Charley Cooper, Chief Communications Officer For Block Chain Firm R3

You should know how to take advantage of opportunities when they are presented to you if you want to maximize your career potential. Listen to host J.R. Lowry as he talks with Charley Cooper about taking these opportunities, recognizing his passions, and focusing on what matters. Charley shares his incredible journey from bartending and waiting tables in Washington DC’s Georgetown neighborhood to working a Presidential campaign to playing a leadership role in a blockchain technology firm – with a wide range of stops in between.  He shares how he has carved out a non-traditional career journey without having to sacrifice what he is passionate about professionally and personally. He covers the concept of soft and hard skills and how you can seize things that are meant for you. He also provides fresh insights on cryptocurrency, politics, government service and banking. Tune in!

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Charley Cooper, Chief Communications Officer For Block Chain Firm R3

On Crypto, Politics, Government Service, And Banking

My guest is Charley Cooper, who I met when we began working together at State Street about 10 years ago. Charley is the Chief Communications Officer at R3, which is a leading provider of enterprise technology and services using distributed ledger or blockchain technology. Prior to joining R3, Charley was a Senior Managing Director at State Street.

Earlier roles prior to that included being a Director at Deutsche Bank, Chief Operating Officer of the US government’s Commodity Futures Trading Commission, Special Assistant to the Deputy Secretary of Defense, an Associate at law firm Kirkland & Ellis, a speechwriter for the US Attorney General, and the Assistant Press Secretary for the Dole/Kemp 1996 presidential campaign. He earned both his Bachelor’s degree and his Law degree from Georgetown University. He is a native of New York City, where he continues to live today. Charley, welcome. It’s great to have you. I’m glad you could join.

Thanks for asking. It’s great to be here.

It’s good to see you again. It’s been a while since we’ve caught up. We had a little bit of a chance to catch up, but we’ll do it in a more structured way this time.

Perhaps let’s start with your role. Tell the audience about R3 and your remit as the Chief Communication Officer.

R3 is a software company. It’s the quickest way to say it. What we do is build enterprise-grade blockchain and private, confidential computing solutions for regulated industry players. If you think about our former employer, other large banks, exchanges, clearing houses or any large institutions that handle robust financial transactions, financial products, and digital assets, we build a software that allows them to play in the new economy.

In terms of my role as the Chief Communications Officer, it is a bit of a misnomer because I oversee the communications and the PR, but I also oversee all of our government relations policy lobbying work. It becomes increasingly important as global actors are paying more and more attention to the technology and want to make sure that what we’re doing comports with what they’re okay with us doing.

You were in R3 pretty much from the beginning, from when you left State Street, where we worked together. What led you there?

It was an accident. I left State Street in the late spring of 2015 with the intent of doing the 2015, 2016 presidential campaign cycle. I was in pretty advanced stage talks to do a super PAC around that campaign. At the same time, [I heard from] the CEO of what had not yet been called R3, a guy named Dave Rutter, who had been the Head of Electronic Broking at ICAP. He and I had negotiated a deal while I was at State Street for his other firm to license some of their software to launch a product. He and I met across the negotiating table and had a hell of a time, at first, not pleasant, and then later, pleasant, renegotiating a deal that he’d originally had in place with State Street.

Over the course of those conversations and occasional heated exchanges, we came to like each other. Fast forward to a couple of months later, in the summer of 2015, it was go / no-go time on the political thing. It wasn’t quite coming together the way I’d wanted it to. While I was trying to determine whether that would work, Dave Rutter laid his chips on the table and said, “I’m putting together a team. If you want to be on the founding team, in the cap table, come join us.”

I went back to a young mathematician who worked for me at the derivatives desk at State Street. I said, “Do you know what blockchain is?” He looked at me like I was a complete idiot and said, “Of course I do.” I said, “Can you explain it to me?” He explained it to me. I came back the next day to see Dave and still did not understand exactly what I was signing on for. I said, “This sounds great. Let’s do this.” Here we are years later and the journey is still going. It’s been a hell of a ride.

How has it been, starting from ground zero and now continuing to work there today? You said that when we recently spoke that you are at 350 people. It’s clearly gained traction. What’s it been like to go from 0 to 350 people?

I would say it’s had its ups and downs. We’re both at the age and point in our career where we don’t do things that we don’t have to do. That’s a fortunate place to be. I very much like what I’m doing and am having a great time, but that’s not to say there haven’t been challenges. There’s a bit of nostalgia for the days when it was just a handful of us in a shared office space that we borrowed from someone or we when we were at WeWork for a while.

We were all jammed in these little desks trying to find room to type, where we weren’t even entirely sure what the product was going to be. We weren’t entirely sure who the clients were going to be, but we knew we were onto something. There was something banging around in this crypto, blockchain, DLT space that none of us understood, but we knew we had to understand.

Charley Cooper: Bitcoin was seen as a hedge against inflation. It was a good place to put your money, because no matter what happened to the global economy, crypto would remain strong. That’s not the way it has played out in recent months.

We were able to get there, and over the course of time, build a business. Between a handful of us, eight of us initially in that original conference room, to 350 and 15 countries, you go through days of unbelievable exhilaration, where you land a bunch of great clients and you feel like you’re on top of the world. You have other days where the market is in trouble or you’re hearing from clients that they don’t understand what you’re doing and there’s no product market fit. It comes and goes. I would say that I am glad that I have done it. I don’t know that, at my age, I would go back and do a startup again. It’s been a hell of a time and it continues to be a hell of a time because we’re still on the rollercoaster, but it feels good.

Everybody’s heard of crypto. I would say a good many people at this point have heard of blockchain. People might not know it by distributed ledger technology. Help the audience understand how what you’re doing is different from crypto itself.

Think of crypto as a token or as a form of cash, a form of currency, which is how most people think of it. [That] can’t operate or exist without a software infrastructure that underpins it. Blockchain itself, in its most traditional form, is the operating system on which crypto, originally Bitcoin, operated.

Now it’s expanded into thousands of new tokens, but originally there was Bitcoin. It was the software that made crypto possible if you think about it. What we do now is we take that software and have built a different version of it called Corda, which is R3’s platform, that is fit for regulated entities and digital assets of all sorts.

Think of central bank digital currencies, stablecoins, digital shares of stock or digital mortgages or digital bonds. The software that we build allows banks or financial market participants more broadly to participate in the new economy in either old assets that have been digitized or some of the new stuff that you see in crypto. It allows it to work within the confines of a regulated environment in which they operate.

Your biggest clients are who?

Our biggest clients are the biggest banks, exchanges, and clearinghouses in the world. They’re household names for guys like you and me who have been in banking for a long time. Our cap table, which is public, includes over 40 banks – Bank of America, HSBC, SBI, you name it – from around the world, and companies like Intel, a major technology company. These are large institutions. It’s interesting that our investors are also our clients. These were strategic investments for them.

They have taken a bet that what we’re going to be able to build is something that they also want to use themselves. Therefore, we build to their specifications. Lo and behold, it turns out that the stuff that works for our investors works for the broader financial services community. It’s asset managers, sell side firms, financial market infrastructure players, you name it, predominantly in regulated spaces.

I have to ask you, since we’re talking about crypto – and admittedly, you are a half step removed from it – but crypto has made a lot of people rich and is completely baffling to other people. What’s your take on crypto?

It’s still completely baffling. We understand what it is and why it operates. I have some small crypto holdings myself. R3 itself is not a crypto company. We build software. We don’t issue tokens, but we very much see the value in the innovations in it. Where I would say it’s baffling, back to the original point in your question, is that there was a feeling among the crypto maximalists, the people who were the original believers, that somehow crypto would be immune from the laws of economics.

You probably heard the statement made a lot over the last several years that Bitcoin is a hedge against inflation and that it was a good place to put your money. No matter what happened to the global economy, crypto would remain strong. That proved to explode pretty spectacularly over the last couple of months. What you have seen is that these new instruments, while they definitely have attributes that have not been created or seen before, are still subject to the law of economics.

There are a lot of people who lost a lot of money. Some of them probably understand why they did. Some of them didn’t. There’s an obvious explanation for some that they got involved in an asset class that didn’t make any sense, and that was new to them, and no one saw it coming.

There were also a lot of people who got hurt because of leverage [borrowing]. If you remember leverage, we had a lot of problems with that in the 2008 crisis. Institutions that were borrowing almost unlimited money to invest in crypto, which is a great business strategy for an asset class that constantly appreciates. If it goes the other direction, leverage becomes a big problem pretty quickly. A lot of people are feeling that pain right now.

Whether you call it a currency or you label it as a more generic asset class, it’s highly volatile. It went up for the most part for a long period of time, but it has had its down cycles. You have to factor that in just like you would any other investment. There are people who said, “How can you lose? It’s crypto. It keeps going up.”

Every asset goes up until it goes down.

Enough about crypto because that’s not the focus of this show. Many other shows, but not this one. Let’s go back to the beginning of your career. You went to Georgetown as an undergrad. You majored in Government. What did you see yourself doing back then? We’re going to get to the political part of your career shortly here, but did you see yourself going into politics then, or were you envisioning something else?

I very much did. My first job when I graduated was working at a bar called The Tombs in Georgetown, where I had spent my college years drinking.

A very famous bar.

It was pretty well known down in DC and maybe some other places. I’d been a generous contributor to its coffers for many years. You say I’m a Government major, which is technically true on paper. The reality is I was a Political Philosophy major and therefore got a Government degree. When I came home and told my parents I was going to be a Philosophy major, I thought my father was going to go into cardiac arrest, I pivoted a little bit. I had enough credits in Government to become a Government major, even though my focus had been on Political Philosophy and Theory. What that all meant was when I graduated college, I was unemployed.

I went to wait tables, which was one of the most important and best experiences of my life, all being short lived because I was terrible at it. I’d always envisioned my career in politics. It was only about a month after – I’d have to go back and look at my initial pay stubs from the Cato Institute – that I got a job. I’d done a bunch of internships in college and high school on Capitol Hill and on campaigns, but my first real “jacket and tie” job after college was working as a public affairs assistant, clipping newspapers, and monitoring media for a think tank in Washington called the Cato Institute.

I had assumed that my trajectory from then on was going to be one in politics and public service. It turned out that way and still may turn out that way. At the time, when I was studying in school, there was no question about what I was going to do, which set me apart a little bit from many of my contemporaries who were thinking that they were going to leave college and then figure it out. I had an idea, which was at least somewhat settling, even though I had no idea how I was going to pull it off.

It wasn’t long after that you went to work on the Dole/Kemp presidential campaign when they were running as a team in 1996. What was it like – you were 23 or 24 years old at that time – to be in the throes of a political campaign back when Dole was running against Bill Clinton in ’96.

It was one of the most invigorating and fantastic experiences of my life. I was 23 years old. I was a press flak. I was talking to reporters sometimes on the record, mainly not – saying inanely stupid things, I’m sure – drafting press releases, and pitching in occasionally to write speeches in the motorcade when the boss didn’t like the speech.

I was banging away on my laptop, which weighed about 40 pounds back then. It was as big as a PC. I started making coffee and clipping newspapers and doing all the junior-level stuff. Right as the primaries began in earnest, the press secretary, a guy named Nelson Warfield, who’s still a dear friend to this day, called me and asked me if I owned a garment bag.

I met him in New Hampshire. I traveled with the candidate from then until election day. It was an unbelievable rush. I learned an incredible amount. I probably got a little cocky along the way. You get to jump in and out of motorcades every day at age 23, and you think you run the world. The day after we lost, the beeper stopped buzzing, no one was calling, and nobody cared anymore.

Charley Cooper: Bitcoin and other crypto-currencies operate on distributed ledger technology that make crypto possible. R3 makes that software and has built a different version of it called Corda, which is R3’s platform that is fit for purpose for regulated entities and digital assets of all sorts.

That was a pretty big come-down for someone of my age. It was honestly one of the most interesting and greatest experiences in my life. It ended up setting the stage for a whole bunch of relationships that would come into play later at the political, legal, and communications levels, and all the stuff that I still do to this day in larger and smaller measures.

Being in the middle of a political campaign is a unique situation. Other than the relationships, what did you take away in terms of skills you developed that you’ve relied on since then?

I’d say there were some hard skills and then there were some soft skills. The hard skill was I learned how to write fast. As a press flak, or as someone who is doctoring speeches on the fly, you need to be able to put things in the written word and condense big concepts or long explanations into tight sound bites. You need to be able to do it in near real-time.

There were actual times I remember pulling up to an event having changed a speech and handing the thumb drive to the advance man who was waiting at the limo to run to the teleprompter to plug it in and download the speech as Dole was walking up the steps to give his remarks. Writing, in general, is a fantastic skill. It is incredible to me how many people, even at top universities, don’t know how to write. Writing quickly is incredibly impactful. That was great. That’s the first thing.

The second hard skill is to know when to talk and when not to talk. That’s interesting as a press flak because your assumption is you always need to get in the story and have an answer to something. Learning what stories to sit out, understanding when a news cycle is going to take on a life of its own that does not require involvement, or is better for you to sit out, is another hard skill.

The soft skills, I would say, are probably two things. One is learning to operate under pressure. There is no instance in which you get given 2 or 3 months on a deadline or even a week on a deadline. It isn’t how it operates. It’s very much minute to minute. That’s super intense. Managing a news cycle is super intense.

That’s very much a soft skill. The other soft skill is the people piece of it. Even as a press guy, I worked a ton of rope lines with the candidate. Senator Dole would stand out and shake hands for hours at a time. I would end up walking along with him and hearing how voters spoke to him, what issues mattered to them, and how he responded to them and made them understand that he was on top of their issues or needed to learn more about them.

Know when you can say, “I understand what you’re talking about,” or know when you have to tell a voter, “I don’t know enough, but I’m willing to come back.” Those sorts of people skills ended up being valuable to learn as well. I learned at the right hand of someone who, while he didn’t win, still got to the point of nearly winning the highest office in the land. That requires a level of political skill that few people have. That was a soft-skill side.

You went to law school at Georgetown. When did the idea of going to law school come into being for you?

I’d been thinking about it for several years, but I wasn’t committed. I took five years between undergrad and graduate school before I did it. It crystallized once when I was having a conversation with a guy named Larry Bathgate, who had been a mentor to me, a Republican operative and fundraiser for many years. He told me to go get a law degree.

I asked him why. He said, “If you’re going into politics, there will always be campaigns that you lose. They’ll be your campaigns, or they’ll be someone else’s campaign that you’re working on. You’ll need a place to go and hang your hat. The one skillset, the one degree that will carry with you and have a clearly defined job attached to it, will be a law degree. Go get a law degree. Spend a couple of years in the private sector so that when those dark times come in politics, you’ll be able to go with credibility to a firm and say, ‘I have skills that you can use. I have a network that you can use. Take me on board for a while.’” That advice turned out to be good because that’s exactly what I ended up doing.

You went to law school. You were writing speeches for the US Attorney General while you were in law school. You ended up at Kirkland & Ellis. Give a little bit of background on how both of those things happened.

The speech writing thing was an accident, but there are no accidents in Washington. It’s all about networks. One of my professors in law school went on to be the Assistant Attorney General for Legal Policy under George W. Bush. He ended up leading the effort to write the Patriot Act in the aftermath of 9/11. After 9/11, about a week later, I was sitting unbelievably frustrated in law school, trying to focus on my classes and unable to do so.

I called him and I said, “You’ve got to get me in. Somehow, I’ll intern. Bring me in so I can help.” He had spoken to the speech writer, a woman named Jessica Guevara. I realized I’m throwing all these names that mean nothing to people, but to me, they’re incredibly important. Jessica was the only speech writer for a person who had overnight been catapulted into one of the most high-profile jobs in the federal government. I went and interned for her. We sat down the first day and looked at the list of public comments that were coming up. I can’t tell you how long the list was. It was mind-blowing.

We divided up and we started writing. We kept writing for months. My legal professors understood what I was doing and were appreciative of it because it was tied to the legal profession. My Justice Department colleagues knew that I was still in law school. They were fine if I was ditching out during the day to go to school, as opposed to showing up at the office.

It was two communities of people that very much respected each other and let me straddle those two worlds. Coming out of it, I went into a private sector job. Kirkland & Ellis was a firm that I had summered at both summers while I was in law school. I was lucky enough to get offered a full-time position. I headed there after taking the bar right after school and dove into pretty standard commercial litigation.

It doesn’t always happen that you get two groups who are aligned and let you live in the intersection of their two worlds at the same time and are willing to take the compromises that go with that. You were lucky that worked out for you.

There are always competing interests. Not just externally but in your own mind. When you’re presented with multiple opportunities, but there are trade-offs between those opportunities, you’re often making sacrifices on one to do the other. Truthfully, my grades probably were sacrificed a bit, because I wasn’t knocking the ball out of the park, but yes, I didn’t have to give up law school to be a speech writer. I didn’t have to give up writing speeches to be in law school. It was a confluence of two communities of people who had both been in each other’s shoes at one point or wanted to be in each other’s shoes at one point. Therefore, they were willing to say, “If you can make it work, go for it.”

You made another career shift. There is a lot of this coming.

All over the map. I’m not sure what this means.

Everybody’s career journeys are different. It’s all good. You went to the Department of Defense and you were working for one of the Undersecretaries of Defense. How did you end up there, making a full jump out of the private legal practice world, out of the political world, into more traditional government service?

This is where the network piece becomes important and is incredibly robust in Washington DC. The people you meet in law school, the people you meet on campaigns, and the people you meet in jobs like at the Justice Department, form a small community of people in Washington. The federal government looks like a behemoth from the outside, but those of us who are the operatives working in the nexus of policy and politics are a relatively small group.

It was a word-of-mouth thing. Paul Wolfowitz, who then was the Deputy Secretary of Defense, was losing his communications advisor, who was going on to work for Vice President Cheney. The role came up, and he knew that he needed to backfill on the comm side, but he also felt that more of a policy and potentially legal bent would be helpful.

When he and I were talking, I argued that [combination] would be useful. He might’ve had the idea that it was public affairs he needed. I pitched him on a broader role about taking some involvement in various policy and legal conversations. Paul brought me in at the beginning of 2004, just as the insurgency was beginning to creep up in Iraq, after the initial combat mission had ended the spring before. While I was technically doing or having some conversations with legal policy people, it became a policy in a spin role and a communications role. It happened because of people that I knew and conversations that I’d had when the role popped up.

A funny story about it, I got a phone call from a previous mentor and a press secretary who said, “You’re about to get a phone call from the Pentagon.” I said, “Okay.” They said, “It’s about a job.” I said, “I have a job.” He responded to me, “It’s the fucking Pentagon. Take the call.” I took the phone call. Another trajectory change in my life. I know, later on, we’re going to talk about some advice to give to folks, but always take the meeting. I didn’t think the meeting was going to be important. It ended up changing the way I looked at my career. It had an impact on me in my personal life and a whole bunch of other things. It was incredibly worthwhile.

How did it change the way that you looked at your career?

First of all, I’d never seen myself in a policy role. I’d always envisaged myself more as a press flak. I’d always envisioned myself more as a campaign guy. To the outside world, government politics all looks the same. There are different camps when it comes to the people who get people elected and the people who work in administration or run for office themselves and then try to do the business of government.

Charley Cooper: Crypto assets definitely have attributes that have not been seen before but they are still subject to the law of economics. And there are a lot of people who lost a lot of money recently. Some of them understand why they did and some of them don’t.

Those two sides don’t always often talk to each other. I always thought I was going to be a campaign guy. The rush of ‘96 was still in my blood. I moved to the Pentagon, and suddenly, the caliber and the weight of the decisions that I was making felt much more palpable and serious. As a result, I felt in a way, far more meaningful. It was a little less of a blood sport, but it was a lot more gravity.

The stakes became higher. That’s interesting to say. The stakes on a presidential campaign, they’re pretty high, but when you’re in a role, certainly at the Pentagon in the aftermath of 9/11 and the Bush administration’s decisions to go to war in Afghanistan and Iraq, you’re at the epicenter of a changing global order. You’re at the epicenter of policymakers that are trying to navigate an entirely new world.

We had not seen 9/11 coming. No one had an idea of how geopolitics were going to shift on a dime. We were part of the group that was making it up as we went along. There were obviously mistakes made, decisions that you go back and you retread in your mind, but being in that room was not something I’d ever anticipated. Once I was in it, I felt a real affinity for it. It ha real meaning to me. It went from a little less politics and a little more public service. I could feel that shift almost in real time.

You then went over to a different part of the government, the Commodity Futures Trading Commission, or CFTC, which regulates parts of the financial markets. A different aspect of public service. I’m sure there’s a network component to this because it’s Washington. You were doing this work you’re describing as meaningful in the aftermath of 9/11 and then you moved over to the financial world. How did that shift happen?

It wasn’t a networking play. Reuben Jeffery, who had been the senior level Deputy for the Coalition Provisional Authority in Iraq, had started his career at Goldman Sachs. He was a lawyer out of law school and then went on to Goldman Sachs and had spent a good chunk of time after 9/11 in the federal government helping coordinate the US response to 9/11. When it was time to come in from the field a bit, he got a call from the White House to see if he would go in and take over the derivatives regulator because it was something that was pretty obvious to him, something based on his skillset, but still being a political and policy role, because it was a public sector role.

He needed a chief of staff and a chief operating officer to come in and keep the trains running on time and to handle a lot of the day-to-day responsibilities for the commission while he focused on the big vision for US regulation and US government involvement or lack of involvement, depending on the issue, in the markets and how they function.

I called Reuben. I said, “Congratulations on the CFTC role.” He said, “Great, do you want to go with me?” I said, “What would you want me to do?” He said, “How about chief of staff?” I said, “I’ll do it.” I’m not kidding, it was like a 5 to 7-minute minute phone call. I made the leap over there. The first thing I did was figure out exactly what the CFTC did and how it worked. I had to learn a lot. I practiced when I was at Kirkland & Ellis. I had had some cases before the CFTC, but I was a young guy. I was doing junior stuff. I didn’t get into the meat of what was going on.

I had a steep learning curve in terms of understanding how the agency worked and what its substance was, but I came to it with a political set of skills that were useful in working with members of Congress, on our oversight committees, on our appropriations committees, as well as at OMB and at the White House, as the executive branch was trying to understand what the driven is market would mean then, and as it turned out, much more importantly, several years, hence.

It was probably an interesting time to be there when you look back because it was relatively close to the time when the crisis hit back in 2008. Derivatives played a pretty big role in that, but presumably they weren’t aware of the scope of what was possibly going to happen. It wasn’t apparent to anybody and was a little bit similar to the 9/11 situation that you talked about earlier.

A couple of things were interesting about it. First of all, at the time, the CFTC’s jurisdiction was over the futures and options markets. It didn’t cover swaps. That’s what would be added to it after the 2008 crisis. In 2007, we were in the President’s working group, the CFTC, SEC, Fed, and Treasury. We began to see more and more turbulence and swings in the market.

The mechanisms of the market felt more and more uneasy and uncomfortable, yet the CFTC’s markets were operating normally. While they would see greater volatility potentially, the mechanisms that were in place, the margining requirements and the backstops that existed in the derivatives markets, turned out to be more robust than many of the other markets. We knew something wasn’t right, but no one could put their finger on it.

In this day and age, everybody looks back and tells you how they predicted the financial crisis. That’s bullshit because if they knew the financial crisis was coming, they would have made a lot of money off it. They didn’t. It caught a ton of people by surprise. We, as an institution, were trying to figure out what was coming in 2007. It felt unstable, but we weren’t sure why. Even though our markets were operating well in the broader context, there was a sense something was coming, but nobody could put their finger on it.

That was your first major foray into the financial services space. Was there something that clicked for you about being in financial services? You’ve largely been in financial services in a variety of different ways since then.

I’ll be blunt. It wasn’t about clicking. It was that I’d spent a good portion of my career in public service. I wasn’t sure what the future would hold in terms of my personal life and potentially settling down. It wasn’t clear where I wanted to go, but I did know that I hadn’t put myself in a financial position yet that would make me comfortable if a rainy day came. That’s the truth.

I had a conversation with the Chairman, with Reuben Jeffrey. He was going to the State Department at the time to take over as Undersecretary under Condoleeza Rice. We were talking about whether I would go with them. I said, “I’ve got to go make some money.” He generously offered to pick up the phone, to anybody in his Rolodex, and he made a set of introductions to me.

During those conversations, I ended up speaking at length with the group at Deutsche Bank, which was then the largest derivative shop on Wall Street. I ended up moving to London to run legal operations for them, which at the time was called LRC, Legal Risk and Capital, right as the crisis began to hit. We colloquially refer to it as risk management. I accidentally found myself at a ground zero place in financial services when I thought I was going to go sit in a job for a while and put some money in the bank. It ended up being a hell of a lot more intense than I’d expected, but that seems to be a trend in my career.

You’ve been in some interesting places at interesting times. There are certainly worse things that you can say when you look back on your career. What did you do after you left Deutsche and before you came to State Street, where you and I met?

I left Deutsche Bank in the spring of 2009. I came back to the States. I put my stuff in the attic, got rid of my flat in London, got in my car and drove around the country for four months. National parks, presidential libraries, visiting old friends. I ended up in Los Angeles and wrote a screenplay with my best friend.

Notice I say screenplay and not a movie because it hasn’t been made into a movie yet, but there’s always hope. He’s Michael Susie, a writer and a director, and he does this for real. I was the former banker / government guy who was looking for something to do. I spent a couple of years, frankly, trying to figure out what exactly I was going to do. Not entirely sure.

The financial crisis was well and truly upon us at that point. There weren’t jobs being thrown around. I continued to road trip for a while. I lived at the beach. I was doing some reading and some writing and ultimately started getting bored and made a set of phone calls, which turned into a guy who knew a guy who knew a guy through the network that introduced me to the State Street team, and in particular, Cliff Lewis, who you and I both know well because we spent a lot of time running the derivatives business for him.

You have an IMDB profile, which I did not know about.

That’s unfortunate and shocking. I can tell you that it is not about the script. That’s probably because I do TV hits for the company [R3] or because I do documentary hits for them. I didn’t put that up. I can claim credit, though. I wish it were more exciting, the fact that I do blockchain documentaries, but it’s certainly not for my acting career, unfortunately.

When you joined State Street, did you have a full sense of what you were getting into in terms of what the job was about?

No, but that was by the design of Cliff. He ran the business by pulling in people of various talents and then throwing them into problems or roles as they came up. I didn’t even know what my title was when I started. I would subsequently graduate to be Martine Bond’s COO for the trading and clearing team.

I do remember a lot of the focus being that this was at the point that the Dodd-Frank legislation in the US was beginning to be written into actual regulations. State Street was launching a derivatives clearings business. They were already one of the biggest custodians on Wall Street for the derivatives business. Dodd-Frank was a big deal for them.

I was brought in to help navigate the change in the business under those regulations and to help shape some of those regulations. I spent a lot of time in DC during that time, working with people to understand what was coming and to try to shape what was coming so that we could then feed that back to State Street and be prepared to take advantage of whatever business opportunities would develop. I don’t remember, honestly, what my title was. It was like, “Come on in here and we’ll figure it out.” We figured it out.

Charley Cooper: One hard skill I learned is when to talk and when not to talk as a PR person. Your assumption is you always need to get in the story and have an answer to something. You have to learn what stories to sit out and understand when a news cycle is going to take on a life of its own.

We were doing a lot of figuring it out. State Street had a sense at the time that they wanted to do more in the derivatives space, for example Dodd-Frank, which was written in response to the crisis to try and put more governance around how the financial institutions were using derivatives. They knew they had a role to play in that. They weren’t sure exactly what it was going to look like. You and I and others spent a bunch of time trying to figure that out and out seeing clients and talking to them about how they viewed the derivative markets. It was interesting, but it was a pretty ambiguous role in many ways for both of us.

I remember several times you and I came out of meetings and compared notes. When we went into the next meeting, we knew more than we went into the last one with. We were learning at the same time our clients were, trying to sound informed, calling Washington, trying to get the latest of what was going on in various different committees, trying to understand what the CFTC was writing so that we went into the meeting after lunch, as opposed to meeting before lunch, we had more updated information based on what they needed.

It was a constant hustle, learning as we went, and helping our clients. If you and I couldn’t give them the specifics of what was going to happen, we could assure them that we were at least on the ball enough that along the journey, we would get them where they needed to go, even if we were learning with them.

Were you in the earthquake meeting in New York?

I don’t think so. Was there an earthquake?

It was down in Virginia. People may remember that. We were sitting in the General Motors building with a bunch of pension funds, and General Motors’ pension was one of them. They called in all the big banks to talk about what they were doing to get ready for Dodd-Frank. I got roped into the meeting with whoever else, clearly not you, at the eleventh hour. We go to the meeting. It was basically a glorified way for the pensions to push us all day. The meeting was going rough. In the middle of the meeting, somebody was going on a little bit of a rant.

The chairs start shaking, and the speaker doesn’t even notice. The rest of us are all looking around at each other asking, “What’s going on?” About two minutes later, we get told to evacuate the building. We walked down 45 flights of stairs. I’ve never been so happy to walk down 45 flights of stairs because that meeting was over. It never got rescheduled. It wasn’t going well. It was good to get out of it. It was one of these funny, funny circumstances that happened in the many meetings that we did over the years.

It took a literal tectonic movement of the Earth’s crust to get you out of the meeting. That was worth it. That seems like a trade-off worth taking. I love it.

Back to your career. Throughout all of this time, you’re still doing the political thing. You’re getting involved in supporting people on campaigns. You were going to conventions. How did all of that play out in the background for you while you were doing your financial services thing, trying to make a little money to put in the bank?

The only way to think of it is that, if it matters, you make time. That could be anything. You could be a painter, a musician, or a race car driver. We’ve all got our thing or our things. If it matters to you, you find the time. I would also suggest if it matters to you, you need to find the time. It’s amazing how many people you and I both know over the course of our careers that found themselves where the job was it, and the rest took a back seat, or they pared down a lot of the things that they cared about. They were making sacrifices that made sense to them. I 100% get it. Given their personal circumstances, it might’ve made sense to make those sacrifices.

I was in a situation where I could continue to drive pretty hard and not sleep as much as I now need to at this age, but I was able to keep pursuing something that mattered and made it work. I was also forthcoming with my bosses. They knew exactly what I was involved in. I still, to this day, while I do run the government relations at R3, I’m involved in various political conversations going on every election cycle and in policy conversations. I spend a lot of time paying attention to what’s going on in Ukraine and Russia. I’ve done commentary on that.

My partners have been good about letting me do that, but that’s also because I’ve been upfront with them that I am going to do it. It’s important to find some of the things that matter to you. If you’re willing to say to them, “This matters to me. I need to make this work for me so that I can continue to work well for you.” A good boss is going to understand that and accept that and realize that the more you generally thrive in life, the better performer you’re going to be for them at your job.

I agree with you. There are certainly circumstances where things are mutually incompatible. I’d say boundaries exist with any employer, but there are also a lot of avenues to make it work. It’s going to become more common as people start to have more portfolio-type careers. You’ve had a portfolio career, but it’s been lots of different things over the course of your career, but more and more, you’re seeing people doing multiple things at once.

You’re seeing people do multiple things at once. You’re seeing, post-COVID, people wax on and on about the impacts of COVID. A lot of it’s overstated, but I do think this is important. More and more people had a bit of a wake-up call that the way they had been operating up until March of 2020 was not the way they wanted to continue to operate.

The way in which they focused maniacally on work oftentimes came at the expense of hobbies that they loved, children they didn’t spend enough time with, community organizations that they felt were important to them, their families or their loved ones. There are a whole host of things that we’re all interested in. The tolerance for giving that up, or the willingness to put that aside purely for financial gain at a day job, working for the paycheck, as opposed to working to live and enjoy life, there’s a lot less tolerance for that.

I would think, in many ways, that’s healthy. We are better performers and better people if we have a more holistic life and we make as much of the opportunities we’re given to try to do as many things as we’re given. We’re better people. We’re happier people if we’re doing things that appeal to us, rather than just going in and punching a clock in a figurative sense.

I agree with you that March 2020 was somewhat of a wake-up call for a lot of people as the pandemic settled in and the work-from-home thing went on and on. We won’t go back to the way that it was before. The question is, what’s it going to look like next? I don’t know that anybody’s got that figured out, but we’ll find out as the months and years progress.

I don’t know, but I can tell you right now that one example staring us in the face is the fact that you launched this show. These topics have been a passion for you for years, and yet it wasn’t until the last few months where you sat down and said, “This is important to me. I have something meaningful to contribute on this. I want to have these conversations to bring them to a broader audience,” and you’re doing it. Would that have happened in 2019? I don’t know, but here you are doing it. I have countless examples of friends of mine who have done similar things. It’s great that people are seizing those things and throwing themselves into things that they’re passionate about.

For me, I learn from it. I take that to work. I benefit from it. It’s fun. I’ve caught up with people I haven’t talked to in forever. I reconnect with people who were in my life in the past, who, in some cases, were important people in my life, close friends. You learn a lot from how their lives and career journeys have progressed since then.

It’s pretty cool. I’m glad you’re doing it.

Obviously, you’re still in the middle of this R3 journey. How do you see the remaining part of your career? Politics is still out there for you. Would you ever consider running for office or do you like just being in the arena?

My clear intent is to stick with R3 until we get this thing where we plan to, whether that’s an IPO, a private sale or what have you. I’m fully invested in the journey. I was one of the guys who launched this thing. I’m excited to be here, but public service and politics are a bit like New York City. Once it gets in your blood, it’s pretty hard to pull that out.

Would I run for office, though, is a different question. I came of age working men and women who played by a different set of rules. We threw punches. We ran tough campaigns, but we did it with civility and respect. Those days seem long since over. I’m not placing blame on anyone. It has been a long deterioration over the course of many decades.

It’s certainly gotten worse in the last few years, but I would say that it’s a bit disenchanting for someone like me who saw the possibility of what politics could be and now sees it and decides that I don’t know that it’s for me anymore. It certainly isn’t for me running.

If I want to get in the spirit of campaign, where we’re debating serious policy issues, that’s one thing. If we’re pissing on each other on a Twitter feed and attacking each other’s individual characters, or we’re attacking each other’s families or loved ones, that’s not a game I want to play. That’s an unfortunate place to be. It’s as if you thought your entire career was going to be one thing, in my case, public service or politics, only to discover that what you thought it was doesn’t even exist anymore. Politics and public service exist, but not in the way that they did. It causes a real recalibration. I’m luckily in a position where for the next several years, I’m here.

I’ve got the ability to spend time on the side, continue to do political things if that makes sense, sit it out when it doesn’t. If politics regains its footing as a place for civil conversation and thoughtful debate, then I’m willing to get back into it. If those days are gone, it may not be me anymore, truthfully. It may be on to the younger generation who has the stomach for it in a way that I don’t.

Charley Cooper: If we pursue a more holistic life and we make as much of the opportunities we’re given to try to do as many things as we’re given, we’re better people.

Our political environment has certainly seen [tumultuous] times in the past. We think this is the worst it’s ever been. I suspect there have been times going back over the prior 200-plus years that it was bad in its own way. It is a different world than it was when you were supporting Bob Dole’s run against Bill Clinton back in the mid-1990s.

You’ve talked a bit about some of the career lessons, taking the meeting, tapping into the network, things like that, and pursuing passions. What other things stand for you that you learned over the years that you would want to share with people who are reading?

You’ve got to be open to things that you didn’t think were on your radar. It’s great to have a set of goals and a general approach, but if all you’ve ever wanted to be is a banker, and someone comes to you with a great job in a different industry, if you refuse to hear them out and consider a broader set of options, you might find yourself unwittingly pigeonholing yourself and looking at the world through a straw and not seeing a broader picture on which you can paint a rich and fulfilling life. That’s an important thing. It’s the expanded version of taking the meeting. Be open-minded about what’s to come. I might be the opposite, where I’ve had ten different careers if you include sailing coach and waiter.

I feel like I’ve always been interested [in what I’m doing professionally.] I always feel like I’m engaged and I’m having a good time with it. There’s that open-minded piece. It’s what we discussed earlier, which is to keep your passion projects alive, and keep investing in things outside the office that matter. It’s incredibly important to who we are as people that we have a wide variety of things that matter to us and nourish us. I know it sounds woo-woo, but it gives us a sense of spiritual fulfillment and feeding that we need. Whatever that means to each different person, it’s important to pursue those things.

The other thing is, and I’m going to sound a little bit frankly like an old man, but you’ve got to work your ass off. Whatever you’re going to do, work hard, go for it, throw yourself into it, make the time for everything that you can, and do it relentlessly. Whatever you’re doing, do it relentlessly. The real opportunities in life don’t just appear out of nowhere. They’re not presented to people who don’t have the ability to work for them and try to make an effort. It sounds old school, but busting your ass is some of the best advice that I could probably give.

It’s interesting that you say that. I wonder how much that mindset still carries, particularly with the younger generation. They’re putting work in a different place relative to other things in their lives. Part of that’s because they’ve seen how their parents’ careers have gone, with a lot of burnout and depression and other issues that I’ll say the Baby Boomers and Gen X generations have faced.

It makes leading in the world nowadays and in an organization a different thing because you can’t necessarily count on people thinking about work in a consistent way to the way you do. You have to bridge those generational differences and figure out a way to make it work. It’s unlikely that you’d have an organization of 50-something-year-olds. You’ve got to be able to come up with a way of creating an organization that gives everybody the degrees of freedom they’re looking for.

The one thing I’d say is that people often conflate working hard with working well. You can be incredibly productive in less time if you work smart and still leave yourself plenty of room to do those things which you find nourishing in different ways of your life. Working hard doesn’t just mean throwing in as many possible hours as you can. In fact, I know some people who worked the longest hours did so because they weren’t good at their jobs. They needed more time to be able to do their jobs.

The new generation would benefit from continuing to work hard, but if they’re doing it smarter, it would still leave them a whole host of possibilities to juggle a portfolio career, different interests, and multiple professional opportunities, and still excel at all those things. It’s not just about putting in as many hours as you possibly can, because a lot of times, that doesn’t end up being productive or helping anyone.

There’s the old adage of working hard and working smart. I learned that personally when I was a new associate at McKinsey. I had a wife and stepdaughter at home. I wanted to have dinner with them at night. I made a solid effort to be on the 6:30 train home from Chicago when we were living out there so that we could have dinner together. If I needed to do [more work] afterward, I did, but I tried to get as much done during the core part of the day as I could, so that I didn’t end up working myself into oblivion.

Any final thoughts, any books you would recommend, or anything else you want to share?

I’ll send you my reading list, but I want to say thank you. This has been great. I love that maybe some of the stuff we’ve been busting our asses doing for all these decades can be useful to someone coming up behind us and trying to figure out their own way. Anything I can do, I’m happy to do it. Thanks for the invite.

I’m glad we did it. Thanks again. Have a good rest of your day.

You too, buddy. I’ll talk to you soon.

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About Charley Cooper

Charley Cooper is the Chief Communications Officer at R3, a leading provider of enterprise technology and services using distributed ledger, or blockchain, technology. Prior to joining R3, Charley was a Senior Managing Director at State Street. Earlier roles, in reverse order, included being a Director at Deutsche Bank, the Chief Operating Officer of the US government’s Commodity Futures Trading Commission, a Special Assistant to the Deputy Secretary of Defense, an associate at the law firm Kirkland & Ellis, a speechwriter for the US Attorney General, and the Assistant Press Secretary for the Dole / Kemp 1996 presidential campaign.

Charley earned both his Bachelors’ degree in Government and his law degree from Georgetown University. He is a native of New York City, where he continues to live today.

To listen to other “Career Sessions, Career Lessons” podcasts, or read the transcripts, visit pathwise.io/podcast/