Khurram Naik: Shashi, I am glad to have you on the podcast. ⁓ I saw you in action recently on a ⁓ at a conference that a friend curated and enjoyed seeing you on the panel and then also separately interviewed Neil Chatterjee recently and he mentioned apropos of nothing that you'd be great on the podcast. So this is ⁓ a confluence that's bringing you here.

Shashi Kewalramani: ⁓ Glad to be here. Thank you for thinking of me.

Khurram Naik: So something that's ⁓ pretty clear from your career is that you've worn a number of hats. And so you've been in private practice in a range of areas. You've ⁓ IP litigation, white collar, criminal defense work. You've been at a large-ish firm. You've had your own practice. You've been a US attorney. You've been a mastery judge. You've done these in different jurisdictions. ⁓ The word you used for this was nonlinear. And at some point your career was linear. You you clerked, you joined a firm, that's linear. Did you prospectively expect to have a nonlinear career?

Shashi Kewalramani: So let me go back and correct something in my background. I was never the US attorney. I was always an assistant US attorney. ⁓ It's a big difference in my mind. One is senatorially approved. One is not. ⁓ So ⁓ have I always had a thought of a nonlinear path? I would say my first nonlinear move was after undergrad to law school. I never expected to be a lawyer. ⁓ And in the South Asian community at the time, there weren't many lawyers who had matriculated through the U S system as lawyers. There may have been some folks who came from countries in Southeast Asia or South Asia who had been lawyers there and then became lawyers here. I had always thought I was going to go to engineering school, go work for a company, ⁓ and potentially then move up the ranks within that company, just as my father did, just as a lot of other folks in my family did. ⁓ the closest thing to any entrepreneurial spirit I had in my family was folks who were physicians who had to open their own practice. ⁓ so I don't think I had thoughts about what my future was going to be, whether linear or nonlinear, ⁓ at any given time, it was just, an openness to different paths that came along the way ⁓ when I wasn't feeling particularly satisfied with the path that I thought I had wanted.

Khurram Naik: And I think you would use a word nonlinear to characterize your career. Is that something different than openness?

Shashi Kewalramani: ⁓ I think they go hand in hand. Linear is what people have in a mind of, ⁓ let me take what my own linear thought was. My own linear thought was get an engineering degree, go to a company, work through the system, ⁓ move around within the industry and move out and then retire. Have a good and fulfilling life that way. ⁓ I have now thought about and understood for me and my personality that ⁓ I had to be open to different opportunities and ideas that came along. And when some people pushed back at it, said like, are you sure you want to do that? You know, the safe path is to stay at the firm, make partner, and then, and then bliss will follow. ⁓ and I didn't think that bliss would follow. So when I say nonlinear, it's probably more nonlinear to other people. ⁓ Though there are definitely, definitely risk aspects within my own life that are, that are nonlinear. For example, leaving a senior associate position at a law firm when you're not far away from partnership to join the U S attorney's office in another state and taking a 75 % pay cut. ⁓ A lot of people would consider that. And I consider that nonlinear. was leaving the safety of. the firm life when I left the court to join Jams after one term as a magistrate judge. ⁓ I recognized I was leaving the cocoon, the safety of the federal judiciary to go out and be an entrepreneur. So ⁓ I guess I'm a little more comfortable with risk taking. A lot of that is ⁓ because of circumstances that I've been fortunate to be in where I can take those risks. My wife works, so that really helps. ⁓ for me to allow to take some risks.

Khurram Naik: You mentioned as associate you didn't see a path and bless and partnership. Why is that?

Shashi Kewalramani: ⁓ at least the path that I was on, I was an associate, I had been on trial teams. What I was looking at for people who made that jump to become the lead trial lawyer, the lead, ⁓ person at the firm who gets the clients, you had to distinguish yourself in some way. and the system started changing where there were fewer and fewer trials happening. at any big law firm. So the experience wasn't going to be there at the law firm. ⁓ I had wanted to get trial experience, but I had also been intrigued of moving out of, I was living in Houston at the time and exploring the opportunities outside of Texas. And that's why I joined and picked the U S attorney's office. Some folks could have said, well, I'll get trial experience. I'll join the DA's office. I wanted to do it in a different manner. I was always comfortable in the federal system because of my clerkship, the practice area I was in. And so I thought US attorney's office was where I wanted to be. And then within that, I wanted to do more white collar work, document intensive work, rather than ⁓ what would be violent crime or narcotics.

Khurram Naik: Did you or do you feel that the federal system is more meritocratic?

Shashi Kewalramani: for the US Attorney's offices or give me, can you give me a little more scope to that question?

Khurram Naik: even in private practice, as a new entrant to litigate in either a state court system or a federal court system, did you feel like would have a clearer path to success for you?

Shashi Kewalramani: So the federal system is much more rules-based, and there is always some level of ⁓ vagary in any system. But my feeling was the judicial officers I had come in contact with, both when I was a clerk and ⁓ practicing, ⁓ because it is much more rules-based, I did feel I knew the... the rules of the game. There wasn't like, ⁓ well, so and so goes to lunch with so and so. So they're going to get a they're going to get a good ruling in state court. Not that that that is like that, but I knew that was not, or at least perceived that was not the case in the federal system.

Khurram Naik: And you mentioned leaving Texas. What was the significance of leaving Texas for California?

Shashi Kewalramani: ⁓ a couple of things. First, the, the offers I got at the U S attorney's office were one, ⁓ I had interviewed, ⁓ in the Northern district of California, which is in the Bay area and the central district of California. I was about to get an interview there when I accepted the offer in the Northern district and applying for, ⁓ an assistant U S attorney's position is similar to a clerkship. You throw out a bunch of darts and see where you can get in. And I had picked five or six jurisdictions. that I thought did a lot of white collar work. ⁓ And the places I had also wanted to live. I had lived overseas as a child, ⁓ but after high school, I pretty much spent my whole career in Texas. And I would come out to California with some frequency and I really liked it. I liked the feel of the place. I liked ⁓ the opportunities that were out here. ⁓ But... I also was lucky enough to get an assistant U.S. attorney offer from that office.

Khurram Naik: Why are you interested in moving into white collar work?

Shashi Kewalramani: ⁓ it is in my mind, ⁓ it was closer to the type of work I was doing, which was commercial litigation, antitrust litigation, and IP litigation. So, ⁓ it is looking through a lot of documents. ⁓ it also has, ⁓ at least perception wise, more transferability back to the private sector. I had never intended to be an assistant US attorney for my career. It was a period of time that I was going to, at least what I was planning on doing was go to a good US attorney's office, get trial experience, do white collar work where you were also against attorneys usually at big firms, and then go back into private practice in big law.

Khurram Naik: And why is it that you, it sounds like you had some early skepticism over institutions and attachment to them. Where did that come from? Like what gave you the point of view that this couldn't be an indefinite home for you?

Shashi Kewalramani: ⁓ I just didn't see, no, was, I wouldn't say it's a, it's a issue with institutions. would say it was something that I didn't see myself at that time with the knowledge I had, being a lifetime prosecutor. I thought it would be a four to seven year term, which was very common in some of these U S attorney's offices, particularly in the Northern district of California, central district of California, Eastern district of New York, Southern district of New York. ⁓ It was very common to do five to seven years, get good experience, work really hard, and then go back into private practice ⁓ versus some other offices around the country where people join the office and they stay there till they retire.

Khurram Naik: So that was the norm ⁓ in that year's attorney's office. And so then ⁓ heading into it, you some expectations of what you'd get out of it. Did you in fact get what you thought you'd get out it? What surprised you that you got out of that tenure?

Shashi Kewalramani: Um, the biggest surprise I think I got was, uh, the, the number of the type of people I came in contact with at the U S attorney's office and, interacting with main justice in the 2003, 2004 time period. really enjoyed the breadth of experiences people had when you are at least when at the law firm I was at, people had a pretty, um, common route to get to the firm. because I was working in an IP place, was undergrad, law school, clerkship firm. And it was very common. There weren't a lot of folks who had, let's say, ⁓ gone undergrad, then taught for a period of time or done Teach for America or joined the military and then gone back to law school and then clerked then come to the firm. The firm I was working at was much more ⁓ stayed in the sense of how people got in. And that's how I saw a lot of folks at the other big firms in Houston, particularly how they came to the firm. At the U.S. Attorney's Office, people had a lot of varied ⁓ paths to the law. ⁓ People taught, people worked overseas, ⁓ people were in government at some point, decided to go back to law school, and then joined the U.S. Attorney's Office at some point in their career. So that was really refreshing to see that there was not a single path to any career goal. And I saw that firsthand with what people had done and I hadn't been exposed to that before. It was always there are steps and you follow those steps and it leads to an outcome versus, ⁓ sometimes those linear steps aren't, ⁓ what we perceive as linear steps don't necessarily lead to the goal. In fact, they do because they expose you to different ideas that really tell you what you're going to enjoy and what you may be good at. So that was one of the

Khurram Naik: What's another instance in your career where experienced something like that, where they had a very analogous insight?

Shashi Kewalramani: ⁓ I would say I saw that at the court too, ⁓ where people had the people who had been selected for judicial positions hadn't necessarily just gone through what you would consider the steps of going through big law, then getting on the bench. were people who came from varied walks of life, had worked at legal defense funds, had worked at public interest entities, had worked at government entities, non-government entities, but still had succeeded in their field by getting nominated, getting appointed as a district judge or an appellate judge. And I found that was also very interesting to see.

Khurram Naik: Can you point to any specific takeaways you had from people who walked these different paths?

Shashi Kewalramani: They learned a lot about the world and I think it made them better people and also better professionals because they weren't thinking in the way that somebody who had just gone through school rather than somebody who'd experienced the world. And I think they had brought insight that ⁓ sometimes I wouldn't think of. And they would have experiences that were ⁓ unique, that would give them really some ⁓ idea of how to handle a situation rather than what had been taught normally, like this is how you deal with this, you dismiss this motion, well, or something like that. it gave them some flexibility and some insight on how to deal with things because I think they had a better idea of human nature.

Khurram Naik: Is there a moment that comes to mind either from the U.S. Attorney's Office or the bench?

Shashi Kewalramani: ⁓ from the U S attorney's office, I remember somebody who had been in the military before they, joint went to law school and we were dealing with the case. ⁓ and one of the, one of the things he told me was the defense attorney was taking some positions that weren't probably beneficial to his client. ⁓ and I was just having a hard time reconciling. Well, why are you not doing things in the best interest of your client. ⁓ I was probably naive. Well, I was naive. And he sort of explained to me certain things that go on in, the real world, in, ⁓ in being exposed to things where he grew up and how he grew up, ⁓ the distrust that probably was there between the client and the council, the council, because of the clients, ⁓ council's relationship with the U S attorney's office and that we had to recognize that the client and the council probably had internal friction that we had to account for and give some grace to.

Khurram Naik: Did that impact you took on in criminal defense matters through the CGA after you left the bench? Did that impact how you approach your practice?

Shashi Kewalramani: 100 % because I appreciated that not only being a court appointed attorney may put ⁓ me in a certain light and in light of my client, but also I've been a former assistant US attorney. And so I would recognize that folks who have been through the criminal justice system, maybe not, this is not the first time they had ⁓ oftentimes rightfully so. the ⁓ hesitancy of disclosing facts to me because they didn't fully trust me and I had to build up that trust over time. So that taught me that I had to give people space to trust me and I also had to take actions that would allow them to trust me. It just couldn't be words. I had to act in ways that showed that I cared about their case and that I was going to fight for them.

Khurram Naik: What specifically didn't they trust about you? My first intuition is they think, ⁓ you're a lawyer and lawyers are more aligned with other lawyers. you have, there's something corrupt about the nature of your relationship with, you know, the prosecutor's office or whatever. And so you're part of the system and you're looking to take advantage of somebody. That's my intuition. But what specifically was it that they didn't initially trust?

Shashi Kewalramani: My sense is that one of the things they don't trust is... Certain clients of mine couldn't afford an attorney. So under the CJA system, the court appoints you and the court pays for it. So they are viewing it as, you're just part of, you and the judge are aligned and judges in the past have done me wrong. Therefore you will do me wrong. And that was it. That was really the first step. And oftentimes what would happen at that first step would be ⁓ you'd get appointed in court. ⁓ The first step in a criminal case is a bail hearing. me, oftentimes people wouldn't fight for bail and I would always, one, I believe the law requires bail except for extraordinary circumstances. And two, I would voice that position aggressively. So that was one aspect. The first time they meet me is I'm going to fight for you from day one on this case. But going back to your original question of why did they not trust me? Because I'm appointed by this judge who and judges are all the same. They're not looking to do the right thing. They're looking to excuse me, railroad me because oftentimes they're working in conjunction with the prosecutors.

Khurram Naik: And then what is it that you did to facilitate trust? If you had to point to one technique, one approach you use, what is it that facilitated that trust? What did you learn?

Shashi Kewalramani: ⁓ to give the folks time, give my clients time. One, you have to fight for them right from the get-go and be fully transparent with your client and explain why you're doing what you're doing. ⁓ So full transparency is a big thing in every aspect of garnering trust, both as an attorney and as a judge. Full transparency would happen with my opinions. I want to put in everything that I am thinking about as a basis to why I came to a decision. You'd see certain rulings that say, I find there's a fact issue period. You're like, okay, well, you got to give me something more like as to your insight. But giving time giving transparency, I would oftentimes meet with my clients for hours, extensive hours, I would go meet them in if they were in custody in the jail for hours to to to talk with them, to learn about them, and give them the opportunity to speak freely, then the fact that I was willing to come into the jail for, let's say, eight hours in one day and be there as long as they wanted to be there, I think showed that I mean what I say. I am going to be here for you. I'm gonna treat you just like the, back then, the $700 an hour client as I would anybody else, even though you're not. you technically aren't paying for me, ⁓ you're going to get the service that all of my clients get.

Khurram Naik: You know, it'd be pretty straightforward for someone who is trying to build a practice and say, like, that's not a good use of my time. Yeah, sure. I'm getting in court and it's a different kind of matter. you know, of course there's a number of benefits to it. But any number of people say like, oh, just, it's just not worth it. I can be focusing on that $700 client and those are the people I'm most likely to work with in future. What mistake are those lawyers making?

Shashi Kewalramani: Well, I was warned about that by other attorneys in the field. Hey, you need to stop doing CJA cases because it's taking away from your other cases and your other marketing and hours and hours. ⁓ My sense is there is a, ⁓ there's a public duty obligation and law firms. didn't see that as much in the central district, but in the Northern district of California, big law firms would be on CJA panels. not only as a way to ⁓ get in court ⁓ with clients, but also to train younger associates of interacting with clients. ⁓ And rather than them sitting at a deposition and watching a deposition being taken, you could take younger attorneys to the jail cell or the meeting room and meet with clients and you would... allow them with your guidance. It's not that, these folks don't matter as much. You just have a lot more freedom of and time of speaking with a client in that setting who wants to talk to you versus private clients may not want to talk to you like, hey, here's the things, get it done, give me a deliverable in two weeks, we'll talk then. These clients are amenable to talking with you and strategizing. And it gives you great insight as to thought processes of what may be going on with clients. So as far as mistakes of why you should do this, I think big firms should do this not only as part of being at the bar, but I think it's great training opportunities for younger folks getting in court. ⁓ And ⁓ being a former federal master judge, I could say I would appreciate it. If I saw somebody from a big firm or a medium firm or a small firm in my courtroom, taking on a CJA case, my level of respect for them went up a little bit. And that transfers to other practices and that transfers to other cases they may have.

Khurram Naik: Can you be more specific? Okay, what is the impact of that respect?

Shashi Kewalramani: The respect is, ⁓ at least in my mind, like, Hey, you, you've put aside, it's not just about the dollar for you. You actually care about your client and you are, ⁓ you are building trust with me because you're taking this thing potentially to your own financial detriment. ⁓ but you are helping the bar at large. You're helping the court as well, because a lot of these folks who are indigent don't get the best attorneys. by being from a big firm, I know they're getting good representation. And we appreciate that because as a judge, I wanted the parties to have good attorneys because that leads to the best outcome.

Khurram Naik: And when you say that trust transfers to their $700 clients, those other matters, can you be more specific? What's tangible? What is the tangible benefit for one, two competently talented lawyers, credible lawyers, one, you're saying earns us trust from doing this other kind of work. What is the tangible payoff to that trust before the bench?

Shashi Kewalramani: Tangible payoff well one is These attorneys who are representing indigent defendants are in court more frequently and when I see an attorney more frequently I Feel they're less likely to play games with me because they're gonna be in front of me in another case So the tangible benefit is I when I when they are telling me stuff when they're making arguments ⁓ I am hoping, it's not always the case, I'm hoping that they know that if I catch them in a lie in this matter, or not a lie, but a misrep or let's say misleading in a slightly way, it's going to transfer to your other client. So you wouldn't do that. Human nature is not to say, hey, I'll do this for the benefit of one and then I'll lose my reputation for all my other cases. It's, it's One more opportunity to build a good reputation with the judiciary.

Khurram Naik: And, know, with the, I think it's really interesting to talk about what you can, the indigent clients, you know, have no bar, they're not paying you by the hour. So they're free to talk to you indefinitely. So you can do more strategizing. I think ⁓ a reaction you could have is, okay, well, great. So you learn how to strategize ⁓ with an indigent client. someone as you're saying is someone who's been ⁓ before judges before for other criminal matters. someone might say, okay, but like how much of the skills can transfer from like learning how to help somebody who has maybe made some mistakes to a big business, know, with, know, business and make mistakes too, maybe that's an answer. But what is it about, it would be easy to make, to call differences between the things that an indigent person who's had trouble with the law, the issues that person poses and the kind of strategy can learn from that for some gigantic tech company or whatever. What is that skill transfer of clients?

Shashi Kewalramani: One skill transfer is learning how to ⁓ obtain information that's relevant to the case. Learning how to be patient, learning to let people speak and tell you what they want to tell you. ⁓ Practice makes you a better attorney. It makes you better at getting information out of whether it's the engineer who was at the bench who gave the specification for the patent or somebody who is not trying to tell you the whole truth about something else. Oftentimes the hardest thing to do, ⁓ representing a client is getting the truth out of your own client and letting them tell you what happened, letting them tell you where the, ⁓ where the bad issues are related to the case. And that takes practice. Sometimes you have to just sit back and listen. Some people are uncomfortable with silence. Some people are very comfortable with silence. I have found the higher up the C-suite, people are very comfortable with silence. They're very good. They're smart. They don't wanna say more than they have to. And sometimes you have to know how to ask those questions and see. the tactics that are taken in order to divert you from answering or giving an answer to the question. and folks who have, ⁓ especially indigent criminals, ⁓ indigent folks who have not, I don't want to use the word criminals. They're, people who have done a bad thing. And one of the best lines I ever heard was just cause somebody did a bad thing doesn't mean they're a bad person. ⁓ sometimes these folks are, are very smart. Oftentimes they're very smart and they've had to get by in society with wits and intelligence. And you learn things through that process that have, that are transferable to speaking with your own clients. And oftentimes your own clients at big companies, they're amateurs considered as compared to what folks on the streets have had to do to get by.

Khurram Naik: Is there a moment that comes to mind? There's a moment of like a particularly sophisticated, you know, someone you represent in the CGA context and that you've learned some technique or, or, you know, there's something that really struck you about what they did that, that you use in, in, in working with these $700 clients.

Shashi Kewalramani: The biggest tell was when somebody wouldn't answer the question in a conference room when it's just you and them. That's the biggest tell. ⁓ that's something that ⁓ I learned how to deal with dealing with my other clients. And sometimes people just need the space and the grace to get to that point in their head to tell you the bad thing. Sometimes people need to be pushed to tell you that bad thing. ⁓ And I can't tell you when one approach is appropriate versus the other. It's just, I've done it so many times. You kind of have a sense that, okay, if I push here, is this gonna rupture the relationship? Or is this what this particular person needs?

Khurram Naik: Is there been a moment where you've taken something that the client in any context, you know, these, these indigent defendants or, or, or big companies, um, is there a time you've taken something that they deemed or was objectively a bad fact and inverted that into something that was beneficial or at least neutral, least neutralized that bad fact.

Shashi Kewalramani: BUM! I would say in certain white collar cases I had had in the past and even in ⁓ civil matters, and particularly in mediations, I do this quite often, which is the other side will rely on a document that they say this is a bad fact and you're speaking with the client. And one of the mechanisms to really understand whether it can be neutralized or at least diminished an impact is Give me the context of this ⁓ document. ⁓ And that allows folks to then discuss, no, this document isn't as bad as you think. And they'll tell me why. And being able to just sit there sometimes for, it doesn't sound like a long time, but for five minutes in silence while that person is talking. ⁓ You do this, five minutes of silence is a long time. But just sitting there and let the other folks speak, sometimes they will give you the answer that actually does neutralize it. Or in their explanation, they come to realize, yeah, this is a bad one. So they internalize the aspect of the document that's going to be harmful to them without me having to tell them.

Khurram Naik: I want to go back to something you said about the nature of the CGA panels in the Northern Districts versus the Central District. And you found that the large firms, that part of the bar was much more active in the Northern District. You've been prosecutor, you've been master judge, you've been in private practice, you know, across two jurisdictions and maybe from anywhere else in the country, they might say, okay, Northern District California, Central District of California, Sure, there's differences, but they're more similar than dissimilar. ⁓ What is your vantage point on that? How can you help people understand, hey, of course there's similarities, but there's actually a lot more differences across ⁓ districts ⁓ than you might expect.

Shashi Kewalramani: it's But when you say differences across the district, mean in the judiciary or the practice? do you sort of, would you like me to focus on?

Khurram Naik: Because you straddled a few different roles, have, you've been, you know, before these in private practice, you've been on the bench, you've been in the prosecutor's office. So it's really, you've got multiple vantage points on differences in powers among these jurisdictions. So you just you pointed to the ⁓ bars, the big law bars participation in CJA, and that impacts know, culture, what are cultural differences among these districts? ⁓ What, you know, what are the natures of the kinds of matters that are prosecuted from the US attorney's office? What's your relationship with the bench? There's lots of jumping off points and I'm curious, you whatever's top of mind for you in comparisons between them.

Shashi Kewalramani: Sure. So for the Northern, let me take the Northern District first. The Northern District of California has a lot, is a lot more tech heavy. Down the, down Silicon Valley, San Francisco has a historically been a financial center. You know, as you probably know, Wells Fargo, Bank of America, they were all based there, but now they've moved, they moved their headquarters elsewhere. But there is a tradition of a lot of financial, businesses as well as tech businesses up in ⁓ Northern California. Northern California also had an SEC office as does the central district. have a culture of prosecuting certain types of or investigating certain types of allegations. San Francisco has an antitrust division office. Central district does not. So as a result of certain offices that have ⁓ priorities in those particular jurisdictions, the practices I think have ⁓ morphed to accommodate those enforcement areas. So San Francisco has a lot more antitrust, private antitrust cases, I understand, than the central district does. ⁓ Another district that has a lot of antitrust cases is Eastern District of PA, Philadelphia. And how those formed over years, I'm sure there's multiple reasons, ⁓ but... At least in San Francisco, they had an antitrust division office there that was enforcing antitrust law. So you have law firms that create and respond to that practice area. ⁓ central district, California, it's just huge. It's massive. It's 19 million people. Northern district isn't smaller. mean, isn't small, but it's not 19 million people. there are a fair number of historically, ⁓ narcotics and violent crime ⁓ prosecutions that were done at a larger scale in the central district of California than in the northern district of California. So ⁓ you had differences in practices of the prosecutors and the type of investigators that would then come to these jurisdictions ⁓ who would investigate cases for you. ⁓ And so from the judiciary standpoint, you would see different types of cases because ultimately we're the client, we were the, ⁓ the attorneys are our clients when I was on the judiciary and they bring you the cases they bring you and you deal with them. So in the Northern District, you would get a lot more ⁓ IP, antitrust and the SEC, though there would be some... ⁓ what I would call guns and drugs and violent crime. It's not nearly as much as the judges in the central district in my mind have to deal with. Though you could take a look at the statistics and it may not be borne out. ⁓ It was just my experience that the judges up there handled a lot more ⁓ white collar and ⁓ IP, SEC, antitrust cases. In the central district, you have a lot of contract cases. There's a lot of commerce down here. Not only is their commerce related to contracts, there is commerce related in the entertainment industry. And that is a big aspect in the Los Angeles courthouse. In the Orange County courthouse, we had a lot of, there's a lot of real estate related businesses and IP because of the companies that are based in Orange County. Riverside has a lot of contract. ⁓ commercial matters, as well as a lot of civil rights investigations just because of the nature of the population. ⁓ even within the districts, the divisions have a different sort of focus because of the types of cases that are generated within the counties that comprise the particular division within the district.

Khurram Naik: And so that's really helpful to understand how these kind of patterns or pockets of expertise that form impact components of the bar. you've got, you described the impact of the expertise that a US attorney's office might have, the impact that has in the private bar. What's the impact on the judiciary? What is the consequence of expertise? Or is there something in the nature of... of resolving contract disputes, if 80 % of your doc is contract disputes versus 80 % is IP and antitrust, what's the impact on how judicial opinions are formed or the approach of the bench and the relationship with the lawyers before them? What changes for the judges as a product of these pockets of expertise?

Shashi Kewalramani: Yeah, I can just speak to myself and what myself what I would see is there's different ways to the way you manage the case is different based upon the nature of the case. ⁓ If it's a ⁓ if it's a let's say ⁓ a P.I. case, a personal injury case involving we would have ⁓ certain sometimes trucking accidents in federal court because they would get removed based upon the on diversity. ⁓ There's a different way you know there's going to be a different discovery, different timeline ⁓ to get that case to trial versus an IP case which may have international components. There are going to be different motions, different discovery aspects. And the more you see of a particular type of case, the more you can anticipate what problems are going to arise and how to put in ⁓ safeguards in the management of the case. to allow that case to proceed more efficiently. Let me give you an example. For example, in a big commercial case, IP versus a relatively, let's say, two-defendant contract case. ⁓ I'm sorry, a two-party contract case versus an IP case. And let's say it's a fairly simple home construction contract versus an IP matter. One of the things you have to be mindful for in either of those cases is what's the scope of discovery and how is that going to impact the deadlines that you're setting for summary judgment and the trial deadline? ⁓ Should you put in a end of discovery date or should you put in a date before that that constitutes what's called a substantial production of discovery deadline? Because there may be lingering things that happen after the discovery has gone out. Well, we've had to work with our ⁓ client in a different country that has different privacy laws, therefore we couldn't provide this material now. Whereas if it's a contract case involving two parties locally, it's going to be a pretty finite sense of ⁓ a finite amount of material that's going to be needed to present that case to a jury. So the more you see of a particular type of case, the better you can anticipate the problems that may arise in managing it.

Khurram Naik: Do you think there's a benefit to codifying that in some way? And so that sets the norm for peers on the bench. Like what are ways to institutionalize this knowledge?

Shashi Kewalramani: Well, certain courts have local rules for patent cases, for example, the Northern District does the Eastern District of Texas, the Central District of California had there. There has been talk about that for now decades and they have not been adopted. But what will happen sometimes is a party will say if the parties will agree, they'll say, well, your honor, we'd like to use the Northern District of California rules for patent cases in this matter. Some people like that, it codifies it. Some people believe it takes away the bespoke handling of every particular case. So you have voices on either side and fundamentally you can't make ⁓ judges do something they don't wanna do. It's very difficult to say, you need a consensus to make that the norm within a particular district. And it can be difficult because People have valid views on both sides of, will this inhibit my approach to a particular case? Let's say it's a really simple patent case. Why should we have all these rules that are more favorable to potentially, let's say, the defendant? ⁓ So that may take away some freedom to manage that particular case in an efficient manner.

Khurram Naik: So what I'm hearing is, well, I first want to mention on this impact of procedure and process is that some has been a running theme on this podcast. It was first raised by Judge Kennelly in his episode. And so he talks about the centrality of process for the administration of justice. Judge Chabria picked up the same theme as well. So this is, think, it seems to me an underrated theme from the judiciary is the role of process in administration of justice. And so the other thing I'm noticing is you're saying, this is something Judge Kennelly also noted in his episode is the pros and cons of how independent every judge is for the same reasons you're identifying. It was part of Judge Chauber's episode because he and one of his colleagues came up with different approaches on an important issue on AI and fair use recently. So, but it seems to me that there's this trade-off between standardization and customization for a particular matter that judges have to consider. Like judges form their own points of view on where they sit on the importance of one or the other. It seems to that's a canonical trade-off that judges consider. Are there other canonical trade-offs that you can identify that judges consider?

Shashi Kewalramani: I guess I'll ask, I don't know what canonical trade-offs mean.

Khurram Naik: Uh, boy, I feel like I'm, I'm, uh, you know, uh, before your courtroom right now. So, uh, look, it just seems like one of the classic issues that, that you're saying that, you know, a judge has to consider is to what degree do I think that, you know, a type of matter is more amenable to standardization or to what degree do I feel like, it's more important to have every matter before me and just make a call on each one of these. Those are trade-offs. There's benefits to one approach, there's benefits to another, there's costs about the approach.

Shashi Kewalramani: Yeah.

Khurram Naik: What are other benefits and costs trade-offs that judges consider? Like, what do you consider as like the, when you're sitting in room with your peers, what do you think are the tension points where reasonable minds, experienced minds can disagree on, on, this seems to be an important one. What are other important ones?

Shashi Kewalramani: Okay, so let me, one of the things, because I was a magistrate judge, I had a lot of discovery matters. There are certain viewpoints in discovery, which is, look, that's the attorneys, they'll deal with it, and when they have a problem, they'll bring it to us, versus putting in procedures to avoid those issues being brought to you. So let me give you one example, depositions. If a party had consented to me, and so I could control a lot of the discovery issues at the beginning of the case where you would have your conference, I would adopt the rules with respect to objections at depositions from the Eastern District of Texas, which were, you can only object to form or you can only... ⁓ tell your client not to answer a question based on either attorney-client privilege or the attorney-work product doctrine. Or you could ask the other ⁓ party, the party you were questioning, you could submit the objection of ⁓ non-responsive. So that does away with speaking objections. And in California state court, they are supposed to do that. You're supposed to do form and only ⁓ be able to instruct your client. to avoid speaking objections. And then if you object form, the questioning attorney has the ability to ask you, what's your basis for that objection? And you would have to say, ⁓ lacks foundation, hearsay, whatever the objection, whatever the evidentiary basis is. Certain judges would say like, we're not gonna put in this controls of how they should, how should they, the deposition should occur. I had enough issues come up before me with, ⁓ speaking objections that were taking the depositions beyond the seven hour time limit and things of that nature that I thought it would be helpful to the council to say, here are the rules. ⁓ you're gonna have these are the only objections you're going to have. And then I don't want to hear, or I think you have less of a leg to stand on saying, well, we didn't get all the information we needed in the seven hours that were allowed for under the, ⁓ federal rules and we need more time. ⁓ so there is an involvement in sort of the process that I thought would be beneficial to what I viewed, again, as my clients were the attorneys at the bar. And other folks said, look, we're just refs until we see a foul, we just sit back.

Khurram Naik: Any number of people, so my experience with master judges is yes, they're feeling so much of the discovery issues across jurisdictions. That's something I observed. Article III judges are obviously the flashy role. That's like, that's kind of the role that people have in mind when they think of judges. What do think people are missing from the opportunity of either being on the bench as a Magisterial Judge, practicing for a Magisterial Judge, clerking for a Magisterial Judge? What do you think is underrated about that part of practice?

Shashi Kewalramani: ⁓ so the role, let me first start the role of the master judge is changing. A lot of districts now have consent programs. The Northern district of California has historically had a consent program where it was, I don't know whether it was considered bad form or why, but when a case is assigned, if it got assigned to a magistrate judge in a civil case, now criminal cases, they have different issues because of the, ⁓ the constitution and how, who can impose sentence on a felony. But in civil cases, a lot of ⁓ parties will consent to magistrate judges. ⁓ And that's becoming more common in the central district. ⁓ It is very common in the northern district. And I can't speak intelligently as to what happens in other districts. ⁓ So the role is changing. From that standpoint of being an MJ, ⁓ I think it's a great opportunity. It's a great job. It's great from a standpoint of ⁓ you're in the federal system. You are getting a lot of consents. You are dealing with a lot of the nitty gritty stuff that happens in cases that actually can help form and moves the process along in an efficient way. ⁓ I think it's I thought it was a great ⁓ opportunity for me to learn also how the ⁓ how to think like a judge and what is really going on behind behind closed doors. What's the thought process even beyond clerking? ⁓ I'd clerked for a district judge. And so when I became a magistrate judge, I had a sense of what happened, but not really. You don't know it until you do it. ⁓ And one of the other things I can speak at least ⁓ to the culture in the central district of California, ⁓ the magistrate judges and the district judges, we interact fairly regularly. ⁓ There was no sort of in certain courthouses or the vast majority of people, there was no distinction. It was like, ⁓ this is Judge so-and-so. You would not hear a district judge say, this is Magistrate Judge so-and-so. I'm district judge so-and-so. You just didn't hear that. so you get a lot of insight into the whole process. As far as clerking for a Magistrate Judge, I just got off the phone with a former clerk yesterday who was arguing with his law firm because somebody had wanted to go off and clerk for a Magistrate Judge. And the biggest thing was like, they will become a better writer. because of the product that we have to get through, especially in the busy districts, ⁓ how many motions we have to decide. And it really trains you to become a better, more efficient writer and gets to the point of what you're trying to convey. You get to see a lot of ⁓ argument by attorneys. You get to see good, bad, and you get to see a lot of ⁓ other materials and just being in a courthouse. You pop in, it's like being a gym rat. You're at the gym and you can pop into a courtroom and see like, we hear so-and-so is giving a closing in this matter. Go check it out. ⁓ And so there's access and there is ⁓ the opportunity to really improve not only your understanding of how the judiciary operates, but also to improve your skills as a writer.

Khurram Naik: To that end, what surprised you the most about how the work that judges do, either in opinions, either in administrative cases, maybe any of these, but what surprised you the most from your time on the bench?

Shashi Kewalramani: volume of cases that we have to deal with and the number of ⁓ complex motions that we have to address in a timely fashion in order to really deliver justice to the parties. ⁓ You hear and you're like, ⁓ we have this many cases, but until you're there seeing the flood and the type of cases, ⁓ so security appeals, bankruptcy matters. ⁓ The most complex issues oftentimes were in pro se matters, particularly pro se 1983 cases, because they were, know, a party would say, would use some loosey goosey language and then we would have to fair it out. ⁓ Hey, what's the constitutional basis for this? And I remember we, and as a magistrate judge, we would have to screen these complaints, these 1983 complaints from oftentimes prisoners and pro se folks. ⁓ which have gotten better with AI by the way. But nevertheless, it is still complex because I I'd remember handing a complaint to, my law clerk. go, here's your new Con law exam. Like what are they, know, Gideon versus Wainwright was a pro se person. And these complex constitutional ⁓ ideas and, and the theories of recovery are oftentimes raised in the most mundane and surprising ways. And so you would see that in cases where, hey, they didn't let me out of my jail cell for blank number of hours. And the other side says, well, there was a lockdown, so we don't have to. It's like, okay, well, there's constitutional tension there. And those types of cases were the most surprising to me of the areas of law that you had to get ⁓ quickly up to speed on. ⁓ Even with the most law clerks are one to or straight out of law school. And yes, they may have some ideas, but you've got this breadth of knowledge and it's difficult. It's difficult one day flipping from an ERISA case to the next moment talking to a fourth amendment issue. That's a little, that's a little quirky.

Khurram Naik: That's profound that ⁓ from the bench's standpoint, the bench is not assigning significant cases based on dollar value or something like that. It's based on legal issues. And so as you're saying, ⁓ some seemingly minor pro se ⁓ case could raise such interesting constitutional issues that in the case of Gideon, just transforms our legal system. ⁓ Yeah, that's interesting. reminds me of the previous episode was with Louis Tompros, very different context, but ⁓ he identified an opportunity to look at pro se patent application ⁓ filings and rejections and look for ones that had raised interesting legal issues that then he could argue at the Federal Circuit. So he took one on pro bono. It's called Enray Klein. so it involved ⁓ the doctrine of obviousness in the wake of ⁓ the KSR Supreme Court decision and got a presidential opinion out of it, got changed the PTO's examination policies. So these seemingly minor matters can have a big impact. ⁓ So from the bench, you're mentioning you're like a gym rat. there's so many, like in the gym, there's ⁓ different theories for what's effective and.

Shashi Kewalramani: Sure. Yeah.

Khurram Naik: different things work for different people, people with different physiques and strengths and et cetera. there's, so when we hear about advocacy techniques, I think most commonly we think of a one size fits all approach. There's just some objective platonic ideal way to communicate before the bar. Sometimes you hear, I think particularly in the context of the Supreme Court, you hear such and such advocate, well, they can get away with that because they can, their blank name and they can do whatever they want up there and their approach. so in some sense, it's just like, maybe it's extremely personality driven in one sense. On the other hand, there's like just these perfect ⁓ approaches. I imagine that the truth is somewhere in between. ⁓ maybe it's certain advocacy techniques apply to certain personalities or certain types of matters. What can you say about what you've learned about advocacy techniques from the bench? What there to what changed your mind about advocacy? Because you had plenty of experience before that in private practice as a prosecutor. What changed? ⁓ And what do you feel like there's archetypes of advocacy techniques?

Shashi Kewalramani: So let's split into two types of advocacy. One is advocacy to the bench in a legal matter versus advocacy to a jury. ⁓ And what works in both cases. ⁓ With respect to the bench, the common theme that I saw across every advocate was they answered the question. first thing out of the box. didn't want to give, they didn't want to preface it with a bunch of stuff. They answered the question. Then they would, then they would give the explanation. ⁓ And that was really appreciated. And that set somebody head and shoulders above the next person. within that answering of the question, and it could have been, it's like, well, it depends. The most lawyerly of all answers, well, it depends. And then the next question you could anticipate from the judges on what. ⁓ If we're gonna go down this flow chart, let's create the flow chart. ⁓ And the best advocates would take you down that flow chart. The people who weren't that good would not. They thought, ⁓ well, I'm not going to get that next question or the anticipate that next question and it would quickly fall apart. All of that is wrapped up with incredibility. Um, as a judge, and this is what I found myself doing, you would oftentimes find within, say there's four attorneys, there are two on either side, the attorney you could trust the most and the attorney who gave you that direct answer quickly with supporting basis, either legal or factual. It all comes down to credibility and who am I going to trust when I don't have everything in front of me and these people are representing, these are what the documents say or these are the amount of documents that we have to deal with versus somebody else saying, ⁓ we have a lot of documents. Like how many? It's like a lot. Okay, that doesn't persuade me. the folks from a legal standpoint, would first answer the question, would be succinct, not necessarily succinct in the sense of not giving the requisite detail, but would often then sometimes put in a little ad hominem attack or would put in why this case is so difficult or something else that's like ⁓ just not related to the merits. ⁓ And they would give you that answer and sometimes they would give you the answer that's harmful to them. It's like, well, no, we don't have that. And that again builds credibility, which is the cornerstone of everything. If you lose credibility, you're pretty much done in arguing before a court. I could say that pretty much across the board. I don't think any judge would say, well, even if you're so and so big name, if you don't have credibility in front of me, I'm still gonna give you a break. It's like, no, it's not gonna. It's not going to happen. ⁓ So that's that's legal ⁓ argument. ⁓ In front of a jury, what I found was there is no archetypal ⁓ manner. People who you would think were like, God, that person is just not prototypically, quote, smooth, but they are winning day in, day out in front of a jury. And I think that comes from genuineness. ⁓ and authentic authenticity to yourself as to what type of person you are. The bigger thing is not being a Juries pick up on that. Judges pick up on that. If you're just a jerk and ⁓ versus fighting for your client, you can do the two things without being a jerk. You can fight for your client ⁓ hard. ⁓ But I don't know if there is a single type. And with juries, again, I think If you get caught misleading or misrepresenting something, particularly a document, it's hard for you to come back from that.

Khurram Naik: Mm. You mentioned what you learned on the bench as a judge. I'm curious about what it's like when you first get on the bench. I imagine early on, like, OK, I'm learning the process. I'm learning what a judge is supposed to do. Of course, you had some indication. You had some guidance heading into it. Was there an early moment where, you ⁓ maybe you go from doing the work of a judge to feeling like a judge? ⁓ If that's true, what was the moment you experienced that?

Shashi Kewalramani: So ⁓ this was an important thing to me. I never wanted to get wrapped up feeling like a judge. Maybe this is not true or not, but there's a story of the Roman emperors would have always somebody whispering in their ear. And I'm not saying a judge is a Roman emperor, but there is such a thing as Robitis. And people start to believe, ⁓ I am funny. People laugh at my jokes. ⁓ I am smart. ⁓ I would affirmatively take steps to, for example, my clerks outside the presence of other judges and not at bar events, I'd ask them to call me by my first name and I'd say it's a security issue. don't know if we're going to lunch someplace, I don't want you to call me judge, just call me shushy. ⁓ But those were little steps that I took and I think I went through my whole career with some level of imposter syndrome of... ⁓ thinking God, you know, there's other people who could do this and you get comfortable with it to say like, no, I, I, can handle this job just as well as anybody else can. You get comfortable with that. ⁓ but I would always keep in mind that my job as a judge was, it was a temp position I was holding. If I retired or if I passed, my chambers would go on to somebody else and I would be forgotten maybe a year later. tops. ⁓ that's just the ephemeral nature of, of the world. ⁓ so I was, I was mindful that I was a public servant. My job was to consider and continue to serve my clients, which are the bar. And I would remind myself of that and remind all our clerks like we are not special. We are all replaceable. We have a job to do. And I, so I never tried to deviate from what my job was, which was to provide timely, efficient, well-explained reasons in an ethical manner. I was a public servant that happened to be in the role of a judge. So I tried never to become like when you say, oh, you feel like a judge. It's like, I think I got better at my job because you would see things over and over again. You built up a database. You built up knowledge on things that could go wrong. in case management or when I would do lot of mediations like things that could go wrong or what would be pressure points that would help in resolving a case. ⁓ But I never really felt that being a judge was something special. It was more of a privilege for me that people had said, yeah, we'll let you be the ref for these games.

Khurram Naik: So you mentioned in a couple of different moments, one moment you mentioned that, look, you know, so. Magistrate judge often, yes, there's matters that are before them by consent, but then also they handle lots of discovery disputes. Also, of course, settlements are often referred to magistrate judges. And then you also mentioned ⁓ that depending on the district, there's different types of matters, maybe one jurisdiction's contracts, whatever. So apart from... those aspects, is there something generalizable about that you were talking about advocacy techniques and the degree of generalizability there are? Was there something about decision making, maybe generally, maybe it's specific to types of matters, et cetera. ⁓ Is there something about your decision making process that you hone from your time on the bench?

Shashi Kewalramani: Yes, for sure. mean, at some point as an advocate, you know what your position is. ⁓ And you are forwarding that position with a larger strategy in mind. ⁓ As a judge, one of the things you would try and separate is the effect of your ruling in the sense of like, ⁓ well, I don't like this person or I don't like, I like this person. you would have, had to separate that from the ruling that you had to make in front of you. It was very much a chips fall where they may attitude and. ⁓ Michael Lewis had a podcast, you he does these podcasts and one of them was he does a very series. He'll do like a series over one season. I think season two or season three was about the rule makers. I'm sorry. The rule enforcers. It was about judges and it started off with refs ⁓ and how we have changed as a culture of attacking the ref. ⁓ whereas before we didn't as much, right? You hear it any baseball game or basketball games, like ref, you suck, you know, and you'd hear things like that. Judges are refs. Right. And so it permeates through society when a judge makes a ruling that, you're doing it for some nefarious reason or you suck and therefore we don't have to follow it or et cetera, things of that nature. ⁓ so I was mindful that I'm not the player here, but I have a role to play, which is I make my ruling and the chips fall where they may. So you have to get comfortable with that. You're going to displease somebody. ⁓ and I was. One of the things in writing that you change is, ⁓ I would write very, very dry because, ⁓ you don't want to. give any indication that it was based on personal animus. And you don't, actually, there's this thing, it's like, right, do good deeds, say kind words, think good thoughts. I think that's a Parsi ⁓ approach to life. But the hardest thing to do is think good thoughts. But you start that by acting and doing good things. And then hopefully it ingrains and you restart thinking good thoughts. So the performative leads to the substantive. ⁓ Saying things kindly, being polite, being measured, then you think that, you start thinking that way. So you have clerks saying, your honor, this guy just lied about the facts. Like, yeah, I get it. Because he blatantly lied. It's like, you would rewrite that. I would rewrite that as saying, ⁓ counsel does not provide proof for this statement. how looking at the evidence, however, comma, you move on, right? You don't need to comment on what somebody did or how they did it when you have the power to make the ruling. There was another, I guess, there was an NBA ref who, his dad was a Chicago PD, and he said, yeah, I learned a lot from my dad who was a Chicago police officer. And he said, you have the last word, don't say the last word. which I thought was telling it's like I don't need to be snarky or anything. This is just the ruling. It is what it is. And so I thought that was ⁓ something that you, it was in my nature not to be snarky. So this was, this came easier to me, but it was still something to be mindful of in any writing, especially when certain counsel would flat out lie about what a case said or what happened in court.

Khurram Naik: Hmm. Is there a decision that you're most proud of?

Shashi Kewalramani: I would say no, I don't think there's a decision. I think what I'm most proud of is that when I was on the bench, particularly in, ⁓ in criminal matters, ⁓ when there were folks before me in, ⁓ detention hearings and bail hearings, I, I heard comments from certain attorneys saying, Hey, even though you detained my client, he really appreciated you listening to him or her. The fact that I gave everybody or tried to give everybody the respect that they were due and didn't and tried actively to suppress any ego I had. I think that has helped me not only as a judicial, helped me in the past as a judicial officer in private practice now and has made me a better person at home. ⁓ Because you do have to internalize suppressing your ego. I didn't view myself as the most important person in the courtroom. I was there, but the client, was the client's courtroom. And when I say the clients, it's the attorney's clients, it's their courtroom. We just happened to be there to facilitate the resolution that has to happen.

Khurram Naik: What were the experiences you had before a judge that helped you get reps in with suppressing ego?

Shashi Kewalramani: ⁓ there are certain judges who I would, who I would model myself after. And these are folks who are highly accomplished, but, ⁓ you would meet them and they were just the most humble people who you can imagine. Like in the Northern district, in particular, everybody would hold up. There's a judge named D Lull Jensen. Judge Jensen was, he was a prince of a man. I had, I tried cases in front of him. he was just, but I remember when I had a two year old daughter. Maybe she was one, we were in a mall. And I hear this Shashi, and he was really nice because he would say my name correctly, which was nice. He'd be like Shashi, like Shashi Kevlar-Romain. Like he would say it perfectly. Because he took the time to learn, like, how do I pronounce your name? ⁓ And he was an institution, I don't know if you've heard of Judge Jensen up in the Northern District. He had been the former District Attorney of Alameda County. ⁓ He had actually then become an assistant attorney general under Judge, under Edwin Meese and Ronald Reagan, even though he was a Democrat, registered, I believe at the time. And then he got back on the bench and he was just such a, he was an institution, but he'd seen me, he saw me at the small, was like, hey, Shashi. It's like, and I looked around, I had my one-year-old daughter in my hand. And he's like, how are you doing? It was like, but he was just that type of a guy. There was no ego. ⁓ and I was like, ⁓ judge, he's like, no, no, no, no, it's, low. It's low. You know, and I really, and everybody would clamor to get in his courtroom. Like if you could get a case before judge Jensen, because of the way it would be assigned, it wasn't going to be easy, but it was going to be fair. and, and that was, ⁓ so those, there are certain officers, judicial officers who I would see all the time who were just very kind, ⁓ would, would, it would, ⁓ let you know that, you know, yeah, they were credentialed. Yeah, they were, they had experience, but there was a, there was a, ⁓ an aspect of just serendipity to where they are. And that was a recognition that I really tried to internalize.

Khurram Naik: Let's talk about your transition ⁓ to private practice as a mediator. ⁓ Of course, this is not rare for someone to go from the bench to mediation. It's not rare to go to place like Jams. ⁓ What about, but I think something that maybe takes a little reflection to notice is that when you're on bench you have you mentioned rules. There's rules ⁓ and as a part of those rules you are able to make determinations that are binding on on on individuals. ⁓ Mediation is different. ⁓ You mentioned this concept of taking a deeming a client-centric approach you know obviously as a judge you you don't have clients but you deemed to have this approach to help you contextualize how to approach. Now you have clients. So what are the skills that transfer from the bench? And then what do you think is the biggest departure?

Shashi Kewalramani: ⁓ So what transfers from the bench first? ⁓ Let me take first the skill sets within that being trained to listen. Some people have it innately. Some people have it naturally. ⁓ I had to work on mine and I think I got much better at doing that as a judge. And before that, I think I got much better doing that as a criminal defense attorney. So it's a constant evolution towards being better in a particular way. recognizing or what transfers, recognizing, ⁓ let's say in a criminal defense setting or even in a civil case setting, when I was on the bench, I would be very mindful of anything I said about counsel, especially in front of their client and also in any written opinion that I would put out because ⁓ let's say a criminal defense attorney is making a bad argument. And I said, I can't use the word. Well, that's ridiculous. ⁓ I would be mindful of making any comment or things of that nature because it could harm the attorney client relationship. Similar in a civil case, I appreciated if I said something, well, ⁓ counsel has misled me or things of that nature. That order sometimes had to go to in-house counsel. In-house counsel would then see, ⁓ maybe or read into it. Well, this judge doesn't like this attorney anymore. maybe I need to find a new counsel. So my words had ramifications beyond just what's said in the courtroom. And I was, I trained on that. got, that really became internalized so that if I was thinking something, you just keep it to yourself. Uh, and oftentimes upon reflection, he goes, the attorney's argument wasn't ridiculous. I hear where they're coming from. So it really trains you to sort of, um, uh, be a little more mindful of your own prejudices and biases and sort of tamp those down. So that has transferred well into private practice, which is, there's mediations and there's arbitrations. Arbitrations, there's the same thing. I'm in court essentially. So I'm very mindful and measured in whatever I say there. ⁓ And I think I've become more mindful and measured in how I think. ⁓ So those thoughts don't pop into my head. In a mediation, I appreciate that the same things where I have to maintain my relationship with counsel, not just as a business generation aspect, but rather in order to get a deal done, I have to empower my jury is, is, is the attorney because when I'm in the other room, he's or she's in the jury room with the client trying to say, well, what that person's, what the judge said was kind of, it makes sense. I need to empower somebody to, and give them the ammo to to persuade their client why they should resolve the matter in a particular way. So that's mannerisms that I think have transferred from the bench and thought processes that have transferred from the bench to my mediation practice. ⁓ The biggest ⁓ difference is... ⁓ Gosh, ⁓ there's the going to, let's say just bar events. I used to go to a lot of them anyway, because I felt it was important to have a South Asian federal judicial officer at as many bar events as possible to see, know, our benches, we were ambassadors for the bench as well. We have a diverse bench, we have different viewpoints, and it was a great way to get intel from the bar as to what we could be doing better as a judiciary to service the bar. Now at the bar events, ⁓ people aren't coming to talk to me. ⁓ They know I'm a former judge. I'm essentially a vendor. get that. ⁓ And so I appreciate that my role is now to be a little more proactive ⁓ in speaking with people. The marketing aspect is a little different ⁓ as to ⁓ how I approach people in the sense that ⁓ You just have to put yourself out there a little more, whereas I didn't have to when I was sitting on the bench.

Khurram Naik: What's been hard about that? What's been surprisingly easy about that?

Shashi Kewalramani: ⁓ hard. I, I'm still surprised at how people, ⁓ certain attorneys don't respond to emails or don't respond to texts in a timely fashion. I'm still surprised by that. Now I had a theory that has been born out, which is the most successful attorneys who you can think of, like the biggest names, they're actually the most responsive. ⁓ there is a direct correlation. between people who are successful and responsive is what I'm seeing. Whereas when you sent an email from the bench or from the court, it's like, oh, you you'd get a response back fairly quickly. And so that has been surprising to me of like, wow, people just don't respond. Interesting. And I'm wondering, you see, and I think clients see this, if somebody's more mercenary versus others, like, oh, they're only talking to me because I need some. thing from you today versus, I'll talk to you just because it's the right thing to do and be polite. If you send, if you say hi, I will wave back. Hello. ⁓ the easiest thing for me has been, I think just because of my involvement, a lot of bar activities before I was on the bench on the bench, it's been relatively easy for me to reach out to networks that I had been a part of before I was on the bench. ⁓ also, ⁓ it's been ⁓ pretty, I just, it's easy for me to go out and grab lunch and talk to people. I'm lucky in that regard where I am not as introverted as I thought I was. ⁓ And so that has been relatively easy to, and then the other thing has been because I did a lot of mediations on the court, ⁓ reaching out to folks who I did mediations for and getting such a positive response saying like, Hey, and I tell them it's like, Look, when I could have been the biggest jerk, you saw what I was in a mediation and I wasn't. So what do think I'm going to be out in private practice? Like I'm going to be forceful, but always polite. Like I was at on the bench, which I think people sometimes like to have in a, in a settlement conference. They don't want a note carrier, you know, Susie thinks they're cute. Well, Tom thinks they're cute too. You know, like they don't, that's, there's no value add to that. this actually relates to my position as a judge, which is I'll make a call. I think this argument's strong, I think this argument's weak, and they may disagree with me, but you gotta make a call, and that's a value add, and that's a deliverable that I can give to any of the attorneys to take back to their clients in determining whether to resolve a case.

Khurram Naik: You mentioned, ⁓ so one thing that you were doing to position yourself is point to your experience in the bench, ⁓ point that you have mediation reps from return bench. You also point to your approach, that it was like, you strive to be ⁓ civil and ⁓ effective on the bench. How else are you thinking about positioning yourself? Because there's a number of other judges and jams. What do you view as your core differentiation? Is it an aspect of niching? Is it an aspect of practice area? Tell me about how you're thinking about how you're differentiating yourself.

Shashi Kewalramani: ⁓ So there's the showing versus saying aspect. Let me go to the showing aspect. In every ⁓ mediation, one of the things, how do I differentiate? I prepare a lot. And I think people see that when I know the details of the case and I appreciate the effort that I put into it. A lot of mediators do that. And I think that's... there's a huge bell curve within the mediation business of ⁓ there's a big middle. There's a, and there's smaller tails on either side. I want to be on the smaller tail on the good side. And part of the differentiation is I have the background in IP. I have the background in commercial, complex commercial cases. I did a lot of securities work and I have ⁓ a very good understanding of federal statutes. So I'm positioning myself more as a commercial and federal person rather than I'm not a, I'm not your best person for, a, a car wreck case and evaluation of soft injuries. ⁓ I can help in that regard. I've done a lot of that, but my positioning is going to be in more commercial IP securities types of cases, trade secrets, those things, those natures. I'm not, I'm not, ⁓ I can do others, but I think that's where my ⁓ sweet spot is. So that's how I'm trying to position myself as compared to a lot of the other mediators. and frankly, my rate is going to dictate that as well. I'm not going to get a lot of the lower dollar value cases because, of my rate tends to be a little higher. So that's, that's, think the differentiator, ⁓ from other folks. And, ⁓ as far as other judges, ⁓ there are, ⁓ I've tried cases. There is a difference between having been a ref or being an ump and being in the batter's box. I've tried like over 15 cases. And so I understand I've had private practice. So I understand the pressures counsel are under as well as giving them an ⁓ insight into how certain arguments may play in court.

Khurram Naik: This is When I'm curious about the ways in which mediation maps onto ⁓ partnership. So one thing we already talked about is niching. That's obviously large law firms or boutiques just. people specialize and so we're already starting to talk about specialization a little bit. Another dimension of practice is thinking about size of matters and there's trade-offs among those. So you can work on high-six matters but there's some constraints you're operating under there or you can get, let's say, there's fewer of them, right? You're chasing whales. Or you can say, you know, I have, I want to work on a higher volume of, know, there's middle market, there's smaller matters within the band of your comp, right? So there's different approaches you could take. Do you have a preliminary view on how you're thinking about the type of matter that you're taking on?

Shashi Kewalramani: Sure, yeah, I'm very mindful of that as well, which is ⁓ the niching versus a broader based approach. So ⁓ in the commercial world, particularly not only just contracts and securities and IP matters and trade secret matters and those things, I think there's a lot of those cases out there. And frankly, the dollar amounts that are at issue, ⁓ they don't have to be that high to... ⁓ Warrant retaining someone like me. So let's say if you're looking at damages above $2 million, there's a lot of cases like that out there ⁓ in the commercial realm. And so I don't feel that I am restricting myself to a small like I'm not looking for like I need three mass torts or one mass torts matter a year. ⁓ I can do that as well. And I have been retained to do some of those. ⁓ But the other matters that I'm, it's interesting that it's sort of like the practice picks you ⁓ where I have resolved cases for particular law firms and now they're coming to me with slightly adjacent subject matters to the subject matter I helped them on. ⁓ And the response I'm getting is we just want somebody who's well prepared is going to dig into the details and the dollar amount meets what we can then tell our client, hey, he's worth it for the day. ⁓ And I was talking to somebody yesterday and on average, even though I'm hired for the day in mediations, I end up spending about 20 hours per mediation ⁓ on prep, ⁓ the mediation itself, and then post prep to get the deal done. So ⁓ I don't feel I am narrowing myself to an area of practice or the types of cases that are equivalent to chasing whales.

Khurram Naik: think another aspect of practice we can compare to practice at a law firm versus mediation is what you already referenced is this concept of repeat business. So I think there's trade-offs to having a whale client that you do a lot of work for versus you're diversified. ⁓ And, somebody put it to me that, you know, patent litigator said, you know, hey, you know, sure, maybe I'd like to have some big tech company as a client, but then how do you say no to that 19th, 20th case, right? Like you just kind of have to keep on dancing and so on. They say dance, right? So that's, it's like a drinking from the fire hydrant kind of aspect to it. So how do you think about that as well for your practice? Like the trade-offs of. maybe having a Ross, let's say one approach is getting 80 % of your work from three firms versus being diversified. Like how do you think about that trade off?

Shashi Kewalramani: I am mindful of that. ⁓ and I want as broad a roster as possible. And so I'm not just focusing on big firms. I've, ⁓ I have a lot of, ⁓ colleagues and cases who I've done ⁓ resolutions for at, ⁓ smaller firms on, the plaintiff side and where the business comes from, just like any marketing, you don't know where it's going to come from. You just need to put as many seeds out there and you don't know what's going to bear fruit. ⁓ But I am mindful that I am not just catering to big firms. ⁓ They don't have as they may or may not have as many cases. And ⁓ that just doesn't seem to be happening. And that's my experience, at least in the mediation world where yes, ⁓ certain big firms will keep coming back to you, but the counterparty may be different every time. And so then the counterparty, if they like you, they'll start hiring you. It's sort of like this web that grows out. At this point in my career, I'm just looking for as much exposure to anybody to see so that they can see what I can do and my abilities and my approach. But I am also, if I don't think any firm or firms would do this, like, hey, we want you for a blank number of cases to the exclusion of others, I would be hesitant to do that for two reasons. One, I don't want to be beholden in that regard. Two, ⁓ it creates an impression of impartial, of, ⁓ of being, not being impartial or being partial to a particular entities. So especially as a mediator or arbitrator, I don't want to be known as, he is a, he's beholden to these blank firms. That's just bad for business. ⁓ whereas if you're an attorney, you can be on the plaintiff's side or defense side and there's plenty of work in that space. ⁓ I'm always amazed and flattered when somebody picks me as a mediator, which is like, to get two attorneys to agree to anything is flattering. And if they agree to me, it's like, that's great. And so I'm mindful of keeping not only that ⁓ reputation, but I don't want that influence on my financial income in that regard either.

Khurram Naik: Mm-hmm. You mentioned something that's different that you have processed, the work that you're putting in. Is there some different about your point of view about how mediation arbitration is conducted? Where you think your oppression points, like what would a reasonable mind, what would your counterparts disagree with you on that you think is a differentiated point of view that you have about how to resolve disputes?

Shashi Kewalramani: ⁓ The differentiating, is, and again, there's a lot of great meters, so I can't tell you what other folks do. I can tell you what I've heard from attorneys who have hired me now. What they say they appreciate is not only the prep, but also I will give them a deliverable in the sense of a media's proposal that I will send out is it's not gonna be like a paragraph, like you should settle for blank. Everybody needs to know the why. If you're settling a case for over, you know, million bucks and you got to go to your in-house counsel, they need to know why. Why should we pay this money or why should we accept this money? And one of things I try to do is always explain why I'm making a particular recommendation. That's sort of an extension of my job as from a judge where I would write probably sometimes a little more extensively than I needed to, but I felt the parties needed to have insight into the thinking as to how I came to a conclusion. That allows the parties then to potentially look at that and say, think ⁓ Judge Cavaromani messed up here. We think he messed up here because these facts are not wrong and that may change the valuation. But that allows them, the parties, to have a meaningful discussion ⁓ after the mediation has ended and while I'm still involved. So the thing that I try to do is probably provide an extensive ⁓ deliverable to the parties. that they can then rely on if they don't resolve it then to resolve the matter a little later as facts change, as circumstances change.

Khurram Naik: So I have two questions to wrap up here. One question, I think both are recurring themes in the podcast for lawyers. So one of the interesting questions or frames the lawyer might have for their career is strategy versus opportunism. And I... there's definitely a yin yang aspect to those and that each encompass a little bit of the other. ⁓ But in various ways you've talked about, I'm hearing a strategy to decision making in your career. In other ways, I'm also hearing opportunistic ⁓ movement and action. Do you identify with one or more to the other or do you have some resolution between two? How do you think of that?

Shashi Kewalramani: ⁓ So your strategy has to change as your life changes, right? There's a difference as a 27 year old attorney with no kids and no spouse that you can take more risks versus you have other responsibilities. You also learn about yourself as you grow, hopefully, saying what is important to you? What do you see as a strategy to say, ⁓ okay, how can I get more clients? What's gonna, as you've indicated, like what differentiates you from somebody else? What is going to be ⁓ important to a client down the road in order to get those clients as a lawyer? ⁓ Not only performance, performance are going to be table stakes. You have to win, you have to do well. ⁓ You have to be responsive to your client. Those are all baseline. But how do you then differentiate yourself? You have to take a look at your own. I took, tried to look, take a look at my own strengths and weaknesses and found where could I maximize my abilities going back to the gym? rat thing. I'm not six three. I can't dunk. Okay, I'm not going to play forward. That's off the table. Where do you fit intellectually, geographically, your platform that allows you to perceive in your mind, where do you see a successful career five years down the road? And one of the things that I think it's very hard to do is predict where you're to be more than five years from Life changes, but you should have a general plan and then it gets hazier ⁓ And then you have to be open-minded to see okay. Well does this opportunity fit within this five-year strategy? You know, there's in one of the hardest things to do is identify the three most important things to you in life I know I think I'm borrowing this from Stephen Covey or something right or you write down the three or four most important things and then how does every decision go to those things, but the hard part is identifying those three things that are important to you. And then how every opportunity fits within that decision. So I've tried to do that. I've tried from time to time, sit down and write, what are the three most important things to me? And how does my decision professionally impact those three things, personally and professionally?

Khurram Naik: Yeah, that's an interesting observation. And the three things, that's exactly how ⁓ my wife, who's my business partner as well, approach ourselves as well. We share the same three priorities around work, family, and business. And that means to the exclusion of things like travel, friendship, creativity, which is not to say we don't experience any of those, but they have to align with those first three. ⁓ She and I also have different prioritization of those three. But what I'll add to what you're saying, potentially it's a difference of opinion, is that I think what's hard, so I don't think we found a hard time to identify those. I think we found a really hard time to apply those and really hold it up. Cause like that involves, again, trade-offs. That's something I keep on coming back to again and again. ⁓ But yeah, I think that's an important observation you're making. And this ties into my other question for you, which is,

Shashi Kewalramani: Yes.

Khurram Naik: you've been, we started the conversation, the first time you and I spoke about this podcast, you proposed this concept of non-literality. So then ⁓ you've been around the block. You've seen this, right? Like you've seen, hey, I've made moves. And so sitting here now, what do you see as prospectively the value of this experience for something else maybe?

Shashi Kewalramani: So prospectively, I think I continue, again, based on my life stage, where I am with our kids, with our family. I'm 54. ⁓ I continue to keep an open mind. You never know what opportunities are going to come down the road. Again, how does that factor into your first three, your top three? I could, if the right opportunity came along, for example, would I pivot from ⁓ being a mediator and arbitrator at Jams? Yeah. But I would have to think about, I'm not wedded to this is who I am. I am a former judge who was a mediator. It is not part of my identity. Work is separate and apart from my identity of who I am. And that takes time and I think confidence to be comfortable with because oftentimes in our society, as you know, People ask you, what do you do? As if that is who you are. And you have to be comfortable saying, well, what I do is blank, but that's not who I am. And so I am continuing to, again, and when I say nonlinear, I compare it to a lot of my peers who had, they haven't done plaintiff side work. They haven't done defense side work. They haven't worked at a big firm. They haven't worked at a US attorney's office. They haven't been a judge. They haven't gone out to the mediation world. It's nonlinear in the sense that it's it's not common Is there a through line to it probably You we can always draw a through line through everything right? That's just statistics but I continue to remain open-minded to opportunities and and I'm not again this this is not who I am. This is what I'm doing now to to fulfill those top three goals in my life.

Khurram Naik: Cool. Well, I'm looking forward to you do with this chapter and I'm looking forward to seeing what the next chapter brings to you. So I'll be staying tuned.

Shashi Kewalramani: I appreciate that. Thank you so much for your time. really appreciate you giving me the opportunities to actually visit with you and get to know you better.

Khurram Naik: I appreciate that.