From Attaché to AWS: Forging Connections on the Future of Geoeconomics with Michael B. Greenwald

Ari Redbord (00:02):

I am Ari Redbord and this is TRM Talks. I'm Global Head of Policy at TRM Labs. We provide blockchain intelligence software to support law enforcement investigations and to help financial institutions and cryptocurrency businesses mitigate financial crime risk within the emerging digital asset economy. Prior to joining TRMI spent 15 years in the US federal government, first as a prosecutor at the Department of Justice, and then as a Treasury department official where I worked to safeguard the financial system against terrorist financiers, weapons of mass destruction, proliferators, drug kingpins, and other rogue actors. On TRM Talks, I sit down with business leaders, policymakers, investigators, and friends from across the crypto ecosystem who are working to build a safer financial system. On TRM Talks, I am joined by friend, former Treasury official and the global head of Financial Innovations and digital assets at Amazon Web Services Michael Greenwald.

(01:04):

But first Inside the Lab where I share data-driven insights from our blockchain intelligence team. Recently, TRM Labs published a report all roads lead to China, North Korean hackers, fentanyl, cartel money laundering, and global organized crime. Chinese underground banking networks often operating in the shadows of the global financial system have become critical conduits for transnational organized crime. These informal banking channels operate outside traditional banking regulations to move value across borders. They enable a vast range of illicit enterprises from cyber enabled financial crime and sanctions evasion to drug trafficking by converting and transferring funds in ways that frustrate law enforcement oversight. In recent years, these networks have increasingly turned to cryptocurrency to facilitate rapid pseudonym cross border transactions. As a result, Chinese underground bankers and their criminal clients, including North Korean hackers, Mexican cartels and Russian crime syndicates have built a sprawling illicit finance ecosystem that exploits crypto assets and underground financial systems to launder dirty money on a global scale. And now I sit down with Michael Greenwald. Michael, I am so glad you're finally joining the show. First of all, you are in a really cool room right now. The first thing I saw was you have an American flag there and also sort of a desk filled with challenge coins. Would you tell folks sort of the meaning of that?

Michael Greenwald (02:37):

Sure, yeah. Everything has a story and the flag is very meaningful for me. A good friend served in Afghanistan and got it flown over our base on 9/11. And so it's just a reminder to me of the counter-terrorism threat. And I used to work when I was a Treasury on countering Al-Qaeda's finance, and so it's a great reminder every day for me of what's important and each challenge coin, as you know from people who serve in government, each of them are stories. Each of them are amazing people that lived a life of consequence, and each of those coins I can pick up and I can just have a flashback to that moment, that handshake, that story, that consequential moment.

Ari Redbord (03:30):

I love that so much. One of the first things I did when I got to TRM about five years ago was I made a bunch of challenge coins for TRM to be able to give out to folks that we're working with. And oftentimes in the private sector, people will sort of look at this like, what is this thing? And I try to explain it's the ultimate show of gratitude for someone who did you a solid, and I love that you tie stories to that gratitude. We're all good at bringing people together. At this point in your career, if you're where we all are, you're very good at what folks would refer to as networking. I think you're a Jedi, you're one of the very best I've ever seen in the world at this, right? Bringing people together for a common cause, common mission. Where did you develop that skill?

Michael Greenwald (04:09):

Well, my parents were always having people over the house, whether it was for Shabbat or for holidays or just a great dinner party. And so I watched my parents do it when I was younger and I loved how they curated the table. They brought people from all different backgrounds and religions together to have interesting conversations. And I'm just inherently a curious person and I like to learn about people and go a couple layers below the surface. I would also want people to bring me in or be around different tables. And so I love convening for that reason, but I also love to bring people together that should be together. And you never know how one relationship, one conversation can lead to an inflection point, a turning point for them. And so for me it's a community of strength and I just think it's so important to convene because I want my friends and my new friends to be successful.

Ari Redbord (05:16):

It's evident. I think most people don't necessarily realize that essentially you were a diplomat for the Treasury Department for a number of years there, but talk about your journey to AWS, right? What you're doing now, obviously in the technology, digital assets, AI space, but really take us back to your career in government and how you ended up in this place.

Michael Greenwald (05:34):

So growing up in the post 9/11 era, I read the 9/11 commission report and there was a monograph about how the attacks were funded and it talked about how 9/11 was funded with $500,000 and use all these different charities and schemes to ultimately fund the attacks. And I must have read that monograph 15 times and I was mesmerized by the idea that we could go after Al-Qaeda this way in terrorists using unique sanctions and tools. And so the person doing it at the time, the person you and I both have deep admiration for was Stuart Levy. And I mean he truly was someone that I and still do have the highest respect for. And I finally got an internship during law school at FinCEN and I emailed Stewart's front office and I was just like, Hey, my last day is this, can I just have a one-on-one with Stewart?

(06:41):

And I just figured that was never going to happen, but you have to send the extra note, you have to ask, you have to raise your hand. And I remember getting the email back and it said, yeah, please show up at this time on this date. And so I made the trek from Vienna to DC beyond excited, and we sat down and we just started telling stories and he started telling me some great stories about his travels around the world. He listened to me why I cared so much about what the office he was leading was doing and why I wanted to make it a career. And he said, well, let me see if I can connect you with our general counsel and we'll see whether there's a slot for you or a seat for you. And so I met with the general counsel and I was like in the law library waiting to get the call and I remember waiting for the unknown number to pop up and I actually remember them calling and I literally running from the library outside to take the call was kind of catching my breath.

(07:47):

And the guy at the time, Mark Monor who was assistant general counsel, he said, listen, we found you a spot. And so I showed up January, 2010 and it was right after the snowpocalypse and I sat in general counsel for the second half of law school. I convinced my law dean to let me spend half a year at Treasury. I got to experience everything about TFI, just an incredible period. And then in that period I decided that I really wanted to go work for the intelligence part of Treasury and that's when I joined OIA after law and got to work with some amazing people during that time. This was the pre-Abbottabad era when Bin Laden was still alive and understanding how Al-Qaeda was moving money and what tools we needed to do and then the post era. And that was just an incredible moment in time to work in government to work in counter-terrorism.

(08:47):

I then had an opportunity to work in the policy office at TFFC and worked on Europe. As many young people will find, there are great moments where you have an opportunity to step up and it happened to be Ukraine, Russia was that moment in 2014, and I was part of a team that was working on those issues. It's just a talented people. I mean as you know this, the most talented people work at Treasury, especially in TFI, and worked on that for a little while and then got asked to go to Doha to open up our at attaché office and work in Qatar in Kuwait. And that was in 2015 and 2017. And that was just, I mean, to represent the Treasury department in the Gulf during that time, it was low oil prices. You saw that geo-economic stress test, you saw the Sovereign Wealth Fund just starting to deploy capital to the US. You saw just sort of a seismic shift happening in the Gulf and globally was just an awesome experience and there's no better experience than representing your country, especially your department out there. And being a Treasury at attaché is one of the coolest jobs, and I have deep respect for people that do that work. Came back, I went into finance for a global investment firm. I became a professor at BU and a senior fellow at Belfort, Harvard and started to write a lot about the space, what was happening. And then I joined AWS and I've been here now for three years. So it's been an incredible journey and I'm very fortunate of the people I've been able to work with.

Ari Redbord (10:33):

Just an extraordinary story and there's just so much there. I love the image of you running from the library to take that phone call. We've had a bunch of great TFI folks on TRM Talks over the years, but for listeners who aren't entirely deep on Treasury org chart, essentially you have the Office of Terrorism and Financial Intelligence, which sits over the entire national security apparatus of the US Treasury Department, which includes FinCEN, which you mentioned interning, which is over OIA, which is the Office of Intelligence and Analysis, which is this tiny, tiny little piece of the US intelligence community that does the work at the US Treasury Department. And then you have TFFC, the Office of Terrorism and Terror Financing, and it is the policy piece. And then you have OFAC, which is obviously the US sanctions regulator, but so cool to have sort of been a part of all of that. One thing I wanted to just get a little deeper on is the attaché part. You're kind of out there on your own.

Michael Greenwald (11:30):

Yeah, so the role you're representing the entirety of the Treasury Department, and I represented in two countries in Qatar and Kuwait. And I had two friends in colleagues in UAE and Saudi at the time, Matt Pellegrino and Will Rich, which were great sounding boards for the end of the day because there's very few people that know what it's like day to day. If you're not in the job, you're basically living two days when you're living in the Gulf because you wake up and you live your golf day and then around 2:30, three o'clock in the afternoon Gulf time DC wakes up. And so the flood of emails, the flood of requests start coming in. But it's a job that requires deep emotional intelligence to do not only diplomacy with the foreign counterparts, but diplomacy in the state department and diplomacy in your embassy. And you're at the ambassadors country team meeting, which is representatives from all the agencies and you are representing your department if there's a visit coming, if there's an important issue, you need a flag for the ambassador.

(12:43):

If there's an issue that whether it's good or whether it's bad, you have to flag that and you have to use your judgment about how you're communicating that. And then you need to be collaborative with others because you are living there for more than one two years. This is not just a one visit type of thing. So it was challenging in the best way, but I would say the part that took the most creativity was the internal diploma because there may be something that Treasury wants to do, the ambassador doesn't or the State Department, and then you have to go into the ambassador's office and you have to disagree and commit. You have to be a diplomat on your own team. But the issues that I covered were obviously counter-terrorist financing and national security. That's a big part of the role. But also there's other parts of the building, there's international affairs, so we would paint the macro picture. There's the tax office, and there was always discussions about double tax treaties. There was understanding how the sovereign wealth fund in the region was deploying capital and what that meant, the energy issues would natural gas, all of these are issues that if you go back to 2015, are coming to the surface today. So it was great to be a student and I really felt like I got a mini MBA when I was on the ground.

Ari Redbord (14:18):

If there's a theme throughout this conversation so far, this really this ability to navigate, to bring people together, it seems like your career is very much like we saw sort of a number of iterations of that. One thing you mentioned really out of the box around 9/11 mostly is how you've spent your really entire career thinking about how to use financial power, soft power or beyond sanctions less soft. Talk me through the way you see the financial tools being used today.

Michael Greenwald (14:43):

Well, I think we've been through a series of chapters in this evolution of financial power and think we've been through different chapters of how the dollar has been deployed. And one thing we learned recently over the last few months is that the market doesn't like uncertainty. And when we were deploying sanctions during the Ukraine era, the most powerful tool was the uncertainty of the market. They didn't understand debt and equity restrictions, which was a novel idea at the time. And so the way I see it, Ari, is that we had an uptick using the dollar to go after Iran, and that pressure campaign was quite successful bringing Iran to the table. What happened after that? I think that is very much in flux and still ongoing. I think then you start to deal with countries that have more exposure to the financial sector and that requires more targeted, more scalpel like sanctions and scalpel like tools of how you deploy the dollar.

(16:00):

And so you have the different provisions in the Patriot Act like Section 3-11, which it's an incredibly powerful tool to say that something is a primary money laundering concern. And so I think that our tools have worked for a long time, and I think the reliance in the situation room has been what can we deploy in the escalation ladder? I think we're reaching a point where our adversaries are getting very good at resisting our tools, and I think we have to look at a playbook of where can there be the art of financial surprise that's targeted, that's scalpel like that they can't anticipate? Because I think that our adversaries are very smart at understanding what the escalation ladder could look like, whether it's in a financial sanction scheme or whether it's in a broader sanctions area. And so I do think that we have to be careful about not becoming complacent about the use of the dollar, and we have to have a dollar innovation strategy, which talks about re-imagining how to deploy the dollar globally.

Ari Redbord (17:25):

I've always argued that we have an entire toolbox of potential financial levers that we can pull that were frankly not because we're leaning so much into sanctions right now. Tariffs is on everybody's mind, but there are other things. When I was a prosecutor, we were the first and still only today to service Patriot Act subpoena on a Chinese bank. The penalty for non-compliance is cutting off correspondent banking. It's the death penalty, right? There are tools available we're definitely not using today. And I absolutely love that

Michael Greenwald (17:52):

With generative AI and these new emerging tools and in quantum emerging data, there's a choice that's taking place about from a security perspective, what is the choice when it comes to cloud providers and how countries are making those decisions? It very much reminds me of countries deciding whether to bank with the dollar or not. And because ultimately, as you know, payments are data. And so it's just sort of reminiscent of how the iteration continues to evolve now in an era of emerging tech where you're seeing the convergence take place between AI in digital assets and really that financial landscape shifting,

Ari Redbord (18:49):

Let's talk through that at AWS. In your role, you're thinking a lot about cloud infrastructure, financial integrity, the future of money. Talk me through a little bit about how you're thinking about these issues.

Michael Greenwald (18:58):

Well, I think the financial landscape, it's been in a constant state of evolution and the way that I have always thought about this, you have stock ticker machines to algorithmic trading systems, and then innovation has always been at the core of finance. And so I always go back to the origins and where we've come from, but among these transformative changes, it's the confluence of artificial intelligence, which we as a company have focused on for many, many years, and digital assets like cryptocurrencies and tokenized assets that really have the potential to be the most disruptive change to finance in decades. And so I think that you see really a reshaping of financial services and infrastructure in the public sector, and I think you see the public sector studying how can they be more productive, how can they be more efficient, and how can they use these tools to not only go after potential adversaries but make their systems work more efficient and secure?

(20:27):

And so the convergence of these two emerging technologies, AI, Ari, the way I think about it with its ability to self-learn, extract actionable insights from vast amounts of data, and then you have digital assets which exists on a decentralized, transparent automated network in my view, it's expected to further amplify the impact of one another, which is why I think the administration has rightly so brought them together. And so I think that you really see the strengths of them being more efficient and robust for the financial system and how the public sector is approaching this right now is really fascinating.

Ari Redbord (21:23):

I love that answer. How do you see AWS's role here as a cloud infrastructure provider?

Michael Greenwald (21:28):

So at AWS, we're really fortunate to be customer obsessed and AWS cloud, it underpins the digital asset landscape. And what I mean by that is we get to work with Web3 customers. We get to work with stable coin customers like Circle and Paxos. We get to work with Coinbase, get to work with you at TRM, we get to work with central banks. And so we have an underpinning gives us a unique perspective on the customer and it gives us a unique perspective on what is customer adoption looking like, how is it evolving, how is the customer trying different things, and then what does the regulatory space look like in comparison? And so I think for us, we want to be part of that journey for the customer experimenting, but working on our cloud in a secure, resilient, scalable mechanism. And for us, security is job number one, two, and three and I think very well wearing your TRM hat how important security is in this space. And so it's a combination of underpinning but also listening deeply to the customer.

Ari Redbord (23:08):

Really fantastic. One of the coolest I think, experiences or meetings I had in my two years at Treasury was actually with the AWS team and Secretary Mnuchin and Sigal Mandelker, who was the undersecretary at the time, Todd Conklin, who was running this massive data project for Treasury. This was pretty early for me in sort of my thinking around technology and innovation. I think I was really taken back by the extraordinary data that's at our disposal that we're probably not taking advantage of today is pretty extraordinary. We've come a long way in the probably seven years that has been, but right, that's what you're doing. You're bringing those private sector services to policy makers so they can make the best decisions that they can.

Michael Greenwald (23:46):

That's exactly right. And Treasury is a great customer. In many different parts of the US government are great customers where whether it's in the national security space or in the federal financial space or the defense or federal civilian space or even globally, I just got back from Saudi Arabia for example. They're doing some very innovative work in blockchain and digital assets and ai. We're seeing public sector institutions lean in and lean in no other before and really asking the question, does this work for us? And if it does, what are the applications? What are the use cases and how can it be better for the customer? How can the experience be better? How can we be more secure and how can we be more efficient? And resilience is really part of every conversation.

Ari Redbord (24:39):

What is your message today as you go around the government having these kinds of conversations? You mentioned Saudi, I know you travel all over the world for this stuff. What's the message right now in this sort of geopolitical moment?

Michael Greenwald (24:50):

So I think in the executive branch and where we're working globally, we usually bring our customers together with public sector institutions. And the importance there is that we're always listening and trying to understand what are they trying to solve for. And so a customer of ours may have a solution that a public sector institution has, and so it's part of that customer obsession already to bring them to the table and to make sure the right people are around the table to attack the problem. I think that ultimately everybody wants to use AI and test generative AI practices implementation. Before you do that, you need cloud as a foundation in your services. So a lot of our first step is explaining what that means, what that journey looks like, and then explaining what's in the realm of the possible for that public sector organization together. And that's why I like to convene customers and partners together. It brings the best minds around the table. And if we can work off our customers, that makes me really happy. And I think it makes different customers in the public sector happy that they know that there are many tools in the arsenal to attack the problem.

Ari Redbord (26:22):

That's fantastic. How have you been able to bring your personal life and meld it together, right? It's not a work-life balance, it's this other thing.

Michael Greenwald (26:30):

Well, you do a very good job of that.

Ari Redbord (26:32):

And so I have my own kind of answers for that, but I don't know a lot of people who have done it as well as you have. And I know there are a lot of people again on here who are looking for that type of guidance as they either start their career or they shift. How have you done that? Well,

Michael Greenwald (26:46):

I work with people I really like and I really respect. And so it's not work. I think that we're really fortunate that a lot of Treasury alumni or folks who worked within the government are working in this sector. And so it's never felt like work. And I guess there may be days that are challenging or long, but I really feel proud of the work we're able to do and you're able to live a life of consequence and help a larger meaning. So I think that I try to always work with people that are super smart that I can learn from, that I can take things away from. And then if there are ways to, I would say bring it all together, that to me is the best formula.

Ari Redbord (27:45):

I remember you moderated a panel really a few months ago, and we'll talk about this in a moment. And I was on the panel, your mother was in the front row. I think that is the ultimate right when you could bring your family into your career and your career into your family. And that was very, very cool. And just for me it was like, yes, this is kind of how you do it.

Michael Greenwald (28:01):

Well, listen, I mean, I wouldn't be here without my parents and every opportunity they gave me. So wherever I can bring them along the journey in some way, that's a win. And I think as you know, get older, you get more sentimental about spending time with your parents. So if you can bring them to that extra event and have that extra moment, that's really special. And then I just like being able to bring people into conversations. And then I've just really started to enjoy moderating. I think you obviously enjoy this podcast. I think if you can learn a few things that maybe you weren't expecting to learn from someone or go a layer deeper, that's special because it helps you understand them better and you learn things. So I have amazing colleagues at AWS and I have a great team, and for me, I'm learning from them every day.

(29:10):

They're truly remarkable. And to me at Amazon, we have a formula where if you have a big idea and you have the data to back it up, they will let you build it. And that's sort of how I approach every day, and that's how the team approaches every day. We think very big. We try to be disruptive in the best way for our customers and let's have some fun along the way and bring great people together and maybe bring people on stage who haven't been on stage before. But once they're on stage, they may find their voice, there may be a message that's different. And so we like to convene whether it's public or in private round tables, but I think it's a critical part of this process.

Ari Redbord (30:00):

That's amazing. One thing I know you are passionate about is where you live in your community. The conference that I was referring to where your mom was in the front row was for really, they call this city of ideas for West Palm Beach, really a place there. This should be an innovation, ai, digital assets hub for America. What is happening there and why are you so passionate about this place?

Michael Greenwald (30:21):

Well, I really grew up here between here and Boston, and I've seen this great evolution of this community and it is a very special community and it really is a city of ideas. And there's so many, whether it's financial or health or education or research, there's just a combustion of activity of innovation that's occurring here. And so when AWS partnered with Related and Steven Ross for the City of Ideas event in which we were lucky to have you at, it was a great beginning of that chapter. So I'm very passionate about my community and I think a lot of us are passionate about our own communities. And I think when you can lean in and tell those stories to a broader audience, that's exciting. I would say when I'm not working, I love art. As you can see behind me, I'm very passionate about contemporary art and I follow the art market very closely and what it means in finance as well as digital assets. And I also just love to travel. If my wife hike, be active, Padel, all the above. Does

Ari Redbord (31:35):

The art collecting extend to NFTs in the digital space?

Michael Greenwald (31:38):

So I think during, I call it the Gatsby era, the Roaring era. When NFTs were really high in the COVID era, I was looking at that market very closely and how auction houses were legitimizing the space in different ways and taking E and so forth, and then converting into dollars. And I think that's a fascinating case study, but I think the art market in how it compares to the global economy and how countries use the art market, I just got back from Doha and Saudi and there's great architecture, great art museums popping up, and whether it's the Luv Abu Dhabi and the UAE and what that means, I find geoeconomics and contemporary art in that convergence to be personally fascinating. And I do think it's important metric of where we are from a macro perspective.

Ari Redbord (32:37):

Oh my gosh, I can't believe we're getting to this last. I feel like we could do an entire TRM Talks, Michael Greenwald talks art markets with us. Michael, seriously, this has been such a fun conversation. Not at all surprising for folks who are listening. It's very much the conversation we've had many times in private. So thanks for joining us.

Michael Greenwald (32:54):

Thank you so much. And let me just say thank you for the great statesman you are in this space. You're a true class act, and I'm very lucky to call you a friend.

Ari Redbord (33:09):

So right after we stopped recording this episode, Michael said to me, I think this was a lot different than anything I'd ever done before. I don't think I've really ever had this conversation about my story, my journey. And I was really struck by, I was kind of proud of that because what I really want TRM to be is a show where we're having true experts talk about critical issues, compliance, illicit finance, regulation policy, digital assets. But I also want it to be a place where we can share the journey of builders in this amazing space. And this was an incredible example of really sharing a really cool story, right? Someone who was at the US Treasury Department, then as an attaché for Treasury in the Gulf, and then who went into this technology finance at one of the largest, most important companies of the world at AWS.

(33:55):

So I loved hearing that journey. And the other piece that I hope folks appreciated is this idea of convening, this really superpower of bringing people together. Something I've done for years with Michael as he's brought me into meetings with senior policymakers within the administration, whether it was Biden or Trump. It's not about the politics, it's about the policy and getting it right. And that's why it's so important that we bring the private sector together with the public sector. And Michael is just so excellent at that. So I think this was definitely one of those, more of those journeys, conversations. How does someone get to this place? You got to ask and ask again and then send a thank you note, right? That was very Michael. So really, really interesting. And I think hopefully listeners will take something from that career journey as much as the deep expertise on a post 9/11 world that we live in. On the next TRM Talks, I sit down with Ryosuke Ushida, chief Financial Officer for the Japanese Financial Services Agency. If you love the show, leave a review wherever you're listening to it and follow us on LinkedIn to get the latest news on crypto regulation, compliance, and investigations.

TRM Labs (35:06):

TRM Talks is brought to you by TRM Labs, the leading provider of blockchain intelligence and anti-money laundering software. This episode was produced in partnership with Voltage Productions. The music for this show was provided by Ikoliksl.

Ari Redbord (35:23):

Now let's get back to building.