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 for new lawyers looking to break into the legal tech world.

Tune in for a conversation filled with career insights, tech trends, and actionable advice for lawyers and legal professionals!

Links:

• Colin Levy's Website: https://www.colinslevy.com

• Malbec.io - Legal Tech Solutions: https://www.malbek.io/

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, scalable innovation in Big Law. He’s also the founder of Legal Metrics, a nonprofit initiative improving how firms and clients measure performance.

In this episode, David pulls back the curtain on what firms are really doing with AI and how change actually happens at scale. We talk about the biggest barriers to adoption (hint: it’s not the tools), how some seasoned partners are leapfrogging junior lawyers in AI use, and what law firms can learn from tech companies.

We also explore:

-How David’s background in client-facing innovation shapes his work inside the firm

-What “working backwards from the client” looks like in Big Law

-Why the hardest part of innovation is behavior—not technology

-The metrics that actually matter for modern legal teams

-How law students and associates can position themselves as innovation leaders

-If you’re curious about the future of legal work and what’s happening behind the scenes at some of the world’s top firms, this episode is for you.

🎧 Subscribe if you enjoyed the episode!

#LegalTech #Innovation #BigLaw #AI #LegalLeadership #FutureOfLaw #LegalOps #LawFirmStrategy

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 businesses, worked at a law firm, and eventually founded his own boutique practice focused on advising startup founders at the intersection of law, healthcare, and AI.

In this episode, we talk about pivoting careers, embracing nontraditional paths, and how he’s using everything he’s learned—legal, technical, and entrepreneurial—to help clients build.

We talk about:

▪️ Lessons from launching multiple companies

▪️ How consulting in Qatar shaped his global perspective

▪️ Using AI to enhance transactional lawyering

▪️ What solo founders need that Big Law doesn’t offer

▪️ Whether a JD is still worth it in the age of automation

Aboud’s career is a case study in reinvention. Listen in if you're curious how law, tech, and healthcare intersect—or what it really looks like to build a practice from scratch.

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-glamorous parts of networking and why some of us struggled with it.

This one’s for incoming law students, current 1Ls, or anyone curious what it’s actually like behind the Reddit posts and glossy brochures.

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 provides strategic legal support to healthcare companies. He also created the Inside Counsel Academy—a program designed to help in-house lawyers think like business leaders and grow into effective legal executives. In addition, he hosts the podcast "Becoming the GC," where he interviews legal leaders on what it takes to thrive in-house.

In this episode, Joe shares his insights on transitioning from Big Law to the GC seat, the value of pairing legal and business education, and how coaching and content creation have become a meaningful part of his journey. We hope you enjoy the episode!

🎧 Learn more at: generalcounselwest.com

📺 Check out Joe’s podcast: Becoming the GC

#LegalLeadersPodcast #GeneralCounsel #InHouseCounsel #LegalLeadership #InsideCounsel #HealthcareLaw #CareerDevelopment #JDValue #MBALawyer #LegalCareer

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 shaped by both deep professional wins and personal battles.

In this episode, Roger reflects on his early years building a business tax–centered law firm from scratch, what it means to truly “own your practice,” and why trying different types of law early matters.

Check out Rogers content on his Youtube at @royselaw or his podcast 10000 Startups; Legal strategies for startup success.

We hope you enjoy the episode.

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, Jon entered the legal field right as the tech industry was taking off. He built his expertise at Wilson Sonsini before joining Venture Law Group, a firm that pioneered taking equity in exchange for legal services, and later transitioned to Heller Ehrman before landing at Cooley.

Jon has worked on major deals, including Halcyon's $100M Series C, Logic.io's $25M Series B, and G2’s $157M Series D, helping companies from early-stage financing through IPOs and acquisitions.

In this episode, we discuss Jon's career, the business development side of law, and what makes a great long-term legal partner. Jon also shares his perspective on how partners approach client relationships and the key considerations for early-stage companies looking to scale. We hope you enjoy the episode.

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 hyper-growth. He previously worked at Facebook and Slack, joining the latter when it was still a few hundred employees and participating in the $27.7 billion acquisition by Salesforce in 2021. Throughout his career, he has worked across platform policy, intellectual property, and privacy, helping shape legal strategy at some of the most innovative tech companies. In this episode, we dive into what it means to be an effective product counsel, how legal teams can work closely with product and engineering to launch new features, and the importance of prioritizing learning and growth in one’s career.We hope you enjoy the episode!

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 built a platform to help attorneys explore new career paths.Both Fordham graduates—Kim with an MBA and Neil with a JD—this is their second successful venture together, having sold their first company in the early 2000s. Since launching Ex Judicata, they’ve had over 100,000 unique visitors and have helped countless attorneys transition into new roles.This episode also marks the first sponsored episode of the Legal Leaders Podcast. Thank to Ex Judicata for sponsoring.

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. He discusses the legal challenges of the crypto industry, his experience representing major players in blockchain and finance, and what it takes to build a successful law practice in an evolving regulatory landscape.You can reach Aaron at [email protected].