Felicia Ellsworth: Welcome to In the Public Interest, a podcast from WilmerHale. My name is Felicia Ellsworth, and I’m a partner at WilmerHale, an international law firm that works at the intersection of government, technology, and business. For this episode, I am thrilled to be joined by Sid Velamoor to discuss his wide-ranging career and journey to become a top litigator and crisis manager. Sid is a partner who specializes in high-stakes, complex commercial disputes and investigations. With extensive experience managing complex litigation and regulatory matters across industries, Sid has particular expertise in relation to operational crises at major companies. Before joining WilmerHale, he was senior counsel at Boeing, one of the world’s largest aerospace companies. He was Assistant United States Attorney in the Computer Hacking and Intellectual Property Crime section, and before that, an associate and counsel here at WilmerHale. We’re thrilled that Sid rejoined the firm this past fall and thrilled that he’s agreed to join us on In the Public Interest. This promises to be a really interesting episode exploring Sid’s remarkable career, his thoughts on what makes a successful, multifaceted lawyer, and his perspective on developments and challenges in aviation and technology. Sid, thank you so much for joining us on today’s episode.
Siddharth Velamoor: Thank you for having me on, Felicia.
Felicia Ellsworth: So let’s start with a little background. You’ve been involved in a number of major corporate and national security events over the last decade or so. Could you describe your practice for us?
Siddharth Velamoor: I think that it’s more important to be lucky than good. And I’ve had the remarkable good fortune of being sort of in the vicinity when once in a blue moon matters emerge. I was at DOJ when the department launched its China initiative in 2018 and ended up on a team that investigated one of the landmark cases under that initiative against a major telecommunications company. I had barely started working as a prosecutor at the time. but just happened to have had a lot of experience with trade secrets law. And that was an immensely educational and novel experience for me as a relatively young lawyer to try and approach the same investigative tools, litigation processes as any other case in the midst of a lot of non-legal considerations, national security considerations, public relations concerns, political issues that were at play. A few years later, I had left DOJ, as you mentioned, to go in-house and encountered that same dynamic. How should non-legal constituencies and concerns affect or maybe even drive legal analysis? And I think that’s not a practice in the traditional sense, but it has sort of typified what my work has looked like over the last 10 years.
Felicia Ellsworth: And would you say that when you were either entering law school or leaving law school, this is the type of legal practice that you thought you’d end up having?
Siddharth Velamoor: Not really. I’d only ever been exposed to lawyers with highly technical practices growing up. One of my uncles was a business immigration lawyer. And so I kind of figured my career might end up looking like that too, like a physician who ends up specializing in a certain medical practice. I thought that would be my trajectory as well, which seemed to be what all the other lawyers I knew growing up had done.
Felicia Ellsworth: As I mentioned, you started your career at WilmerHale nearly 14 years ago before leaving us for government service and then to go in-house. Can you talk a little bit about what brought you to this firm to begin with?
Siddharth Velamoor: Well, I think ours is a firm really built around practitioners and is designed to support and enhance their practices and their dedication to their craft. And I remember interviewing as a rising 2L in law school with the late John Harwood, who was a partner at Wilmer Cutler Pickering in its telecommunications practice. And this was back in the day when we were in kind of a hotel in Times Square, speed dating partners at firms for summer associate positions in New York and DC. And the instruction was, I remember, be the kind of person they’d like having a beer with. And so you end up talking about where you like to go on vacation, what kinds of fancy restaurants you like to eat at. And then I walked into my interview with John, which I remember believing was utterly unlike any of the others. He wanted to talk about practicing law the whole time. And he was decidedly serious about it. I could tell that he loved his work regardless of outcome, regardless of financial reward. And he was, I’d say, pretty unforgiving and laser-focused on finding people on the other side of the table who would approach the work with that same dedication. And I think that’s because he cared so much about finding people who wanted to be great practitioners. And that was my experience at the firm when I joined and why I came here.
Felicia Ellsworth: I always say to people that WilmerHale is a place for lawyers who are real law nerds, people who really love the law and love to practice it and love to talk about it and love to think about it. So it sounds like you had that experience from not even day one, but minus day one.
Siddharth Velamoor: Minus day one. That’s true. I don’t think I had the typical profile that lawyers have growing up and really liked the liberal arts that much. I didn’t have a burning desire to learn about the law. So I was drawn to the law, I think, because when I was a kid, it seemed like the only white collar profession where one got paid to engage in direct competition and win. And I was just a total competitor growing up. I turned everything into a competition, often lost, often was very upset about it, often practiced like disproportionately hard to try and win inane contests. And so I think that’s kind of what drew me to the law. But I think it was great for me to be here to work with people like John, to work with some of the other folks that I worked with really early in my career because They paired that with a real dedication to the craft, which I think is more important for long-term satisfaction.
Felicia Ellsworth: So let’s talk about your first stint after you left the firm in the Computer Hacking and Intellectual Property Crime section at the U.S. Attorney’s Office in Washington. Can you talk a little bit about your experience as a federal prosecutor? What was that like?
Siddharth Velamoor: Yeah, we’ve got a lot of federal prosecutors at our firm, and I’d say there are certain aspects of the practice that are very typical. You spend a lot of time in court, you understand judges well, and I think you build relationships with the bench and bar that have a depth to them that you wouldn’t have in private practice as a young lawyer. I enjoyed some parts of being a prosecutor immensely and missed some things about private practice. One big distinction is that in private practice, it’s certainly not our design to work on the basis of imperfect information. We have the time to turn over at least the big rocks before we make any big decisions. That’s not always true. As a prosecutor, you might have an emergent issue where you know some of what’s going on, but you also know there are unknowns. And I think being able to work in that type of a fog, because you have no choice but to do something, you might have a cybercrime organization that’s moving quickly and covering its tracks, and you’ve got an opening to try and do what’s called a takedown in the industry. You have to execute on that, even if you know there are pieces of the organization that aren’t within view. And so I think it was a good experience for me as a young lawyer to learn how to make decisions with imperfect information, where you’re trying to balance the interests of knowing everything with the interest in having an effective outcome right there operationally.
Felicia Ellsworth: So you’ve talked a little bit about how different in some respects that is from your experience in private practice. But how did your time at WilmerHale help prepare you for some of those experiences as a federal prosecutor?
Siddharth Velamoor: I think judges are pretty unforgiving if you’re not presenting them with arguments that are credible on sight. And you don’t want to end up with a skeptical judge. Definitely don’t want to end up with a skeptical jury. I think being in an environment like our firm, you become pretty good at ferreting out bad arguments because you’re surrounded by people who have what my kids refer to as “radical candor.” When they see flaws in your position, you hear about it. And if you’re paying attention as a young lawyer and want to improve, you tend to internalize that skepticism and approach your own work with the same relentless scrutiny. That helped me from the get-go. When I was prosecuting cases, I was able to look at arguments objectively to understand how they would play with an audience, what the attacks would be, and to distill our arguments down to what I knew would be indisputably persuasive on site.
Felicia Ellsworth: Any interesting trial experiences or war stories from your time as a prosecutor to share?
Siddharth Velamoor: Well, I’d say one big lesson was don’t take anything for granted when preparing witnesses. We had a big cryptocurrency laundering trial, and the key witness in that case had been prepped really well on the substance. But one thing we hadn’t prepped him on was what to do in the moment when we’d ask him to identify the defendant in the courtroom. So he’s up on the stand, he’s really nervous, and we asked him to point to the person who had engaged in the fraud, and he pointed right at me. And we then had to take the unprecedented step of noting for the record that the witness had identified counsel for the government as the person who engaged in the crime. The jury got a good laugh out of that, and I learned that it’s worth prepping a witness for quite literally every question they might receive. The other thing I learned is that judges are humans too. If you haven’t presented them with a narrative that really captures their interest, their desire to do something about it, you’re not going to see the outcomes that you want. That was a misperception I had going into the job was that juries are the ones that you’re trying to appeal to, but judges, you can just sort of present them with arguments and they’ll come to the right conclusion. Over years of having conversations with them in court, you understand that they need to be appealed to just like anybody else.
Felicia Ellsworth: Let’s talk about what you did next, going in-house to Boeing, yet another very different experience from the prior two. What made you want to join Boeing and become an in-house lawyer?
Siddharth Velamoor: I grew up in the Seattle area. Boeing, for me, was an icon of American achievement. My mom worked at Boeing soon after we immigrated to the U.S., and so it felt fated to be able to give back to this great company that had done so much for my family and other families that I knew well growing up. In a sense, it was a deeply personal decision for me to join and very rewarding.
Felicia Ellsworth: I’m sure it was a very interesting place to be an in-house attorney over these past several years. Can you talk a little bit about your experiences there?
Siddharth Velamoor: Yeah, it is a really interesting experience to work as an in-house attorney, particularly in a very sophisticated, complex legal department at a company that’s deeply institutionalized in the sense that it’s been around for over 100 years and it’ll be around for another 100 years. There were a couple things that I found fascinating about the experience. The first is how operational, commercial you are in your thinking. You hear this all the time from people, but you don’t really understand it unless you’re on the inside. It’s like you’re sitting in the front seat of the car next to the driver, looking ahead, identifying risks and hazards, and figuring out what to do, which is very different from the work of a litigator. We tend to look backwards and try and figure out what happened. The other thing that jumped out at me is business clients are very intuitive at understanding what the law must be. And it made me feel I had imposter syndrome, I think, after a couple weeks in the job, because I’d get on these calls after researching the law, and before I could even tell them what the law was, they had pretty fairly described what they thought it should be. It made me appreciate how when you’re really steeped in the business, you kind of intuit the rules that ought to apply to your work pretty well. I mean, it was a great set of clients to work with because they were interested in and I’d say naturally inclined towards understanding the legal issues.
Felicia Ellsworth: Yeah, that’s an interesting observation. And those of us in private practice work a lot with the in-house legal team and less so with the business team. But obviously, as an in-house lawyer, your clients are the in-house business folks. Can you share any experiences or perspective from having had those closer interactions with the business teams during your time in-house?
Siddharth Velamoor: Yeah, well there’s a couple things that I think I will never stop thinking about, especially at a firm like ours. We use the term “bet the company” a lot, as a way to distinguish the really big cases, company-defining, career-defining cases. I certainly was guilty of using that term as a younger lawyer. When you’re in a company, I think you realize that every case, even the small ones, are bet the career, bet the reputation, bet the project, bet the budget cases for someone, for some team, for some sort of initiative at the company. And it’s a referendum on what happened, what they did, how well they did it. You come to the conclusion that all of this stuff really does matter. It’s not bet the company, but it feels that way for someone on the client side. And so it left me with a renewed sense of urgency to make sure that when I’m working on a matter, no matter how small, no matter how apparently inconsequential, I’m feeling and channeling the same urgency that I expect someone at the client has about it.
Felicia Ellsworth: I want to talk about your practice here at the firm and a little bit about the crisis management aspects of it. But before we do that, what made you want to come back to the firm? What brought you back home?
Siddharth Velamoor: I’d love to say that it was the only way I could think of to be invited onto this podcast. And now that I’ve experienced it, it’s truer than I believed. I’m a nostalgic, I think, and I had some of the best years of my career here working alongside superlative litigators, and I really missed that. You kind of pull together on common cause on this matter, and it’s kind of this collective effort to build something that really impresses whoever you’re trying to persuade. It was very meaningful to me early in my career, and I knew I wanted to come back and restart that.
Felicia Ellsworth: Let’s talk about your practice now that you’re back here. Crisis management is a practice area popping up everywhere now, but it wasn’t even maybe five years ago a recognized practice area for an outside law firm to have. How would you describe crisis management and why is that something that clients increasingly feel they need?
Siddharth Velamoor: Well, I find the term odd because I also sort of feel like great lawyers avoid the crisis or eliminate it. But my guess is that crisis eliminator sounds like an action movie and not a legal practice. And so here we are. President Obama had this advice to young professionals, which is, “get stuff done.” He might have used a different word for “stuff.” I think a lawyer in this practice area knows what stuff is coming and knows how to get it done, consistent with the client’s commercial and stakeholder interests. There’s a lot more you can layer onto the practice, and obviously it’s much more complicated than that. But my sense is that a lot of the market demand for the practice comes from understanding that an operational crisis can generate a lot of different types of stuff to deal with and having someone who can anticipate what that might be and figure out how to get ahead of it or to deal with it is valuable. And there are a lot of practitioners who have done that really well.
Felicia Ellsworth: How has your experience informed the lens through which you view crisis elimination practice? Let’s try and rebrand it.
Siddharth Velamoor: I imagine a picture of Arnold Schwarzenegger on the screen would help. I had certain matters as a young attorney where I realized that we can’t just send criminal process in this case, or we can’t just write the same indictment without thinking about external non-legal interests or considerations at play. And so my view is that in any corporate crisis, you’re going to have a variety of potentially competing interests that you have to balance. You might have investors, you’ve got the customers of the company that’s going through whatever it’s going through. You’re going to have employees, you’re going to have messaging issues within the company and others. Being able to think about decisions you’re making and how each of those constituencies is going to respond is the heartland of what I think a crisis management or crisis elimination practitioner does. Making sure you’re mindful of the various constituent interests that are affected by any particular decision. I’ll give you a great example because I’ve been thinking about this. If there’s a litigation, a typical litigator response is to throw all the affirmative defenses you can into the answer. And so you might bring an affirmative defense that says that some other third party was partially at fault for whatever the claimed harm was. Now, if it turns out that third party was a really important customer or supplier or investor in your client, then there are constituent interests not to bring that affirmative defense, even if it means waiving it and losing the chance to assert it later in the case. And so I think being able to think that through when you’re making legal tactical decisions is one of the ways that I think crisis management practice shapes out.
Felicia Ellsworth: Let’s talk a bit about litigating in corporate crises. How is that different than what I would call run-of-the-mill litigation? Obviously, there’s the same rules, same discovery objectives, presumably the same legal arguments. What makes crisis litigation different, if it is different?
Siddharth Velamoor: We talked earlier about being very thorough. The typical private practitioner’s approach to litigation is that in most cases, you want to take the time in litigation to try and understand what’s going on and then to litigate the case in due course. Now, if you’re in the middle of a crisis, there are extrinsic factors that might drive you towards accelerating the timeline of the litigation, elongating the timeline of the litigation so you kind of fall out of the crisis and your decision makers aren’t influenced by what’s happening. The idea is that if you’re in a crisis, it’s likely something that’s very public, and it’s likely something that the people who you are trying to persuade have already started to form opinions about. And so you’ve got to be mindful of that public discourse around the issue when you’re litigating the case, either to take advantage of it, if you’re on the right side of the crisis, or things have started to turn in your favor, or to kind of drift back a little bit if you feel like the crisis is now being litigated in a different arena and your litigation needs to take a backseat to it. Great in-house legal teams, like the one I was just at, have great counselors. And great counselors inside or outside the company aren’t reactive, but can forecast legal and compliance risks and challenges for their clients. And so I think having someone on the outside who can help you to look around corners, anticipate what your clients, your shareholders, your stakeholders within the company and other interested parties might do or ask you about, that’s going to give you a lot of room to do your job well if you’re on the inside.
Felicia Ellsworth: Thank you so much, Sid, for joining us on the podcast today. This was super interesting to hear about your many interesting exploits and the different skills and experiences that you brought back to the firm from this time away. I really appreciate you taking the time to chat with us today.
Siddharth Velamoor: Thank you, Felicia. Really enjoyed it.
Felicia Ellsworth: And thank you to our listeners for tuning in to this episode of In the Public Interest. We hope you’ll join us for our next episode. If you enjoy this podcast, please take a minute to share with a friend and subscribe, rate, and review us wherever you listen to your podcasts. If you have any questions regarding this episode, please e-mail them to us at [email protected]. For all of our WilmerHale alumni in the audience, thank you for listening. We are really proud of our extended community, including alumni in the government, the nonprofit space, academia, other firms, and in leadership positions and corporations around the world. If you haven’t already, please join our alumni center at alumni.wilmerhale.com so we can stay better connected. Special thank you to the producers of this episode, Jacqueline Vieira and Walker Schneider. Sound engineering and editing by Bryan Benenati. Marketing by Andy Basford and his team, all under the leadership of executive producers Kaylene Khosla, Matt O’Malley and Jake Brownell. See you next time on In the Public Interest.
