022: Nimesh Gupta on therapy, moving from biglaw to bigtech to startups, and generative AI in law

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