Technically Legal - A Legal Technology and Innovation Podcast
Technically Legal is a legal tech podcast exploring how technology is transforming the legal landscape. Each episode features insightful interviews with legal innovators, tech pioneers, and forward-thinking educators who are leading this change. Our guests share their experiences and insights on how technology is reshaping legal operations, revolutionizing law firm practice, and driving the growth of innovative legal tech companies. We also explore the broader implication of technology on everyone involved in the legal system, from practitioners to clients. The podcast is hosted by Chad Main, an attorney and founder of Percipient, a tech-enabled legal services provider. Chad launched Percipient on the belief that when technology is leveraged correctly, it makes legal teams more effective. Technically Legal Podcast is an ABA Web 100 Best Law Podcasts Honoree.
Episodes
Jamie Tso and Ray Sun, the founders of LegalQuants, discuss a fundamental shift in the legal profession: the transition from legal engineering to "legal quant" work. The conversation explores how technically fluent lawyers are using vibe coding, frontier AI models, and first-principles thinking to move beyond mere efficiency and toward the complete redesign of legal services.
Jamie and Ray share their back...
We welcome back Sabastian Niles, President and Chief Legal Officer at Salesforce, to discuss his recent "Open Letter to Law Firms." As the legal industry hits a critical inflection point, Sabastian argues that the era of "AI theater" and small-scale pilots is over.
The conversation dives deep into the Innovator's Dilemma facing law firms, the shift toward agentic AI, and how firms must reimagine their busi...
Ayana Dow, Senior Counsel at the DeFi Education Fund (DEF) shares her unique career trajectory from Big Law and Capitol Hill to the forefront of decentralized finance policy. The discussion centers on the critical need for regulatory clarity in crypto, the distinction between decentralized protocols and centralized entities, and the ongoing efforts to educate lawmakers on blockchain technology.
Key takeawa...
Kara Peterson and Richard DiBona, the husband-and-wife co-founding team behind Descrybe, discuss the legal research platform they built designed to "democratize access to the law." The discussion explores the unique dynamics of married cofounders and how they are leveraging Generative AI to disrupt a landscape long dominated by high-cost legacy providers.
Richard, a software engineer, and Kara, a marketing...
The legal industry is not confronting a single disruption but a redistribution of work, capital, and regulation across a system under stress.
The boundaries of Unauthorized Practice of Law (UPL) in the near term may be defined more by what regulators must allow than what they restrict.
These are just a couple of conclusions from author and legal business strategist Ken Crutchfield in a recent ...
Donald Beshada, former litigator turned legal tech entrepreneur and CEO of Covalynt shares his journey from big-law to the forefront of using data science in litigation. Specifically, to address systemic fraud in class action settlements.
The conversation explores the evolution of claims administration—from the traditional "People Magazine" notice era to the current digital landscape dominated by targeted ...
Akshay Verma, COO of SpotDraft explores his non-linear journey through the legal industry. From his early days as a big-law paralegal to lawyer to a business development role to leading legal operations at tech leaders like Facebook and Coinbase, Akshay shares his unique perspective on why the most successful legal departments prioritize process over technology.
The conversation dives deep into the realiti...
Sophia Contreras Schwartz, General Counsel at Nextdoor, discusses her unique journey of building a legal department from the ground up. Sophia discusses how her background as a musician and fitness instructor informs her collaborative leadership style and why Nextdoor identifies as "Middle Tech"—a category of companies often overlooked by one-size-fits-all regulations.
The conversation explores the strateg...
Lucas Moskowitz, General Counsel at Robinhood returns to the show to talk tokenization of Real World Assets and the current state of crypto legislation.
Lucas updates us on Robinhood's evolving demographics, noting that while the platform remains a hub for first-time investors, the customer base is maturing alongside the platform's product offerings, such as retirement matching and advisory services. Mosko...
In this episode, James Barclay, CEO of Passle, discusses how legal technology is evolving to solve a big challenge in the legal industry: cross-selling. James shares the journey of Passle—from its roots in the early internet gold rush to becoming a leading thought leadership platform for the Am Law 200.
The conversation covers Passle's new AI-driven tool, CrossPitch, which helps attorneys overcome the "tru...
One of the most listened to episodes in 2025 featured a conversation with Andrea Muttoni, President of Story Protocol. The discussion explores how blockchain technology is being used as a foundational infrastructure for intellectual property (IP), aiming to simplify and modernize the process of registration, licensing, and monetization for creators and IP owners. Muttoni details his journey from a bedroom music produce...
Avaneesh Marwaha, the CEO of Litera, visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law.
The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company to its curr...
In one of the most popular episodes of the year, Legalbenchmarks.ai Founder Anna Guo discusses her organization's research that tests whether artificial intelligence custom-made for legal tasks better than general AI tools.
Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for colleague...
In the most listened to episode of 2025, author of "Systemology" and business systems expert, David Jenyns, discusses the importance of systemizing business processes, even in the nuanced field of law. Jenyns debunks the myth that legal work is too bespoke to be systemized, explaining how just like any other business, documenting legal workflows unlocks scalability and creativity. He shares his journey from digital SEO agency owner...
Meredith Kildow, President of Consilio discusses her career path from finance to leading global operations and delivery for one of the largest companies in the legal and eDiscovery space.
Meredith shares insights into building a revenue organization from the ground up and the shift to her current role overseeing operations and delivery for a highly acquisitive company. The conversation focuses on the pract...
This episode features a conversation with Cecilia Ziniti, Co-Founder and CEO of GC.AI. Cecilia traces her career from early the early days of the internet to founding an AI-driven legal platform for in-house counsel.
Cecilia shares her journey, starting as a paralegal at Yahoo in the early 2000s, working on nascent legal issues related to the internet. She discusses her time at Morrison & Foerster and her ...
In this episode, Sabastian Niles, President and Chief Legal Officer at Salesforce, takes a deep dive into the intersection of corporate strategy, in-house legal careers, and the transformative power of Agentic AI.
Sabastian shares his unique career path from a near two-decade tenure at a prestigious law firm before joining Salesforce. This conversation is essential for anyone interested in the evolving rol...
Is artificial intelligence custom-made for legal tasks better than general AI tools like Google Gemini and ChatGPT? That is the topic of this episode featuring Legalbenchmarks.ai Founder Anna Guo. Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for colleagues quickly reve...
Justin Wales, Head of Legal for the Americas at Crypto.com, and author of The Crypto Legal Handbook visits the show to provide his unique perspective on pivoting from a career in Constitutional Law, including work on high-profile appellate cases like the Obergefell gay marriage decision, to becoming a trailblazer in crypto law and blockchain technology.
He shares his serendipitous journey stemming from a ...
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