarcoat or I have a little bit of this like, what's the thing like? Truth with Novocain?
13:00 Harry Stebbings? Yeah.
13:00 Speaker 00 I try to make it feel good sometimes. And that's not always like the most effective way. So we all have things to work on and I gotta think through that. But it sounds to me like that directness that you're describing is really good and really important. As you get older, do you sometimes like become a little bit maybe more mellow?
13:18 Harry Stebbings? No, I become less patient.
13:20 Speaker 00 But you're not as older. Maybe there's some sort of like moment where it flips a little bit. I'm gonna make you laugh with this. I'm, you know, 54.
13:28 Harry Stebbings? Oh, you're not Billy. You look so young.
13:30 Speaker 00 I'm 54 going on 65. I'm probably more intense in certain ways at 54 than I was at 34. I guess I'm nicer now at 54 than I was at 34. I'm a little more like understanding of people, probably try to be.
13:46 Harry Stebbings? Do kids make you nice? Is that it? Do they make you more patient, more understanding?
13:51 Speaker 00 Maybe like being around love when you leave the office in that kind of way. Maybe mellows or kind of softens you. I think you can be pretty nice, but also like pretty exacting and pretty rigorous. And I think you can have very high expectations of people. So I can be nice. I can be a little bit, sometimes not quite as direct as I need to be. Everyone that works for me understands when I'm angry. It's probably a bummer when I'm angry because it maybe takes a little bit to get me angry or get me disappointed.
14:19 Harry Stebbings? Do you care about being liked?
14:20 Speaker 00 Yeah. I can understand how people would perceive it as a weakness. My overall instinct, Harry, is if you're authentic and you're yourself, then that's a lot of it all. Not to say that like no weaknesses can emerge, but you lead with who you are. So I've always probably wanted to be liked. I feel like getting along with people is like, let's start there. I'm not easily pushed around. I mean, I'm gonna make you laugh with this one. I don't always get what I want, but I tend to get what I want a fair amount. So I'm not a pushover. But if someone doesn't like me, does it bother me? Yeah, a little bit.
14:59 Harry Stebbings? When do you dictate versus when do you welcome opinion? This is another challenging one, which is like, no, no, I'm the CEO. We're going this way versus open for thoughts. Let's discuss the right plan together.
15:09 Speaker 00 If I feel like it's a decision that ultimately there's a tremendous amount at stake around, and there's going to be a fall guy on the decision if it doesn't wind up working out, I will make sure to make an obvious point that it's mine because I don't think you can pass the buck on big decisions. That being said, dude, I have a lot of smart people that work with me and I have a lot of really smart, by the way, clients in my world. So I do like to get people's opinions and I do like to hear from the people around me. And my general view is if you can get a consensus, that's better.
15:47 Harry Stebbings? I get you. In venture, consensus often needs to, needs to a bit of a challenge. Yeah, 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?
16:04 Speaker 00 So let me describe it for you this way for a second. So my company, TradeWeb, has largely gotten to where we are today through a lot of like really good organic investments and organic growth, right? So we are not some company that's arrived here through lots of like M and A. 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. And so one of the things I've been doing a little bit is like using the language of change, right? Which is like, we've gotten here and 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
16:49 Speaker 00 one specific way. Let's start talking about 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 start using the language of like real ambition. Like, why not? I sometimes like play golf like too often and for sure, like not well enough. When you take a golf lesson, they'll make a change and that change will feel so awkward because they're trying to get you to feel something. So sometimes you, well, I do this a lot. I will enunciate a point pretty loudly to sort of push us in the direction of change.
17:31 Harry Stebbings? It totally makes sense. I think the biggest thing also with leaders is enunciating change. I always hear people say, oh, I'm so bored of saying the vision and the mission. And it's like, yeah, but for someone, it's the first time that they're hearing it. And you always have to remember that. You mentioned there, like, how do you take bigger bets? How do you be more courageous, more bold?
17:50 Speaker 00 Yeah.
17:50 Harry Stebbings? Super direct, Billy. I think about talent brands a lot. Where do the best software engineers want to go to work?
17:57 Speaker 00 Yeah.
17:57 Harry Stebbings? And with Stripe, with Shopify, with the Silicon Valley names, do the best software engineers want to go to TradeWeb? And how do you think about that?
18:06 Speaker 00 I think the goal is for the answer to be yes. The history of the company is interesting because you don't always have companies that have been private for so long and then go public kind of later in the company's history or evolution. So like the roots of the company is really around being a little bit private. There are advantages to being sleepy. So I'll describe for you an advantage, or maybe we can talk about this. TradeWeb, Harry, has a lot of clients. Goldman Sachs, Morgan Stanley, PIMCO, WAMCO, the central banks, Norges, like all these big like, you know, hedge funds, right? We travel along back and forth between like giant egos. At the end of the day, it's really simple.
18:49 Speaker 00 We're the electronic interface that connects like Citadel and Goldman. We've been pretty smart around understanding like there's a totem pole. There's always been a totem pole. Understand where you sort of live in that totem pole. And we don't always have to be the sort of like biggest ego in the room. We don't always have to have the biggest brand. We can, you know, flourish. And amplify a little bit sometimes behind the scenes and let our clients ultimately at the end of the day have the biggest, most important presence out there. Um, I don't know if we've like always like thought that through like perfectly exactly. I think that's how we evolved in a certain way.
19:29 Harry Stebbings? I think it's fascinating in terms of the strategic positioning of kind of knowing where one sits. And also being the enabler means that you don't always have to be front of house.
19:38 Speaker 00 Dude, one time I was out with a guy, this is like a long time ago. He was a nice guy. He was a little bit of like out of central casting, hard-nosed like Bond guy. And this is like probably like 10 years ago. He was working at Credit Suisse at the time. And we were talking and I kept referring to BlackRock as my client. And he just reminded me in a really nice way. He's like, oh yeah, like they're actually like my client. And I didn't want to get into a debate with him about like who actually was providing more value to BlackRock or who BlackRock was more of the client to. But he was letting me just understand like, hey, look, I'm gonna say this in a nice way. There's no way that relationship with BlackRock is more important to you than it is to me. Human beings are very like interesting, right?
20:20 Speaker 00 Because there's like so quickly almost like, I don't want to say like a competitive dynamic, but people have like egos, dude, like big egos.
20:27 Harry Stebbings? Do you have an ego?
20:28 Speaker 00 Definitely. Yeah. I have an ego. You have to have an ego. I'm a person that was, you know, president of my company, the number two person in my company, you know, for a long time. And I had a great working relationship and a friendship and a partnership with the CEO. And we would talk about it where I would say to him like, this can't be Coldplay where like everyone knows like Chris Martin and like no one else. Like this has to be a band where at least there's two of us.
20:55 Harry Stebbings? Why?
20:56 Speaker 00 Because my ego, I guess my ego was bruised. I was like, oh wait, I don't want to be Mike Pence standing in the back.
21:01 Harry Stebbings? What did he say?
21:02 Speaker 00 He said, I got you. I hear you. And that's why we will co-brand. We'll work on making sure that it's always understood that this is a two-man partnership at the time. That being said, he was the CEO, you know, so there were certain things he would do by definition that I would be the person standing on the sides. And I felt my ego then, like, oh, what would it be like to do? That myself, right? And so, of course.
21:25 Harry Stebbings? How was it when you became Freddie Mercury or Chris Martin?
21:28 Speaker 00 It was comfortable and normal. It felt like a process that had worked. And for me, it felt like a moment in time, maybe 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. It did not feel, honestly, and I think you know very well that I would 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. I've done a lot in my career and I'm ready for like this next chapter.
21:57 Harry Stebbings? Was there ever a time where you had to check yourself on your ego? I remember when I was like 21, made like a certain amount of money and I was like, I am fucking cool.
22:06 Harry Stebbings? And I believed the bullshit too much.
22:08 Speaker 00 Professionally, it has not felt challenging for me to do that. Because I think there's like a little bit of like an easygoingness that I bring to the equation that feels less ego driven. So what I think about is like, how do you make sure that your casualness does not allow a scenario where someone thinks their results are casual? I'm aware of all of that stuff.
22:32 Harry Stebbings? Do you worry about that? You are informal and human and it's wonderful for me.
22:37 Speaker 00 I do because like I'm more driven now than I was when I was building my career, but I don't always show it. I wouldn't say it's like a technique because it's like, it's my personality and it's who I am. I'm comfortable in my own skin and I come across that way. I'm also, again, let's throw this other thing back in the mix. I think like firmly aware of like this totem pole thing, right? When someone takes themselves like so seriously, it's like, come on, guys. Like, let's remember, there are bigger problems in the world. There are bigger problems in the financial service industry. Like, I'm gonna make you laugh when the famous line when, you know, the financial crisis was kind of roaring. And the story was that Lloyd was in a town car headed down to see the Fed.
23:19 Speaker 00 And kind of one of the bankers in the car said to him, like, I don't, I don't know how much more I can take of this. Cause they were stressed. They were working really hard. Everyone was going like a hundred miles an hour. And I think the guy was like, I don't know how much more I can take all this. It's like the pressure is like building. Lloyd said like, come on, like, we're not like storming the beach at Normandy. Right? Like, let's keep this all in perspective. We're all pretty lucky here.
23:41 Harry Stebbings? Do you feel the pressure?
23:42 Speaker 00 I feel the pressure, and maybe this is a little bit of a, of a concept of what you're saying in terms of ego. I sometimes feel the pressure when I go home and I find myself like slightly having a harder time to relax and unwind and be present with my family. And I feel like distracted. And so I'm thinking to myself like, why am I carrying all this stuff home? Maybe because of like how I'm dealing with pressure, maybe how pressure is kind of running through my system. Someone asked me like, do I feel nervous? And I don't feel nervous. Well, you make everyone feel very comfortable. So I wouldn't feel nervous in this situation. Sometimes when I'm doing a part of a board meeting that isn't necessarily out of my central casting sort of comfort zone, I'll feel a little nerves.
24:23 Speaker 00 Like, oh, I'm in 10th grade. I'm going in to take a biology test. You know, have I studied hard enough?
24:28 Harry Stebbings? I do have to ask, on the like, you feel the pressure when you go home? I don't. I feel the guilt because I'm like relatively uninterested by the conversation. And that sounds awful. And if I'm, if anyone from my family listens, I'm sorry, it's true. But my point being like, you spend all day stimulating.
24:45 Speaker 00 Your, your brain's tired.
24:46 Harry Stebbings? Yeah, but then they want to talk about the weather.
24:48 Speaker 00 And I feel that too. It's like, it's a challenge. It's like something's not quite right. If at the end of the day, I haven't figured out a way to keep that engagement thing running. And maybe it's like run out of gas a little bit. I feel that way too, where it's sort of like, how can I be unbelievably aware of the details of these five business issues? But struggle with my, you know, my 12th graders, the name of her history teacher.
25:13 Harry Stebbings? 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.
25:18 Speaker 00 The broad answer is definitely yes. The truthful and the more recent answer is no. I have three kids and my younger daughter, she's a senior in high school and she's got like all these like big basketball games. You know, it's her last basketball games and I missed a bunch of them, you know, because I was working. 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 missing those moments the most, I think.
25:48 Harry Stebbings? Did you really need to be there? Like often we can over amplify the importance of it and it's like, no one will remember those in a year.
25:55 Speaker 00 Good question. I think it's impossible to know the answer of like, was it worth it? If you're asking me today, my answer is like, probably not. But at the time, I must have thought yes.
26:05 Harry Stebbings? Has your style of parenting changed over the years, Billy?
26:08 Speaker 00 No, I think I was always probably a little bit of like the yes dad. I struggled saying no. So it was easy to kind of, you know, surround them with love and to try to be the person that did a lot of fun things with them. And I find myself doing different, obviously versions of that, but being similar along those things. Fifteen years later, that sort of dynamic is kind of still in place.
26:33 Harry Stebbings? How do you inspire children to have the same hunger, ambition, tenacity when they're brought up in a wealthy family, bluntly? You know, you went to a betting shop in the Bronx. Like, they don't need to. But how do you encourage them to be really ambitious?
26:50 Speaker 00 Super hard. I would say that like from a parenting perspective, that's like the number one thing on my mind. 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 spoiled and being unmotivated. I learned a long time ago, a little bit of a lesson, which is like other people's successes like aren't your success. I've also learned a lot around the concept of like, I'll make you laugh with this one. The beer's not as cold when it's like not yours. So there's a really nice feeling to go into like your house
27:30 Speaker 00 with your cold beer in your house and having a sip of that and knowing like, hey, like I earned that. I go out of my way in the best possible way as a father, just to reiterate those kinds of things with my kids. But yeah, they live a different life than I did. Yeah.
27:46 Harry Stebbings? I often ask myself, I often ask myself, would I work as hard if I've been brought up in different situations? And the honest answer is, I don't fucking know.
27:52 Speaker 00 You can't, right? It's like hard to know. Like, what's that little like extra motivational thing? I went to schools, I grew up pretty, you know, Manhattan, like, middle class. I went to schools with like a bunch of friends, much more wealthy than I was as a kid. I was motivated, not necessarily by like money or status or all that stuff, but I was for sure motivated to prove myself. And that, as you know very well, that can be like a super strong blessing.
28:23 Harry Stebbings? Money, fame, power. How do you rank the three in what's important to you?
28:28 Speaker 00 Fame, distant third. It would be really easy to say like money first, power second. I think power is like pretty interesting. So I think if you dismiss power, so obviously, maybe you're not quite being super true or super assessing like how you really feel. I've always thought like a little bit of like prospering below the radar is not a terrible place to be. You know, you're gonna blow up my Instagram account with this one. So I'm gonna become less, less below the radar at some point. But like, I think like prospering below the radar is cool.
28:55 Harry Stebbings? One thing I often think about is like, do richer leaders make better leaders? And the reason I say that is because you remove downside fear. You can be more courageous when downside is relatively removed. And you don't need to constantly be fearful, like one is if they are not financially independent or free. Do you think richer leaders make better leaders?
29:13 Speaker 00 Not, not a hundred percent positive. It's a good way to think about it. I would say there's certainly examples where that seems to be true, right? If you think about like a lot of these private equity founders or hedge fund founders who are extraordinarily wealthy, who have become wise, I think really important kind of traits. I think that the opposite way to think about it would be like by not having as much at stake, do they lose some credibility? It doesn't seem like it.
29:41 Harry Stebbings? The best are like machines. They're just animals and the money is just like a scoreboard. And it's just a way to show that you win.
29:48 Speaker 00 You know this really well, Harry Blackstone, at one point was a majority shareholder in my company. And there was a moment in time before the company went. Public, I went to very casually, meeting Steve Schwarzman in a casual kind of setting. You know, speaking of like, you're almost describing him perfectly. And it was very quick to say he would never remember it is a understatement. But he grabbed me a little bit by the arm and he said, like, very aware that the Blackstone role in the company and the fact that my company was going public. And he said, as a sort of wise man, like, it's nice to win, enjoy it. And I felt that when he said it, I was like, well, this guy knows like winning.
30:27 Speaker 00 And if he's telling me like to not lose sight of that moment where you've worked really hard for something and it's happening or it's coming true, I'm gonna remember this moment for sure, knowing he's not. But I'm gonna remember this moment because like, he knows. And so maybe in that model that you're describing, like, those guys like know, like what it takes. You might as well listen.
30:51 Harry Stebbings? Do you like being public company, honestly? And I have so many friends who are public company CEOs now.
30:56 Speaker 00 Yeah.
30:56 Harry Stebbings? And I'm like, do you like it? And they're like, no, I hate it. I wish.
30:59 Speaker 00 Yeah. I mean, when you said honestly, like, you're kind of leading the witness. Anyone would say there are things about it not to like.
31:07 Harry Stebbings? Like what?
31:07 Speaker 00 You wind up spending a lot of your time on corporate governance, regulation, things that you feel like are occupying more of your time than you wish they could. And almost everyone feels that way a little bit, like burdened by the structure of it. That being said, genuinely, there's like a lot of things to also like about it. Are you and I doing this today if we weren't public? Maybe not. So there's a profile thing that works. This is gonna make you laugh because I told you I was like a pretty poor student in a lot of different ways. There's like that report card thing around like, how is your company like ultimately performing in the bright lights of a stock price?
31:46 Harry Stebbings? Do you check that daily?
31:47 Speaker 00 Yeah.
31:48 Harry Stebbings? Okay, I tie my mental happiness and my mental state to the performance of my company.
31:52 Speaker 00 Yeah.
31:53 Harry Stebbings? Kind of harder for me because there's no ticker. How do you not get depressed when your ticker's down? And how do you detach from the performance of the company?
32:01 Speaker 00 It's hard. Is it down because the market's getting repriced around?
32:06 Speaker 00 An extra genius event, 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 kilter your reaction differently. We've been lucky because we've performed really well, 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, you know, a negative reaction to your business and you're human.
32:33 Harry Stebbings? Can I ask you, what's been the biggest bet that you've made as CEO? That's worked out and what did you learn from that?
32:40 Speaker 00 There's a part of me that wishes like I had, it's a really good question, like a super almost like dramatic kind of response to that. We've done a couple of important deals that have been not big bets, but they've been smaller bets that are moving us in the direction of kind of what you and I are talking about in terms of like the big bets.
33:01 Harry Stebbings? I really like this in you. If there's not a big bet that comes to mind straight away respectfully, and I'm so pushing. Do you think you've been courageous enough as CEO making big bets?
33:12 Speaker 00 I placed big bets on people in my tenure as CEO and I'm not kind of like sugarcoat the answer. Like I really have.
33:19 Harry Stebbings? What does that mean? You bet on people who don't have the qualifications and the experience, but you believe?
33:23 Speaker 00 I have taken what I would describe to you as like honestly, like risks in sort of relationships that I felt like were beneficial to both me and the company. And I've, I think benefited from having very strong intuition about people.
33:39 Harry Stebbings? If you would put a number on it, what percent of your bets on people prove outright?
33:44 Speaker 00 Shockingly, not as high as you would think.
33:47 Harry Stebbings? You can put a number on it for me after this, but there's a trope that basically 50% of the.
33:51 Speaker 00 Yeah, I was gonna say 50, like the concept of being able to have like intuition. All of those things should be like bright lights pointing towards like 75% or like, like a hundred percent, like everyone, but like the answer is no.
34:06 Harry Stebbings? But in the 50% that don't, are there commonalities in why it doesn't work out?
34:10 Speaker 00 Maybe chemistry, 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 wanna 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 kinda like, can you get unstuck? You know, can you find another kinda run at this whole thing? You know, and I've had to like assess like a little bit of of the very first things that you and I were talking about. And this is turning into like an amazing therapist session, which is have I been clear enough? Have I been direct enough? Have I given enough kinda feedback along the way? Most of the time, the answer is yes. And I don't put a lot of blame for myself when something doesn't work out.
34:54 Speaker 00 But as you know really well, like, there's always like a co-created dynamic. And and when you're CEO and you place a bet on someone and it doesn't work, you know, you're bummed.
35:02 Harry Stebbings? Oh, yeah. And then there's time delays and there's lags. And then you have to go through the process of getting rid of them. And then the process of finding someone new and then onboarding is three steps, getting rid.
35:12 Speaker 00 All painful, all bad outcomes.
35:15 Harry Stebbings? All all long processes. How quickly do you know if a bet on a person is a bad bet?
35:21 Speaker 00 It can really depend. And then there are these moments where truthfully, like, someone clearly turns it around. And that initial instinct can be wrong. If 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 all of this sort of importance on the line, um, there's a reason why they're having that impulse. And it's gonna be tough to ultimately resurrect the relationship. I have not found that to be the case. 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 sometimes it's a struggle of like, hey, I see this in you. You can do better here.
36:06 Speaker 00 I'm gonna 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.
36:16 Harry Stebbings? I'm gonna get in trouble for this one. But I you said like pushing you and demanding. I am the same, but I think that the younger generation, which I am in, are entitled and do not wanna work as hard and wanna prioritize balance and life. And I think it's very challenging to have the same work environment that you had in the eighties.
36:36 Speaker 00 Yeah.
36:36 Harry Stebbings? Which was fucking grind.
36:37 Speaker 00 Yeah. Yeah, like people like smoking on desks.
36:41 Harry Stebbings? Yeah, and people used to pull all nighters in banks.
36:44 Speaker 00 Yeah, yeah, it was a tough culture. There's like no doubt about that.
36:48 Harry Stebbings? But it but it was actually an efficient culture in many ways in terms of output. Do you worry that this generation is too soft?
36:54 Speaker 00 Some of that stuff got played out a lot around, as you know really well, like around COVID and work from home. And there felt like there was like, if not a power struggle, there felt like there was this like tension in the system about like, what's really gonna work here? And I don't want to sound like, you know, the old guy on the chair on a lawn kind of thing. Like, you know, making pronouncements about like what the kids are like these days. But sometimes there's so much benefit that you get from hustle and grit and perseverance. There just is.
37:28 Harry Stebbings? I agree. I fucking emailed Benial 53 times with a separate email for every week for a year and a week.
37:35 Speaker 00 Yeah. Is that switch permanently turned on all the time? I will say this, and tell me what you think about this, like the kids that have it like switched on, like, wow, do they have like a lot of like trajectory in front of them?
37:49 Harry Stebbings? Oh, 100%. But I also find with the ones that have it switched on, they show early signs of exceptionalism. It's why whether I'm hiring you or I'm investing in you, I will always go back to your early childhood. No great person who was hugely ambitious fell out of McKinsey and Bain and thought, oh, now I'm gonna be really ambitious and courageous.
38:07 Speaker 00 It's a process along the way. Some of that process can be about positive momentum. So I know people who have only been successful and they will only be successful. And they were successful when they were in sixth grade. They were successful when they were sophomores in high school. They went to Harvard. They went to Harvard Business School and they've been exceptionally successful, straight out of Central Casting in their professional careers. All of that is like positive momentum that has just built over time.
38:37 Harry Stebbings? I would never hire them or invest in them. Those guys are the ones that break the minute something breaks. They never ever have experienced being bullied, being the fat kid in the corner with no friends.
38:49 Speaker 00 Yeah, the sort of like Tom Brady theory of like, I'm gonna use every slight that's ever existed to continually motivate myself and create this kind of resilience thing. There's like no doubt that's the sort of like the two types. I don't know. So you and I were like joking about the kind of EQ thing and like the sort of like self-awareness and all of that stuff. I sometimes gravitate towards people like who aren't like me at all. And when I say that to make you laugh, like the out of central casting, like the smartest people like in the room. I've always been the smartest. I will always be the smartest. And that switch, that cognitive switch is just like turned on. I see the benefits of just like straightforward, like wow, like a really smart person.
39:34 Harry Stebbings? No, I didn't like them too small. Very bad, very bad trait.
39:37 Speaker 00 There's a, there's a decent chance that you're a very smart guy. For me, it's easy.
39:41 Harry Stebbings? There's a decent chance that I'm a charmer and I'm a stylist. But no, I, okay, I would rather unwavering hustle than I would unwavering.
39:48 Speaker 00 Yes. Well, listen, you know, you get both and then you're really on to something. Let's be honest, right? You get both. I've been with you on the side of like hustle and resiliency. And really what we're talking about are like offset skills.
40:02 Harry Stebbings? The hardest thing, the thing that I'm, I've made mistakes on now, which is I used to hire the pedigreed person and that was the wrong hire. And then I went binary and I would suddenly go to the really inexperienced, really hungry, ambitious, and that didn't work either. It was just inexperienced and immature.
40:21 Speaker 00 You know what's interesting? Like in my world, Harry, and you'll, you're going to appreciate this. To make an obvious point and I'll mangle this for you. There were a ton of really bad consequences to affirm like Bear Stearns going through like the struggles that Bear Stearns went through. One of those is that when I grew up, like in the bond trading world where Bear Stearns had like tremendous levels of respect and really talented people and they like lived.
40:48 Speaker 00 In that ethos of what you're describing, like it's not about pedigree, it's not about polishedness, it's not about what school you came from and who you know, it's about old fashioned grit and resiliency and street smarts and that entire firm for a lot of years, and even when that firm was like extremely successful for a lot of years, kind of lived by that code, to see that code kind of die by the sword a little bit hurt because it was kind of cool to kind of feel that culture in the world.
41:20 Harry Stebbings? My question to you is like, hearing you there speaking about Bear Stearns, and final one before a quick fire, a lot of younger people look at where we are today and feel very worried about the state of the economy, the state of the world. You've seen some real, oh shit, man. How does this compare? How did it feel when Bear Stearns went through its troubles, Lehman's went through its troubles, 2008 happened?
41:44 Speaker 00 You know, my company was on the 51st floor of the North Tower. I was in the building on 9/11 that day. So when I think about like trauma, you know, it starts with kind of 9/11. And then I think about like the sort of like professional trauma around the crisis. I mean, that was some pretty scary stuff. Is there going to be cash at the ATM at Citibank? You know, there was this like just like massive unwind and it can feel like that never happened, but it did. And so for like a company like TradeWeb, we saw like our clients like, you know, with this like amazing business model and then saw our clients going down one by one, you know, and Ted Pick as CEO at Morgan Stanley, he's talked about it. There was a moment where Morgan Stanley felt like next in line,
42:26 Speaker 00 like super shaky, right? Like where can this thing go? And then cut more recently, even a year ago, like the shocks to the system around the regional banks and all of that, you realize you're living in this like fragile place, you know, and I didn't even mention obviously with the pandemic, the world feels like obviously like scary right now.
42:46 Harry Stebbings? But does this feel better than it did then in 2008, in 2000 with the dot com?
42:52 Speaker 00 The markets feel better and more resilient and in an obvious way in better Shape. There's a playbook in place around preserving the structure and the and the high functioning ness of the market in a way that should people should feel in a good way 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 an 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.
43:30 Harry Stebbings? Does geopolitics impact your business?
43:32 Speaker 00 Yeah, just from the standpoint of like volatility in the marketplace. We've gotten much stronger in the EM regions. And so we've gone through periods of time where we've planted flags in terms of like how we've wanted to build business in like China markets and things like that. So there's always like a little bit of like a real world impact to what we do.
43:51 Harry Stebbings? I mean, I think people forget seven of the major nations are having political election year. But listen, I could talk to you all day, but I want to do a quick final.
43:58 Speaker 00 Yeah.
43:58 Harry Stebbings? What have you changed your mind on in the last 12 months most?
44:03 Speaker 00 I have changed my mind on Trump being electable. 12 months ago, I did not think the Republican Party would get behind him, and I didn't think he could win the election.
44:12 Harry Stebbings? And now you think he will?
44:13 Speaker 00 I think he will. And I it starts with he can, but I think it ends with he will.
44:17 Harry Stebbings? Is it that bad if he does?
44:19 Speaker 00 I mean, I think it's bad for like my nervous system.
44:22 Harry Stebbings? But like, he was right about China. He was right about a lot of the economy.
44:26 Speaker 00 You know, you and I can talk about like, what do you was right about and wrong about, you know, he brings so much negative energy into the into all the situations, but we can probably have a thoughtful conversation about like things that he got right. I mean, I think we're allowed to do that.
44:41 Harry Stebbings? Is New York City still a capital of the world?
44:43 Speaker 00 Yeah, you talk about resiliency, you talk about grit, you talk about all of those qualities that make someone awesome. New York City has like all that stuff like times a million.
44:54 Harry Stebbings? What's the best book on financial markets and why?
44:57 Speaker 00 The best book on financial markets is going to surprise you. Reread all of the financial part of Sherman McCoy in Bonfire of the Vanities. The way
45:08 Speaker 00 Tom Wolfe is able to get inside, you know, a trading firm that was modeled after Solomon Brothers is incredible. Like the language that he describes, like transactions and the cadence of the markets off the charts.
45:22 Harry Stebbings? What do you know now that you wish you'd known when you started as CEO? You can call yourself the night before your first day as CEO and say, ah, Billy, you should know this.
45:31 Speaker 00 Create boundaries quickly. So don't always entertain every new relationship, which can be a concept of like a banking relationship. It can be an external relationship with a client, like preserve your time in a very structured way. Because time is one of the most valuable things that you have.
45:52 Harry Stebbings? That's a good one. So many people say to me, I wish I wasn't as nervous and I wish I'd known that it would all be okay. And I think it's the most bullshit one because the fact that you worry that it won't be okay means you work harder. You put in more hours. If you would always know that it's okay, I probably wouldn't have worked.
46:07 Speaker 00 Yeah.
46:08 Harry Stebbings? Fine. You can have dinner with anyone, dead or alive. Who do you have dinner with and why?
46:12 Speaker 00 My father passed away when I was younger, so I would definitely always pick him.
46:16 Harry Stebbings? How old were you when he passed away?
46:18 Speaker 00 I was 26. So if I could pick him, like have a fun sushi dinner with him, I think I would probably pick him. That'd be fun.
46:24 Harry Stebbings? Does it upset you that he doesn't see your success?
46:27 Speaker 00 I, I don't think about it like constantly, but the answer has to be kind of like deep down, you know, yes. And so you live with like a bunch of regrets sometimes and that has to be one of them because, you know, you feel that, but you also regret that he didn't get a chance to spend time as a grandfather. That's the part of life that gets tough.
46:45 Harry Stebbings? Penultimate one. What are you most excited about or optimistic about today? We just spoke about geopolitics and global conflict and the challenges. What are you most excited or optimistic about?
46:55 Speaker 00 I'll kind of answer this one like a little bit like personally, like I'm really optimistic and excited, both about where I feel like this company is going to go. Not to be like narcissistic, but to be honest, you know, my own personal kind of evolution and growth and how I feel like I can continue to lead and run this company. I'm very, very enthused and I think this comes through to you and excited about the opportunities in front of the company and myself personally.
47:23 Harry Stebbings? Okay, there'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?
47:36 Speaker 00 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 new directions, some of which 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 a forward march for us. So we're going to be bigger, stronger and a better company. Complacency is the killer of the whole thing. Getting the things that matter wrong is the killer. You stop placing like idea generation at the top. You start putting like office politics ahead of that. You lose sight of like who the customer is. Bad traits.
48:18 Speaker 00 I'm very determined and I'm going to work my best to make sure like those things don't enter our world, but those are the killers.
48:24 Harry Stebbings? Billy, I've so enjoyed this. I know it turned into a bit of a therapy session, which I love.
48:29 Speaker 00 For me, for sure. You're going to send me a bill.
48:31 Harry Stebbings? No, I'm not actually. I greatly appreciate the flexibility. This is why schedules are shit. Thank you so much for being so brilliant.
48:38 Speaker 00 My pleasure and thanks to Rana and thanks to you. This was great.
48:42 Harry Stebbings? I so enjoyed doing that show with Billy. I love it when you have a meandering discussion and you have the schedule, but it goes off into the directions of relationships to money, ego, identity, parenting. If you want to see the full video, you can check it out on YouTube by searching for 20vc. But before we leave you today, Merge is the leading product integration platform, offering a suite of unified APIs across key software categories from HRIS to CRM. That allows organizations to offer hundreds of customer-facing integrations. Merge also handles the full integration lifecycle, from an easy initial build to handheld end-user onboarding, to maintenance support and management tooling for all your integrations.
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Previous 20VC: a16z's Chris Dixon on Who Will Win the Next Generation of Venture, The Two Ways to Make Great Venture Investments and Find the Best Entrepreneurs & Why AI Will Strengthen the Position of the Incumbents Moving Forward Next 20VC: Founders Fund's Trae Stephens on Why The Most Competitive Deals are the Worst, Why No Company is Successful Because of their VC, Why We are Making ZIRP Mistakes Again Today, Why Loss Ratio is BS and Upside Maximisation is Everything Page updated September 29, 2026 · transcript and summary are machine-generated
