Rule-Breakers

Ep #14: Information Architecture and Structured Documents in an AI world

In this episode, Sean McGrath sits down with Alex Smith, Global Product Lead for Knowledge, Search, and AI at iManage, to unpack what’s really happening at the intersection of AI and the world of legal practice. With a career spanning nearly two decades at LexisNexis, leading innovation at Reed Smith, and now shaping AI-driven knowledge systems at iManage, Alex brings a rare, perspective on how legal information actually works, and why many people misunderstand it. Sean and Alex explore the evolution of digital information from CD-ROM publishing to today’s AI-powered knowledge management systems, the enduring importance of structured data, and why “IA before AI” – Information Architecture before Artificial Intelligence - might be the most important consideration for anyone building legal knowledge management systems with modern AI tools. Along the way, they tackle hallucinations, trust in citations, knowledge graphs, and the gap between what today’s AI can realistically generate and what legal professionals can safely rely on being accurate. This is a deep dive into the infrastructure behind legal knowledge—and why the future of AI in the world of law depends less on better and better AI LLMs models, and more on the quality of the information we feed to these models.

Ep #13: Identity, security and privacy - with digital identity pioneer, Eve Maler

In this episode of Rule Breakers, Sean McGrath sits down with Eve Maler, a pioneer in digital identity and a long standing member of the XML community who was influential in shaping XML itself, based on her expertise in its predecessor SGML. Eve has accumulated decades of experience shaping the digital identity landscape, from her role in developing the XML-based SAML (Security Assertion Markup Language)  to today’s User Managed Access (UMA) OAuth extensions. Eve shares insights into why authorization—not identity—is now the frontier of innovation, and how emerging models empower users to define and manage access to their own data online. This episode is both a historical journey and glimpse into the frontier of digital identity where traditional person/role-centric authentication/authorisation meets fast moving world of autonomous Agentic AI.

Ep #12: From SGML (1986) to LLMs (2026): Jon Udell on The Tools That Make Digital Knowledge Work

In this episode of Rule Breakers, we’re joined by author and software developer Jon Udell, a longtime explorer of the tools that shape how we write, publish, and work with knowledge. From the early days of SGML and semi-structured content to the modern web and today’s AI-powered knowledge management workflows, Jon shares a sweeping perspective over the  last forty years of knowledge management innovations.

Ep #11: XML, HCI, and a retrospective on markup and the Web with Steven Pemberton

In this episode, we speak with Steven Pemberton, a pioneer of the early web, the first user in Europe to connect to the open internet, and a long-time contributor to standards at the W3C including CSS and XHTML. He also worked on the ABC programming language that heavily influenced Python. Steven traces the origins of the web from Tim Berners-Lee’s original vision of a connected information system to the standards that followed, reflecting on how ease of use is sometimes in tension with ease of implementation. Steven talks about one of his recent projects - Invisible XML – which rethinks markup from a schema inference perspective. Steven also talks about HTML5 and framework-driven web design application design.

Ep #10: Markup Goes Beyond Tags: Rick Jelliffe on Language Markup, Structure & Semantics in XML

Dive into an in-depth conversation with Rick Jelliffe, one of the most influential figures in the world of markup languages and structured data. Rick's contributions to markup and markup standards span from SGML in the 1980s, XML in the Nineties, up to the present day. He brought his extensive expertise in character encoding to the work on the XML standard.  This was a pivotal feature of XML, ensuring that multilingualism was baked right into the XML standard itself taking advantage of the Unicode standard. He is perhaps best known as the inventor of the Schematron XML validation language, ingeniously utilizing XPaths to greatly extend what structures/constraints can be automatically validated in XML documents.