Mar 29, 2024 · 1h 5m · news
Billy Hult: 27 Years of Compounding Growth Leading to the Market Leader with $1.4BN in Revenue|E1134 · 20VC with Harry Stebbings
0:00 / 0:00
▶ Watch on YouTube →
gold bands on the timeline = statements, start to end. Hover to read, click to jump. CC turns on captions
In this episode of 20VC, TradeWeb CEO Billy Hult shares his leadership philosophy, emphasizing the value of raw grit over elite pedigree, the realities of balancing ego and execution, and the personal sacrifices that come with high-stakes executive roles.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 18.2% of the talking time here. How this is scored →
Harry as informed peer 2.6 Guest teaching 3.6 Guest disagreement 1.4 Harry pushing back 2.0
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 20:52 Billy challenges host's polite phrasing
Billy directly confronts Harry's framing on talent recruitment, asking if Harry is implicitly calling Tradeweb too sleepy and below the radar.
Hardest push from Harry ▶ 44:33 Harry presses on bold leadership betsHarry refuses to accept Billy's vague answer about smaller deals and directly challenges whether he has been courageous enough as CEO in making transformative bets.
Biggest teaching moment ▶ 24:01 Wall Street client power dynamics breakdownBilly educates the host on the subtle hierarchy of Wall Street relationships by recounting how a Credit Suisse trader set him straight on who held true power with BlackRock.
Harry holds his own ▶ 52:30 Harry defends his anti-pedigree hiring thesisHarry forcefully asserts his investment and hiring framework, explaining why candidates with uninterrupted elite credentials break under pressure compared to those with early adversity.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| 20VC Title Card | 1 | 1 | 0 | 0 | Friendly introduction and rapport building where Billy expresses excitement to be on the show. Light discussion on childhood and early schooling characteristics. | |
| Hard First Jobs: The School of Hard Knocks in the Bronx | 2 | 4 | 1 | 1 | Billy shares his experience working at an off-track betting parlor in the South Bronx and discusses leaning into strengths versus passions. Harry pushes a counter-quote on doing what you are good at. | |
| Defining the Role of a CEO: Strategy and Execution | 2 | 5 | 1 | 2 | Billy outlines the responsibilities of a CEO, emphasizing strategy, execution, and client management. He illustrates his point with an anecdote about Jamie Dimon at a JP Morgan conference. | |
| Vulnerability, Personal Growth, and Maya Angelou Quotes | 3 | 3 | 2 | 3 | Harry asks for personal managerial advice regarding his direct style and fear-inducing leadership. Billy offers advice on directness and truth with novocaine while trading Maya Angelou quotes. | |
| Parenthood, Managing Anger, and the Vulnerability of Being Liked | 2 | 3 | 1 | 2 | Discussion turns to the desire to be liked and how parenting softens leadership styles. Billy explains that while he wants to be liked, he is not a pushover. | |
| The Language of Ambition and Driving Change | 3 | 4 | 1 | 1 | Billy explains the importance of using ambitious language to drive organizational change, using a golf swing modification analogy to illustrate enunciation of strategy. | |
| Brand Exposure, Recruiting, and Operating Below the Radar | 4 | 4 | 4 | 4 | Harry challenges Tradeweb's talent brand compared to Silicon Valley giants. Billy picks up on the implicit framing and reframes the strategic value of operating below the radar while navigating Wall Street egos. | |
| Navigating Elite Clients and the Competitive Dynamics of Wall Street | 3 | 5 | 2 | 2 | Billy recounts a story about a Credit Suisse bond trader putting him in his place regarding BlackRock, and explains managing ego balance in executive leadership using a Coldplay band dynamic analogy. | |
| Casual Leadership and Keeping Perspective Under Pressure | 2 | 4 | 1 | 1 | Billy discusses balancing casual leadership with high standards and quotes Lloyd Blankfein during the 2008 financial crisis to illustrate keeping perspective under pressure. | |
| Coping with Pressure and the Sacrifices of Fatherhood | 3 | 3 | 1 | 3 | Billy opens up about carrying professional pressure home and missing his daughter's basketball games. Harry gently pushes on whether the work was truly urgent enough to miss those moments. | |
| Parenting and Instilling Ambition in Privileged Children | 2 | 4 | 1 | 1 | Billy discusses parenting privileged children and instilling ambition and self-reliance, sharing his concept that beer tastes colder when you earned it yourself. | |
| Ranking Money, Fame, and Power | 3 | 3 | 1 | 2 | Harry asks Billy to rank money, fame, and power, and posits that wealthy leaders make better leaders due to reduced downside fear. Billy offers a nuanced perspective on leader credibility. | |
| Meeting Steve Schwarzman and the Joy of Winning | 2 | 4 | 1 | 1 | Billy shares an encounter with Steve Schwarzman before Tradeweb's IPO and discusses the pressure of managing stock price fluctuations as a public company CEO. | |
| Placing Bold Bets on People | 4 | 3 | 2 | 7 | Harry directly challenges Billy on whether he has been courageous enough to make big corporate bets. Billy responds by shifting the definition of big bets to placing high-stakes bets on people. | |
| The 50% Success Rate of People Bets and Chemistry Breakdowns | 3 | 4 | 2 | 2 | Billy candidly admits that personnel bets only work out around 50% of the time, discussing chemistry breakdowns and how optimism leads him to attempt resurrecting troubled executive relationships. | |
| Generational Shifts: Grit, Hustle, and the 1980s Grind | 3 | 3 | 1 | 2 | Harry criticizes younger workers as entitled and soft compared to the intense grind of the 1980s and 1990s. Billy acknowledges cultural shifts while noting high potential in switched-on young people. | |
| Hiring Debate: Pure Hustle vs. Pedigreed Intelligence | 5 | 4 | 3 | 4 | Harry strongly asserts his preference for raw hustle over pedigreed elite graduates who break under pressure. Billy counterbalances Harry's view by defending the value of pure intellectual horse-power. | |
| Navigating Extreme Crises: 9/11 and the 2008 Meltdown | 2 | 6 | 1 | 1 | Billy shares his personal memory of being in the North Tower on 9/11 and navigating the 2008 financial crisis, offering historical perspective on system fragility versus current geopolitical tensions. | |
| Quick Fire: Geopolitics, New York City, and Book Recommendations | 2 | 3 | 1 | 1 | In a quick-fire round, Billy discusses political predictions, New York City's resilience, financial market literature recommendations, and losing his father at age 26. | |
| The 10-Year Vision & Fighting Corporate Complacency | 2 | 3 | 1 | 1 | Billy shares his ten-year outlook for Tradeweb and warns that corporate complacency and office politics are the ultimate company killers. |
Statements from this episode (26)
Billy Hult: Success comes from grit and street smarts, not pedigree
“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.”
Billy Hult worked as an off-track betting clerk in the South Bronx
“My first job, and it was like You know, for sure either end of high school or kind of early college, kind of one of those summer jobs, was working Harry at a place they called, like, OTBs. It was off-track betting a place where people would go in back in the e…”
Hult: Advising people to follow their passion is naive and misleading
“It's a little bit of, 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 early in…”
Billy Hult: CEOs who disconnect from execution breed organizational passivity
“I try to get my kind of sleeves rolled up and my hands around execution, because I do think that's where companies kind of ultimately make their bones around like, how good are you at really ultimately executing on a game plan? And if you get yourself like too…”
Hult: Leaders shouldn't just get out of the way of great hires
“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.”
Hult: Jamie Dimon sets the benchmark for ego-free client engagement
“He's amazing with clients. Like you talk about a guy that can kind of 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 JP Morgan's clients, his …”
Stebbings admits he used to lie when nervous and act arrogantly
“I did stupid shit. I used to lie when I was nervous. I would be too arrogant because I believed that bullshit.”
Billy Hult: CEOs must take full ownership of high-stakes decisions
“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 yo…”
Hult: Tradeweb built its business through organic growth, not M&A
“So my company TradeWeb has, you know, largely gotten to where we are today through a lot of like really good sort of, you know, organic investments and organic growth. Right. So we are not some company that's arrived here through lots of like M&A.”
Hult: Tradeweb is the electronic interface connecting Citadel and Goldman
“Like we're the, you know, we're the electronic interface that connects like Citadel and Goldman.”
Hult: B2B infrastructure can flourish without demanding the biggest brand presence
“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 alway…”
Billy Hult: Corporate leaders must possess an ego to succeed
“You have to, I mean, I have an ego. You have to have an ego.”
Billy Hult insisted on co-branding Tradeweb's leadership as a two-person partnership
“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 band where it, you know, at least there's two of us.”
Billy Hult experiences nerves in board meetings outside his comfort zone
“If I was doing like CNBC, I wouldn't feel nervous. If I'm doing an earnings call, I won't feel nervous. You know, maybe that's like everything's going well. That helps. But sometimes when I'm doing a part of, and I'll wind up having a bunch of board members pr…”
Billy Hult ranks power above money, with fame a distant third
“Fame, distant third. It would be really easy to say like, you know, like money first, power second, but I think I think power is like pretty interesting.”
Billy Hult: Public CEOs spend excessive time on governance and regulation
“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.”
Tradeweb CEO Billy Hult admits only 50% of his people bets succeed
“I was gonna say 50. You know, and I, and I'm like, man, like if I'm filling out like a survey or a form and I'm listing my strengths, I'd like, oh, like the way I think about things, the way I get to know people like that, the kind of antenna thing that we wer…”
Hult rejects 'fire fast' leadership advice on failed hiring bets
“As someone was telling me recently, you know, the first time a CEO feels like, you know, something hasn't worked out, they should act on it. Because, like, if they have that impulse with, like, you know, all of the sort of importance on the line there's a reas…”
Stebbings: Great ambition stems from childhood, not top consulting firms
“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 going to be really ambitious and courageous.”
Stebbings refuses to hire or invest in people with unbroken track records
“There's a reason why 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.”
Hult: Bear Stearns succeeded by prioritizing grit and street smarts over pedigree
“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 pol…”
Billy Hult was inside the World Trade Center on 9/11
“My company was on the 51st floor of the North Tower. I was in the building on nine 11 that day.”
Billy Hult: Financial markets are more resilient today than in 2008
“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 high functioning-ness of the market in a way that should, people should feel sort of, …”
Billy Hult predicts Donald Trump will win the presidential election
“I think he will, and I, you know, it starts with he can, but I think it ends with he will.”
Billy Hult: 'The Bonfire of the Vanities' is the best financial markets book
“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 Tom Wolf is able to kind of get inside you know, a trading firm that was sort of modeled after Solomon brothers i…”
Billy Hult: New CEOs must quickly set boundaries to protect time
“Create boundaries quickly. So, so, so don't always entertain sort of 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 at a, in a very, very structured way.…”