Technically Legal - A Legal Technology and Innovation Podcast

Sabastian Niles, President and Chief Legal Officer at Salesforce, is a longtime legal executive focused on AI adoption and legal tech. He urges leaving pilots behind and building integrated AI platforms. Conversation covers agentic AI, breaking silos with unified systems, rethinking client relationships, and four core systems firms must establish to compete in the AI era.

Ayana Dow, Senior Counsel at the DeFi Education Fund who moved from Big Law and Capitol Hill to DeFi policy. She discusses regulatory clarity for crypto and the distinction between decentralized protocols and centralized entities. She explains efforts to educate lawmakers and agencies, why protecting developers matters, and how market structure bills could shift oversight to the CFTC.

Richard DiBona, software engineer and co-founder who built Descrybe’s AI-native research stack, and Kara Peterson, marketing and systems thinker focused on access to justice, discuss building an affordable legal research platform. They cover starting from a personal legal problem, building a cleaned legal corpus, why they built from the ground up rather than wrapping models, and their multi-step, verification-first research workflow.

Jim Doppke, an ethics lawyer and former Illinois regulator; Bill Henderson, a law professor studying legal innovation and access to justice; and Ken Crutchfield, a legal business strategist on AI and UPL. They debate how AI and LLMs are shifting legal work toward consumers and ALSPs. They cover regulators’ struggles to define advice versus information, AI as a labor-replacing ROI driver, and where allied professionals and managed services fit.

Donald Beshada, former litigator and CEO of Covalynt, builds data science tools to stop sophisticated class action fraud. He traces the shift from print notice to digital bot attacks. Conversation covers real-time fraud scoring, identity resolution, courts demanding defensible evidence, and a future where purchases map directly to people.

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 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 him to the startup world and the future of AI in legal workflows. Key Takeaways: Process First: Technology is not a "magic pill" for broken workflows; centralized repositories and defined approval chains must come first. The Power of BD: Business development skills (evangelism and resilience) are critical for successful legal operations leaders. The "Holy Trifecta" of Legal Tech: Every department needs a CLM, a Spend Management tool (at scale), and an agentic Workflow/Intake tool. AI vs. Lawyering: AI will replace non-legal tasks, not the lawyers themselves, making AI literacy a new standard for the profession. Episode Credits Editing and Production: Grant Blackstock Theme Music: Home Base (Instrumental Version) by TA2MI

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 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: The First Legal Hire: Companies should consider their first GC when they start generating significant revenue or enter highly regulated spaces. "Middle Tech" Challenges: Nextdoor faces unique regulatory hurdles, like age verification laws, which are often designed for "Big Tech" giants but create significant operational burdens for mid-sized platforms. Force Multipliers: Investing in Legal Ops early allows a small team to scale by focusing on process design and vendor management rather than just manual intake. AI as a Strategist: Using tools like GC.AI doesn't just speed up drafting; it helps in-house lawyers ask better questions of their outside counsel by identifying nuances that general AI might miss. Things We Talk About in this Episode Legal Tech Tools: Ironclad, SimpleLegal, GC.AI Organization: Chamber Music America

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 legislative clarity under a new administration. Moskowitz breaks down the concept of Tokenization of Real World Assets (RWA), explaining how blockchain technology can democratize access to private markets, art, and real estate. The discussion covers the technical and legal differences between "native" tokens and "wrapper" products, the benefits of 24/7 liquidity, and why the United States risks falling behind global jurisdictions like the EU and Asia if regulatory frameworks do not evolve. Key Takeaways Robinhood's Evolution: The platform now serves 26 million customers. While half are first-time investors, the company is expanding into advisory and retirement products to serve users throughout their financial lifecycles. Crypto Regulation: There is a shift from "regulation by enforcement" toward legislative clarity. Moskowitz discusses the importance of comprehensive market structure bills and stablecoin legislation to provide long-term durability for the industry. Tokenization Mechanics: Tokenization is the digital representation of a real-world asset on a blockchain. This innovation promises to increase liquidity, allow for fractional ownership of high-value assets (like private equity or art), and enable faster settlement times. The "Wrapper" Concept: Moskowitz explains Robinhood's EU offering, where customers trade a tokenized "wrapper" that represents a share of US stock held in custody, distinguishing this from companies issuing native tokens directly on the blockchain. Why Lawyers Should Care: Even those outside of securities law must pay attention to tokenization, as it is poised to impact the documentation and transfer of all real-world assets, including real estate deeds and commercial contracts. Things We Talk About in this Episode Robinhood RWA Policy Paper: Read the policy papers mentioned in the episode regarding Tokenization. Episode Credits Editing and Production: Grant Blackstock Theme Music: Home Base (Instrumental Version) by TA2MI

James Barclay, CEO of Passle, a legal tech innovator, dives into how AI can enhance cross-selling within law firms. He reveals how his firm was born from the early internet boom and evolved to tackle the silo problem. With their new AI-driven tool, CrossPitch, attorneys can easily discover each other’s expertise, solving internal awareness gaps. The discussion also touches on data visualization for managing partners and how effective communication can boost collaboration and significantly reduce lost revenue.

Andrea Muttoni, President of the Story Foundation and former Amazon product manager, shares his journey from music production to blockchain innovation. He discusses the mission of Story Protocol, which aims to simplify intellectual property registration and licensing using blockchain technology. Muttoni introduces the Programmable IP License, ensuring transparent rights for creators, and unveils Poseidon, a marketplace for sourcing IP-cleared data to support AI training. His insights highlight how blockchain can reshape copyright in the AI era, securing fair compensation for creators.