Earlier this year, Benjamin Gruenstein left Cravath Swaine & Moore, his professional home for almost two decades, and founded his own boutique, Gruenstein Law. Ben and I first met around the time that he launched his firm, after we were introduced by a mutual friend (but not his brother, former Wachtell Lipton partner David Gruenstein, with whom I used to work). I greatly enjoyed my conversation with Ben and thought that I’d love to have him on the podcast at some point.

And now, the time has come. In our conversation, Ben discussed three topics in the news: (1) his departure from Cravath, which has seen higher-than-usual partner turnover this year, and why he wanted to launch his own firm; (2) Fernandez v. United States, a noteworthy case that was recently decided by the U.S. Supreme Court, which Ben argued before the justices; and (3) how AI is transforming the practice of law—and the role it played in Ben’s decision to leave Biglaw.

Thanks to Ben for his insights—in our interview and more generally—and good luck to him and his colleagues at Gruenstein Law.

Show Notes:

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Benjamin Gruenstein (courtesy photo by Erin Patrice O’Brien)

Three quick notes about this transcript. First, it has been cleaned up from the audio in ways that don’t alter substance—e.g., by deleting verbal filler or adding a word here or there to clarify meaning. Second, my interviewee has not reviewed this transcript, and any transcription errors are mine. Third, because of length constraints, this newsletter may be truncated in email; to view the entire post, simply click on “view entire message” in your email app.

David Lat: Welcome to the Original Jurisdiction podcast. I’m your host, David Lat, author of a Substack newsletter about law and the legal profession also named Original Jurisdiction, which you can read and subscribe to at davidlat.substack.com. You’re listening to the 102nd episode of this podcast, recorded on Thursday, July 16.

Thanks to this podcast’s sponsor, NexFirm. NexFirm helps Biglaw attorneys become founding partners. To learn more about how NexFirm can help you launch your firm, call 212-292-1000 or email careerdevelopment@nexfirm.com. Want to know who the guest will be for the next Original Jurisdiction podcast? Follow NexFirm on LinkedIn for a preview.

As I’ve covered in the pages of Original Jurisdiction, Cravath Swaine & Moore, one of the nation’s most prestigious law firms, has witnessed a fair number of partner departures this year. Some went to other firms, some went in-house—and one decided to start his own firm.

Meet Benjamin Gruenstein—who is, upon information and belief, the first partner to leave Cravath to launch his own boutique since David Boies almost 30 years ago. A former federal prosecutor and Chambers-ranked practitioner for white-collar litigation and government investigations, Ben spent around 18 years at Cravath, where he was a founding member of the firm’s investigations and regulatory enforcement practice. Why did he decide to depart from a legendary firm to hang a shingle? That’s one of the topics we tackled in our podcast conversation—along with AI, which makes now an exciting time to strike out on one’s own.

I also wanted to have Ben on the podcast for another reason. A few weeks ago, the U.S. Supreme Court decided Fernandez v. United States—in my opinion, one of the most interesting cases of October Term 2025, even if it didn’t get as much press as some others—and Ben represented the petitioner in that case. So I wanted to talk to Ben—who clerked for the Supreme Court, but never argued before it—about what it was like to argue before the high court for the first time. Without further ado, here’s my conversation with Ben Gruenstein.

Ben, thank you so much for joining me.

Benjamin Gruenstein: Thank you, David. It’s an absolute pleasure to be here.

DL: So tell us about your background and upbringing. Where did you grow up?

BG: Sure. I grew up right here in New York City, in the Yorkville section of the Upper East Side. My father was a refugee from Nazi Germany. He came here in 1938 when he was 14 years old. My mother was the daughter of Russian Jewish immigrants. I went to Ramaz, a Jewish private school, through high school, and then once I graduated from there, I went to Harvard College and then Harvard Law School.

DL: And I actually know the answer to this question, but for the benefit of my listeners, did you have any lawyers in the family or any early exposure to law?

BG: I did, and you certainly know this all too well. I am the youngest of three boys. I have two much older brothers. My oldest brother is a hematologist-oncologist on the Upper East Side; he’s 21 years older than I am. And the brother that you are referring to cryptically is my brother David, who is 17 years older than I. He was a longtime partner at Wachtell Lipton, and I believe that he was someone that you had the pleasure of working with.

DL: Yes, that’s right. Given the age gap, though, did his being a lawyer affect your decision to go to law school? I don’t know how exposed you were to what he was doing.

BG: Well, certainly David and I have always been very close. There are 17 years separating us. What he and my other brother would tell me whenever I misbehaved is that if I continued to misbehave, they would do to me what they did to all the other brothers that were in between us. But David and I have always been very close, and I certainly was exposed to his practice of law and learned a lot from him. But in truth, it’s not clear to me that he always loved the idea of me becoming a lawyer. He had a fantastic career; he practiced at the pinnacle of the profession at Wachtell Lipton, and he found his career very satisfying and happy. But he certainly knew a lot of lawyers who weren’t, and I think he was concerned about me, as his baby brother, and whether I would find a legal career as satisfying as he did.

DL: I did have the pleasure of working with your older brother at Wachtell. He was a great mentor and supervising lawyer, and so I really do think he had a wonderful career practicing at the pinnacle, as you were saying.

What inspired your decision to go to law school? When you went to HLS, what kind of career did you have in mind for yourself?

BG: Well, with one older brother who was a doctor and one older brother who was a lawyer, it was a fun parlor game at family events for people to speculate in whose footsteps I would follow. When I went to Harvard, I took the pre-med classes for the first year and was thinking about going to medical school. In my second year, I started to take philosophy classes, in addition to the math classes I had taken my first year, and ultimately I decided to major in philosophy and math. So for me, I saw law school as a natural intellectual extension of the coursework I had done. My major as an undergrad was in logic. The topic was the liar’s paradox, which is, “This sentence is false”—which if it’s false, then it’s true, and if it’s true, then it’s false. And thinking through those sort of logical problems led me to think that law school would be something that I would intellectually enjoy and also that I would enjoy ultimately practicing law.

DL: Well, it’s interesting—I’m guessing you did very well in the logic games, which for better or worse are no longer part of the LSAT. When you went to law school, did you have a sense of what your practice might entail? Or what kind of practice environment you might prefer?

BG: No, not really. I went to Cravath as a summer associate for my second summer, and one of the reasons I went there is because I thought it would give me the truest idea of what it would be like to practice as a litigator in New York. And I certainly did get a very good sense of that from my time there. I knew that I wanted to be a litigator—I was interested in the argumentative side of law—but I didn’t really know much more than that. But I had a great time at Cravath, and it led me to think that I could see myself one day practicing law at a law firm in New York City.

DL: So you did eventually return to Cravath, but we’re getting ahead of ourselves. What was your first job out of HLS?

BG: So when I graduated in 1999, I had the pleasure of clerking for Judge Stephen Williams on the D.C. Circuit. Judge Williams was a great mentor to me. He was well-known in the law-and-economics circles for many of his opinions, and I really learned a ton from him and enjoyed the year immensely.

DL: And then after that, you did what many former law clerks to Judge Williams did and went to the Supreme Court.

BG: That’s correct. I went to clerk for Justice Souter, who also, like Judge Williams, was a great mentor to me. Really, it was the honor of a lifetime to clerk for him. He passed away in the last year and a lot has been written on him, but he truly was the most gracious, humble, smart, funny person I’ve ever had the pleasure of being in touch with.

DL: That is definitely what I’ve heard from people who knew him—he seems like a true mensch—so I’m sure that was an amazing experience. Where did you go after your clerkship with Justice Souter?

BG: After clerking with Justice Souter, I knew I wanted to come to New York, and while I was clerking, some AUSAs from the Southern District came down to the Supreme Court to recruit, and I took the bait. I was very excited about becoming a prosecutor. So I went to the U.S. Attorney’s Office for the Southern District where I became a criminal prosecutor for roughly the next five years. Most of that time I spent in the organized crime unit.

DL: It’s interesting you went straight from a clerkship to the Southern District, which at least back then was unusual. Was that through the DOJ Honors Program, or was that just through a regular career hiring?

BG: At the time, they would hire straight out of Supreme Court clerkships—and I think they still do.

DL: Yes, there are definitely exceptions to their practice of hiring experienced lawyers. Sometimes judges who were well-connected to the office would have a clerk go directly, after not that much experience. And as we have been hearing in the news, the DOJ is now willing, in theory, to hire any lawyer directly out of law school. You don’t need a SCOTUS clerkship—they are a little hard up for personnel—but again, we’re getting ahead of ourselves.

So tell us about that experience in the Southern District of New York. It’s a renowned office. There have been amazing alumni, including many I’ve had on this podcast. Tell me about your five or so years in the office.

BG: It really was a wonderful job. For me, I came into that job thinking that I was somewhat of a law guy, having done two appellate clerkships, and when I started, I learned how important it was to be a facts guy, both in the investigations and in trying cases. And one thing that I found very gratifying about trial work at the Southern District, especially because you’re trying cases before such an esteemed bench, is that you really need to bring both the facts and the law to bear. And while I certainly did focus a great deal on facts, both developing them in investigations and presenting them in trial, I felt that my focus on law and my ability to make legal arguments—not only in appellate arguments to the Second Circuit, but also to district judges, even in the midst of trial when I was dealing with, say, evidentiary objections—was very helpful. And I really loved trying cases at the Southern District. It was immensely challenging as well as immensely gratifying.

DL: So it’s interesting what you were saying about having both the law and facts in terms of the ability to argue both. That makes sense to me because the Southern District gets a lot of cutting-edge cases, including some brought under novel theories, and so I could understand why even as a trial lawyer, you would need to be on top of the law. Did you have a particular case or trial or investigation that jumps out to you as a highlight from your time at the S.D.N.Y.?

BG: I would say towards the end of my time, I did an organized crime case against the Genovese organized crime family, or members of the Genovese family—in particular, one captain who was 86 years old when we prosecuted him. He had never done any time in jail, but we prosecuted him for racketeering, extortion, and other related crimes. Ultimately, we convicted him, but that case actually came out of an investigation that we had done of the school bus union, the yellow school bus union in New York, where both the president and the treasurer were connected to organized crime, and ultimately that led to the prosecution of this captain in the Genovese crime family.

DL: Did that matter go to trial, then?

BG: It did go to trial. Another legal media giant, Elie Honig, and I tried the case together, and this captain was convicted. Unfortunately, he died a few years later in jail, but we had a very interesting rapport during trial. Usually the prosecutors and the defendants don’t talk very much to each other during trial, but he took a different approach. And I remember after I had done the summation, which I thought was a pretty hard-hitting summation, and when the jury went out, the defendant turned to me and said, “You couldn’t say one nice thing about me?” And then he said, “Even Meatballs said I was a nice guy.” He was referring to “Sammy Meatballs” Aparo, who was also a captain in the Genovese crime family, and we had played a recording of Aparo saying that this defendant was a nice guy and that he had just become a captain in the Genovese crime family. So we got along well at trial. He was a gentleman, and he certainly treated the prosecutors and the FBI agents with respect.

DL: Oh my gosh, that’s great—I love that. Elie, of course, was a guest on this podcast too, a little while ago. So tell me, then—where did you go after the Southern District?

BG: So when it came time to leave the Southern District, I reached out to Cravath, where I had been. I called Bob Joffe, who was the partner that I was assigned to as a summer associate—he had been the head of the firm—and I called him and said, “Do you have any interest in developing a white-collar practice at Cravath?” Because at the time Cravath did not have a dedicated investigations practice. And he said he would get back to me. He got back to me very soon after that and set up an interview, and I interviewed with several of the partners and then ended up going to Cravath.

DL: You then essentially founded what would turn into their white-collar defense and enforcement practice?

BG: So I started as an associate doing litigation and investigations, and when I made partner, I was the first partner who would have a dedicated white-collar investigations practice, and I worked with another partner who also did a lot of that sort of work and litigation as well. And we dubbed ourselves the investigations group because I thought it was important—both externally facing, to clients, as well as internally—that we be a dedicated practice group. Even though Cravath typically and historically has been a generalist litigation practice, I thought it was valuable to have that specialized practice and to promote that to the outside world.

DL: You’re totally right about that. That is just the way of the world, and you were picking up on a trend that has continued to this day. Did that practice end up expanding over the years, beyond you and the one other partner or colleague you mentioned you worked with?

BG: It did. We brought in some additional partners, one of whom had been an associate before he went off to DOJ. We brought in additional partners from DOJ, as well as from the SEC. So it did grow significantly.

DL: And so tell us, big picture, about your time at Cravath, as both an associate and then later a partner. How many years were you there, and what would you say was a highlight, or what were some of the highlights, of your time there?

BG: So I was there from 2008 until I left earlier this year, four months ago. I became a partner in 2012, and my practice generally was a corporate investigations practice focused on government and internal investigations, but I also did litigation. As far as the highlight, I think certainly the overall highlight was helping to develop the practice. We took the practice from the work of a few partners who would do this sort of work on a one-off basis, and we developed it into a coherent investigations practice. And certainly by the end of my time there, we were handling some very significant matters, really just as we’ve been handling throughout, and that was very gratifying.

One of the matters that I spent a fair amount of time on was the Avon FCPA investigation, which was an investigation of Avon Products related to work they had done in China. Evan Chesler and I were brought in towards the end of the investigation and ultimately helped settle that investigation, and that was a very professionally gratifying event that also led to many of the professional connections that I have today. I can trace many of my clients back to their time at Avon. They’ve since dispersed, and I’ve worked for many companies because their general counsels and the like started off at Avon.

DL: That’s interesting. I actually worked on an Avon matter at Wachtell, Lipton, although it was a civil litigation involving a large commercial lease. But anyway, small world.

So I’m curious: when you were at Cravath over those 18 or so years, what changes did you observe in the practice or the profession? Is there a particular thing that jumps out at you, in terms of what changed over that almost two-decade span?

BG: Well, there certainly were changes over time. In the litigation department, something that we saw was increased specialization. One of the great things about Cravath litigation partners is that they are primarily generalists. They can try any case. And while that does remain true, there was increased specialization. There is a very robust antitrust practice that Christine Varney, who came out of the DOJ Antitrust Division, led for a number of years. We had our investigations practice. We had a specialized IP practice. And not to say that all of these people didn’t work on other things—they all did, and many of them were generalists—but there was increased specialization within the litigation department.

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In that spirit of being a generalist and being able to do things that are a bit of a stretch, or that perhaps test different talents or cause you to explore something that maybe you hadn’t explored before, one of the reasons I wanted to have you on the podcast is that you argued a case before the Supreme Court in the last term, Fernandez v. United States, which the Court decided fairly late—so the opinion was actually issued not that long ago. Your practice at Cravath, as you mentioned, was primarily an investigations and enforcement-type practice, not a Supreme Court and appellate practice. Did you ever think, perhaps when you were clerking for Justice Souter, that you might want to someday argue before the Court?

BG: Well, certainly when I was there, that was a dream that I had that I would one day be able to argue. During the Term that I was there, Ted Olson had been the solicitor general, he was coming off the job, Seth Waxman was going into the job, and those were really two giants of the Supreme Court Bar—and Seth Waxman still is, of course. So seeing them argue certainly led me to think that this would be a dream come true. Although as you mentioned, my career did go down a different path in that I became a trial lawyer at the U.S. Attorney’s Office, and then when I went to Cravath, I was really more of a corporate investigations lawyer, and the goal of every investigation is to stay as far away from the courtroom as possible, and certainly from the Supreme Court. So yes, it was a dream, but not one that I really spent a lot of time thinking was ever going to happen.

DL: How many appellate arguments did you have under your belt by the time you stepped up to the podium at One First Street?

BG: I’d probably done around 20 at that point—mostly in the Second Circuit, from the time that I had been at the U.S. Attorney’s Office, as well as when I left the U.S. Attorney’s Office, I went on the Criminal Justice Act panel for the Second Circuit and was appointed to represent indigent defendants in their cases in front of the Second Circuit.

DL: So actually mentioning that you were on the Criminal Justice Act or CJA panel ties us into Fernandez. That was a criminal case, and it was not a white-collar case but a murder case—that’s not usually Cravath’s bread and butter. So did you receive that as a CJA case initially, I’m guessing?

BG: That’s correct. So in addition to being on the CJA panel in the Second Circuit, I’m also on the CJA habeas panel in the Southern District, and that involves assignments related to habeas and other post-conviction proceedings. In the Fernandez case, it was a motion for compassionate release. Judge Alvin Hellerstein appointed me to represent Joe Fernandez.

DL: I have written about Fernandez a little bit in Original Jurisdiction, but for folks who might not recall, what was the key issue in the case, or at least the issue that went to the Supreme Court?

BG: So the issue that went to the Supreme Court is whether, in a motion for compassionate release, one of the “extraordinary and compelling reasons” to warrant a sentence reduction, i.e., compassionate release, can include an attack on the conviction or sentence. So in Fernandez’s case, we argued for compassionate release because the judge had expressed in other proceedings, including on habeas, the view that Mr. Fernandez might actually be innocent (he has always maintained his innocence).

And we also argued that there were significant disparities between his sentence, which was life in prison because he went to trial, and the sentences of other of his co-defendants, including the alleged getaway driver who received a two-year sentence to a lesser narcotics offense, which actually was one of the key facts that led Judge Hellerstein to have significant concern that Joe Fernandez may have been innocent. And the reason was that the key cooperating witness who had testified against Joe Fernandez, and on which basis his conviction was obtained, also said that this other fellow was the getaway driver, and the fact that the government pled the alleged getaway driver down to a two-year count led Judge Hellerstein to wonder whether the government itself had doubts about the veracity of the cooperating witness and in turn the guilt of Joe Fernandez.

DL: You actually prevailed in the district court. Tell us how the case made its way to the Supreme Court.

BG: So after we prevailed in front of Judge Hellerstein, the government took an appeal. They also sought a stay of Judge Hellerstein’s ruling, which was denied. So Joe Fernandez was out of jail for around a year and a half before the Second Circuit ruled on his case. I argued the case to the Second Circuit, and then ultimately the Second Circuit reversed Judge Hellerstein’s ruling and said that questions about innocence or about sentencing disparities are really criticisms of the verdict, the conviction, and the sentence that should be raised on habeas and should not be raised through a motion for compassionate release.

DL: Just a reminder: there are actual human beings behind the captions of these cases. So your client, Mr. Fernandez, was out for a time. After the Second Circuit reversed, was he taken back into custody then?

BG: Immediately, yes—the very day.

DL: Wow. Okay. Interesting. So then the case goes up to the Supreme Court. What was it like to argue before the Court? Were you nervous?

BG: I was nervous for months before the argument, but it was really the good kind of nervousness, the type of nervousness that led me to prepare a ton for the argument. When I would have free time, I would sit on my couch at home and have Gemini ask me questions that I might receive as the lawyer for Joe Fernandez, and I thought Gemini did a tremendous job in doing that and I would practice with Gemini. Then on the actual day of the argument, I remember being in the lawyer’s lounge and thinking to myself, “I don’t feel all that nervous. I feel the same level of nerves that I do when I argue in front of the Second Circuit or appear before a district court.” And then that led me to think, “Well, what’s wrong with me? I should really be more nervous.” And that itself led me to become slightly more nervous. And then as I was talking to my other colleagues who were arguing that day, one of them told me that it was his 62nd argument in the Supreme Court, which led my blood pressure to go up a little bit. But I did feel very well-prepared and it probably was because of all the preparation, including with Gemini.

DL: So who was that lawyer on his 60-somethingth argument? I could probably just look it up on the day calendar, but I’m curious.

BG: It was David Frederick from Kellogg Huber.

DL: Oh, yes. Or Kellogg Hansen now, I guess. But go ahead.

BG: Yes, from Kellogg Hansen. He was arguing a related case to mine, and he split time with Dave O’Neil from Debevoise, and Dave had been in law school with me and clerked the same year I had. He clerked for Justice Ginsburg, and he was also at the U.S. Attorney’s Office with me. So it was nice to be there and to go through that with an old friend.

DL: So when my husband Zach Shemtob interviewed Cecillia Wang, who argued the birthright citizenship case, she said that she was nervous beforehand, but once you’re in the moment fielding those questions from those nine very engaged justices, you kind of almost don’t have time to be nervous; you’re just really in the moment, focused on their questions. Did you feel that way?

BG: Well, certainly. And you really end up having a conversation with nine different people at the same time, and your neck keeps swiveling around as you talk to the different justices. But I found it to be incredibly exciting and fun to be doing it, and very quickly the nerves went away.

DL: How many moots did you do—as in standing up with human beings, rather than Gemini?

BG: I did three moots. I did one at Georgetown, I did one at Northwestern—both at their law schools—and then I did one with a bunch of former Southern District AUSAs that are in my network, friends of mine. They all came to Cravath, and we did a moot around a conference table. All of the moots were fantastic, and that moot in particular was probably the most predictive of what the actual argument was.

DL: You and I had coffee while the case was pending before the Court, and you were not super optimistic about the bottom-line outcome. Were you surprised by the outcome of the case? And maybe you can also explain to my listeners what the court did hold in Fernandez.

BG: Sure. So ultimately what the Court held was my argument that Fernandez might be innocent really is an attack on the conviction and that had to be brought on habeas and could not have been brought on a motion for compassionate release. While I was disappointed in the ruling, I’m not sure I was surprised. During the argument, it was very clear that the Court had concerns about the “floodgates” problem, which is that if they allowed this case to go forward on compassionate release, then it is likely that the floodgates would open and that all sorts of motions for compassionate release would be made.

I was disappointed, however, for a few reasons. One, I had pitched this case very much as a textualist case, and I thought it would appeal to a textualist court. The question was whether the phrase “extraordinary and compelling reasons” could capture really anything that could be found to be extraordinary and compelling. And I was very frank with the Court during argument that I thought it would be rare that an attack on a conviction would be extraordinary and compelling in a case like this (which frankly wasn’t really an attack on the conviction because we never said there was insufficient evidence, we just said that he very well could be innocent and because of that, he had already served enough time). So it was disappointing that the Court interpreted the words “extraordinary and compelling”—which, while they do set a high bar, are very broad words—to establish what I refer to as an atextual limitation on those words.

And I was also disappointed because I really do feel strongly that judges should have the discretion, certainly in very rare cases, to exercise justice when they feel that an injustice has been done, and that’s what Judge Hellerstein did here. And while I do understand the floodgates problem, it’s unfortunate that the floodgates problem eclipsed what is another problem: in some number of cases, hopefully very rare, there is a real injustice, and the judge should be able to reduce a sentence. Here, Judge Hellerstein couldn’t after trial because it was a mandatory life sentence, but it was certainly my view that he should have the discretion to do justice down the road.

DL: The Court ultimately split 8-1, although Justice Sotomayor wrote a concurrence in the judgment, which was joined by Justice Kagan. Justice Jackson filed a dissent. And I think some of the arguments you just outlined to me, including your point about how to read the statutory text, really were very important to Jackson’s dissent.

BG: Absolutely. So Justices Sotomayor and Kagan agreed with me on the question that was presented—that an attack on the conviction or a criticism of the conviction can be extraordinary and compelling—but what they said is, “But there need to be some changed circumstances,” which there weren’t in this case. Justice Jackson agreed with us on the question, but also on the application to this case, which is whether the potential innocence of Joe Fernandez could be extraordinary and compelling. And she basically said, “Well, what could be more extraordinary and compelling than a judge being concerned that an innocent man was sentenced to life in prison? And shouldn’t the judge be able to do mercy as a matter of statutory language?” Because Congress said extraordinary and compelling. And while there was no evidence in the legislative history that they had this case in mind, Congress did refer to the statute as a safety valve, that it should be kind of a last-ditch opportunity for a judge to reduce a sentence, and Justice Jackson really did make that textual argument that the words should be read as they are understood in a dictionary. And that understanding does not allow for a categorical limitation for arguments that could have been raised on habeas.

DL: Yes, I do think that was actually one of the strongest points of her dissent. One last question about Fernandez. It’s interesting: the case was argued in November, but the opinion didn’t come down until the end of May, practically June. You’ve been on the inside of this, as a former Supreme Court clerk. Did you have any thoughts on the delay?

BG: So what I thought was going on, as I was speculating and waiting for the decision to come down, is that there would be one justice who would write both majority opinions, and that could slow things down and that they would have to be coordinated because there was another case that came down, the Rutherford and Carter decision, and it raised a very similar issue. So Justice Barrett ended up writing both of those majority opinions, and then Justice Jackson wrote the dissenting opinion in Fernandez and Justice Sotomayor wrote the dissenting opinion in the Carter/Rutherford case. So my guess is that there was some cross-case thinking that kind of took a little bit longer to get the two opinions out.

DL: Okay, fair enough. And I would urge my listeners to go and check these cases out. They’re quite interesting, even if they didn’t generate as many headlines as birthright citizenship or tariffs.

Now let’s turn to another reason I wanted to have you on the show: your recent departure from Cravath to launch Gruenstein Law. I believe you’re the first Cravath partner since David Boies left Cravath to leave the firm to go hang a shingle, so to speak. What led you to leave such a storied firm and strike out on your own?

BG: I think what you just said about David Boies is right, certainly in my memory. And you’re right that Cravath is a storied firm. It is a fantastic firm, and I had an amazing experience there. I learned a tremendous amount. I mentioned Evan Chesler earlier: he was the head of the firm for a long time, and he really taught me to be a corporate litigator. I very much valued my time as one of the founders of the white-collar practice and ultimately a senior partner in that group. And then I was also the hiring partner for the litigation department for four years before I left. So all in all, I had a wonderful experience.

Ultimately, however, starting my own firm is something that I’ve dreamed about for a long time. I very much want—and I’ve always wanted—to practice law in precisely the sort of way that I want to practice law, to take on the matters that I want to take on and the clients that I want to take on without certain constraints, to have flexibility around things like rates and conflicts, and to join forces with friends and other like-minded people who want to practice law in exactly the same way that I do.

DL: Cravath has experienced an unusually high number of partner departures this year. When I was working in private practice, I think the only way people left Cravath was in a box. Any thoughts on that?

BG: Well, I certainly wouldn’t draw any conclusions from the recent departures. Cravath is a fantastic firm, it’s doing extremely well, and everyone I’m sure has their own reasons for why they left. I certainly can speak to the reasons that I left, and certainly it has nothing to do with how the firm is doing; as I said, it’s doing great.

DL: So it’s interesting what you were talking about in terms of moving toward this opportunity to practice law in the way that you would like. One thing about Cravath is it’s a very storied firm, and it’s very traditional. People would even say—I don’t know if it was a joke or not—that they had firm conventions for how you would do a letter and where the indents would go and all of this. It’s a very traditional firm, and things have to be done “the Cravath way.”

Tell us more about why you decided to launch your firm. What are some of the things that you can do now at Gruenstein Law that you couldn’t do at Cravath—not through any fault of the firm, but just because it wasn’t the Cravath way?

BG: Well, I’m not sure I would say it wasn’t the Cravath way and that I’m looking to do anything differently. In fact, for me, Cravath was a very transformative time and led me to be the lawyer that I am today. Really what I’m talking about is having the flexibility—primarily through rates, but also avoiding conflicts—to take on any matter that I want to take on, regardless of things like whether it’s a big client or a small client, or what the rate structures or the fees might be. If there is a matter that I want to take on, I want to have the flexibility to do it.

Also, there are areas of my practice that I want to develop and hopefully will, which I was not able to do at Cravath for understandable reasons. For example, I would like to do more of a white-collar criminal defense practice in addition to the corporate investigation, to represent people in their white-collar trials. I also want to develop a criminal appellate practice, which is something that I got much more of a taste of during my Supreme Court argument, and I would love to be able to do more of that sort of work. So those are all things that I have in mind and that I look forward to doing.

DL: What’s your vision for the firm? If I check in with you five years from now, where would you like to be?

BG: Well, I don’t really have a particular vision for where I’ll be in terms of the size of the firm or the like. My number one goal is to continue doing the sort of high-quality work that I did at Cravath, to continue doing it at this firm, and to do it with the best lawyers that I can find who would be willing to join me, whether it’s associates or partners, and together we’ll serve our clients extraordinarily well. And if I’m still doing that five years from now, I will be extremely happy. I don’t expect that this firm will grow as large as Boies Schiller did in its first five years, but I would certainly expect growth. I am looking to grow, but I’m also looking to really focus on the quality of the work and the quality of the people who join me.

DL: So Boies Schiller did grow very quickly. I interviewed David about that a number of years ago, and I don’t know, they initially set up in some kind of barn or stable or something, which they very rapidly outgrew. [Ed. note: it wasn’t a barn or stable but a loft, about four miles from where David and Mary Boies lived.]

How big is your current team?

BG: Currently, we have an associate as well as a law clerk. The law clerk is a lawyer from Israel who is now studying for the bar, and she principally handles everything related to AI for the firm, and it’s great to have someone of her background. She’s very technical and can really help navigate the firm’s AI tools.

DL: That actually leads me to an additional reason I wanted to have you on the show: over the past few months, you and I have had some interesting conversations about AI and the practice of law. Besides what you mentioned earlier about helping prepare for oral argument with Gemini, are you using AI in your own practice, and if so, how?

BG: Yeah, absolutely. When I started the firm, I started completely on my own. I didn’t hire my first employee for two months. So I was using AI extensively at the beginning myself. When I had to do interrogatories and document requests, I would use Claude to help me draft it. I didn’t like using Claude to draft things start to finish—I feel like I lose too much control over the document if I ask Claude to just draft—but I would do one interrogatory at a time. I would tell Claude I want an interrogatory about X, and Claude would write it, and then I would edit it, and I would go one to 20 that way. So I was using it extensively.

Right now we are using it extensively. We’re demoing a few products to see which we like best. And ultimately, I actually think it’s going to be very similar to how firms use both Westlaw and Lexis: people have different preferences, there will be different AI tools that will appeal to different people, and firms may offer several of them. And that’s what I aspire to do—to have the right tools for anyone who joins me.

DL: That’s really interesting. I’ve been talking to a lot of lawyers about that, and that’s exactly what people are saying: the different tools often have different things that they’re especially good at, and it’s your job as a lawyer to figure that out.

Taking more of a 30,000-foot view, what do you think AI will mean for the legal industry or the business of law? And, of course, the question everyone’s wondering about is: are lawyers going to be out of jobs?

BG: Well, I think AI is going to have and already is having a profound impact on the legal industry. On the business side of law, you have to imagine that as law firms can use AI to engage in certain low-level or menial or repeated tasks, they won’t need as many human associates to do it. It just seems natural that that is going to be the outcome. Now, whether law firms can redeploy associates, whether they can use associates to do different things… I’ve always thought that associates don’t spend enough time when they’re writing briefs actually reading the cases, as opposed to just pulling out snippets to quote. So hopefully associates will find more time to think deeply about cases and read the case law. So in that way, certainly associates can do other things. But I certainly think some of the work, or even a lot of the work, that junior associates are doing can be replaced by AI, at least in part.

And for law firms, I think the question is going to be, well, how do you bill clients when it doesn’t really seem to make a lot of sense anymore to bill clients on an hourly basis, because the value you may be giving to clients may really not relate to the hours that are being worked because the AI time is really saving a lot of work. So I think those are ways in which the business can be changed.

There’s another way that I think that AI is really going to change the legal industry, which is the question of how associates are going to learn how to be lawyers at law firms. Historically, and even today, the way associates learn how to do something like document requests is that they’re told go find some templates or some samples and adapt them to the case that we’re working on. Now, that’s something that AI can do really well; AI is great at pattern recognition. So you really shouldn’t have an associate doing that from scratch. The associates should use AI.

And in my view, the way associates are going to learn is not through the 10 hours of drafting document requests, but rather in having AI do it and then going over it with the partner and the partner saying, “These are the things I like about this draft, and these are the things that I don’t like.” And what that starts to look a lot more like is the apprenticeship model, and it’s interesting to think that as technology advances, we’re actually going to go back to the apprenticeship model. But that certainly strikes me as a good thing, and it strikes me as a way in which smaller firms or boutique firms or firms with far lower leverage, a much lower associate-to-partner ratio, will be very well-equipped to work because with fewer associates per partner, it’s much easier to have that apprenticeship model.

DL: That’s such an interesting point, and it was certainly the way that I learned in many ways. If I would draft something and your brother would edit it, I might sit down with David and he would go through and explain why he made each change, and that was tremendously educational for me.

You mentioned earlier the billable hour. Your former partner, Evan Chesler, famously wrote an article years ago predicting the demise of the billable hour, and I think it has lasted longer than he expected. And I think it is still, when I talk to lawyers, the dominant method of billing for many people in so-called Biglaw. What is your own approach at Gruenstein Law to fees and to billing arrangements? How much of your work is still on the billable hour, and how much of it is on alternative fees? What can you say about that?

BG: Some of my work is still on the billable model because it’s just really too hard to predict at the beginning of a matter how long something’s going to take, but on several of my matters, I’m using alternative fee arrangements and doing flat fees because my goal is to bill clients according to the value that I provide them, and the number of hours that I work or that anyone on my team works is not necessarily correlated with the value that they’re getting out of it. So what I like to do is to hear from a client about what the problem is, what the matter is, if it’s an actual case or if it’s just advice, and to think what is the value that I can add, and then to suggest a fee that I think is appropriate.

So I think currently I’m probably doing flat fees in around a third of my matters, but I really would like that to increase as I get a better sense of the matters and how they’re going to go in the future, and I’m better able to assess the value that I’m going to be able to provide to clients. But I very much would like to work as much as possible on a flat-fee model because I want to align my interests completely with the client’s.

DL: And that’s a great point about perhaps being able to do more on alternative fee arrangements once you have more experience, because one thing that firms that are very good with AFAs have is a lot of data. They have a lot of historical data about how long a matter of this type took us. So when you’re just starting out on your own, it’s probably harder—but I’m guessing that over time, your work done pursuant to AFAs is going to increase.

BG: I think that’s right, and it really is very consistent with my overall approach, which is that I want to do the best work for the clients whose matters I want to handle, and while sometimes it’s hard to justify very high fees simply because that’s what it takes to do the work, I think it is possible to justify fees based on the value that I’m providing. And if I can bill on that basis, I think that’s something that clients would appreciate, and that’s certainly a way that I would appreciate working.

DL: Let’s now turn to my speed round. These are four standard questions, which are the same for all my guests. My first question is, what do you like the least about the law? And this can either be the practice of law or law as an abstract system.

BG: On this one, the issue really relates to my corporate investigations practice, and there companies feel a very strong pressure to settle with the government when they’re undergoing investigations, and I find it frustrating that there’s such a trial penalty in the corporate space. I don’t think it’s good for companies, I don’t think it’s good for shareholders, and frankly, I don’t think it’s great for the justice system. So I wish companies would be willing to fight a little bit more when they’re under investigation.

DL: That’s a great point, and you’re not alone in that. I would refer my listeners to the writings of one of my past podcast guests, Judge Jed Rakoff.

My second question is, what would you be if you were not a lawyer?

BG: Well, I’m not sure what I would be, but I do know that if I do retire or start to slow down in the future, I really would love to open a kosher deli.

DL: Okay, that’s a good one. I had a meal today from a deli—not a kosher one, but a very good deli.

My third question is, how much sleep do you get each night?

BG: I get around seven to eight hours and often will sleep in on the weekends a bit.

DL: And my last question is, any final words of wisdom, such as career advice or life advice, for my listeners?

BG: I certainly made a big career change in the last few months, and what I would encourage your listeners to do is to enjoy their career and to try to get the most out of it. This is a very exciting profession, but they should spend time every now and then assessing what it is that they enjoy and what it is that they find satisfying and to make tweaks along the way.

DL: Well, I totally agree with that. And as someone who enjoys my career, including speaking to folks like you, thanks so much for joining me, Ben.

BG: My pleasure. It’s great seeing you, David. Thank you.

DL: Thanks so much to Ben for joining me, and congratulations to him on the launch of his firm.

Thanks to NexFirm for sponsoring the Original Jurisdiction podcast. NexFirm has helped many attorneys to leave Biglaw and launch firms of their own. To explore this opportunity, please contact NexFirm at 212-292-1000 or email careerdevelopment@nexfirm.com to learn more.

Thanks to Tommy Harron, my sound engineer here at Original Jurisdiction, and thanks to you, my listeners and readers. To connect with me, please email me at davidlat@substack.com, or find me on Twitter, Facebook, and LinkedIn, at davidlat, and on Instagram and Threads at davidbenjaminlat.

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The next episode should appear on or about Wednesday, August 5. Until then, may your thinking be original and your jurisdiction free of defects.