Home Podcasts Technically Legal - A Legal Technology and Innovation Podcast
Technically Legal - A Legal Technology and Innovation Podcast

Technically Legal - A Legal Technology and Innovation Podcast

Percipient - Chad Main 100 Episodes Jun 11, 2026

Technically Legal is a legal tech podcast that explores 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. The podcast covers topics such as legal operations, law firm practice, and the growth of legal tech companies. Hosted by Chad Main, an attorney and founder of Percipient, a tech-enabled legal services provider.

Episodes

Affordable & Accessible: The Democratization of Legal Tech (Tyler Foreman VP of AI - Rocket Lawyer) Jun 11, 2026 31:59 Tyler Foreman, the Vice President of AI at Rocket Lawyer, joins the show to discuss the intersection of artificial intelligence and the legal industry. Foreman shares his untraditional legal tech career path, spanning engineering at Intel, drone data analytics, and ultimately making the move to legal via contract lifecycle management (CLM) at DocuSign, before diving into his current work at Rocket
Building Software for Less: The Death of Expensive SaaS in the AI Era? (Nathan Wenzel - LegalOperatorAI) May 28, 2026 51:29 We catch up with legal tech entrepreneur Nathan Wenzel to discuss his journey from founding and exiting SimpleLegal to launching his newest venture, LegalOperator.ai (formerly Lexiomatic). Nathan shares insights on the evolution of private equity (PE) structures, the shifting economics of the enterprise software market, and how artificial intelligence is disrupting traditional software development
The Rise of the Legal Quants (Jamie Tso & Raymond Sun) May 14, 2026 34:54 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 t
The AI Pilot is Over: Legal's Moment to Move Beyond Experiments and Avoid the Innovator's Dilemma (Sabastian Niles, President & CLO Salesforce) Apr 30, 2026 40:18 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 t
Ayana Dow on Updating Crypto Regulation and Preserving the Freedom to Build (Senior Counsel, Defi Education Fund) Apr 16, 2026 36:26 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. Ke
Descrybe's Quest to Democratize Legal Research (Kara Peterson & Richard DiBona) Apr 2, 2026 38:41 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
The Uberization of UPL? How AI Is Outpacing the Unauthorized Practice of Law (Ken Crutchfield, Bill Henderson, Jim Doppke) Mar 19, 2026 45:05 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 tri
From Water Pistols to Tanks: Why Data Science is the Gold Standard to Counter Class Action Fraud (Donald Beshada, CEO, Covalynt) Mar 5, 2026 56:02 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
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) Feb 19, 2026 37:37 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 th
The Legal Ops Force Multiplier: How Nextdoor GC Sophia Contreras Schwartz Built a Lean Legal Team From Scratch Feb 5, 2026 30:59 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 th
Tokenization of Real World Assets: From Art to Real Estate to Private Equity (Lucas Moskowitz, General Counsel, Robinhood) Jan 22, 2026 27:24 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 servic
Bridging Law Firm Silos: How Law Firms Can Maximize AI-Driven Cross-Selling (James Barclay, CEO Passle) Jan 8, 2026 27:29 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

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