Hi, I'm Georgie Dickens, host of Stratospheric Leaders, the podcast where I get to have inspired conversations with extraordinary leaders from across capital markets. Join me to hear their game-changing strategies, the personal stories, and powerful sound bites behind their stratospheric success. Every episode packed with wisdom, insight, and real-world lessons. The stuff they simply don't teach you in business school. If you want to elevate your game and most importantly elevate those around you, this podcast is for you.
I was delighted to welcome the wonderful Doug Cifu to an episode of Stratospheric Leaders and what an enjoyable conversation we had. There were many laugh out loud moments for me. And what struck me was how real this conversation felt. And I imagine that whether you meet Doug in the boardroom or equally if you bump into him in a restaurant, he's exactly the same, which is he's warm, he's charming, he's funny, and he's a serious business person, but refreshingly, he doesn't take himself too seriously. And when we talked about the world of work, it all started from an early age. Eager to make his own money, he started off cutting grass. And then in his teenage years he became a golf caddy and like many of us that have had jobs in our youth, there are so many valuable lessons that feed into our leadership. And for him as a caddy, he learned how to treat people, how to treat them with respect and how to connect with people across all walks of life. Post high school he went on to Columbia to study law. And this is where his mother said to him, 'Douggeie, you're either going to make a lot of money or you're going to get yourself into trouble.' Fortunately, he chose the former path. Doug was a successful lawyer for many years before he joined forces with Vinnie Viola and they founded Virtu. And this is a company which specializes in high frequency trading and market making across a wide range of asset classes. And I was really curious around why did you name the company Virtu? It was after the word virtuous because everything they do, he said, we want it to be virtuous. There's no gray. It's black and white and we're always going to be on the good side of white. Now in 2025 Doug has been with the company for 17 years. He's the CEO with a market cap of around $6 billion. And having worked with the organization, I can confidently say it's a firm with some of the very best people in the industry. It's a great episode with some exceptional leadership lessons and also some genuinely brilliant personal insights. I trust you're going to enjoy this episode as much as I did recording it.
Doug, I am delighted to welcome you to Stratospheric Leaders. In fact, I'm thrilled to welcome you to your episode of Stratospheric Leaders. You and I first met at a Christmas lunch several years ago and I remember it vividly because it was during this brief window between COVID lockdowns where we were able to gather in person before everything shut down again. So I think not only did we share Christmas cheer amongst the group but also a few microbes. But since then I've had the privilege of working with the Virtuians and you have such an extraordinary group of people working at Virtu as part of one of the programs I ran last year. You and I did a fireside chat and as I shared with you at the time it was packed with such powerful lessons, rich insights and so much humor. We talked everything from markets to hip flexors, your daughter calling you cheap. We talked about sweater vests. I mean, we covered a whole range of topics. And the conversation really left a lasting impression on me. So, I have very much been looking forward to our podcast recording. And so I would love that I always do my prep and we know each other really well, but I was googling you and there's all about the Florida Panthers is there too, but yet again you're a private person as well. So, I was going to ask, well, not going to ask. I'm going to ask if I was to Google search you, what's one thing I wouldn't find out? What's a lesser known fact that people wouldn't know about you?
Wow, that's a great one. I would say, and my wife would disagree with that, that I actually think I'm a terrific dancer. Which is my wife actually, yeah, it's one of those things where like she says, 'You're a great dancer, but you're all about yourself.' So, like I just like having fun. So she's like I'm like an afterthought. In fact, I've been married for 25 almost 26 years and when we first started dating, you know, we go to this wedding it's at the Metropolitan Club. I don't know why I'm telling you the story but it's like a funny dance story. And this is like we'd been dating maybe like three, four, five months and it was like her best friend was getting married and she's in the wedding party and she's kind of rolling me out and it was like a big Jewish wedding. I'm not Jewish. And so she was concerned, you know, blah blah blah. All the nonsense and BS that people worry about, my wife used to worry about. So she's like, 'Don't drink that much.' And I was like, 'All right, that's like putting meat in front of a dog. Don't ever tell me not to do anything.' Long story short, she goes off with the wedding party. She comes back. I don't really remember this that well. And I was hammered. And I was kind of like, I'll say dirty dancing. It wasn't like inappropriate with the groom's mother, Mrs. Miller. And she was like, 'What in the?' So, that was literally the only fight we ever had because she was like, 'What are you doing?' And she tried to cut me off from drinking. Long story short, you know, she got over it. And we're still married. 27 years later, I guess. So, there you go.
So, she did marry you. So, I love the fact you like having fun. And I'm sure that is a golden thread that's run through your life.
Yeah. Yeah, like I don't want to say I don't take myself seriously because I do serious kind of business things, I guess, but like I kind of am who I am. I just figured out a long time ago. I don't know. It probably was my upbringing. I had a fantastic mother. I'm not just saying this because you're a great mother because I've met your children. It's 98% the mother, right? And so I had a great mother. You know, 2%, you know, the guys, you got to be there, you know, provide kind of keep the kids in the fairway a little bit, but the mother's doing everything in the fairway. I'm a golfer, so I use golf analogies. And so I kind of figured a long time ago when I started business, like I've always had like kind of a personality, if you will. And so I was like, I can't really change who I am. I just can't. I'm not a great ass-kisser. I'm not a good, you know, I have a hard time being super phony. And you know, it's just it was hard. So like I learned I started as a lawyer and I was like, 'All right, if I'm skilled and people, you know, most people like me, some people can't stand me.' And at the end of the day, you just can't worry about you got to control what you control. So I don't really worry about like what the world thinks of me, if you will. And I just want to like, you know, live every day and be happy and run my little firm and go to hockey games and be happy and hopefully play like some nice golf with friends and, you know, that kind of stuff. Just keep it simple.
I love what you said there about personality because I think as leaders ascend like IQ is table stakes. It is about personality. We're in the business of people. You want to engage people and equally you want to have fun in life. Like life is the journey.
Yeah, it really is. And I really actually like people. I like meeting different people. I mean that's like one of the best things about the job I've had for the last 17 years like starting and then running this little firm called Virtu Financial. It's first of all the colleagues and friends and partners I've had over the years and do still have at Virtu and watching them grow. And like Cindy who you know very well our CFO she started when she was like this big and 12 years old and kind of a sheepish junior accountant and now she's the CFO of this public company that's pretty cool. And like people from different cultures different places. I love when I take an Uber I always talk to the Uber drivers and I ask them where they're from and we talk about like Kazakhstan or like Georgia, the country, not the state, you know, and I learn like a lot about different people and their backgrounds and whatnot. I just think it's like kind of part of the joy of life.
Yeah. I remember a leader once said to me, be interested and be interesting. And that be interested, he said, it sets you apart when you're curious about others. You want to learn.
Yeah. Yeah. And I'm saying this and I'm not trying to be like the everyman guy, but like frankly, I've had much more interesting conversations with like caddies and people working in my house or landscapers. I used to be a landscaper when I was a kid. Or Uber drivers. Than I have like really uptight businessmen and billionaires who like just bore the shit out of me, you know, like I don't have like a ton of the master of the universe kind of friends. I never got that. Like these guys seem to all socialize with each other. It's like they're not that interesting. Oop, sorry. I cursed. They're just not that interesting. And like everyone's like, 'Oh, I got this house in the Hamptons. I'm on the board of this.' It's just like, 'Ah, forget it. I don't want to do any of that crap.'
Keeping it real. And look, you mentioned 17 years at Virtu, and I know you were in law before that, but I want to rewind even before that. The young Doug Cifu, what was his first ever job?
Well, it's a great question. My first I had a number of I was self-employed first. Depends what you ask. So, like I always wanted I was always fascinated by money because we didn't have a ton growing up. I grew up very comfortable. My dad was an electrical engineer. My mother was a nurse that worked at night. So, like two salary home and you know, but they had to put three boys through college and then graduate school and pay for all that kind of stuff. And that wasn't really that easy in the 1970s and the early 1980s. And I had two brothers that went to college and graduate school and they paid for everything. I never had any student loans, right? So like I was always very eager to like make my own money and have my own money. So I started literally I used to have to I loved cutting grass and like I'm an Italian so Italians love landscaping and stonework. I was shitty with stonework. So I gravitated towards landscaping. I still to this day like I love trimming bushes and cutting trees. I'll tell you a really funny story. When I first I meander and I'll come back. I apologize. When I first moved out to Short Hills, New Jersey, we moved to this like really fancy house, like this great house. I was a lawyer and I didn't know any better. We never had a landscaper. No one ever did anything. We were kids. We did everything ourselves. My father had three boys that he had built in help. So, we get to the house and it was a little overgrown. So, I got like a tree saw and all this other stuff. I know how to do this stuff. Saw me in the front yard like literally trimming trees, cutting the grass, and all this stuff like making it nice because it was my house, you know? I'm proud of it. And my neighbor across the street, I hadn't met him. And I was probably dressed like an animal, like a slob, like I always am on weekends. And I was all full of stuff. So the neighbor pulls in, I wait, I go, 'Hey, how are you?' And the guy looks at me and goes, 'Runs in the house.' Cuz he thought I was the landscaper. What I learned is when you move to suburbia, you don't do any of your own stuff anymore. So anyhow, I digress. Now 25 years later, I do have the landscape, but I go out. Actually, the guy was cutting the bushes yesterday at my house here in Florida and I went out and talked to him and like made sure he was doing it the way I like because I like an Italian. I love landscaping. So, that was my first kind of job. Then I was a caddy at the local country club that I never could belong on. I learned a lot of lessons being a caddy. I did not grow up in a country club. And some people were nice to me, some people were like not nice to me. Like people were mean to me. I remember vividly one of these conversations I was like 15 or 16 and the guy asked me what I wanted to be when I go to college. I said, 'I'm going to be a lawyer. I'm going to go to like Harvard, Yale, Columbia, Princeton, one of the Ivies.' And he kind of laughed at me and I was like, 'Why is this dude laughing at me? That wasn't very nice.' And I ended up going to Columbia and here I am. So, it was one of the life lessons. And to this day, I'm unbelievably just cuz I like them generally, but I'm really really nice to caddies and my nickname at the club is called BT for Big Tipper because I always want to take care of caddies because I remember how people used to look down on me when I was a caddy. But then my first real job was at You're not an American, so you won't get this, but it was an American New York institution called Carvel, which is an ice cream factory. It's not just a store, it's a factory. And you made everything there. And I started working there when I was 16. And I was really good at it. Like really good. I made cakes. I made flying saucers. I loved it. I made $3.35 an hour. I got a promotion. I ended up being the manager. I worked for this lovely Italian grandmother named Mrs. Munia. I never called her by her first name, Mrs. Munia. She loved me. I made the cakes. They had a cake called a cookie puss, which they still make today. So you could be a little creative. The only thing I was really hard I have terrible handwriting and when you write on a cake, you know, when you write like happy birthday and you do with the icing bag, your handwriting still sucks even if you're using icing bags. So I was not good at that. But I love that job. The best part of that job, which was not good for my physique, was if you made a mistake, Mrs. Munia said if you make a mistake, you can eat it. So, I would like if you fucked up a cone and did like vanilla instead of chocolate, you'd put it to the side and then eat it. So, I gained like 20 pounds. But other than that, it was a great job.
And I love this. And going back to your caddying, you said you learned many life lessons. One is about how you treat people. What other lessons did you learn that have really stood the test of time?
The other thing was really interesting, I'm glad you asked that. So like the way it works at country clubs is they have like a caddy yard and they have like this generally disgusting building. Now it's nicer where you sat in and think of this. I was like a 15 or 16 year old white kid and this was in Syosset. So the name of the club was called Woodcrest. It doesn't exist anymore. It was kind of a high-end club in Woodbury. I'd ride my bike there. But the other people and there were a couple other kids there, but there were a lot of adults that were caddies and this was not like the higher end of society, if you will. So there I am as a 16-year-old and guys were like throwing dice and drinking and there were African-Americans there and other minorities. I had never interacted with these people before. So it was like you had to learn one how to interact with a large swath of society. And then the other thing is then you went on a golf course and you had like rich people that I'd never really interacted with that you know from the area that you had to like be an adult with and kind of interact with and some of them didn't want you to talk some of them would engage you some of them were super nice. So I learned like a good life lesson on how to deal with people from like the bottom of society up to like back then doctors were like the most prominent people and there were some Wall Street people at this club. These were like other forms of humanity for me. I'd never met anybody. I grew up in a very kind of not blue collar but a very basic family oriented place where nobody had like a ton of money like that. So it was like these people that had like money and drove Mercedes and all that kind of stuff. So how do you deal with that large swath of society? So you learn how to deal with different people.
And you went like law was you mentioned you went to Columbia. What was it about law that interested you?
You know it was a little bit I guess it's my personality. My mother said to me and I've said this to people before like when I was young and she was unbelievably supportive so I could just like do what I want. Not I didn't run like wild right? I was a great student and whatnot. So, but she said, 'Dougge,' she always called me Douggeie, you know, 'you're either going to make a lot of money with that mouth or you're going to get in a lot of trouble' and both, you know, kind of both have happened. And it was like I was always like very verbal and kind of almost had like ADHD talking to people and having a personality. So, I thought at first I thought and I was a high school debater. I don't know if you have that in England, but we had like it's a kind of a big deal here. And I was pretty good. I was president of the debate team. Kind of a geeky guy, right? I went to states and the nationals for it. I won some trophies. So, I thought I was going to be like a courtroom lawyer. You know, kind of like Clarence Darrow or something like that. And then when I got to law school, I was like, these litigation people are just angry all the time and arguing about like nonsense. It was too much stress, too much just being angry about nothing. And being a business lawyer or a corporate lawyer really fit my skill set. It was like, you know, intellectual, you had to be smart, you had to study, you had to really know the law, you had to keep up with the case law, but you had to interact with high-end clients, private equity firms, big corporations, individuals on sophisticated securities, you know, I did everything, mergers and acquisitions, bankruptcy, intellectual property, tax, all that kind of stuff, and give advice. And then you had to go interact with an adversary who was on the other side of the transaction, whatever it was, and get along well enough with them to come to a compromise that both parties could accept, right? So it really kind of fit very nicely into what I thought I was good at.
And so what was the defining moment then when you were in law for a period of time that then was like, you know what, I'm going to leave. You co-founded Virtu.
Yeah. No, I never had any intention of leaving. I was very well regarded at the firm. You know, I won all these idiotic awards that lawyers give to themselves like super lawyers and I was in all these books and I was like private equity lawyer of the year and all this shit. Like I was on the management committee of Paul Weiss, which is a great great law firm. It's been in the news recently, but a great law firm and I was a corporate lawyer making a good amount of money. But I had this client named Vinnie Viola that I had been referred to by General Atlantic Partners, which was my big client. Bill Ford who I owe a lot of my life to Bill Ford but so Vinnie needed a lawyer. General Atlantic had invested in New York Mercantile Exchange and Vinnie was chairman so Vinnie called up Bill Ford and said hey who was that loudmouth guy he didn't say who was that guy that represented you if he's good enough for you he's probably good enough for me and that's how I first met Vinnie and I was his lawyer for a couple three years he had a couple very significant personal business matters that I helped resolve for him. And when you get into the trenches with an individual client, like it means the world to them, right? It's not like I'm representing some big company and if they make or lose half a billion dollars, yeah, it matters, but it doesn't really matter. Like this was Vinnie's life. And so I had a bet the company litigation, if you will, or situation for Vinnie. And I did a really, really good job. Partly because I was a good lawyer, but partly because I was really into it. You know, when you represent an individual and you really like the person, you're sort of super motivated, you know, like I'd make a lot more money doing some deal for some private equity firm as opposed to representing Vinnie. But, you know, we really clicked on a personal level. We're both Italian-Americans. We have very similar kind of views of life. We both like sports and this and that. We both have family and just we both He's a West Point grad. I love military history. So, we just had all these common interests. He's very different than me. But we really clicked on a personal level. And I'll say this, he must have seen something in me. And he said to me after like a couple years of me being his lawyer at Paul Weiss. 'Hey, you know, Doug, you're wasting your effing time being a lawyer. You're really smart. I want to start this business in New York and it's going to do X, Y, and Z.' And he described what Virtu was going to be and what it is today, right? So, I was like, it was one of those moments in life where I was like, and I had never really thought about leaving Virtu. And we always like I think lawyers are always like look at their clients and say, 'Man, I'm freaking smarter than this guy. I should be the guy making all this money and I should be the client.' But it's hard to like transition. And I So, I met a crazy man who was crazy enough to trust me. And here I am 17 years later in a really cheap trading vest with a nice view of the Cheesecake Factory talking to you. So life comes at you fast.
It does come at you fast. I didn't realize the Bill Ford connection because he kind of did the intro to my book. So I met him through
I know and I know he knows Lance really well. He invested in Lance's company. So yeah,
Actually I did that deal for GA.
I love what you said there with Vinnie. You did a great job. There was like rapport. There was trust. You know, there was consistency. And the Virtu I'm again, how did you call it Virtu? Was it something Vinnie had really decided on the name?
work, which I did. I'm going to get more work than I can imagine. And then clients are going to then I'm going to make partner because they're going to see how good I am. And clients are going to like me and I'm good with people. I'm a good schmoozer. I'm good on a golf course. I'm not half bad in a pub. So like I'll get clients and I'll get work and I'll always be I'll always have a business. Maybe it won't be, you know, $100 million of legal fees. It might be 10 million or it could be 20 or whatever it is, but I'm going to always be successful as a lawyer because I have all those skills. So screw it. Who cares what people think about me? I don't have to, you know, I'm not looking to be everybody's best friend. I'm looking to, you know, have great colleagues, you know, collaborate with people and have a really good practice that I'm proud of. And so it was that kind of mentality when we started Virtu. I was like, 'Okay, all right. I'm a talented guy. I'm going to figure this out.' I remember like I had like I used to put on my wall in my first office in the temporary office I'd have like little stickies on all the acronyms because people would say like EBS, Espeed, you know, they'd have like all of the months for crude would have different abbreviations and I didn't know any of the stuff. So I began these, you know, you're the president of the firm and people expect you know what the hell left from right is and I didn't know. It's like learning a new language, you know, I mean it's like I was literally like an immigrant dropped off a boat at Ellis Island and I didn't speak English. I was speaking Swahili, you know, so it was like I had to learn a whole new language.
But to your point, you were a voracious learner and if you, you know, you figured it out. If you don't know the answer, you go, as you said, I'd go away. I'd listen to case studies. I'd, you know, it's that desire to want to grow.
Yeah. And the other thing is I'm not, again, the right way to say this is I'm not afraid to be embarrassed. So I would ask questions where it was very clear I didn't understand something but I was smart enough and worked hard enough to have context around the question I was asking if that made sense. I didn't just go up to our technology and say, 'Oh, what's an operating system?' right? Like I'd learned enough about it and then I would go to our CTO Aaron Simons who sits a couple doors down in 2009 and I would ask him a question about like, 'Oh, how does the PCI bus work? What's a kernel bypass like? What's an FPGA card? How does it really work? I think I understand it. How does this really work?' And I'm sure he would roll his eyes sometimes like, 'I cannot believe I work for this schmuck and doesn't know any of this.' But he was a great teacher and he would teach me a lot and then I would recall a lot of it and I would grow and then I would read a lot of the stuff that our technologists did. So, like, you know, for a guy who is, I don't know what I am, a baby boomer, whatever. I'm born in 1965, right? Like, who missed like the computer age, if you will, in a material way. Like when I was in college and law school, I didn't have a laptop. When I did my law review note, I had to go to like a room, the computer room, and type it out, right? You know, it was like we didn't have laptops, right? So, and to this generation now, our technologists, it's like an appendage. And so, it's a different language. So to be able to interact with them on a, you know, kind of a pure managerial but a pure basis, you know, that's been a struggle but a struggle that I'm willing to undertake.
Yeah. And I love what you said there. It's, you know, and it's asking the question providing context and I suppose the key thing if you're asking the same questions several times then that's when it's going to irritate people.
And we referenced your daughter, Rachel. I haven't met her. I've met your wife, Melissa, who's fabulous. But you, in our fireside last year, you spoke about Rachel, who's a STEM graduate working at a PE firm and I was just curious because I've worked with a lot of your female leaders.
No, by the way, they're no longer called PE firms. They're alternative asset managers.
Alternative asset managers. Sorry.
They do more than private equity. Anyhow.
