Rule-Breakers

Edd Wilder-James joins us in this episode for a wide-ranging conversation that begins in the early XML and SGML communities and stretches all the way to today’s AI-driven world. Along the way, we revisit the rise of pivotal standards such as DocBook, HTML and DITA. Edd and Sean discuss the unique culture of the structured document markup conferences that brought together technologists, publishers, academics, and information architects from radically different disciplines ranging from hi-tech engineering to the liberal arts.

Edd reflects on the optimism and intellectual energy of that era, including debates around standards, schemas, hypermedia, and the Semantic Web, while also acknowledging some of the orthodoxy and “tech tribalism” that shaped those communities. The discussion explores how ideas from SGML, HyTime, RDF, and structured publishing continue to resurface in modern systems, often under different names.

The conversation also looks at the Big Data (Hadoop) era in the formative years of cloud computing, the evolution of open-source ecosystems at Google and Microsoft including his current work at GitHub around Copilot and large-scale agentic AI systems.

Throughout the episode, Edd offers a thoughtful perspective on recurring patterns in computing: the tension between elegant models and practical systems, the repeated reinvention of timeless old ideas, and the enduring importance of context when interpreting information.

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.

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.

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.

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.

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.

The latest episode of Rule-Breakers features Liam Quin a pioneering figure in the world of electronic publishing and generalized markup. In this conversation, we learn about Liam’s journey from a childhood fascination with typesetting that started with the fonts used in his copy of The Lord of the Rings, to a lifelong passion for digital documents that included working at the W3C on the XML standard.
Liam and Sean explore the early days of structured content, the massive buzz that surrounded the emergence of the Web, the early Mosaic web browser, the world’s first HTML editor (HoTMetaL) and much more.

Join Rule-breakers host, Sean McGrath and our latest guest, Anthony Coates, for a deep dive into the history and necessity of structured content. Drawing on his experience at Reuters and his work on major financial standards such as FPML, Tony recounts the various factors that allowed XML to break out and become successful, how FPML played a role in encouraging XML tool vendors to fully support W3C XML Schema language standard. In this wide ranging episode, other topics include Tony's thoughts on literate programming and vibe coding for AI.

Ever wonder how websites and apps are built to look organized and work the way they do? 
In the latest episode of Rule-breakers, Sean talks to James Clark, a true pioneer who helped create the hidden rules and structure that make the modern web possible. James talks about his incredible journey from the early days of computers and typesetting to becoming a central figure in shaping foundational technologies like XML. 
He shares how he helped simplify complex coding languages to create a common 'blueprint' that everyone could use, influencing everything from how you browse articles to how data is shared across the internet. This is the story of a quiet innovator, whose work laid the groundwork for the web's biggest breakthroughs — even those you don't see. 

Sean talks to Tim Bray, a true pioneer in the world of digital documents and computing. Tim talks about his early work, including the groundbreaking Oxford English Dictionary (OED) project at the University of Waterloo. Tim went on to co-create the foundational XML standard that powers so much of the web today. Exploring the surprising prevalence of XML in places like WhatsApp, Tim offers his perspective on the growing importance of Markdown in an AI-driven world and its bright future for entry-level text styling.