Deep conversations with underrated lawyers.
Jamie Nawaday is Head of Seward & Kissel's Government Enforcement and Internal Investigations Practice and the founder of Disrupting Drinking, where she speaks on personal change and cultural change to disrupt the corporate cocktail culture. Jamie has the unique insight that drinking isn't just about wellness - it reflects how the legal profession handles stress, bonding, and belonging. We explore how storytelling and authenticity are not side skill, they're core to both legal persuasion and personal transformation. That change doesn't have to come from quitting your job and going all in - you can start a courageous conversation from within.
Vishal Shah is the founder of Shah Litigation, a high-stake employment litigation firm. This is a unique opportunity to examine the strategy and values a biglaw associate used to launch and grow a successful law firm. We talk about the decision to switch to the other side of the v., how he researched the opportunity to identify his niche, his approach to a national trial practice, the unique dynamics of the plaintiffs' bar, and business development strategy.(01:30) - from small-town Alabama to big-city biglaw (15:35) - how personal tragedies and a desire for control over Vishal's career motivated his move to launch his own firm (19:05) - key insights from successful law firm founders (21:31) - how Vishal leverages his network, LinkedIn, and relationship-building for client development (33:21) - case selection philosophy (38:46) - litigation approach and pre-trial blueprint (01:04:49) - the impact of the unique collegiality of the plaintiff's bar (01:19:39) - advice for rising biglaw associates
Pratik Shah is the Practice Head of Akin's Supreme Court and appellate practice. Pratik breaks down his achievements and shares the values and principles he used to challenge himself and create opportunities. This conversation explores three underdiscussed topics, the market for appellate litigation, the business of appellate litigation, and the seismic shift in appellate practice in the past couple decades. We also explore how to make decisions about the kind of practice to join and build.
Tim Yoo is a partner at Bird Marella and probably one of the few lawyers who can reference both the second fundamental theorem of calculus and The Undertaker. This free-ranging conversation explores how lawyers can use basic concepts from applied mathematics for decision principles and strategy. We also cover what lawyers can learn about storytelling and character development from professional wrestling.
Lora Krsulich is an associate at Goodwin and a rising star. After clerking in the Central District of California and the Ninth Circuit, Lora litigated at Susman Godfrey before joining Goodwin. She shares her story of finding her voice and confidence in law as a first-gen lawyer, and the values she's followed as she's pursued success and excellence. (00:58) - - “Covered in Masking Tape”: Lora's father's pride in his work and how it influenced her. (08:01) - - “Fear as Fuel”: Facing debt and fear in her first year of law school, then finding her footing with other first-gen lawyers (12:32) - - Clerkships: the transformative experience of clerking for two federal judges. (22:06) - - Role of Advocacy: Always advocating subtly, even in procedural moments. (38:16) - - Parenting and Litigation: How becoming a mom reshaped her work habits and time management. (49:46) - - Lora reflects on how her experience of being "swindled" as a first-generation student seeking financial aid information led her to be more open to asking for help and building trust-based relationships. (01:07:18) - - “Knowing When a Witness Needs a Bathroom Break”: How her deposition skills reflect her ability to connect. (01:09:11) - - “I Wanted to Be Trusted”: Laura's early courtroom experiences at Susman Godfrey. (01:18:06) - - Transition to Goodwin: Why she joined Goodwin and her focus on IP litigation. (01:25:00) - - “Inverting Weakness into Strength”: Turning her non-technical background into an asset in IP cases. (01:26:47) - - Being Strategic and Ambitious: Embracing those traits to focus her career path.
This episode with Sonal Mehta is a masterclass on decision-making. We explore her early rise to partner and the path that led her to the management committee at WilmerHale by walking through the tradeoffs and opportunities she identified at each step. We also explore the role intuition plays in legal analysis. And we discuss Sonal's journey through challenging parts of her practice and what's led to her success. Sonal is remarkably down-to-earth for her accomplishments, so this was a fun interview.
Silpa Maruri graduated from law school in 2011, but she's already been partner at renowned trial firm Quinn Emanuel and is now founding partner at Elsberg Baker Maruri, an elite commercial litigation firm. How did she do it? In this episode, we discuss the techniques and principles Silpa used to practice creativity and self-advocacy. Launching a new firm can seem daunting, but Silpa breaks down some of the key components and the path that got her here.
Listening to this episode, you can't miss Samuel Levine's passion for consumer protection. It would be a mistake to look at his remarkable ascent from Harvard Law School to become Director of the Bureau of Consumer Protection at the FTC as a strategic arc to power. Samuel's story illustrates why lawyers should get their hands dirty and find work you're passionate about.I've largely advocated for a more strategic approach to career, and Samuel's approach is a nice counterbalance. I enjoyed this conversation, I hope you will to.
Heather Stevenson went from litigator at Sullivan & Cromwell to running a juice bar, then returned to law as a transactional lawyer at the Boston Globe where she rose to Deputy General Counsel, then became General Counsel at Red Cell Partners, an incubation firm. I've been influenced in more ways than one by Heather's adventurous career, and I admire her first-principles approach to thinking about what's important in career.
Kalpana is known as one of the top trial lawyers in the country. She's also co-chair of one of the leading trial firms in the country, Susman Godfrey. That's a rare combination. I took this opportunity to explore themes in Kalpana's career and professional decisions, there's a ton of great principles covered in this conversation. In this episode, we talk hip-hop dancing, the role of gut decisions in career, how she approaches business development, and more. (00:00) - why Kalpana practices hip hop dancing (10:27) - the role gut decisions have played in her career (15:27) - how to benefit from gut decisions (18:57) - how should lawyers think about joining a growing office (26:47) - what Kalpana is willing to sacrifice for success (31:27) - how Kalpana allocates her time and effort to new cases (36:17) - how the firm gets new ideas (45:07) - a firm Kalpana admires (51:57) - how a trial practice helps with running a firm and vice versa (01:00:47) - how Kalpana balances the history of the firm and its future (01:04:47) - the most impactful tip she picked up in her training (01:12:07) - how Kalpana litigates differently from Steve Susman (01:13:47) - Kalpana's favorite phase of litigation (01:22:27) - my take on Kalpana's superpower (01:26:17) - how Kalpana approaches business development (01:36:37) - “show, don't tell” (01:40:27) - what Kalpana is most excited about in her career (01:45:37) - why she believes in doing both plaintiff and defense work (01:50:47) - Kalpana's advice for lawyers
Ryan McCarl is a founding partner at Rushing McCarl LLP and author of Elegant Legal Writing. I was intrigued by the practicality and the eclectic range of influences Ryan draws on for this latest contribution to the pantheon of legal writing books. Ryan pulls ideas from disciplines like graphic design and marketing and from authors in nonfiction and fiction alike. The result is clear guidance on how to write to be helpful, enjoyable, and original.
Moez Kaba is the managing partner of Hueston Hennigan, the elite trial firm. Moez's father drove a cab, and now Moez is one of the most sought-after trial lawyers in the country, and he's only 42. We spent a lot of time exploring Moez's approach to trial and the role serendipity and boldness played in guiding his path through law. (00:45) - how he joined his firm based on a conversation on the subway (09:51) - how boldness can help first-gen lawyers get a seat at the table (19:45) - what's special about cross-examination (22:07) - what's the trial moment he keeps revisiting (31:03) - trying cases the Hueston Hennigan way (33:01) - what's a principle from everyday life that impact your practice (34:50) - how Moez found his voice at trial (41:00) - why the best trial teams are like an orchestra (48:01) - how to respond to events out of your control (59:24) - how has Moez related to ambition over time (01:01:19) - what drove Moez to go to law school (01:14:15) - Moez react to headlines about him (01:25:15) - who would play Moez in a biopic
Nimesh Gupta is the founder of Briefly, a legaltech generative AI company. I met Nimesh through a mutual friend, and we hit it off - our patent litigation background, views on parenting, therapy, and entrepreneurship. We take Nimesh's unconventional moves from biglaw to big tech to startups and dig into the decisions. We explored how to assess risk and opportunities in new technologies and businesses, including legaltech and generative AI. Along the way we explore how mindfulness and authenticity provided a north star for career decisions.Disclosure: I'm an advisor to Briefly.
Neel Chatterjee is a partner at Goodwin. Neel is fascinating because on one hand he's a trial lawyer that handles serious high-stakes tech disputes, and on the other hand he's the kind of guy who has “partner and very handsome man” written on his firm business card. We spend some time going deep on these aspects of Neel, where they came from, and how they converge. (31:40) - a counterintuitive decision career (00:00) - Chapter 2 (36:00) - a pattern in his career (00:00) - Chapter 4 (38:30) - his rule of thumb of building a book of clients (00:00) - Chapter 6 (42:30) - how Neel gets things done (00:00) - Chapter 8 (45:40) - how Neel manages peers (00:00) - Chapter 10 (49:00) - the inflection point to rainmaking (00:00) - Chapter 12 (01:01:30) - how do you think about risk and diversification in your career (00:00) - Chapter 14 (01:05:30) - is Neel a salesperson? (00:00) - Chapter 16 (01:06:50) - Neel's superpower (00:00) - Chapter 18 (01:10:40) - how Neel crafts trial strategy (00:00) - Chapter 20 (01:17:30) - how Neel balances all the work (00:00) - Chapter 22 (01:31:50) - why aren't there more people experimenting with outsized marketing? (00:00) - Chapter 24 (01:36:10) - does Neel feel like he's arrived? (00:00) - Chapter 26 (01:46:20) - where Neel's practice is heading (00:00) - Chapter 28 (01:49:40) - how should lawyers figure out where to direct their career (00:00) - Chapter 30 (01:51:30) - ChatterjeeGPT
Paul Grewal is the Chief Legal Officer at Coinbase. As the highly visible head lawyer at a company perennially making headlines, much of Paul's story and approach is well-known. This interview explores the lesser-known aspects of Paul's career moves: how Paul thinks about risk, the key question to ask in making a career change, and a conspiracy theory he can't shake. (09:12) - the financial and emotional changes in leaving practice for the bench (15:30) - the most challenging part of being a judge (22:10) - the most skillful advocacy he observed (48:27) - what made Coinbase an asymmetric bet (01:07:12) - how can more lawyers take risks (01:15:32) - what's a decision he made that he wasn't sure he got right (01:20:02) - what's a conspiracy theory Paul believes in (01:26:20) - why Paul is so active on social media (01:36:40) - what Paul's learned about storytelling (01:39:48) - the number one question to ask to make career decisions (01:41:55) - what his peers would say Paul is particularly good at
Alamdar Hamdani is the U.S. Attorney for the Southern District of Texas, one of the most important jurisdictions in the country. What I love about his story is that it's the classic American story of how the son of poor immigrants in small-town Texas became the US attorney for one of the most important jurisdictions in the country. But I discovered another equally American part of this story I hadn't heard elsewhere - the story of the entrepreneurial civil service that led him to where he is today. (16:00) - the decision that changed his career (19:00) - how selling Sesame Street books led to the decision that changed his career (39:30) - how the South Asian bar led Alamdar to the US Attorney's Office. (42:30) - the shocking story of how Alamdar accepted his role as Assistant US Attorney (47:00) - what role does taking big risks in your career (58:00) - the lawyers Alamdar met early in his career (01:11:30) - the “Mama rule” (01:27:30) - what's the most underrated risk the US faces (01:32:30) - what are national trends in enforcement
Gurbir Grewal's meteoric ascent to the Director of the SEC's Division of Enforcement may seem charmed, but here Gurbir shares the tradeoffs and costs of the steps he took. Gurbir is uniquely down-to-earth for someone so public and prominent, and this interview went deep into the decisions and experiences that shaped his path.
It's inspiring to hear the origin of The Sikh Coalition in the aftermath of 9/11 and the disproportional impact on the Sikh community. But it's all the more remarkable to hear how Winston & Strawn partner Amandeep Sidhu and his cofounders built an organization around consensus-building causes that benefit multiple communities. And how Amandeep did it by getting stakeholders at his law firm to support him along the way. This episode is for anyone looking to make a social impact and learn how to develop thoughtful responses to the inevitable crises and opportunities.
As the CEO of Litera, Avaneesh Marwaha is responsible for setting the pace of innovation at a leading legaltech company. So when Avaneesh shared some of the goals he set for himself at 25 that he's still carrying out at 40, I had to dig in to learn more. A company like Litera has a powerful lens on the legal industry and where it's headed. So we spent a lot of time talking about core insights like what makes clients stick with law firms. We also discuss the three areas Avaneesh sees opportunities for lawyers to move into legaltech, and the #1 skill lawyers need to develop now to advance their practice. This conversation is for anyone interested in learning what it feels like to bet on yourself and to move into a growing frontier.
When I was introduced to Kenneth Anand, I was equal parts excited and anxious. I'm no more than a casual fan of Kanye's work and I've never been into streetwear. But how could I say no to meeting the ex-GC of Yeezy? Kenneth and I ended up having a sprawling conversation about his new book Sneaker Law and how it departs from traditional legal casebooks. We talked about his journey from producing hip hop to law and how after 15 years of practicing law he oriented himself back to his roots in streetwear. We talked about how the methods and culture around sneakers and streetwear is moving into other industries. And we talked about lessons learned from Kanye himself.
It's hard to picture a better time to grow a cold chain technology company like Therma, and it's even harder to picture the legal clinic origins of the business. Manik Suri has made a career out of synthesizing surprising insights and finding talent to partner with. In this episode we discuss what Manik learned from a friend that ended up as a presidential candidate on how to channel your inner confidence. You'll learn a new question to ask yourself "what kind of energy am I burning?" And we talk about how to manage downside risk by getting over the fear of failure.
Federal judges are fascinating because they resolve high stakes matters addressing a wide swath of issues touching on every aspect of society. And because of their limited resources and the 30-some new cases they get a month in a busy court like the Northern District of Illinois, they have to become experts at building systems for making decisions. So I'm happy that I got to spend two hours with Judge Matthew Kennelly to learn about what he does. We explored the tools he's developed for helping bring disputes to resolution in the 22 years he's been on the bench. We talked about some of the interesting implications of lifetime tenure, how he's changed how he manages his docket, new ideas and how they spread among judges, what's difficult about sentencing, and the tradeoffs between standardization and individual attention on cases. Judges are used to people laughing at their jokes, but Judge Kennelly is actually funny (although I won't repeat that he's a "pillar of our community" because apparently he's heard that enough times). I hope you'll enjoy this rare in-depth conversation.
I'm thrilled to share this interview Chief Judge James Holderman (ret.) formerly of the Northern District and now a mediator at JAMS ADR. Externing for Judge Holderman in law school was an inflection point in my legal development, and I feel like I've been riding that wave ever since. It's rare to get a chance to sit with a federal judge and explore lessons from 30 years on the bench. We talked about his upbringing on a farm in Southern Illinois and some of the surprising legacy that's had on his judicial career. We discussed how he wielded authority from the bench, and the hardest task he faced on the bench. Judge Holderman shared some of his prescriptions for improving how federal litigation is conducted.
When Archit and I planned to do this episode in the new year, we didn't quite expect this much attention on Robinhood. We explore Archit's arc from the first lawyer at Robinhood to general counsel. We talked about the lessons learned from building a team of dozens of lawyers, and how he approached the novel legal and regulatory issues along the way. We covered the regulatory landscape for fintech companies, reasons to be bullish on crypto, and yes, we talked about Gamestop.
I didn't expect to interview someone at another Florida sports franchise so soon, but I'm glad I had a chance to talk to Megha Parekh, Chief Legal Officer of the Jacksonville Jaguars. One of the most interesting themes from the conversation was around work-life integration and the systems she's used to foster it in herself and others. There were insights into the relation of remote work and inclusivity, and lessons on the perils of perfectionism. This interview is for anyone interested in being unapologetically yourself and refusing to cut out the fun in your life.
Kunal Patel and I something less of a conversation and more of a jam session. We explored his career as a creative and a lawyer to creatives and the multi-year grit it took to land the roles he took on. I don't know how many lawyers once drove for Uber or took a paralegal role to get a foot in the door at the right company. We also explored his ambitions for South Asian creatives and why representation in media really matters. One quote from Kunal has stayed with me: "there can't be a first unless there's a second and a third and a fourth." This interview was a first.
Bilal Zaidi is the host of one of my favorite podcasts, Creator Lab. We explored the genesis of his podcast and the connections it drew between his influences from Pakistani, the UK, and the US. We dove into some of the patterns Bilal has discerned from interviewing CEOs, investors, and writers. We also compared experiences growing up Pakistani in the UK and the US and some of the surprising differences.
You probably know more about baseball than me, but I'm glad I had a chance to learn a little about the business of the game with Ashwin Krishnan, General Counsel of the Miami Marlins. As soon as you start talking with him, you can tell he's built differently than other attorneys - there's no jargon and he's high-energy. It was fascinating to hear about how the Marlins is thinking about its place in entertainment as it competes not just with other franchises but Disney, gambling, and even Netflix. For those contemplating a move to Miami, Ashwin has the perfect pitch. And for those who want to forge their own career, Ashwin's example is inspiring.
Sachin Shivaram is CEO of Wisconsin Aluminum Foundry Co. I was fascinated with Sachin's journey that started with every credential imaginable and led him to running an aluminum foundry in Manitowoc, WI. We talked about the surprising revelation he had from reading Atlas Shrugged that led him to the steel industry, a panic moment when hosting Joe Biden, and what's special about Wisconsin.
Avanti Bakane is a partner at Gordon Rees. I've known Avanti for some years now, and I've been consistently impressed with her ability to collect and connect people. I sat down with Avanti to discuss her people-driven approach to her career and what she's learned about building allies and how to manage by playing to your team's strengths. Avanti is just easy to talk to and I admire how even-keeled she is for a big-firm lawyer.
Rudhir Kristhel is the founder of Krishtel Coaching and a former attorney. We started the conversation talking about how his beard helped me strike out on his own and ended it with Rudhir's three-part framework for how to think about growing relationships. The theme of this conversation is how to tune in to yourself to be a better player in the game of career and life.
Vivek is founder of Jayaram Law. He went from biglaw to opening his own firm in the depth of a recession, which now has three offices and is growing. We talked about how much of his growth has come from a core insight around aligning the legal work to clientele and firm culture. That lead to some interesting conversation about how to think about diversity and why contemporary culture matters for lawyers.
Vineet and I talked about:picking the right narrative for your careercareer home runs v. singlespolitics as venture capital how to make losses as useful as winsthe benefits of taking a pay cut
Learn more about Adam at https://www.glscap.com/our-team/Learn more about Khurram at https://www.naik.co.
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