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, an interesting and important 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:

* Benjamin Gruenstein bio, Gruenstein Law

* Cravath Partner Gruenstein Launches Boutique Firm in New York, by Meghan Tribe for Bloomberg Law

* Cravath Investigations Partner Launches His Own Boutique, by Ryan Harroff for Law.com

* Cravath Partner Launches Corporate Investigations Boutique, by Daniel Connolly for Law360

Sponsored by:

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 [email protected].

Last Tuesday, June 30, the U.S. Supreme Court issued its final opinions in argued cases for October Term 2025. So it’s an ideal time to review the Term that was—and to look ahead to what’s on the docket for OT 2026.

I could think of no better guest for this project than my husband, Zachary Baron Shemtob. Zach is the executive editor of SCOTUSblog—a leading news outlet, if not the leading news outlet, about the Supreme Court. Before joining SCOTUSblog in May 2025, he practiced at two top law firms, clerked for the Second Circuit and Southern District of New York, and graduated from Georgetown Law, where he served as editor-in-chief of the law review. Prior to his legal career, Zach was an assistant professor of criminology, where he focused on legal decision making.

Thanks to Zach for joining me—and thanks to him and the entire team at SCOTUSblog for their excellent work.

Show Notes:

* Zachary Shemtob author page, SCOTUSblog

* Zachary Baron Shemtob, personal website

Sponsored by:

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 [email protected].

Defending some of the Trump administration’s most controversial policies in court, before frequently skeptical judges, can be difficult. But Abhishek “Abhi” Kambli, who recently stepped down as deputy associate attorney general, took on this challenge—repeatedly. During 15 months at the U.S. Department of Justice, he personally argued more than 20 consequential cases, involving subjects including the Biglaw executive orders, the Alien Enemies Act, and military service by transgender individuals.

Earlier this month, Kambli joined Holtzman Vogel—a boutique known for its political-law practice, state attorneys general work, and government investigations expertise, as well as its high-level connections in Republican and conservative circles. Having completed his government service, Abhi is freer than before to speak his mind—and graciously agreed to sit down with me to talk about his time in the administration.

Thanks to Abhi for a thoughtful conversation, which included fielding difficult questions, and congrats to him on his latest move.

Show Notes:

* Abhishek Kambli bio, Holtzman Vogel

* Abhi Khambli, X (fka Twitter)

* Ex-DOJ Lawyer Who Defended Trump’s Big Law Attacks Lands at Firm, by Tatyana Monnay for Bloomberg Law

* DOJ’s Kambli Entrusted to Pull Off Win in Trump-Big Law Fight, by Justin Henry for Bloomberg Law

Sponsored by:

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 [email protected].

For longtime observers of the legal profession, here’s a headline we wouldn’t have expected a few years ago: “The Eight-Figure Talent Race for Supreme Court Lawyers.” According to Ryan Barber and Erin Mulvaney of The Wall Street Journal (gift link), superstar SCOTUS advocates—including former solicitor general Elizabeth Prelogar, now at Cooley, and former acting SG Jeff Wall, who recently joined Gibson Dunn—are commanding pay packages previously unheard of for appellate practitioners.

For such a small and elite group, the Supreme Court bar has seen a striking amount of movement in the past few weeks. In April, Wall led a four-partner group that decamped from Sullivan & Cromwell to Gibson. A few days later, another leading high-court litigator, Kannon Shanmugam, left Paul Weiss and joined Davis Polk & Wardwell, where he now heads the firm’s new Supreme Court and appellate practice group.

What explains this flurry of movement in the SCOTUS space? Why are top firms investing so heavily in Supreme Court and appellate practices? And what broader trends might this reflect?

I could think of no better guest to explore these topics than Kannon Shanmugam. Not only did he recently go through the recruiting process as a lateral partner, but he’s now going to be doing some hiring of his own, as he and Masha Hansford build out what Kannon hopes will be “the very best appellate practice in the country.”

Thanks to Kannon for speaking with me, and congratulations to him and Masha on their move to Davis Polk.

Show Notes:

* Kannon Shanmugam bio, Davis Polk & Wardwell

* Kannon K. Shanmugam profile, Chambers and Partners

* Davis Polk Looks to Appellate Star Shanmugam to Elevate D.C. Build, by Meghan Tribe for Bloomberg Law

Sponsored by:

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 [email protected].

The trend of leading litigators launching their own boutiques continues. Last month, three Chambers-ranked trial lawyers—Jessie Liu, Justin Shur, and Jonathan Kravis—left their respective firms to found Liu Shur Kravis in Washington, D.C.

What makes LSK particularly interesting is that it’s a “bipartisan boutique”—unusual in D.C., where boutiques tend to have a partisan valence. Liu was the Senate-confirmed U.S. attorney for D.C. in the first Trump administration, while Kravis worked in the White House Counsel’s Office in the Obama administration.

To learn more about how LSK came together and what its launch might reflect about the evolving legal industry, I welcomed Jessie Liu to the podcast. We first discussed her journey as the daughter of Taiwanese immigrants from a small town in Texas to the top of the legal profession—including her service at Main Justice, her tenure as U.S. attorney, and her years as a Biglaw partner, most recently at Skadden Arps. We then tackled events in the news—and Jessie shared her thoughts, as someone who served at a high level in the first Trump administration, on how the second Trump administration differs from the first.

Thanks to Jessie for joining me, congratulations to her and her partners on the launch of LSK, and good luck to them in the years ahead.

Show Notes:

* Jessie K. Liu bio, Liu Shur Kravis LLP

* Jessie K. Liu profile, Chambers and Partners

* Jessie Liu bio, Wikipedia

Sponsored by:

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 [email protected].

State attorneys general have been playing an increasingly important role in American law and politics in recent years, as I discussed in my recent podcast interview of former New Jersey attorney general Matthew Platkin. Continuing the conversation on this interesting evolution, last week I interviewed Rob Bonta, the 34th attorney general of our nation’s largest state, California.We began by discussing Rob’s early life, including how he immigrated to California with his family as an infant, and his legal career, including his service in the San Francisco City Attorney’s Office and the California State Assembly. We then turned to current events, including the Supreme Court’s recent ruling in Louisiana v. Callais; the 67 lawsuits his office has filed against the Trump administration since January 2025, including election-related cases; and Rob’s own future plans, including whether he might run someday for the U.S. Senate or governor of California.

I’ve known Rob for decades, ever since we were members of an informal (and very small) group of Filipino-American students at Yale Law School. Rob is now the first person of Filipino descent to serve as California’s AG—making him an especially fitting guest for May, which is Asian American, Native Hawaiian, and Pacific Islander (AANHPI) Heritage Month.

Thanks to Rob for reconnecting with me and for sharing his thoughts on a wide range of timely topics.

Show Notes:

* Rob Bonta bio, Office of the Attorney General of the State of California

* Rob Bonta bio, Wikipedia

Sponsored by:

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 [email protected].

Artificial intelligence is transforming the practice of law in countless ways, as I’ve explored in this podcast and newsletter. Thus far, I’ve focused mainly on AI’s implications for lawyers and law firms. But how is AI affecting clients, what they expect from their firms, and the attorney-client relationship?

Sabastian Niles, the president and chief legal officer of Salesforce, tackled these topics in an open letter he published last month, “How Law Firms Can Lead the Agentic AI Era—And What Clients Now Expect.” After reading his letter, I thought he’d be the perfect guest to help me explore these critical subjects.

We began our conversation by covering Sabastian’s path from mock trial champion to Wachtell Lipton M&A partner to CLO of one of the world’s leading technology companies. We then turned to AI in legal—discussing what “agentic AI” actually means, how Salesforce evaluates outside counsel on AI adoption, and why Sabastian believes that trust and innovation, far from being in tension, go hand in hand.

Thanks to Sabastian for speaking with me—and for his invaluable insights into the future of law and the legal profession in the age of agentic AI.

Show Notes:

* Sabastian Niles bio, Salesforce

* How Law Firms Can Lead the Agentic AI Era—And What Clients Now Expect, by Sabastian Niles for Salesforce

Prefer reading to listening? For paid subscribers, a transcript of the entire episode appears below.

Sponsored by:

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 [email protected].

Sarah Isgur is one of the busiest people in legal media. She hosts the delightful Advisory Opinions podcast (on which I sometimes appear); serves as an editor of SCOTUSblog, the leading online outlet covering the Supreme Court; and appears regularly on ABC’s This Week with George Stephanopoulos. And now, as of yesterday, she’s a first-time author.

The thesis of Sarah’s new book—Last Branch Standing: A Potentially Surprising, Occasionally Witty Journey Inside Today's Supreme Court—is deceptively simple: almost everything the media tells you about SCOTUS is wrong. The conventional 6-3 framing obscures far more than it reveals. And compared to Congress and the presidency, the Court is genuinely trying to do its job.

In our wide-ranging conversation, we covered Sarah's unconventional path to legal media (she was inspired by Legally Blonde to apply to Harvard Law School, and was fired from the DOJ and CNN before reinventing herself at The Dispatch); her book’s core argument, which will be controversial in some quarters; Justice Sotomayor’s recent, pointed criticism of Justice Kavanaugh; and possible picks for the next Supreme Court justice and attorney general. Thanks to Sarah for joining me, and congratulations to her on the publication of Last Branch Standing—a must-read for anyone interested in the U.S. Supreme Court.

My latest guest is an acclaimed appellate and Supreme Court advocate, Jennifer Bennett of Gupta Wessler. To introduce her, I’m going to turn over the floor to a former podcast guest: Judge Vince Chhabria (N.D. Cal.), for whom Bennett clerked. When I mentioned to Judge Chhabria that I was going to be interviewing Jennifer, he immediately moved into testimonial mode:

"Funny, I was going to email you to suggest that you interview her! She is truly one of one. She recently won her fourth Supreme Court case, GEO Group v. Menocal. Despite representing workers in all four of her cases (the first three on arbitration), she has won all four of them, and each one of them has been unanimous. In other words, this lawyer for working people has never lost a vote in her four cases on behalf of working people at the current Supreme Court!

She also just argued her fifth case at the Court, Flowers Foods, Inc. v. Brock—the arbitration case about ‘last-mile’ drivers. It seems like she might win that one, too.

Jenn was my very first law clerk—I refer to her as Chhabria Clerk Zero. For around three months, before the other law clerks started, it was just me and her in chambers, sifting through our new cases and figuring out how to handle them.

Steve Berzon came to my informal swearing-in, I was lamenting not having immediate law clerk help, and he mentioned that this person who clerked for [Judges] Marsha [Berzon] and Jesse [Furman] had about six months to kill before starting a fellowship at Public Justice and might be interested. I was so lucky to have Jenn. Given how amazing she is and given her experience in Jesse’s chambers, she was able to get me up and running in a way that would have been impossible otherwise. She played a big role in teaching me how to be a good district judge."

Thanks to Judge Chhabria for the intro, and thanks to Jenn for joining me.

Show Notes:

* Jennifer Bennett bio, Gupta Wessler LLP

* High Court Bar’s Future: Gupta Wessler’s Jennifer Bennett, by Jeff Overley for Law360

* US Supreme Court weighs bid to narrow worker arbitration exemption, by Daniel Wiessner for Reuters

Prefer reading to listening? For paid subscribers, a transcript of the entire episode appears below.

Sponsored by:

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 [email protected].

I’ve interviewed many law firm leaders on this podcast, usually from one of two extremes: brand-new boutiques or long-established Biglaw institutions. But the most interesting moment in a firm’s history may be the middle—when the early bets have paid off, but the long-term trajectory is still unfolding.

That’s where Glenn Agre Bergman & Fuentes is today. Founded in February 2021, in the depths of the pandemic, the firm is now one of the nation’s leading boutiques—and recently marked its fifth anniversary with a celebration at The Pool, a fabulous venue inside the landmark Seagram Building.

I was there at the invitation of my longtime friend Jed Bergman—a former Wachtell Lipton colleague and co-founder of Glenn Agre, where he recently became the chair of litigation. After catching up at the party, I invited Jed to join me on the podcast to talk about what it’s like to be five years into building a firm.

Five years is a revealing moment: long enough to have learned lessons, but early enough that the future remains wide open. Jed and I discussed why he and his partners launched Glenn Agre, what he knows now that he didn’t then, where the firm is headed—and why he thinks AI could give boutiques a competitive edge over Biglaw.

Congratulations to Jed and his partners on the milestone—and best of luck in the years ahead.

Show Notes:

* Jed I. Bergman bio, Glenn Agre Bergman & Fuentes LLP

* Jed Bergman profile, Legal 500

* Jed I. Bergman Appointed Chair of Litigation Department at Glenn Agre Bergman & Fuentes LLP, PR Newswire

Prefer reading to listening? For paid subscribers, a transcript of the entire episode appears below.

Sponsored by:

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 [email protected].