RAG is Not Dead: Josef's Sam Flynn on Legal Tech That Works

This week, we sit down with Sam Flynn, COO and co-founder of Josef, to separate substance from hype in the rapidly evolving world of legal tech. Sam shares his passionate stance that “RAG is not dead,” defending Retrieval-Augmented Generation (RAG) as a foundational and still deeply relevant method for deploying AI in the legal industry—despite the flashy allure of agentic AI. His nuanced take reminds listeners that success in this space depends not only on the sophistication of the technology, but on doing the “boring” foundational work: ensuring data integrity, context-aware chunking, and responsible workflows.

Throughout the discussion, Sam champions the idea that great legal technology should not just enhance expert workflows but make legal information accessible to non-experts. With examples from Josef’s clients like L’Oréal, Bumble, and Bupa, Sam illustrates how Josef’s tools allow legal departments to offload routine work through reliable self-service systems—freeing up time for more strategic thinking while improving speed, compliance, and consistency across organizations. He makes the case that empowering end users with trustworthy tools isn’t just good tech—it’s a new model for scaling legal and compliance services.

A key highlight is Josef’s Roxanne project, developed in collaboration with Housing Court Answers and NYU. Roxanne is an AI-powered tool designed to help tenants in New York navigate the complexities of housing law. Sam outlines the safeguards that ensure Roxanne’s answers are accurate and compliant, such as closed-domain data sources, human-in-the-loop validation, and smart escalation workflows. The conversation touches on the broader access to justice (A2J) implications of this technology—arguing that when designed carefully, AI can amplify the reach and impact of legal aid organizations by orders of magnitude.

The episode doesn’t shy away from the tensions legal professionals feel when automation enters their domain. Sam offers a powerful reframing: instead of seeing these tools as a threat, lawyers should view them as opportunities to offload low-value tasks and expand their influence. The goal, he says, is not to cut jobs—but to redefine the kind of work legal professionals do, making space for more proactive, strategic, and meaningful engagements within organizations and communities.

As the conversation wraps, Sam shares his optimism about the future—tempered by a clear-eyed understanding of the human factors that will determine success. While the technology is ready, the question is whether legal professionals will step up and take the lead. His call to action is clear: focus less on the hype, and more on the systems, safety, and trust that make tech transformative. Whether you're a legal technologist, innovator, or cautious observer, this episode offers a grounded and inspiring look at what it takes to build legal tech that actually works.

Listen on mobile platforms:  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Apple Podcasts⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ |  ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Spotify⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ | ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠YouTube⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠

Special Thanks to