Skip to content
The Twenty Minute VCThe Twenty Minute VC

Billy Hult: 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue|E1134

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. ----------------------------------------------- Timestamps: (0:00) Intro (01:03) Billy’s Career Journey (06:22) The Path to CEO (12:30) Leadership and Management Insights (20:15) Cultivating a Talent Brand (23:53) Strategy in Positioning and Branding (31:35) Work-Life Harmony (34:09) Parenting with Ambition (37:37) Valuing Money, Fame, and Power (38:28) Wealth’s Influence on Leadership (41:19) Public Company Pros and Cons (42:49) Stock Performance and Well-being (43:54) Betting on People as a Leader (49:53) Young Generation Work Ethic (54:28) Balancing Hiring Strategies (56:12) Financial Market Challenges (Assigned to Luca) (59:23) Quick-Fire Questions ----------------------------------------------- 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? ----------------------------------------------- Subscribe on Spotify: https://open.spotify.com/show/3j2KMcZTtgTNBKwtZBMHvl?si=85bc9196860e4466 Subscribe on Apple Podcasts: https://podcasts.apple.com/us/podcast/the-twenty-minute-vc-20vc-venture-capital-startup/id958230465 Follow Harry Stebbings on Twitter: https://twitter.com/HarryStebbings Follow Tradeweb on Twitter: https://twitter.com/Tradeweb Follow 20VC on Instagram: https://www.instagram.com/20vchq Follow 20VC on TikTok: https://www.tiktok.com/@20vc_tok Visit our Website: https://www.20vc.com Subscribe to our Newsletter: https://www.thetwentyminutevc.com/contact ----------------------------------------------- #20vc #harrystebbings #billyhult #tradeweb #ceo #venturecapital #businesstips #investing #businessstrategy

Billy HultguestHarry Stebbingshost
Mar 29, 20241h 5mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:001:03

    Intro

    1. BH

      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 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.

    2. HS

      (instrumental music) 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 wanna have Billy on the show. Please make the intro." So grateful to her for doing so.

    3. BH

      Yeah.

    4. HS

      And thank you for joining me today.

    5. BH

      Well, thank you for having me. Rana is amazing. I wanna tell you, Harry, I think this is, like, like, maybe, like, a bucket list thing for me to do with you. 'Cause I've been watching, you know, your growing kinda YouTube presence, and, um, I was hoping to get the invite. And sometimes you get lucky and actually get it.

    6. HS

      Do you know, I remember-

    7. BH

      So thanks to you and Rana.

    8. HS

      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-

    9. BH

      Well-

    10. HS

      ... tiring life.

    11. BH

      ... mo- more than presentable.

    12. HS

      (sighs) Yes.

    13. BH

      I think you're ready for, um, you know, the bigger, th- the biggest platform available.

  2. 1:036:22

    Billy’s Career Journey

    1. BH

    2. HS

      Well, you're very kind.

    3. BH

      (laughs)

    4. HS

      Charm will get you a long way. But I wanna 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, and what would their description be?

    5. BH

      I, I, I do agree with your premise that, like, it's amazing, you know, how, how much of you gets formed from, like, the age of, like, zero to six or zero to eight. If you had known me then, I think maybe there are parts of me that would, um, you know, not surprise you and maybe some parts that would surprise you. So I think I was, like, a much more quiet kid, um, and I think I've become a, a fairly, um, you know, boisterous, um... I'm not a young adult anymore. I think I'm, like, middle-aged now-

    6. HS

      (laughs)

    7. BH

      ... believe it or not, Harry. Um, but I was a quiet kid. And what I would say maybe, um, in a more interesting way, um, 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, um, 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 from, like, zero, you know, to eleventh 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.

    8. HS

      (laughs)

    9. BH

      You know? As soon as I was emotionally kind of engaged on a topic, then I would do okay. But I struggled with everything that was, um, sort of, like, not straightforward to me. I was not, like, by any stretch. I was no Rana. I was, I was no, um, you know, no straight A student by any stretch.

    10. HS

      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, uh, doing lawn mowing when you were seven all day or, like, doing paper rounds. Did you have that hard though?

    11. BH

      I did. I mean, I, you know, I grew up in Manhattan, like, like, you know, so there were no lawns to mow.

    12. HS

      (laughs)

    13. BH

      Um, but I'm gonna make you laugh with this, 'cause, 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 kinda early college, kinda 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 '80s and '90s 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, 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 Brother- Brown Brothers or Morgan Stanley.

    14. HS

      (laughs)

    15. BH

      It was the school of (laughs) , the school of, a little bit of the school of hard knocks.

    16. HS

      You said about kind of earlier that you're... you 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.

    17. BH

      Yeah.

    18. HS

      Do you think people should lean into their strengths and discard their weaknesses?

    19. BH

      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 As 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 s- you know, inherent strengths that you wanna kinda 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.

    20. HS

      I love it. Someone said to me the other day, "Everyone says, like, do what you love." I say that's bullshit. They say-

    21. BH

      Yeah.

    22. HS

      ... uh, do what you're good at, because what you're good at, you'll generally like.

    23. BH

      Uh, that-

    24. HS

      And if you don't, suck it up. (laughs)

    25. BH

      I, I think that's true. It's a little bit of you can, you can be misleading when it's sort of, like, you know, "Just follow your passion, Harry. Just do what you love." You know, life can be a little more kind of exacting. And sometimes, you know, decisions you make early in your career or early in your life have, like, longer term consequences. So you can be... sometimes I think you can be 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?

    26. HS

      (laughs)

    27. BH

      Like, wouldn't it be nice if we could all just do, like, things that we love?

    28. HS

      You were P-

    29. BH

      (laughs)

    30. HS

      You were, you were PM way back, weren't you?

  3. 6:2212:30

    The Path to CEO

    1. BH

    2. HS

      Did you find being CEO very natural? It is a very different role. Every CEO-ship is different.

    3. BH

      There are aspects of the job that I have found to be natural, and there are aspects of the job, um, that I think I gravitate towards and I enjoy, um, and then there are kinda things about it that I think maybe aren't, like, in my perfect sweet spot and are harder.

    4. HS

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

    5. BH

      Um, 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 kinda 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 dem- demotivate people. So, I do think there's a concept of, like, re- 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 kinda 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, uh, passivity.

    6. HS

      Oh, on that note, uh, you see, I write on my hands. (laughs)

    7. BH

      Yeah, I saw that. I noticed that.

    8. HS

      Yeah, yeah. Y- you see, like, it looks really-

    9. BH

      Yeah, it's very-

    10. HS

      ... pro, yeah, yeah.

    11. BH

      You don't need a, you don't need a, um, a piece of paper. What would that be for?

    12. HS

      Uh, sod, sod that.

    13. BH

      (laughs)

    14. HS

      Let's, uh, but, but my, my question to you is, like, you said there about, kind of, you don't wanna be too far removed. We often hear the statement, "Hire great people and get out the way."

    15. BH

      Yeah.

    16. HS

      How do you think about that, and then micromanagement and the balance between the two?

    17. BH

      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, um, 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 JPMorgan, 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 JPMorgan, he's there, but, like, JP's hosting, you know, this event for their clients. Um, he's amazing with clients. Like, you talk about a guy that can kinda flip the switch from, you know, he's the most well-regarded, esteemed person in a lot of ways at that event, he makes it all about his engagement with, you know, with JPMorgan's clients. 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 kinda 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 kinda cool.

    18. HS

      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."

    19. BH

      Yeah. I think that is true. Um, you know, the other thing she says, by the way, like, which I love, we're gonna get into, like, a quote contest-

    20. HS

      (laughs)

    21. BH

      ... is like, is like, you know, "When people show you who they are, like, believe them," right? And so, I've always kinda thought of that, which is like, you know, good and bad. When people reveal themselves to you, like, it's happening for a reason.

    22. HS

      Okay. Help me understand that. Do people not change, though? I look at myself and, you know, now, I'm, I'm not old, but I, you know, 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, you know, another person figuring life out. And so, I don't know if that's fair. Do you know what I mean?

    23. BH

      Well, people grow, for sure, and I think that's a very kind of, um, sort of, uh, 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 believing them all the time, but you're seeing who they are, sort of, right? And so maybe there was a moment where you showed some- 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 kind of evolved the right way, you know, they're seeing your growth along the way.

  4. 12:3020:15

    Leadership and Management Insights

    1. BH

    2. HS

      Can I ask you a question? (laughs) I mean, you know, when we, we were chatting before and you were like, you know, preparing for the show and the schedule, 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. Um, it's not great actually.

    3. BH

      (laughs)

    4. HS

      I mean, my response is, "You should be." (laughs)

    5. BH

      Yeah, yeah, yeah.

    6. HS

      Uh, but, but, uh, what would you advise me? I don't wanna have a culture of fear. How do I not, but also be very direct, set the direction, and, and lead?

    7. BH

      Um, you don't s- you don't s- seem unbelievably scary, but I, but I hear you.

    8. HS

      Okay.

    9. BH

      Um, I think the most important thing is, 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. So if you're, if you're-

    10. HS

      Do you sugarcoat?

    11. BH

      If... I sugarcoat? It's like, if I could tell you, like, you know, we all have things to work on. I... Either I sugarcoat or I have a little bit of this like, what's the thing? Like, you know, truth with Novocaine.

    12. HS

      Yeah.

    13. BH

      You know, I, I, I make it, I try to make it feel good-

    14. HS

      Mm-hmm.

    15. BH

      ... sometimes. Um, and that's not always like, like, sort of like the most effective way, so we all have things to work on, and I gotta think through that. But like, it sounds to me like, that directness that you're describing, um, is really, really good and really important. I think... I don't know. Like, as you get older, do you sometimes like, sort of become a little bit maybe more mellow? And do you become-

    16. HS

      No, I become, I become less patient.

    17. BH

      But you're not, but you're not as older. You know, may- maybe there's some sort of like moment where it flips a little bit. You know, I, I'm gonna make you laugh with this. I'm, I'm, you know, 54.

    18. HS

      Oh, you're not, Billy. You look so young.

    19. BH

      Yeah, I know. Uh, I'm, I'm 54 going on 65.

    20. HS

      (laughs)

    21. BH

      Um, I'm probably more intense in certain ways at 54 than I was at 34.

    22. HS

      Mm-hmm.

    23. BH

      Um, but I'm probably... I don't know, may- 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.

    24. HS

      The kids make you nicer. Is that it? Do they make you more patient, more understanding? Uh, why do you think you get nicer and nicer?

    25. BH

      Yeah, maybe the, may- maybe, maybe, maybe like being around love, sort of when you leave the office in that kinda way, maybe mellows or kinda 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 un- unfortunately like sometimes not quite as direct as I need to be. Everyone that works for me understands when, when I'm, when I'm angry. You know? I, I'm probably a b- it's probably a bummer when I'm angry, you know? 'Cause it maybe takes a little bit (laughs) to get me angry or get me disappointed.

    26. HS

      Do you care about-

    27. BH

      That's a word.

    28. HS

      Do you care about being liked?

    29. BH

      Yeah.

    30. HS

      Hmm.

  5. 20:1523:53

    Cultivating a Talent Brand

    1. BH

    2. HS

      It totally makes sense. I think the biggest thing also with leaders is an- 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. Uh, you mentioned that, like, you know, how do you take bigger bets? How do you be more courageous, more bold? Super direct, Billy, um, I think about talent brands a lot, whether the best software engineers wanna go to work. And with Stripe, with Shopify, with the Silicon Valley names, do the best software engineers wanna go to Tradeweb? And how do you think about that?

    3. BH

      Yeah, so I think, you k- you're being, uh, you're being, like, uh, like, like polite maybe a little bit. Are you kinda saying, like, we're, like, a little too sleepy, a little too below the radar? Like, um-

    4. HS

      I, I'm saying like how do you progress-

    5. BH

      ... how do we up the, how do we up the game kind of? Like, how do we-

    6. HS

      How do you get there?

    7. BH

      ... how do we get more of that recognition stuff? So-

    8. HS

      Yeah. What

    9. NA

      Yeah.

    10. HS

      Are you an incumbent?

    11. BH

      Yeah, I mean, look, I think the goal is for the answer to be yes. Is it yes? Like, we, you know, um, we have some work to do on sort of continuing to increase the, the brand and the exposure of the company, and that might, that might, um, sort of play into effect in the way that you described around, like, recruiting, not just with technologists, but, like, with business people too. Um, I think we've come a long way in, in, in certain ways. Like, the history of the company is kinda interesting 'cause you don't always have companies that have been private for so long and then go public kinda 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, um, to being sleepy sometimes. So, so, so I'll describe for you an advantage, or maybe we can talk about this.

    12. HS

      Sure.

    13. BH

      Tradeweb, Harry, has a lotta clients, right? Goldman Sachs, like, you know, Morgan Stanley, PIMCO, WAMCO, um, GSAM, the central banks, like, you know, Norges, like all these big, like, you know, hedge funds, right? We sort of, like, travel along back and forth between, like, giant egos, you know? At the end of the day, it's, uh, really simple, like, we're the, you know, we're the, we're the electronic interface that connects, like, Citadel and Goldman, and so 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, like, 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, you know, the biggest brand. We can kind of, 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 kinda 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 sort of evolved in a certain way. To your point, as a, as a public company, I think, like, increasing brand is important. That's wh- that's, like, not the only reason why I'm doing this, but like, a- a- as you can tell, it's a concerted effort on our part to, like, increase, you know, exposure. Um, I think the more people learn about and understand and hear about our company, the better off we are. We have a good story

  6. 23:5331:35

    Strategy in Positioning and Branding

    1. BH

      to tell.

    2. HS

      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.

    3. BH

      You know, um, dude, one time I was out with a guy, this is like a long time ago, with, uh... He was a, he was a nice guy. He was a little bit of, like, out of central casting, um, sort of, uh-... you know, hard-nosed, like, bond guy, you know. Um, at- and this is, like, probably, like, 10 years ago. And he was at, uh, he was working at, at Credit Suisse at the time, and we were talking, and I kept referring to, you know, BlackRock, you know, 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, sort of," right? And, and I didn't wanna get into a debate with him about, like, who, 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, you know, 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? Because there's, like, so quickly almost, like, I don't wanna say, like, a competitive dynamic, but people have, like, egos, dude. Like, big egos.

    4. HS

      Do, do you have an ego?

    5. BH

      You have t- I mean, I have an ego, you have to have an ego. And I would, you know, I'm an, I'm a, um, 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. Great working relationship and a friendship and a partnership with the CEO, you know. And we would talk about it, where I would say to him, like, you know, "This can't be Coldplay, where, like, you know, everyone knows, like, Chris Martin and, like, no one else." Like, "This has to be, you know, a, a band where, uh, you know, at least there's two of us-"

    6. HS

      Why?

    7. BH

      "... that we know."

    8. HS

      Why, why is that?

    9. BH

      Because of my ego. I w- I guess my ego was bruised.

    10. HS

      Ooh.

    11. BH

      You know, I was like, "Oh, wait, I don't wanna be, you know, Mike Pence, like, standing in fr- you know, standing in the back, you know?" (laughs)

    12. HS

      W- what did h- what did he say?

    13. BH

      He said, "I got you. I hear you." You know? "And that's why we will kind of, um," you know, you know, co-brand. "We'll work on making sure that it's always understood that this is a, you know, a really, you know, a two-man partnership at the time." That being said, he was the bo- you know, he was the CEO, you know, so there were certain things he would do by definition that I would be, you know, the person kinda standing, you know, on the sides. And I felt my ego then, like, "Oh ... what would, what would it be like to do that myself," kind of, right? And so, of course.

    14. HS

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

    15. BH

      It was comfortable, and normal, and it felt, um, it felt, um, sort of like a, like, um, a process that had kinda 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 you, and y- I think you know very well that I would kinda tell you if it was true, it did not feel, like, laden with, like, anxiety.

    16. HS

      Huh. (laughs)

    17. BH

      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."

    18. HS

      Was there ever a time when you had to check yourself on your ego? I remember when I was, like, 21, and I made, you know, made a, a certain amount of money and I was like, "I am fucking cool." (laughs)

    19. BH

      (laughs)

    20. HS

      And, and I believed the bullshit too much.

    21. BH

      Maybe when ... Professionally, it has not felt, um, challenging for me to do that, because I think there's, like, a, a little bit of, like, an easygoing-ness that I bring to the equation that feels less ego-driven. So, what I think about is, like, um, how do you make sure that your casualness does not allow a scenario where someone thinks their results are casual?

    22. HS

      Hm.

    23. BH

      Right? So, I, I'm, I'm aware of all of that stuff.

    24. HS

      Do you worry about that?

    25. BH

      Yeah.

    26. HS

      'Cause you are-

    27. BH

      Because-

    28. HS

      ... yeah. You are informal, and human, and it's wonderful, for me.

    29. BH

      Yeah.

    30. HS

      But-

  7. 31:3534:09

    Work-Life Harmony

    1. HS

      I, I do have to ask, on the like you feel the pressure when you go home, I don't. I feel the guilt, and let me just... Because I'm like relatively uninterested (laughs) by the conversation. You spend all day stimulated with-

    2. BH

      You, your brain's tired.

    3. HS

      Y- yeah, but then they wanna talk about the weather and more.

    4. BH

      Your brain's tired.

    5. HS

      Yeah.

    6. BH

      Yeah. I mean, I feel that too. It's like, um, it's a challenge. It's, it's like something's not quite right if at the end of the day, you know, I haven't figured out a way to kind of keep that engagement thing kinda running, and maybe it's like run outta gas a little. But I feel that way too where it's sort of like, how can I, um, be unbelievably aware of like these five sort of the details of these five business issues, but struggle with my, you know, you know my 12th grader's, um, the name of her history teacher, you know, or-

    7. HS

      Do you feel, do you feel like you've been that for your kids like you would like to have been?

    8. BH

      (laughs)

    9. HS

      It's really hard when you're CEO of a public company.

    10. BH

      I miss... You know, the, the, the broad answer, and it's, it's a really, it's a genuine question. Um, the broad answer is definitely yes. 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, and 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, um, of her, probably like of her life. And I missed a bunch of them, you know, 'cause 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.

    11. HS

      Did you really need to be there, uh, in terms of for the work? Like often we can over-amplify the importance of it, and it's like, mm, no one will remember those in a year.

    12. BH

      Good question. Is that like pressure? Is that how pressure kinda seeps into your system, where you kinda like overwork in a certain way because you feel pressure maybe? It's possible. Like, I'll never know really... I think it's impossible to know the answer of like was it worth it? If, if you're asking me today, my answer is like probably not. But at the time, I must have thought yes. That, that might be pressure.

  8. 34:0937:37

    Parenting with Ambition

    1. BH

    2. HS

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

    3. BH

      No. I mean, I think I was like, um... You know, I think I was always, um, probably a little bit of like a, 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 kinda still in place.

    4. HS

      How do you inspire children to have the same hunger, ambition, tenacity when they're brought up in a, a wealthy family, bluntly? You know, you went to a betting shop in the Bronx.

    5. BH

      Yeah. (laughs)

    6. HS

      Like, they don't need to. (laughs)

    7. BH

      Right.

    8. HS

      H- how do you encourage them to be-

    9. BH

      Hard.

    10. HS

      ... really ambitious?

    11. BH

      Super hard. I would say that like from a parenting perspective, you know, that's like the number one thing on my mind.

    12. HS

      Mm-hmm.

    13. BH

      Um, I think, I, I think there's a difference between sort of having... I don't know. What are we talking about, like privilege?

    14. HS

      Mm-hmm.

    15. BH

      Like having access to privilege or maybe being privileged, and I think that's like a, that'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 kinda 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 kinda earned that." You know? And so, I really, you know, I, I, I, I go out of my way and, uh, 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.

    16. HS

      I often ask myself, would I work as hard if I'd been brought up in different situations? And the honest answer is, I don't fucking know.

    17. BH

      You, you-

    18. HS

      Maybe, though.

    19. BH

      ... you can't, right? It's, it's like hard to know, like what's that little, like, extra motivational thing? You know, I went to schools, I grew up like, you know, pretty, you know, m- you know, Manhattan, like, middle class. Um, but I, you know, I went to schools with like a bunch of, you know, you know, friends, um, but much more, much more wealthy, um, you know, friends than I was as a kid. I was motivated. You know, not necessarily by like money or status or all of that stuff, but I wa- I, I was for sure motivated to prove myself. And that, as you know very well, that can be like a super strong

  9. 37:3738:28

    Valuing Money, Fame, and Power

    1. BH

      blessing.

    2. HS

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

    3. BH

      Fame, distant third.

    4. HS

      (laughs)

    5. BH

      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, 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 gonna blow up my Instagram account with this one, um, so I'm gonna become less, less below the radar at some point. But, but like, I think like, you know, prospering below the radar is kinda

  10. 38:2841:19

    Wealth’s Influence on Leadership

    1. BH

      cool.

    2. HS

      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?

    3. BH

      Not 100% positive. It's a good way to kind of think about it. I would say there's certainly examples where that seems to be kinda true, right? If you think about like, you know, a lot of these sort of like private equity, um, you know, founders or hedge fund founders who are, you know, extraordinarily wealthy who have become sort of almost sort of wise people in certain ways around, like, you know, I think really important kinda traits. The opposite way to think about it would be like are they, you know, by not having as much at stake, do they lose some cre- credibility? It doesn't seem like it.

    4. HS

      No, 'cause the b- the best are like, uh, uh, machines. Like, they're just animals and the money is just like a scoreboard where it's just like beating the other fucker on the other side of the table. (laughs) And it's just a way to show that you win.

    5. BH

      You know this really well, uh, Harry, Blackstone at one point was a, was a, um, was a majority shareholder in my, in m- in my company, and, um, there was a moment in time before we went, um, before the company went public where I wound up kind of like very casually, um... And they've, they've been a great firm to work with. I, I, I wound up very casually meeting Steve Schwarzman in a, in a casual kinda setting, you know, speaking of kind of like you're almost describing him kinda perfectly. And it was very quick and he would, like... To say he would never remember it is a understatement. He kinda grabbed me a little bit by the arm and he said, like, you know, very aware that, you know, the Blackstone role in the company and the fact that my company was going public and he kinda said, you know, as a, as a sort of wise man, like, "It's, it's nice to win. Enjoy it." And I felt that when he said it. I was like, "Well, this guy knows, like winning." (laughs) You know? 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, like I'm gonna, I'm gonna kinda like, like remember this moment for sure, knowing he's not. But I'm, but I'm gonna remember this moment because, like, he knows, you know? And so maybe in that model that you're describing, like, those guys like know like what it takes, you know? You might as well

  11. 41:1942:49

    Public Company Pros and Cons

    1. BH

      listen.

    2. HS

      Do you like being public company, honestly? I think yeah, that it's fucking horrible. (laughs) No offense. And I have so many friends who are public company CEOs now.

    3. BH

      Yeah.

    4. HS

      And I'm like, "Do you like it?" And they're like, "No, I hate it."

    5. BH

      Yeah.

    6. HS

      "I wish that I could probably."

    7. BH

      I mean, when you said honestly, like you're, you're kinda leading the witness, um, there are... Anyone would say there are things about it not to like.

    8. HS

      Likewise.

    9. BH

      Right? Um, you wind up spending a lot of your time on, um, corporate governance, regulation, things that you feel like are, are, um, occupying more of your time than you wish they could. And almost everyone kinda feels that way a little bit, like burdened by the structure of it. That being said, there are, you know, just genuinely, there's al- like a lot of things to also like about it. Are, are you and I doing this, um, today if we weren't public? Maybe. I mean, maybe. The company's got enough profile and we know enough people and Rona's amazing that she's connecting us no matter what. But are you as interested in doing it? Maybe not.So, there's a profile thing.

    10. HS

      Mm-hmm.

    11. BH

      Kind of, that works. There's a, you know, this is gonna make you laugh because I told you I was like, a pretty, um, you know, 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.

    12. HS

      Do you check that daily?

    13. BH

      Yeah.

    14. HS

      Like, yeah, it's like a...

  12. 42:4943:54

    Stock Performance and Well-being

    1. HS

      Okay. So like, I tie my mental happiness and my mental state to the performance-

    2. BH

      (laughs)

    3. HS

      ... of my company.

    4. BH

      Yeah.

    5. HS

      Kind of harder for me because there's no ticker. Um-

    6. BH

      Yeah.

    7. HS

      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?

    8. BH

      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 kinda kilter your reaction differently. I think when it's like, you know, it's not that, you know what, we've been lucky because we've performed 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

  13. 43:5449:53

    Betting on People as a Leader

    1. BH

      human.

    2. HS

      Can I ask you, what's been the biggest bet that you've made as CEO that's worked out on the first front, and what did you learn from that?

    3. BH

      We've done, you know, a couple of, of, of important deals that have been not big bets, but they've been kind of 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.

    4. HS

      Can I push you a bit, Billy? I- 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-

    5. BH

      Yeah.

    6. HS

      ... do you think you've been courageous enough as CEO, making big bets?

    7. BH

      So, I almost was finished, but you caught me like, kinda like, in a, in a, because I, I, I do these like, super like, long run-on sentences, as you know. I've placed big bets on people in my, in, in, in my tenure as CEO, and I'm not kinda like, sugarcoat the answer. Like, I really have.

    8. HS

      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?

    9. BH

      I've brought people into my world who I took, took a, 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 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.

    10. HS

      If you were to put a number on it, what percent of your bets on people prove outright?

    11. BH

      Shockingly, because I feel like I'm really damn good at that stuff, not as high as you would think.

    12. HS

      Well, uh, there, there's a trope-

    13. BH

      Mm-hmm.

    14. HS

      ... and so you can put a number on it for me after this. But there's a trope that basically 50% of the time-

    15. BH

      Yeah.

    16. HS

      ... it will work out.

    17. BH

      I was gonna say 50.

    18. HS

      Yeah. Yeah.

    19. BH

      You know? And I, and, and I'm like, man, like if I'm filling out like a, like a survey or, um, a form and I'm listing my strengths, I'm like, oh, like, the way I think about things, the way I get to know people, like that, the kinda antenna thing that we were talking about, 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, 100%, like everyone. But like, the answer is no.

    20. HS

      No, uh, listen to- I'm totally with you. I'm terrible at it, bluntly. (laughs)

    21. BH

      (laughs)

    22. HS

      Um, so but in the 50% that don't, are there commonalities in why it doesn't work out?

    23. BH

      Maybe chemistry.

    24. HS

      Huh.

    25. BH

      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 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, you know, can you, can you sort of get unstuck? You know, can you find another kinda, 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 kinda 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 kinda 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.

    26. HS

      Oh, yeah.... and, and then there's time delays and there's lags.

    27. BH

      Yeah.

    28. HS

      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. It's three steps; getting rid, new-

    29. BH

      Yeah.

    30. HS

      So-

  14. 49:5354:28

    Young Generation Work Ethic

    1. BH

    2. HS

      I'm gonna get in trouble for this one.

    3. BH

      (laughs)

    4. HS

      But I, you said, like, pushing you and demanding, I am the same, but I think that the younger generation, which I am in, uh, 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 '80s and '90s-

    5. BH

      Yeah.

    6. HS

      ... which was fucking grind.

    7. BH

      Yeah.

    8. HS

      Like-

    9. BH

      Yeah, like people, like, smoking on desks.

    10. HS

      Yeah. And people used to-

    11. BH

      (laughs)

    12. HS

      ... pull all-nighters in banks, often.

    13. BH

      Yeah. Yeah. Like, like, like a really tough sort of, like, there was a, it was a tough culture. There's like, there's like no doubt about that.

    14. HS

      Yeah. But it, but it was actually an efficient culture in many ways-

    15. BH

      Yeah.

    16. HS

      ... in terms of output.

    17. BH

      Yeah.

    18. HS

      Do you, do you worry that this generation is too soft?

    19. BH

      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, you know, what's really gonna work here, you know? And I don't wanna sound like, you know, the old guy on a ch- on the chair on a lawn kind of thing, like, (laughs) making, you know, making pronouncements about, like, what the kids are like these days. But sometimes, you know, like, it's sort of like there's so much benefit that you get from, like, hustle and grit and perseverance. There just is. I will say this, and tell me what you think about this, like, the, the kids that have it, like, switched on, like, wow do they have, like, um, a lotta, like, trajectory in front of them.

    20. HS

      Oh, 100%. But I-

    21. BH

      You know?

    22. HS

      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.

    23. BH

      Mm.

    24. HS

      No great person who was hugely ambitious fell out of McKinsey and Bain and thought, "Ooh, now I'm gonna be really ambitious and courageous."

    25. BH

      It's a, it's a process along the way. Some of that process can be about sort of 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. There's a reason why that is.

    26. HS

      I w- I w- I would never hire them.

    27. BH

      Yeah.

    28. HS

      Or in- 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.

    29. BH

      Yeah. The, the, the sort of like, the, the sort of like Tom Brady theory of, like, "I'm gonna use every slight in the, in the, that's ever existed to continually motivate myself and create this kinda resilience thing." There's, there's, there's, there's, like, no doubt that that's the sort of, like, the two types. I don't know about I would never. I mean, I, you know, s- so, so, so you and I were kind of, like, joking about, you know, the kinda EQ thing and, like the, the sort of, like, self-awareness and all of that stuff. Like, I sometimes gravitate, 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. Like, the, the, the, like, "I've always been the smartest, I will always be the smartest," (snaps fingers) and that switch, that cognitive switch is just, like, turned on. I am really attracted to and I am, um, I see the benefits, you know, of just, like, of just, like, straightforward, like, wow, like, a really, really smart person.

    30. HS

      Oh, no. No, I don't like them too smart. Very bad, very bad trait, I think.

  15. 54:2856:12

    Balancing Hiring Strategies

    1. BH

    2. HS

      The hardest thing and the thing that I'm, I've made mistakes on now, which is I used to hire the pedigreed person from amazing... And that was the wrong hire. And then I went bla- from, like, you know, binary and I would suddenly go to the really inexperienced, really hungry ambitious, and that didn't work either. It was not, it was just inexperienced and immature.

    3. BH

      Yeah.

    4. HS

      And-... it's-

    5. BH

      Well-

    6. HS

      ... says about finding the na-

    7. BH

      You know, you know what? You know what's interesting, like, in my world, Harry? And you'll, you'll, you're gonna appreciate this. Like, you know, to make an obvious point, and I'll s- and I'll, I'll mangle this for you, there were a ton of really bad consequences to a firm, um, you know, to a firm like Bear Stearns going through, like, the struggles that Bear Stearns went through, you know? One of those is that, you know, when I grew up, like, in the bond trading world where, you know, Bear Stearns had, like, tremendous levels of respect, right? And really talented people, and they, like, lived in that ethos of what you're describing. Like, it's not about pedigree. It's not about polishedness. It's not about, like, you know, where y- what school you came from and who you know. It's about, like, 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, kinda lived by that code. To see that code kinda die by the sword a little bit hurt. You know? Because s- because it was kinda cool to kinda feel that culture in the world.

  16. 56:1259:23

    Financial Market Challenges (Assigned to Luca)

    1. BH

    2. HS

      A lot of younger people look at where we are today and feel very worried about the state of the economy, the state-

    3. BH

      Yeah.

    4. HS

      ... of the world. You've seen some real, "Oh, shit" moments.

    5. BH

      Yeah.

    6. HS

      How does this compare? And how did it feel when Bear Stearns went through its troubles, Lehman's went through its troubles, 2008 happened?

    7. BH

      You and I will talk more. This is not, this is not our first conversation. You know, um, you know, my company was on the 51st floor of the North Tower. I was in the building on 9/11, that day, so, you know, when I think about, like, trauma, you know, it kinda starts with kinda 9/11. Um, and then I think about, like, the sort of, like, professional trauma around the, around the crisis, um, and that was some pretty scary stuff. You know, is there gonna be cash, you know, at the ATM at City, at Citibank? Like, it, it, it was, you know, there was this, like, just, like, massive unwind, and it, it can feel like that never happened, but it did. And so for, like, a company like Tradeweb, like, we saw, like, our clients, like, you know, with this, like, amazing business model, and then saw our clients going down one by one by one, you know? And, and there was a moment where, you know, and Ted Pick as CEO at Morgan Stanley, he's talked about it, there was a moment where Morgan Stanley felt, like, you know, next in line, like, super shaky, right? Like, "Where can this thing go?" And then, you know, cut, you know, cut more, you know, more recently, um, you know, even a year ago, like, the shocks to the system around the regional banks and all of that, you're, you're, you, you realize you're living in this, like, fragile, kind of fragile, um, you know, place. And, you know, and I didn't even mention, obviously, you know, the pandemic. The world feels like, obviously, like, scary right now-

    8. HS

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

    9. BH

      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 f- and the high-functioningness 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, kinda Russia, and then we haven't, you know... I'm not a, I'm not a political expert, but everything even around China feels pretty fragile. So that's, or pretty volatile. So that, that's, like, that has to keep us all a- all up at night.

    10. HS

      Does geopolitics impact your business?

    11. BH

      Yeah, you know, just from the, from the, from the standpoint of, like, volatility in the marketplace, um, you know, we've gotten much stronger in, like, in the EM regions, and so we've, you know, 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

  17. 59:231:05:46

    Quick-Fire Questions

    1. BH

      do.

    2. HS

      I wanna do a quick fire with you.

    3. BH

      Yeah.

    4. HS

      So what have you changed your mind on in the last 12 months most?

    5. BH

      I have changed my mind on, on Trump being electable. 12 months ago, I didn't think the guy ... I di- I did not think the Republican Party would get behind him, and I didn't think he could win the election.

    6. HS

      And now you think he will? I'm unwavering in the fact that I think he will.

    7. BH

      I, I think he will, and I, you know ... It starts with he can, but I think it ends with he will.

    8. HS

      Is it that bad if he does?

    9. BH

      I mean, I think it's bad for, like, m- you know, my nervous system, um ... (laughs)

    10. HS

      Well, hey, he was right about China. Uh, he was right about a lot of the economy. I mean, COVID really was ch-

    11. BH

      You know, w- you and I can talk about, like, what he was right about and wrong about. To m- from ... You know, he brings so much kind of negative energy into the, into all the situations, but, you know, we, we can probably have a thoughtful conversation about, like, things that he got right. I mean, I think we're allowed to do that.

    12. HS

      I find Kamala Harris brings so much positive energy to the situation, Billy. You all right? (laughs)

    13. BH

      (laughs)

    14. HS

      No comment.

    15. BH

      Yeah.

    16. HS

      Uh, what do you ... Oh, okay. Is New York City still the capital of the world?

    17. BH

      Yeah. New York City is ... You talk about resiliency, you talk about grit, you talk about, um, you know, all of those qualities that make someone kinda awesome, New York City has, like, all that stuff, like, times a million.

    18. HS

      What's the best book on financial markets and why?

    19. BH

      The best book on financial markets is gonna surprise you. R- reread-... all of the financial part of Sherman McCoy in Bonfire of the Vanities. The way Tom Wolfe is able to kind of get inside, um, you know, a trading firm that was sort of modeled after Salomon Brothers, um, is incredible. Like the language that he describes like transactions and the cadence of the markets, off the charts.

    20. HS

      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."

    21. BH

      Create boundaries quickly. So s- so- so don't always entertain sort of, um, every new relationship, which can be a concept of like a banking relationship. It can be, um, an external relationship with a client. Like preserve your time at a v- at a v- in a- in a very, very structured way, because time is sort of- was one of the most valuable things that you have. Um, and be very, very diligent about your time is what I would say.

    22. HS

      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."

    23. BH

      (laughs)

    24. HS

      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-

    25. BH

      Yeah.

    26. HS

      ... more hours. If you'd always known that it's okay, I probably wouldn't have worked as hard.

    27. BH

      It's okay, by the way.

    28. HS

      Yeah. Fine.

    29. BH

      It's okay.

    30. HS

      Won't bother. Won't bother fundraising.

Episode duration: 1:05:46

Install uListen for AI-powered chat & search across the full episode — Get Full Transcript

Transcript of episode dis1jsDO-lA

Get more out of YouTube videos.

High quality summaries for YouTube videos. Accurate transcripts to search & find moments. Powered by ChatGPT & Claude AI.

Add to Chrome