Ben Chiriboga (Nexl) on Legal Tech, Innovation, and the Future of Law
Technically Legal - A Legal Technology and Innovation Podcast
Release Date: 09/11/2025
Descrybe's Quest to Democratize Legal Research (Kara Peterson & Richard DiBona)
Technically Legal - A Legal Technology and Innovation Podcast
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 expert, share their journey from a personal legal issue to building a platform that processes over 100 billion tokens of legal data. They explain why they chose to build an AI-native system...
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The Uberization of UPL? How AI Is Outpacing the Unauthorized Practice of Law (Ken Crutchfield, Bill Henderson, Jim Doppke)
Technically Legal - A Legal Technology and Innovation Podcast
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 he penned about the pressure artificial intelligence is placing on legal service delivery and regulations barring the unauthorized practice of law. In this episode, Ken is joined by Indiana...
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From Water Pistols to Tanks: Why Data Science is the Gold Standard to Counter Class Action Fraud (Donald Beshada, CEO, Covalynt)
Technically Legal - A Legal Technology and Innovation Podcast
Donald Beshada, former litigator turned legal tech entrepreneur and CEO of 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 advertising and sophisticated fraud bots. Donald explains how his company uses data science and identity resolution to bring "scientific rigor" to ensure class action settlements reach legitimate...
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Stacking Legal Skills: How Stints at Big Law, Biz Dev and and Legal Ops Paved the Way to the C-Suite for Akshay Verma (COO, SpotDraft)
Technically Legal - A Legal Technology and Innovation Podcast
, COO of 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 realities of Contract Lifecycle Management (CLM), the evolution of the "agentic" legal tool, and why change management is the biggest hurdle for legal innovation. Akshay also discusses the "underdog mentality" that drew...
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The Legal Ops Force Multiplier: How Nextdoor GC Sophia Contreras Schwartz Built a Lean Legal Team From Scratch
Technically Legal - A Legal Technology and Innovation Podcast
, General Counsel at , 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 strategic value of hiring Legal Operations early, the specific tech stack that keeps a lean team of eight efficient, and why "versatility and curiosity" are the most important traits for in-house counsel today. Key Takeaways: ...
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Tokenization of Real World Assets: From Art to Real Estate to Private Equity (Lucas Moskowitz, General Counsel, Robinhood)
Technically Legal - A Legal Technology and Innovation Podcast
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. Moskowitz also highlights the company's commitment to financial literacy. The core of the conversation shifts to the shifting regulatory landscape regarding cryptocurrency and the potential for...
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Bridging Law Firm Silos: How Law Firms Can Maximize AI-Driven Cross-Selling (James Barclay, CEO Passle)
Technically Legal - A Legal Technology and Innovation Podcast
In this episode, CEO of , 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, , which helps attorneys overcome the "trust and awareness" barriers that prevent internal collaboration and revenue. James explains that while content marketing is essential for lawyers to showcase expertise, the real value lies in how that expertise is shared...
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Best of 2025: Building a Modern IP Infrastructure and Protecting Creators in the AI Age (Andrea Muttoni - President Story Foundation)
Technically Legal - A Legal Technology and Innovation Podcast
One of the most listened to episodes in 2025 featured a conversation with Andrea Muttoni, President of . 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 producer to a product manager at Amazon and eventually to a leader in the blockchain industry, driven by a passion for the intersection of technology and creativity. The conversation delves into the...
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Best of 2025 - From IP Lawyer to Investor to CEO to Legal Ecosystem Builder (Avaneesh Marwaha, Litera CEO)
Technically Legal - A Legal Technology and Innovation Podcast
Avaneesh Marwaha, the CEO of , 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 current role as a comprehensive legal tech ecosystem. Avaneesh highlights the company's strategic shift from acquiring to building new technologies. He also emphasizes the importance of Litera’s...
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Best of 2025 - Benchmarking Legal AI: Measuring the Delta Between Man and Machine (Anna Guo Legalbenchmarks.ai)
Technically Legal - A Legal Technology and Innovation Podcast
In one of the most popular episodes of the year, Founder 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 colleagues quickly revealed a strong community interest in a systematic approach to evaluating legal AI tools. This led to the creation of Legalbenchmarks.AI, dedicated to finding out where...
info_outlineA conversation with Ben Chiriboga, Chief Growth Officer at legal CRM company Nexl and host of the This Legal Life podcast. Ben shares his journey from a litigator to a legal tech innovator. He recounts how an early e-discovery tool using natural language processing completed in six hours what had taken him six months, leading to an epiphany about the power of legal technology.
The conversation delves into the legal industry's historical resistance to technology, prioritizing billable hours over efficiency, and how Ben leveraged his legal experience to transition into a new role in tech. Ben discusses the challenges of building a legal tech company and the critical distinction between a general CRM and one designed specifically for law firms. The episode concludes with a thought-provoking discussion on the impact of AI on the legal profession, focusing on what aspects of law are truly "fundamental" and what new roles and jobs AI will create.
Key Takeaways
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The Power of Tech: Legal tech tools can drastically improve efficiency, as demonstrated by an e-discovery tool that performed six months of work in just six hours.
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Transitioning Careers: A background in law can be a valuable asset in the legal tech sector, but success requires adapting to new skills like sales, marketing, and growth strategy.
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The "Why" Behind a Legal CRM: General CRMs are built for sales teams with built-in incentive structures, whereas a legal-specific CRM, like Nexle, is designed to passively collect and enrich data without requiring lawyers to manually input information.
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The Fundamentals of Law: The human element—relationship building, counseling, and strategic advisory—is the core function of a lawyer that AI cannot replicate.
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The Future of Legal Jobs: AI's true impact will not be in better-drafted motions, but in the creation of new "legal adjacent" roles and business models that merge legal expertise with technology and data.