Legal Leaders

We're officially 3L's! After finishing our 2L year at Berkeley Law, I sat down with classmates Riya Dhanjal, James Courser, and Rameses Neale to reflect on law school, Big Law recruiting, AI, burnout, networking, and student life. We discuss Berkeley Law’s culture and grading system, the realities of accelerated Big Law recruiting, the growing role of AI in legal practice, and what we wish we knew...

Dina Segal is the Chief Legal Officer at Gusto, where she leads legal, compliance, and government affairs for a platform serving over 400,000 small businesses across the United States. In this episode, Dina shares her journey from growing up in Ukraine—where she was inspired by her grandfather’s work as a lawyer advocating for his community—to building a diverse legal career across BigLaw, fintech...

Lisa Gorman is one of the most accomplished legal executives in tech. She spent nearly nine years at Eventbrite, rising from employment counsel to General Counsel and Chief Legal Officer. During her tenure, she helped lead Eventbrite's legal strategy through its IPO, global expansion, the pandemic's devastation of the live events industry, and ultimately a $500 million acquisition by Bendi...

In this episode, I sit down with Dennis Adsit, an executive coach with over a decade of experience helping leaders navigate transitions and build high-performing teams. Dennis holds a PhD in industrial psychology and has coached everyone from startup founders at Techstars to C-suite executives, with prior experience leading Six Sigma implementation and global call centers at Intuit. Dennis reveals...

I spoke with Dan Haley, Chief Legal Officer of Flock Safety, to walk through a career that spans nearly a decade in Big Law and senior legal leadership roles at some of the fastest-growing technology companies in the country. Dan shares what it’s really like to make the transition from law firms to in-house, including the tradeoffs, surprises, and lessons he learned along the way. We talk about na...

Justin McCallon is the Founder and CEO of StrongSuit, an AI platform built to modernize and accelerate core legal workflows. Justin started his career as a practicing attorney before leading large-scale analytics, transformation, and AI initiatives at AT&T and DIRECTV. In our conversation, we cover his path from law to consulting to building a legal AI company, what he’s seeing in the legal te...

Ian Poirier is the Associate General Counsel at Toyota Research Institute (TRI), where he works at the intersection of autonomous vehicles, robotics, safety, and policy. We talk about how autonomous vehicle regulation has evolved over the past decade, including Ian’s experience moving from Lyft’s early AV efforts to Toyota’s long-term research and safety programs. Along the way, he explains why on...

Julia Taylor is the Chief Legal Officer at Coupa and a Berkeley Law alum. We unpacked her path from Big Law to becoming the first lawyer at Eventbrite, where she spent nearly twelve years and helped guide the company through its $1.8B IPO. Julia reflects on her early influences, including her time working on Capitol Hill for Senator Dianne Feinstein and Jerry Brown, and how those experiences shape...

Jason Barnwell just joined Agiloft as Chief Legal Officer after 15 years at Microsoft, where he most recently served as GM and Associate General Counsel for Monetization and Business Planning. I spoke with Jason about his career path from MIT engineering grad to software engineer to leadership at one of the world's leading tech companies. We discussed his work driving digital transformation wi...

I spoke with Colin Levy, General Counsel at Malbec, an innovative CLM company. Colin shares his in-house journey, his passion for legal technology, and how he's helping bridge the gap between law and tech. Colin discusses the importance of building a personal brand, embracing AI in the legal industry, and the future of law schools adapting to tech innovations. He also offers insightful advice...

David Cunningham is the Chief Innovation Officer at Reed Smith LLP, where he leads legal tech transformation for 2,000+ lawyers across 34 offices. But his focus goes far beyond technology—he’s rethinking the culture and workflows that shape how legal work gets done. With a background in legal operations and data analytics, David has become one of the leading voices in the push for practical, scala...

Aboud Chaballout was on track to become a doctor. He studied human biology at Cornell, completed a Fulbright, and even worked in healthcare consulting in Qatar. But somewhere along the way, he realized his interests pulled more toward entrepreneurship than medicine. He went to law school, launched a startup after 1L, and never looked back. Since then, he’s built and sold multiple healthcare busine...

I sat down with three of my classmates—Alex Kang, Laith Hourani, and Aman Madan—to unpack the highs, lows, and everything in between from our 1L year at Berkeley Law. We talked about: What brought us to law school How we navigated the pressure of grades and early recruiting The good, bad, and weird of law school social life Advice we wish we had on day one And yes, we even got into the not-so-glam...

Joseph Schohl is a five-time General Counsel and former Fortune 500 CLO who became a public company GC by the age of 35. Over the course of his career, he’s held leadership roles at Baxter Healthcare, DaVita Kidney Care, and Radiology Partners, while also building a reputation for empowering the next generation of in-house counsel. Joe is the founder of his own firm, General Counsel West, which pr...

Roger Royse is a partner at Haynes Boone and the founder of the Royse Law Firm. Over his career, he’s advised thousands of startups, built a name in tax and startup law, and authored two books sharing hard-earned lessons with founders and lawyers alike. Roger’s story goes well beyond law. He’s a CPA, an entrepreneur, an athlete, an author, and a pancreatic cancer survivor. His perspective is shape...

Jon Gavenman is a seasoned corporate attorney and partner at Cooley, where he’s been advising startups and public companies since 2008. With a career spanning more than three decades, Jon has had a front-row seat to Silicon Valley’s evolution—helping companies scale, navigate acquisitions, and raise capital. Starting as a math major at Pomona College before earning his JD from UC Hastings/UCSF Law...

Mark Pike is the Associate General Counsel at Anthropic, an AI research and safety company experiencing explosive growth. At the time of this podcast, the company raised a $3.5 billion Series E round, bringing its valuation to $61.5 billion, solidifying its position as a leader in AI development. Mark has a proven track record of making strategic career moves at companies on the verge of massive h...

Ex Judicata is an employment platform and job board designed to connect attorneys with nonlegal career opportunities that make the most of their JD. https://exjudicata.com/⁠ In this episode, I sit down with Kim Fine and Neil Handwerker, the co-founders of Ex Judicata. With extensive backgrounds in business development, recruiting, and the legal industry, they recognized a gap in the market and bui...

Aaron Brogan is the founder of Brogan Law, a boutique law firm specializing in cryptocurrency, fintech, and emerging technology. After graduating from Harvard Law, Aaron spent six years in Big Law in New York, first as a litigator before pivoting to crypto and fintech law at McDermott. In this episode, Aaron shares his inspiring journey—from navigating Big Law to launching his own firm in New York...

In this episode, we’re joined by Kevin Liu, a partner at Goodwin Procter and a member of the firm's Strategic Technology Transactions and Licensing and Data, Privacy & Cybersecurity practices. Kevin shares his impressive career journey, which blends engineering and law, offering a unique perspective on the intersection of technology, privacy, and intellectual property. Kevin’s expertise spans...

Lindsey Mignano is the founding partner of SSM Law, a WBENC corporate law firm redefining the delivery of BigLaw services at affordable rates. SSM Law specializes in representing emerging technology companies, venture capital funds, and industry-adjacent service providers in critical areas like venture financing, M&A, tax law, and commercial contracts. As a fully virtual, women-led firm, SSM c...

Simi Raina is the Head of Legal at Webflow—one of the fastest-growing companies on the Forbes Cloud 100 list. Simi’s impressive career has taken her through some of Silicon Valley’s top tech companies, during major phases of hyper growth including Salesforce, Uber, and Visa. In this episode, Simi shares invaluable insights on networking, job hunting, and the unique aspects of in-house legal work,...

Dr. Ali R. Alemozafar is a partner at Wilson Sonsini. He focuses on IP counseling and works with companies at various stages of growth, from pre-financing startups to public companies. Prior to practicing law, Ali was an accomplished academic, acquiring his bachelor's in chemical engineering from Cornell and earning a Ph. D. in chemical engineering from Stanford. Ali was exposed to the field of pa...

Bradley Krack is a partner at Gunderson Dettmer in Silicon Valley. A former engineer and submarine officer, Brad specializes in guiding high-growth tech companies through complex deals. He recently celebrated his thirteenth year with Gunderson, where he represents companies in their financings, IPOs, and M&A transactions. His experience spans a variety of technology firms, including consumer i...

Mehdi Ansari is a partner at Sullivan and Cromwell in New York. He serves as Co-Head of the Firm’s IP and Technology Group and the Firm’s Artificial Intelligence Practice. Mehdi’s practice focuses on advising clients on a wide range of transactions involving intellectual property and technology, including mergers and acquisitions, joint ventures, licenses, collaborations, research and development...