EP 38: Reflecting on 2L at Berkeley Law - Recruiting, Grading, AI & Law School Culture
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 before starting law school.
Topics include:
• Big Law recruiting and networking advice
• AI in legal education and practice
• Berkeley Law culture and student life
• Practice area selection and firm differences
• Journals, externships, and extracurriculars
• Burnout, balance, and imposter syndrome
8 May 2026
EP 37: How to Build a Successful Career in Law: Insights from Dina Segal, CLO of Gusto
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, and high-growth technology companies.
We dive into her path through tax, litigation, and FCPA work during the 2008 financial crisis, her transition into corporate law, and her move in-house—where she ultimately rose into executive leadership roles at companies like Intuit before becoming CLO at Gusto.
This conversation covers:
- How to successfully transition from BigLaw to in-house- What it takes to grow into a Chief Legal Officer role- Why understanding the business is critical for in-house lawyers- How to approach career pivots with a “learning mindset” -Building and scaling legal, compliance, and government affairs teams- How AI is transforming legal workflows, decision-making, and team capacity
Dina also shares practical advice on promotions, leadership, and why the best lawyers today are not just advisors—but builders embedded within the business.
If you’re a law student, practicing attorney, or operator working closely with legal teams, this episode offers a clear look at how modern legal careers are evolving—and what it takes to stay ahead.
“Every change is a combination of intentionality and a leap of faith.”
A great reminder that careers aren’t planned—they’re built.
3 Apr 2026
EP 36: From Employment Lawyer to CLO of Eventbrite - Leading Through IPO, Pandemic, and $500M Exit
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 Bending Spoons.
In this episode, we discuss her unconventional path from English literature major to tech CLO, how she transitioned from law firm partner to in-house counsel by organically becoming part of her client's team, and what it takes to expand beyond your core expertise. Lisa shares how she went from employment law to leading litigation, content moderation, product, privacy, regulatory, and the entire legal function. We explore the value of building trust and tenure at a single company, the role of legal AI tools like GCAI in modern practice, and her experience leading Eventbrite's content moderation program and DSA compliance. Lisa also addresses what the future holds for junior lawyers in an AI-driven world and reflects on her biggest career highlight of leading the $500M sale to Bending Spoons.
Lisa offers candid advice for law students and early-career lawyers about finding work that doesn't feel like a grind, the value of staying when you find the right fit, and keeping an open mind about where your legal career might take you.
#Eventbrite #ContentModeration #TrustAndSafety #DSACompliance #LegalTechnology #GCAI #LegalOperations #MergersAndAcquisitions #BerkeleyLaw #LawSchool
Who has been a guest on Legal Leaders
Names identified in recent episode analyses. Showing up to five guests.
Abboud Chaballout
Alex Kang
Laith Hourani
Aman Madan
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Podcast Authority Score: 48 / 100
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YouTube
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