Andrew Ross Sorkin
Journalist and Author
“I do think they're genuinely curious. They're on the phone asking everybody a million questions because they want to know how to think about these things. They're talking to their employees. They're asking them about their lives. I think some of the great leaders of great companies have a genuine curiosity.”
Summary
In this episode of Leadership Matters, Alan and Andrew Ross Sorkin discuss the traits of successful leaders.
Andrew worked under Stuart Eliot at the New York Times before, during, and after attending Cornell University. In 2001, Andrew founded “DealBook”, an online daily financial report published by the Times. He is also a co-anchor on SquawkBox.
In this wide-ranging conversation, he discusses how persistence trumps talent and gumption, in terms of success. He and Alan reflect on the increased attention on CEOs in terms of moral leadership, and Andrew commends leaders that take a decisive stand.
Mentions & Resources in this Episode
Too Big To Fail is Andrew’s book about the 2008 financial crisis
DealBook is the New York Times’ daily financial newsletter
Squawkbox is CNBC’s morning news and talk program
Stuart Elliott is a journalist for the New York Times
Warren Hoge is a journalist and the former Chief of the London Bureau for the New York Times
Guest Bio
Andrew Ross Sorkin (born 1977) is an American journalist and author. He is a financial columnist for The New York Times and a co-anchor of CNBC's Squawk Box. He is also the founder and editor of DealBook, a financial news service published by The New York Times. He wrote the bestselling book Too Big to Fail and co-produced a movie adaptation of the book for HBO Films. He is also a co-creator of the Showtime series Billions.
Follow Andrew on his website, AndrewRossSorkin.com
Clips from this Episode
CEOs that are willing to make tough decisions in order to do good
Modern companies that choose to speak out & take a moral stand
Back in March, America needed to make a large, systemic COVID-19 testing program
Episode Transcription
Alan Fleischmann
Today, I'm joined by one of the most influential journalists and true renaissance man, Andrew Ross Sorkin, a CEO in his own right. Andrew is a columnist for The New York Times and editor-at-large of DealBook Newsletter, which has become the first read for CEOs and investors across the world. He is co-anchor of CNBC’s flagship morning show, Squawk Box, and is well known for being a co-creator of the hit Showtime drama Billions. He's also the best-selling author of Too Big to Fail, which chronicles the 2008 financial crisis. Many see Andrew as the conscience of Wall Street. He is unafraid to speak his mind on the most important issues of our time and is a forceful advocate for the role of finance to solve big problems, like incoming inequality, and social and economic justice. Andrew, welcome to Leadership Matters.
Andrew Ross Sorkin
Thank you so much for having me on.
Alan Fleischmann
I'm thrilled to have you on. We get to have some of the most extraordinary leaders and CEOs from public, private, and civil society on the show. And our listeners are also, in many cases, leaders in their own right who are looking to get inspired by other people's life stories and get words of wisdom and get personal about what you've seen in the world. What I love about you is that you do that in your day jobs, and you have jobs. You're not afraid to get personal, and that ties things back to what matters to each one of us. And that's kind of what we try to do here and Leadership Matters. So I am thrilled that you're here. I also do really truly see you as a renaissance man, because you do with such ease so many different things, that I don't know how you do it. And each one seems to be your number one passion and focus.
Andrew Ross Sorkin
It's a privilege. I appreciate you saying all those things. I will tell you, none of it is with ease. And I don't think anybody who's had any success. I don't think it's with these but hopefully, it looks that way.
Alan Fleischmann
No, it looks, I wouldn't say easy. Because you can't work the hours that you do and juggle what you do if it were easy, but you do it with ease. You look like it's with ease.
You know what, I will say this. And I think you may feel the same way about your own quote, unquote, job. I don't feel like I've ever worked a day in my life. I truly feel that way. I feel blessed. I feel so blessed in that way to find opportunities and things to do that I just love doing.
Alan Fleischmann
I love that. And there's definitely something that keeps me passionate about what I do every day. I watch you closely and see it's a big part of who you are. This insatiable curiosity. I mean, every human being that I see you meet is someone you just you're fascinated by quickly if they're worth being fascinated by. Not everybody is.
Andrew Ross Sorkin
You know what, that's not true. Can I say something about that? There is something fascinating about everybody. And occasionally, you meet somebody where you overhear someone say, Oh, that person's a dud, or they're not interesting. If you spend enough time with somebody, you will find that nugget, that thing that really makes somebody unique and interesting. I have found even people that may be despised and hated and despicable, in many ways to be fascinating, utterly fascinating.
Alan Fleischmann
You'll see a side of them. But also maybe that's a journalist in you and maybe that's the guy in you that became a journalist, but you ask lots of questions. And you unravel the story. You make something very human very quickly.
Andrew Ross Sorkin
My mother will tell you this started when I was four years old. I used to annoy all of her friends who would come over to the house and I would quiz them about their life and what they did, and why they did it. And for whatever reason, I think I was born with some kind of curiosity gene, to try to understand what drives people.
Alan Fleischmann
Let's talk about that for a little bit. The young Andrew. Your mom was a playwright?
Andrew Ross Sorkin
Yes, a playwright.
Alan Fleischmann
And your father was a lawyer focused on trade regulation and trust. So you must have maybe from them, which it seems like your life has a little bit of left brain, right bait brain dynamic going on in your house. So I'm just conscious it was something that was like you learn from one party who became part of you and another influence the other.
Andrew Ross Sorkin
I think, in many ways, they had a huge influence over me. I think I learned to write to the extent that I learned to write it all, from my mother. I still find writing to be a very painful exercise. I know, I'm supposed to be a professional writer, but I sort of had visions of people like Michael Lewis, playing the keyboard like a piano. And I sit there and it's very difficult. But I think I learned to write from my mother and to be able to try to find the drama in a story to try to find that the crux of the story from her. And my father was somebody who I think taught me a certain logic pattern. We used to sit around and discuss antitrust cases. I mean, you'll probably think this is crazy as a child that we would have debates about what just happened to Microsoft around our dinner table. But I think spending time with my father really thinking through the various permutations of an argument. And I think that combined, and together, frankly, with their support, because they're some of the most remarkable and I think supportive parents, I'm sure lots of children would say about their parents, but I feel especially so of mine, that i's helped lead to a lot of the things that are happening later.
Alan Fleischmann
Is your mom still writing?
Andrew Ross Sorkin
My mother is still writing. And if she was on this broadcast, she’d be upset with me now, because I don't have a play to promote of hers right now. But oftentimes, in non-COVID times, we have lots of places to promote. And my father is not practicing but teaching law at Fordham Law. And he was teaching law at Yale Law School. So they're still quite active. I need brothers and sisters. I have a sister in the finance business, who lives in Denver.
Alan Fleischmann
Oh, wow, a great place to live. That's great. And then I also think of you as this renaissance man, Drew. You got an entrepreneurial bug really young. The difference between an entrepreneur and a non-entrepreneur is someone has a big idea and then does something with it. You seem to do a serial amount of things when you were a kid. And you said, I'm going to do that. And you did. And then you started sports magazine when you were 15. And you’ve been writing ever since.
Andrew Ross Sorkin
I never wanted to be a journalist, I should be very upfront. The idea of being a journalist was not on the list as a child. What was on the list was being quote, unquote, in business. And in particular, in the media business. I was always fascinated by the media business I watched too much television as a child, but I was just as fascinated by the advertisements as I was by the programming itself. I used to read AdWeek, and AdAge, and all the trades. And in particular, I used to read a columnist named Stuart Eliot, who was my hero in so many ways because he wrote about the advertising business. Most people picked up the New York Times every day, and they'd go to the front page, or they go to the sports page. I would go usually to page C four, or five or six, which was in the business pages, which is where Stuart's column is. It was about what was happening on Madison Avenue. And it was a bit more of a Mad Men age, of course, during that period. And when I was 15, I ended up starting a sports magazine at my high school. But I will be honest with you, it wasn't that I was necessarily interested in sports though I follow the Knicks and loved Michael Jordan like everybody else at that time. I started the magazine in large part because I thought it was an opportunity to sell advertising and get the advertiser’s message in front of students inside a school. That was the play. So it was much more of a business than a journalistic effort in that regard at that time. And that really led to a role that I took on as an intern when I was 18 with Stuart Elliot. The sports magazine, in my high school, we tried to turn into a national sports magazine. The New York Times wrote a brief story about it back then when we were trying to build it. It ended up by the way flopping and failing quite miserably, but one of the great educations to this day of my life, and really because of it, I ended up writing Stuart some notes, some letters and calling him and calling all sorts of people to try to get to him. And eventually, he decided that he would be kind enough to take me to lunch on a Sunday and take me on a tour of the building. Back then there were no internships for high school students, as he used to say, this is a Union Shop. We can't do this. But somehow he was kind enough, or maybe I somehow persuaded him to allow me to come there for five weeks for free. I was an unpaid intern, we could talk about the white privilege and other things that are related to that today, in retrospect. But I ended up going there. I used to stand and wait for him in the morning. And I used to get a visitor pass every day because I was not supposed to be there. I was not on the rolls of anything. And by accident, it was about three weeks in, there was a woman named Felicity Behringer, who I owe much of my career to in addition to Stuart, who had no idea who I was, I was wearing a suit trying to look like I deserve to be there. And she overheard me talking about this thing called the internet. This is now in 1995. Back when you can see the word modem, a device that transmits data over a phone line. I mean, that's sort of maybe dates me a bit, but she overheard me talking about it. And she said, Can you write a story about that? And she didn't know who I was. She thought I was a news clerk or something. And I went back and I told Stuart and he dropped the F-bomb. But he said, you're in high school, go tell her and go tell who you are. You can't do this. Somehow, I don't know, we decided not to tell her at least initially. And I ended up writing the story. And Stuart did a lot of editing. I showed it to my mother first. And they ended up running the story in the newspaper. And that was the beginning of my career as a journalist.
Alan Fleischmann
There's so many things that I want to unravel. The idea that you were so entrepreneurial. The gumption part of you. You always hear every great story about someone embarking on something, there's always a part of the story, which is that I didn't give up that persistence part. The fact that you kept calling me or writing this guy who you admired from afar. You said, I want to come work with you. Right? It's like he gave in, you know?
Andrew Ross Sorkin
Well, I think there's a lot to be said about persistence. To me, persistence always trumps talent. I believe that to this day because I think I'm probably more, frankly, persistent than talented. I know so many people who I think have genuinely true talents. But I do think that persistence really matters. And I am somebody who believes that most people don't really like to say no. It kind of hurts to say no. Actually, most people want to say yes. So if you can somehow get yourself in front of somebody and you can push and you don't want to seem too aggressive, because sometimes that can be too much. But if you can push and not just appear, but actually offer some sense of value to the other person, I think there's a tremendous opportunity for people who can do that. My sense has always been that persistence matters so much more than talent. I genuinely believe that. And I think if you can get yourself in front of somebody and try to offer some sense of value, there's a great opportunity because nobody wants to say no to you. Saying no hurts. I hate saying no, I want to say yes. Everybody wants to say yes.
Alan Fleischmann
I think it's the gumption and persistence part. And it does speak volumes, which is a very important issue today of mentorship. This idea that you found a mentor or mentors, it sounds like, who've been very valuable to career but Stuart, obviously to your point, wanted to say yes, and he did. And then, therefore, you got in the gate.
Andrew Ross Sorkin
Yeah, 100% and he was a great mentor and a great adviser, and a great friend to this day.
Alan Fleischmann
So let's fast forward a little bit of college. You wrote for the Times still while you're in college.
Andrew Ross Sorkin
I went to Cornell University, and during my time at Cornell, I wrote a number of stories. My junior year, I went abroad to London. Second semester was at the London School of Economics and ended up writing—I used to go to the after school—to the London Bureau for the New York Times, and I’d write in the afternoons. And it was one of the great experiences of my life. I worked for Warren Hogue, again, one of the great mentors of mine, he was the bureau chief at the time. And then, of course, when I graduated from Cornell, I was thinking about lots of different things I could do. I didn't think I'd get a job at the time. So I actually desperately wanted a job and didn't look like they were going to give me one and then randomly, towards the end of my senior year, they called me back up and they said, Hey, what about going back to London and covering mergers acquisitions for the paper. Because I’d done some business news before and this was at the peak of the M&A boom of the late 90s. So it was a very exciting thing. But again, I didn't think I'd be a journalist, I thought I'd go there. I had so many friends who were going into consulting jobs. And the idea was they were going to go work in a McKinsey or a Bain or BCG, they learn about different industries, they meet interesting people, and then they'd go to law school or business school. And I thought that's actually a little bit of what this might be. I thought I'd go do M&A with lots of different industries. I covered pharmaceutical deals, and banking deals, and media deals. And I thought I, I've learned a lot about how these businesses work, maybe meet some interesting people along the way. And then I'd go off and follow a more traditional path. And of course, I loved that so much, I never left.
Alan Fleischmann
And so you came back to the States, you ended up finishing college.
Andrew Ross Sorkin
I finished college and then came back to the states and then went back to London, and I was in London, and then returned in 2001. In 2001, I continued covering mergers and acquisitions. But that's actually where I also got a little bit of an opportunity to sort of flex a little bit of these entrepreneurial muscles because I had this idea for this thing called DealBook. And so in a way, I got to do the journalism park that I didn't think I would necessarily do, but then also got to be a bit of an entrepreneur in building a small business.
Alan Fleischmann
It's amazing to me because I know you and I know you're genuinely a very humble man and I love that about you. But do you ever look back and then say that thing that you created with the DealBook—that actually did spawn, create. Other media publications came after that? I mean, so many folks have, I won’t say copy the DealBook, but certainly have been inspired by the DealBook in other media.
Andrew Ross Sorkin
You're very kind to say that. Look, I'm actually very jealous of all of those creations. So I look at Politico, of course, and Axios and Business Insider with great admiration in so many ways. And I appreciate you saying that, but there was something in retrospect. Now back then, we didn't really know what blogs were. The idea of linking out hyper-linking to competitors seemed like a crazy idea. The New York Times, by the way, that idea that we were going to link to the Wall Street Journal or the Financial Times, people thought that was anathema. That was nuts. So yeah, there was something very exciting about it.
Alan Fleischmann
And the idea of taking something and creating another brand within a very prominent brand like the New York Times. Now you see that everyone's trying to come up with their own lane. That didn't exist until the DealBook, really. I mean, that was something where—I mean, others will say there are other things, I know. But honestly, you created something that had its own identity, even though it was New York Times.
Andrew Ross Sorkin
So again, I appreciate you saying that. I will say that being part of the Times though, and it's been my home in so many ways for now 20 plus years has been one of the great blessings of my life. And I also think that DealBook has been a great beneficiary of that. I say that because I think a lot of times, you look at Axios, or Politico or these things that ultimately got spun off the journalists who have left a larger organization, I think there's been a great benefit by being part of the Times.
Alan Fleischmann
Yeah, so let me ask you about this. When you think about the best of times or the worst of times of journalism, you’ve been through that too. I mean, because when you started your career, and you weren’t trying to be a journalist, you're looking at the world and you're saying this is a great way for me to do all these different things that turned out, you did a lot of different things, but it's been a mainstay part of you. Media has been going through its own struggles, as it’s digitized, as the world changes, the industry suffered. But it’s also you're living through a time right now, what I would argue, we've never paid more attention or felt more needing of journalism. So I guess I'm just curious. And I want to get into like the leaders you've interviewed. I want to get a sense of leadership. But I want you to give us an assessment a little bit here of—.
Andrew Ross Sorkin
So this is a very difficult question, actually, for me, because oftentimes, I'll go speak at a university, or I'll talk to kids in high school or college, who invariably will say, should I try to go into a career in journalism today? And the answer to me is not actually, as straightforward as you might think it should be from someone who loves this business as much as I do. Because I know that I'm one of the lucky ones. I mean, truly lucky ones. And it's a hard, hard business. It's been a struggling industry. And I'm thinking more in regards to the print industry and online industry than necessarily the TV business. Though, I think that the TV business may ultimately run into the same challenges that the newspaper business did. Now, of course, right now, the New York Times as a business and franchise is excelling in all sorts of ways, including as a business again, very happily. But in terms of people who plan to make their livelihood this way, for a lot of people, it's not the easiest career. And so what I tell people is if you genuinely love it, if you love asking questions, I mean, I will say that is one of the things that's so fascinating of the business. You're basically paid, you're given a license to ask people questions. If that excites you, it's worth a try, right?
Alan Fleischmann
And if you can't help but ask questions and you want to be paid for it. The other thing I see is who you get to meet, which I want to talk about in a second. You're listening to Leadership Matters on Sirius XM, I'm your host Alan Fleischmann and I'm here with Andrew Ross Sorkin. And we're talking about his journey as a leader, entrepreneur, influencer, and frankly, thought leader, as both the co-anchor of CNBC Squawk Box, as the founder of the DealBook at the New York Times, as a journalist, and then obviously, as a best-selling author, and co-creator of a television show with Billions. And then obviously Too Big To Fail, which I want to get too. Too Big To Fail was a huge success. Obviously, I'm thinking about it a lot now. Because there's a lot of thought about what happened then what happened right now 2008 financial crisis. And now I'm sure you asked us a lot. There's something about writing the first draft of history. I'm sure there's a part of you that every day when you're going on television, or every day when you're editing and writing for the DealBook, you're thinking, am I part of history right now? You are. You're chronically things that, frankly, we're gonna look back on. I'm just curious, did you know it was gonna be a breakout success that it was? It really is truly the blueprint of that time. And you're such an optimistic guy. But does that create also a fascination about crisis? Because you've become the guy who shows us the way during not only the good times the bad.
Andrew Ross Sorkin
Well, so I am fascinated, I shouldn't say I'm fascinated by crisis. I'm fascinated by bad news. I hate to say that, but I think bad news is unto itself fascinating. I did not know, at all that Too Big To Fail would have the success it had. I remember when I got the book deal with Penguin at the time. I told my wife I'm gonna have to get the advance back. Because how am I going to write this book? I’d never probably written more than a couple thousand words. I think I'd written a magazine story at that time. So the idea of writing at 100,000 words, I think Too Big To Fail ended up being 120,000 words. So yeah, I just thought it was inconceivable. My mother would tell you, given how difficult was for you to write a term paper, how I was going to write a book. And so even I think I still find it somewhat inconceivable that it happened. But I've always been interested in the story about people. And I think that oftentimes, especially in a crisis, we look at these large institutions and these big systems. And that's how people look at these stories. But I always thought that if you told the story through people and their motivations and what led to their thoughts, and why were they doing what they were doing, it all becomes a lot, in some ways clearer. Because oftentimes, we have very black and white views of what's happening. We're reading the papers every day, or watching television, and we have these we have the black hats and the white hats. And we have very strict thoughts about these things. But if you can get inside the room, nothing's black and white. Never is, it's all very gray. It's all shades of gray. And if you can tell that, if people can see that. If people can see how people were making decisions. You can agree with the decisions disagree with the decisions, but it changes your perspective. And that's what I wanted to do more than anything else. And that's what I try to argue with all my journals.
Alan Fleischmann
Yeah, that's why I love the way you write. And the way you approach. Even when you do your conferences, you're bringing human beings together and talking about not only their businesses but their ideals or visions, their personal sides of them. And that's a huge part of what we love on the show. And what I love to do in my day job is, at the end of the day, we are about people and you connect with companies, or you connect with franchises or enterprises, because you want to know who the leadership is. I mean, it's not a disconnect. Your curiosity gets personal. I mean, like, Who are you? And why are you doing this?
Andrew Ross Sorkin
Totally, because people have this view that business is oftentimes about numbers and math. And that's a part of it. But it's really about the people who are oftentimes both leading the company. So I'm fascinated by the leaders at the top. But I'm also so fascinated by people frankly, at the bottom and the relationship between both.
Alan Fleischmann
What's really fascinating, I had the great pleasure once of being in a dinner where I spent really high-quality time with Warren Buffett. And the two of us talking, and he told me that—and he was sad because things were changing around the annual reports. He used to love reading annual reports like you would read a biography. And then when he was looking at a company he would buy, he actually could walk away after several meetings and tell you all about the family tree of that person. How many siblings they had, where they came from, he never forgot it. So when people think, oh, Warren Buffett and all the number crunching, he cares about numbers, and all these accountants would come running in the room. He would walk away often with a feel about the person where they came from, what they hungered. And when you think about it, he barely ever changed investing when you invested in the company because he actually said he was investing in the person or the people.
Andrew Ross Sorkin
And I would also say a great judge of character. A great judge of character.
Alan Fleischmann
Yeah. So tell me a little bit about that. Because you, I mean, you obviously decided to get—Billions is a huge success. It's a favorite show for so many people. I imagine that was also a concept you came up with because of the people. I mean, you looked and said that we can actually do a show around this crazy world of billionaires and telling it in a really personal way. I mean, what was the inspiration there?
Andrew Ross Sorkin
Well, for me, I just worked on Too Big To Fail. The book had been published and then I ended up helping produce a film, Curtis Hanson was the director of Too Big To Fail, an adaptation that ran an HBO and after that project, I had such a great experience learning so much about film and editing and how something like that could be put together. I thought to myself, you know what, nobody's ever really done a TV show. And this is now 2010/11, about the world of hedge funds. And at that time, with this sort of billionaire class on the rise, I thought that was such a unique world that should be explored. Now I will tell you that, at least initially, because I remember going to California, this is again back in 2011. And started to talk about well, could you do a show inside a hedge fund and what's it like and to me, it was not just being inside the hedge fund, it was being inside like the family of a hedge fund. And everybody said to me Sorkin, you're an idiot. Nobody wants to watch a show about Wall Street. People don't like Wall Street. People have tried to do dramas around Wall Street before. They've all failed. This is a terrible, terrible, terrible idea. And I went home. And my wife was watching reruns of Law and Order on USA Network, because they're always doing these Law & Order marathons. And I'll never forget saying to her, you know what kind of TV shows work? Procedurals. People love the law. Why do they love the law? They seem to understand the law, they get the law. And that, for me, at least was a bit of a eureka moment. Because I thought to myself, okay, well what happens if you were to pit the legal world against the hedge fund world? Now it's a bit of a cat and mouse story. People get that. It's a bit of a Trojan horse actually into this other world. And what happens if you set the two reads against type. So actually, the hedge fund manager who think you're not supposed to like. You may fall in love with. And maybe the prosecutor who you think is doing everything in the name of right, is just as conflicted as the person you think you don't love. So that was sort of, for me the initial sort of gestation period of it. And then I happily went on a long tour of meeting lots of different people in the business but ended up meeting Brian Koppelman and Dave Levine, who were my co-creators and the showrunners of the show. And we wrote the pilot in 2013. Maybe we sold it in 14, and it aired in 16. So it's funny. TV, there's a long sort of gestation period for how these things come to be.
Alan Fleischmann
It’s like writing books, too. It's a long gestation period for that. I mean, I imagine there must be one of the great moments of joy because people talk about it. The show is so popular. People still are looking at the early parts of the series now. I'm sure there's a lot of binge-watchers right now that are catching up on that as well.
Andrew Ross Sorkin
Oh, no, it's funny because you think to yourself, you have articles that people read, or maybe they read Too Big To Fail or things like that. But millions of people watch TV, and they watch Showtime and they watch dramas and they watch Billions and knowing that people get entertained by it. As one of the proud Papa's of it, it’s a thrill.
Alan Fleischmann
That's so cool. Tell us a little bit about—you interview some of the most extraordinary leaders, I mean, business leaders, globally. You tell the stories of other people, you ask questions, you've gotten a great team at the New York Times. What are the collective traits... I can tell you that you fit. I get to work with leaders and CEOs every day, we have them on the show, I get to work with them. You have those traits of curiosity, the idea that you ask questions you don't necessarily come in with all the answers, which is why I think you would have been terrible as a management consultant. Because they always come in with a PowerPoint, they don't necessarily want to hear what you have to say, I hope I don't offend anybody, but I may have. But I'm curious what traits you see collectively across the board among leaders/ You also deal with a lot of diverse leaders. So it's not like they all come from the same place.
Andrew Ross Sorkin
So okay, so I think there are two qualities to a great leader, and one of them, you probably will know. And the other may be counterintuitive, I don't know. The first is I do think they're genuinely curious. They're on the phone, asking everybody a million questions, because they want to know, they want to know how to think about these things. They're talking to their employees. They're asking them about their lives. They're running into the janitor, and they care about the janitor because they want to understand the janitor’s experience at the company and they walk into a store and they are talking to the person on the floor of the store to understand how different product is selling. You go back and think of the great merchant kings or the merchant princes of the world. I’m thinking of Mickey Drexler. He would walk into any store. I remember having lunch with him once, and he looked at the bill. And he started asking the waiter why is the water costs this and why is it? I think some of the great leaders and have great companies have a genuine curiosity. But the other thing I was gonna say, this may be maybe more counterintuitive. I think that a lot of the great leaders I know—I wouldn't say just great leaders, but people who have had great success are actually remarkably insecure. That actually a lot of what's driving this. So I spend a lot of time trying to think of what's why people are doing what they're doing. A lot of people have a lot to prove. And I say this, by the way, this is true myself, I know. But if you look at some of the great Shoot the Moon success stories, I think a lot of those leaders are trying to prove something. Sometimes, they're trying to prove something to themselves. Sometimes that's trying to prove something to their mother. Sometimes just trying to prove something to somebody else. And it's not just can I create the thing? It's then can I stay there you can I make it better? And I've always been surprised by that. And I think the real trick is, I think about this even about my own children, is you would normally say to yourself, Well, I don't want to create insecurities in my children. So the question is sort of how do you create a healthy enough insecurity, that they're driven? But not an insecurity that's so dis-motivating that they can't move? And is there a way to create that balance? I don't know. But I think about that a lot.
Alan Fleischmann
100% when you think about the people that you most admire who have that persistence, that tenacity, they're confident, but there is this vulnerability. They've overcome adversity, and they're scarred. And the scar tissue may be tougher than normal tissue, but they're scarred. So you will see them, not panic, but they'll never let good be good enough, right? And then with your own kids and you're thinking your job as a parent is to protect them from all bad things.
Andrew Ross Sorkin
Correct.
Alan Fleischmann
But the reality is you want your kids to have diversity, overcome it, understand what risk is, but you don't want them to fail. Although failure is what made a lot of the people we admire the most so successful.
Andrew Ross Sorkin
How do we do it? How do we do it? I don't know. We’re not going to know till, well, in my case, my kids are so young. We'll find out we'll find out.
Alan Fleischmann
The truth is, life offers adversity on its own. And you know what? That's part of the deal. Do everything you can to protect them and they feel loved and secure with hope when that adversity happens. But your parents did something to do, or maybe your mother said that you were wired at four. I don't know, maybe that's the answer is that some of this is wiring and not just the environment. Or wiring that led you to take advantage of the environment. Maybe it's both?
Andrew Ross Sorkin
No, no, no, you should know I think I'm gonna fail in every moment. At every moment I think it's over. I'm convinced at every turn, that something bad's gonna happen. You may think this is being humble. It's not humble. It's I feel lucky because I know that so many things broke my way. And could have gone
a totally different way you feel like you can't be that.
Alan Fleischmann
I always refer to myself as the chief worrier and chief warrior. That I'm always worrying, but we advance. But you have a wonderful disposition, optimistic people think I am, and I am. But they have no idea how much I worry. And to your point, it can't get better than this. And so, therefore, God forbid, it's only going to go down from here.
Andrew Ross Sorkin
It’s very funny you say that, because the other thing about leadership, which I do think is true, is great leaders, I think worry, but they worry privately. I don't think that great leaders worry publicly. I think they worry privately all the time. I think that they may be an anxious ball, but they don't project it.
Alan Fleischmann
I guess part of their role is that they have to inspire. They have to make their people—imagine this, you're living through it right now. We're living through one of the most complex leadership moments, probably ever. The idea that we're communicating through zoom, and we've got everybody at home, and there's no more hierarchy the way it used to be, the response as a leader, you yourself with the different folks you work with and then the folks who work and talk to, they got to show confidence right now, but vulnerability too.
Andrew Ross Sorkin
But that was the other thing I was gonna say. And I do think this has been a shift probably over the last three to five years. And it's a word I hate but I think we have moved to a moment where people do want to see leaders be vulnerable to be quote-unquote, authentic. And so how do you balance this idea of showing that set sense of confidence and not try to pretend you don't worry all day long, even though you may be knotted up inside? And striking that balance I think is a very tough challenge.
Alan Fleischmann
I mean, one of the things that's been very interesting to me and not only interesting, but it's been wonderful to see front and center is that we started talking you were a big part of it. You wrote a extraordinary piece at the end of the year of 2019 that I thought was heart-wrenchingly honest about the gap. The realities of people living and working out of their car, but they're not considered to be in poverty. I mean, this idea that we wake up and understand. Before inequity became the Great Awakening, you were already very personally striking out in your platforms and your writing in particular on the need for, if you're going to talk about stakeholder capitalism, you better really talk about all stakeholders in a different way. One of the things I've been most pleased by is the idea that these leaders are coming out. That thre are CEOs who are speaking about stakeholder capitalism in a way that you hadn't seen before. And obviously, after the death of George Floyd, and this whole awakening, and talking about systemic racism and inequity is there and the Black Lives Matter movement, and then you're talking about how do we work with our stakeholders? I'm just curious. Are you seeing a fast forwarding authentically of leaders doing things differently? And trying to address this differently? Are you seeing a gap of my leaders, those who are and those who are not?
Andrew Ross Sorkin
I’m going to say this and is I hope this isn't an unsatisfying journalistic objective answer. I think it's a little bit of both is the real truth of it. I think there are genuine leaders who are doing remarkable things. And I'll give you an example. So I would say, this isn't on the issue of race right now. But if you look at Ed Stack who runs Dick's Sporting Goods. He made a decision about two years ago now, to not sell guns in his stores. That is true leadership. I mean true leadership, because he was making a moral stand, a moral decision that can have a real impact on the economics of his business, on the reputation of his company. And it was not an easy decision. It was a bit of a jump ball of even whether we're even whether it would work. And happily for hi, it it. But that was a hard decision. I think there are a lot of CEOs today and I commend them. And I think we're all on a journey. So even those that haven't taken the full step. Look, if you put out a press release saying something, I'm not gonna slap you around. Because I think we're on a journey. Even if it's just lip service, it's a journey. It's the beginning of a journey, hopefully. Do I think that all CEOs are really willing to take on truly hard decisions that would potentially hurt their business in the short term, the benefit of long term? That's harder. I'm not sure we're totally there yet. I do think actually, though, and I'm heartened on the issue of race in this country, that I think there is a real conversation happening at the board level and managements across this country right now, about what it means to truly have a diverse management team. What it means to have a diverse board. And I think that people are taking that very, very, very seriously. And I think over the next several years, you're going to see a real shift in terms of what the profile of some of these boards and managers look like. And I think especially as this next generation comes up, I'm hoping that we're not going to have the conversation we do today, which is that there are really only four black CEOs in the Fortune 500, which is a disgrace.
Alan Fleischmann
Yeah, horrible.
Andrew Ross Sorkin
But I'm hoping two, three, four or five years from now, that that would be a very different story.
Alan Fleischmann
That's great to hear. Obviously, we need that direction and that compass that says we're moving.
Andrew Ross Sorkin
I think we're moving in the right direction. I mean, I think the hard part about this is we all want move so fast. And as fast as I would love us to move, and we would all like to teleport ourselves to this version of some form of a future. I think the flip side is that we have to be careful about the complexities of doing it. And frankly, not moving too fast. Because what I don't want to happen is I don't want there to be a backlash, I don't want there to be a situation where people get promoted into roles that they might not be ready for. And then they don't succeed. And that to me, would be the worst of all. And so I think trying to find the balance is going to is is a very tricky, tricky thing to do.
Alan Fleischmann
Which is why we need to have it at the governance level, like you were suggesting at the board level, but also pipeline of talent, right? Real scalable mentorship as well, where you're seeking talent on the board of Morehouse. So how do we actually create those pipelines of opportunity, as well? One of the things also, which has been a big shift, and I know you've thought about it, talk about it, and deal with it. There's this expectation that no longer government is doing the things that it would be doing normally in the days when you were starting a career. We look at corporations differently. Corporations when it comes to public policy. Corporations and CEOs when it comes to values. Things that you would have thought your everyday politician or the federal state level or even local level would be doing. They are or they should be. But we're looking at corporate leaders to do the same.
Andrew Ross Sorkin
So I wrestle with this, because I am oftentimes advocating in columns and the like, and on television that corporations need to speak out, they need to take moral stand. If they claim to believe something, they need to actually do it. And increasingly, that has a political element to it. What I wonder is whether this is just a particular moment in our in history and in time, which is to say that right now, Washington feels so broken and so devoid of leadership, and I'm not trying to make a comment on this administration or anything else. But the larger system in Washington right now. That as a result, the business community is having to step up and take these positions that they otherwise wouldn't need to take because they would be able to follow the rules of the road that would be set by our democratic process. For all of the the backlash against Milton Friedman today around his thoughts around profit and purpose and the social purpose of a company being to make profit. One of the things he said was that he didn't want business leaders in politics. He didn't believe it was the role of business leaders to get involved in politics. But the reason he said that was because he said they're unelected. They're unelected. And that's true. They are unelected. And so many of them have become sort of unelected statesmen. And should shareholders be supporting that? Should consumers be supporting that? I think there's some real questions about it. I'm not 100% sold on all of any of it really.
Alan Fleischmann
The balance of it. Yeah.
I think this may be a particularly unique moment that companies need to step in. And in many ways, I would love it if we had a functioning Washington that actually created real rules of the road, so that you didn't have to have unelected business people get involved.
Alan Fleischmann
And I don't want to get you involved in politics here. Because I know that wouldn't be fair. But you do talk to a lot of officials, both public and private and civil society leaders. If you were a politician, which is the one area you've never been, and I don't see any interest, though, and you're doing it. If you were Washington, or if you were Albany or if you were Sacramento, what would you be doing differently right now? Are there things that you think should be done in partnership with private sector that isn't being done? So that we would be able to avoid some of the things we're gonna have to deal with in the coming months or years.
Andrew Ross Sorkin
Well, there's one particular thing I would do. And it's unique to this COVID moment. It's not a larger idea. And that is that I'm convinced that back in March, this country needed to make a big effort in a large systemic testing program for the country for COVID. That if we had a large testing surveillance program, effectively, you could recreate some real confidence in the system, irrespective of when you get a vaccine or when you get a therapeutic. And by the way, I think we're going to be living with this for many years. Even when we do get a therapeutic and a vaccine, we're still going to be living with some version of this for years. And so if I told you that when you got to the airport, every single person who went on a plane was tested, I think you'd have great confidence getting on that airplane. I think if I told you that if you went to a public school in the United States that every student and, frankly, every parent and caregiver who goes to that school in the morning to bring their kids to school or take them home has an opportunity to get tested on a on a weekly basis, you would have great confidence in the system. I think that would change the entire dynamic with which we're even having this conversation. But that probably needed to happen back in March and April and probably needed to involve an investment in the hundreds of billions of dollars, but I think it would have paid dividends in ways that we will be paying unfortunately for for many, many years, because we haven’t done it.
Alan Fleischmann
It sounds like there's still time to do it but we wasted time.
Andrew Ross Sorkin
I think it's completely wasted time. I would still do it if possible. The hard part today is that if you're an investor or a venture capitalist and people are approaching you with different new testing devices and this and that, there's a lot of people who say I don't know if I should invest in this because who knows when the vaccine is going to come. Who knows about the therapeutics. I do think you need to have a public-private partnership and there needs to be some form of government backstop and I think that it is demonstrably in the public interest.
Alan Fleischmann
How do you explain the stock market right now? I mean, how do you explain that?
Andrew Ross Sorkin
Not well. I scratch my head often. I can give you the rationale for why the market has moved the way it has. I'm not sure I personally agree with it. But I think there's a couple of arguments to be made. One is that the Fed is providing so much liquidity and printing money in remarkable ways. And therefore, you probably want to own stocks. You want to own assets because cash is going to be worth less and less over time. I think that if you are part of the S&P 500, it means you're one of the biggest 500 companies around. And guess what? The biggest 500 companies around should do better over time, because so many small businesses in this country have been disadvantaged during this period. So if you're a Walmart or an Amazon, and I give them enormous amount of credit for what they did during this pandemic, but they've also been advantaged, got advantage by the government. And they will consolidate power. And so those 500 companies will do better and better and better. They're gaining market share. And so if you own one of them, that to me, makes a lot of sense. Now at these multiples, that's a harder question.
Alan Fleischmann
One of the things that we're seeing right now, which I think is unprecedented. I get to have a bird's eye view in many of these collaborations that are occurring between companies. You're seeing sectors where there's been enormous historic competition, where maybe because it's those who are involved in science will be more more collaborative because of the race for the vaccine. But there are other industries, we know where there's collaboration going on. Is that happening in the real way? Is that really happening at scale? Is that something that you are noticing as well? And then I'd love you to share a little bit of what makes you feel—the non warrior side of you, the optimistic side of you during the pandemic, what are the things that you're seeing you hope do scale? Collaboration be one of them, I hope?
Andrew Ross Sorkin
Well, I'm actually a believer—and it's funny, because I just interviewed Reed Hastings, and we were having a conversation about work from home. And he said he thought there was nothing good about it. There was nothing better to him about a zoom meeting than a meeting that can happen in person. He thinks a meeting person is so much better. I may be on the other side of that argument. I think that there are certain meetings that need to happen in person, there's no question that they need to happen in person. But at least from what I do every day, I feel like we've been remarkably productive. I feel like when I work with our DealBook team, we've hired new people into the team, even during this period.
Alan Fleischmann
Who you only met on zoom.
Andrew Ross Sorkin
And I did the job interview to decide to hire them on zoom. Yes. And I give the team at Northside credit for being as creative as ever, if not more. So because I think they met the moment. We’ve always been trying to meet the moment. So I think there are some benefits to this. What I'm trying to figure out about the clinical benefits to a remote life is how do we keep the best parts of this when the world goes back to normal? And are the best parts of this also, though, at odds with regular life? And that's what I'm not so sure about? I think I think they may be. So look, I find people are collaborating. People are picking up the phone more. I feel like we're back in the 80s and 90s when people just pick up the phone. Six months ago, people would schedule calls. They'd send you a text message and you'd send them a text message saying what can I call you this afternoon. Now people pick up the phone and if the other person picks up, they pick up. If they don't, maybe they leave a voicemail or send a text message and they call you back. There’s a spontaneity about it.
Alan Fleischmann
And I think that's true of leaders too. And you're more accessible than you've ever been because you're home. There’s no airport or I'm running to a meeting or I'm somehow rushing to a restaurant for another meeting, board meeting. None of that's happening where you have to leave your home.
Andrew Ross Sorkin
So it's very interesting because some people think I would actually argue that there are a number of CEOs and leaders I know who I think are more present today than they've ever been. In large part because if you're running a global company, oftentimes you're quote unquote leading that company from from 30,000 or 45,000 feet in the air.
Alan Fleischmann
The other thing too, you obviously are great convener and the small, medium, and large level because you pulled together this incredible DealBook, you've also done amazing convenings of your own with the New York Times. Obviously, I would argue CNBC, your platform there is probably one of the greatest computers on a daily basis. And you are doing it from home now. When you're looking at like, who you want to spotlight who you are spotlighting and who you think will have the spotlight, I’m ust curious. Is there a certain quality in a leader? Is there a certain industry or sector? Is there something you'd want us to be looking out for that you think will be the—if you had the perfect interview? Or you wanted to spotlight the perfect sector industry? What would that be? I want to put a lot of my last questions. I know we're running out of time and I want to try to get a few of those in there.
Andrew Ross Sorkin
Oh, goodness. I've interviewed them before, but I'd love to go sit with with Jeff Bezos right now. Right now, given the moment we’re in, given the the heat and spotlight that's on big tech, given what he's doing in space right now. Given the way he thinks about the future, and what the future looks like, and what progress looks like. And you're talking about great leaders, he to me is actually in very many ways at the top of the list, because—and by the way, he's oftentimes had something to prove. Because I remember back in the late 90s, when people call it amazon.com. Right. And people thought it was never gonna work, never gonna work, the whole thing was was crazy. There's no margin, they were losing money. This, this, and that. And he's proved them wrong. And I think that that's driven him. But I also think that he's had a longer time horizon. And I think that's another thing that actually is a significant differentiator between some of the best leaders and also best investors. Oftentimes, people are looking 1,2,3 years out, I think he's looking 5,10,20 years out. And if you can just change that horizon just even a little bit, that's a remarkable differentiator.
Alan Fleischmann
And this philosophy that he has of always day one. Every day is day one. That goes back to the insatiable curiosity or the the idea that that you can’t rest on your laurels from yesterday, which I think he's been a big part of it.
Andrew Ross Sorkin
He's one of those people that, to this day, has that curiosity. He'll ask you anything he wants to know about what's happening in the newspaper business. Now, by the way, he owns a newspaper. So he has a particularly unique interest. But he was always somebody who was interested in other people and wanted to understand what was driving them and what interested them. And I think that that's led to a lot of the innovation that he's helped create.
Alan Fleischmann
So one last question for you. Your wife. I hear you talk about her and she's an extraordinary influence on your life as wel, because she seems to be a very steady advisor, co-partner. And then you've got these kids. When you're talking about heroes when you're talking about the conversation you're having at home. Do you have heroes? Is your wife share her heroes? Are you sharing with your kids your heroes? Is there someone you would say to your kids you need to admire or do we not have heroes anymore?
Andrew Ross Sorkin
Oh, that's so interesting. It's a that's a very deep question. Because I do think that between media and social media, it's been a lot harder to have heroes than it used to be. It's gonna sound like some kind of cheesy cliche, I will tell you that my wife I do think is a super woman. And I say that often, or at least I tried to she says I don't say it enough. But she's a remarkable steadyhand. I often say that, I worry so she doesn't have to, but I think that she keeps the whole both of us so grounded and balanced. I don't know if I ever told you this. When I first met her. I was actually scared to date her because I felt like I met somebody that I couldn't believe I'd met them. And I felt like I know that my whole life like it was prenatural. It was like crazy.
Alan Fleischmann
Like it was destiny.
Andrew Ross Sorkin
Yeah, it was such a strange thing. I was so nervous I about the whole thing. I thought how can I never have met this person? I feel like I've known her my whole life. And I feel that way to this day.
Alan Fleischmann
Do you both have the same heroes are yours. Are you sharing your heroes with your kids?
Andrew Ross Sorkin
I feel like I'm gonna fail you on this answer because I don't know if we talk about heroes in that way. I mean, I think my wife is a literary agent. So she talks a lot about great authors and great writers and great storytellers. But I don't know if we talk about heroes in that way. Maybe we should.
Alan Fleischmann
So as we're wrapping this show up, and I wish we weren't because I'd love to talk to you for another hour. What is the next big thing for Andrew Ross Sorkin? Obviously, what I love about you is you don't give up on the things that you do every day. So it's not like you ever say, Okay, I got to replace this with another. I don’t know how you do it, but you do.
Andrew Ross Sorkin
I like layering more things on top of other things. By the way, my wife would tell you, she thinks that's not the best strategy. But I'd love to write more books, I'd love to produce, films and documentaries, and maybe come up with another TV show over time. But I think for me more than anything, being a journalist has been the great love of my life, oddly enough, with this sort of entrepreneurial piece layered on top, and by being able to have this license to ask questions, and satiate this, what feels like an insatiable curiosity, oftentimes, I think it helps drive and create so many other things. And I just to be honest with you, I just enjoy being part of this conversation and the conversationI'm having with you.
Alan Fleischmann
That's so nice. I will say, you bring trust to everything you do. So whether you're talking about a TV show that we love, now Billions, or a show you might produce or the things you do when you interview people on the show and Squawk Box, but also books and other interviews you do, honestly, there's a trust that if you're going to do it must mean something. And it must be valuable. What I love, though, about you, which I'm looking forward to seeing more and more of a just be candid, is when it becomes your point of view. You're not just the curious guy that brings it out of others, which you do beautifully. And probably brilliantly. It's when you start to say what you feel and you get passionate like you've done and very important points in the during this pandemic, and certainly in the lead up to it and before. Even then. And it's in those moments where you just tell us what we need to know. And you put that spotlight on and I encourage you to do more of that. Because when Andrew speaks, we do read it and we do listen.
Andrew Ross Sorkin
I appreciate it. I will tell you that I actually don't like to do it that frequently, in part because I'm always nervous I'm offering my perspective. And also because I think there's a lot of people who offer opinions every day, oftentimes. Frequent, constant opinion. And I think, first of all, it's it's hard to be right all the time. Let's be honest, you're gonna get a lot more wrong than you're going to get right. And so I'm hoping that I choose my spot.
Alan Fleischmann
No, I think if it is quality, not quantity, I look forward to it. I think you come out like you've been extraordinarily humble and thoughtful during this whole period of talking about systemic racism, inequality. You've asked questions, which obviously open our minds, but you've also told us what you feel. We had a conversation you and I about when you have people of color on. You're bringing the best-talented people to talk about what they do as disruptors of their industries, who may be a black man or a black woman.
Andrew Ross Sorkin
I remember that conversation. To me, it's important that we're having them on because of what they do, not to come on and talk simply about their color and their own story. Though I do think their own stories an important story to be told oftentimes because there's a modeling piece that relates to what I do.
Alan Fleischmann
Well Andrew, this has been an enormous pleasure to have you on Leadership Matters because you do tell stories. You are insatiably curious. You are an entrepreneur and I mean, 100% when I said we have leaders on here, CEOs, you are the CEO of many, many things. And we're grateful to have you on here and grateful for what you do on your day job. So thank you.
Andrew Ross Sorkin
Thank you so so very much for having me.
Alan Fleischmann
I love it. And I look forward to more. We'd love to have you back here again.
Andrew Ross Sorkin
You bet. Thank you.
