Rory O'Keeffe
Beyond The Fine Print: The Tech Law Podcast
Overworked, under-resourced, juggling complex legal challenges? If this sounds familiar, Beyond The Fine Print is the podcast for you. Managing high-stakes decisions on tight deadlines leads to stress and burnout, and keeping up with what’s coming next in law and the world of tech can feel like a full-time job in itself. Beyond The Fine Print cuts through the noise, delivering digestible insights on legal trends and developments in tech while breaking through the jargon. I’m your host, Rory O’Keeffe and each episode I’ll be bringing you a conversation with a thought leader in the space. This i...
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Rory O'Keeffe
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Podcast website
Latest episode
Jun 18, 2026
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Episodes
A Lawyer’s Guide To Building A Successful Legal Tech Company with Wanne Pemmelaar 18.06.2026 53:39
Some problems seem too boring to solve. Data retention is one of them. And Wanne Pemmelaar noticed this when he was tasked with reading every data protection rule across nearly 100 countries. A task which rapidly drifted away from its budget. In this episode, I'm joined by Wanne Pemmelaar, CEO and Founder of filerskeepers, data protection lawyer, legal tech entrepreneur, and CEO and Co-Founder of...
Will AI Tear Down The Velvet Curtain? The Future Of Law with Stephanie Sylvestre 04.06.2026 55:54
AI is making legal expertise more accessible. The curtain is being pulled back. But if anyone can get answers from a machine, where does that leave the profession? In this episode, I’m joined by Stephanie Sylvestre, Co-Founder of Avatar Buddy, TEDx speaker, Harvard Advanced Leadership Initiative Fellow, and a technology leader with over 30 years of experience spanning Burger King, Subway, HP, and...
You Built the Career… So Why Doesn’t It Feel Right? with The Midlife Mentors 21.05.2026 46:32
If you’re a lawyer somewhere north of 40 and you’ve recently found yourself staring out the window during a Teams call thinking “is this it?”, this episode is for you. On paper, everything looks right. The job. The salary. The postcode. But something feels off. A sense that the version of success you chased for the last couple of decades doesn’t hit the way you thought it would. And let’s not call...
The “Dark 5 Traits”: How Corporate Sociopaths Make It To The Top with Jonathon Grantham 30.04.2026 1:01:07
There are five “dark traits” that so many people working within organisations secretly hold. Some of these traits have no benefit to anyone, others are getting people promoted. In this episode, I’m joined by Jonathon Grantham, Director of Nexoid, author of “Corporate Sociopath Handbook” and long-time observer of corporate behaviour, who has spent decades studying the traits that help certain peopl...
Are We In A Bubble? What Needs To Change In The Legal Profession with Dana Denis-Smith OBE 09.04.2026 52:18
The legal profession can sometimes feel like The Truman Show. Inside the comfort of a bubble with everything in order and running like it always has. That is until someone taps the glass. In this episode, we’re joined by Dana Denis-Smith OBE, founder of Obelisk Support and the Law Society of England & Wales's incoming president for 2027. Dana has spent over 20 years reshaping the legal profess...
What CEOs Really Think About Legal Risk (And How To Communicate It) with Nick Jain 19.03.2026 40:06
Just because something matters to legal, it doesn’t mean it matters to the leadership team. When legal advice reaches the C-suite, it often arrives in the wrong form. Too much detail and not enough focus on what the CEO actually needs to hear. In this episode, I’m joined by Nick Jain, Partner at Eagle Rock and former CEO of IdeaScale (amongst other organisations). Nick is a growth architect and $1...
The Legal Guardrails We Need To Prevent An AI Disaster with Allen Martinez 05.03.2026 48:25
AI isn’t a risk in itself. AI without oversight and guardrails is. And in this episode, we’re cutting through the hype, the panic, and the broken promises that are leading businesses into AI chaos and liability. I’m joined by Allen Martinez, Chief AI Architect/Growth Strategist and Creator of BXAIOS. Allen has had an interesting career path, from directing for Quentin Tarantino’s commercial divisi...
Is The Law Ready For The Impending AI Identity Crisis? With Dina Ovsepian 19.02.2026 50:28
We’re facing an AI identity crisis. Deepfakes are becoming more than just internet pranks and slop content. They’re becoming industrialised deception. And with millions of deepfakes now circulating, and most people being unable to reliably detect them, the line between what’s real and fake is wearing thin. And the law is struggling to keep up with its pace. In this episode, I’m joined by Dina Ovse...
The Biggest Cyber Security Risk And How To Fix It With Robert Siciliano 29.01.2026 49:18
It’s easy to leave cyber security in the hands of the IT department. And to blame the hackers when a breach does happen. But there’s usually a human in the middle of it all. And that’s where the risk usually sits. I know I’ve clicked on things I shouldn’t have before… And that’s why, in this episode, we’re joined by Robert Siciliano - security analyst, author, media voice, and one of the most reco...
Stop Wasting Money on Legal Tech! How to Get Rollouts Right with Merlin Beyts 01.01.2026 52:48
In-house legal teams are constantly under pressure to move fast and adopt AI, but rushing into new tech can be a fast track to wasted time and money. In this episode, we’re joined by Merlin Beyts, Content Director at LegalTechTalk, one of the biggest legal tech conferences around. Merlin sits at the intersection of legal and technology, asking the blunt questions lawyers often avoid. We unpa...
How To Stop Being The “Department of NO” And Earn Trust At The Leadership Table with Dr. Heidi Gardner 18.12.2025 51:03
If you want to move beyond being seen as the department of “no,” this conversation is for you. Most legal teams are fighting a similar battle. They want influence, they want trust, and they want a seat at the strategy table. But siloed cultures and broken communication keep pulling them back. In this episode, we’re joined by Dr. Heidi Gardner, a force in the world of collaboration and leadership....
Every Lawyer Needs To Do THIS. We Cut Contract Cycle Time By 40%! with Sarah Derbyshire 04.12.2025 38:59
Legal departments need to evolve fast, and it’s not just AI that’s applying the pressure. In this episode, we’re joined by Sarah Derbyshire, General Counsel at Baringa. Sarah is a calm and collected, yet fiercely driven legal leader who’s built legal functions from scratch, helped pilot AI effectively, and co-founded a career-shaping network for in-house lawyers. Sarah’s career looks more squiggly...
Inside the Legal Strategy Powering the World’s Boldest Ads 20.11.2025 41:05
You can’t scroll past it, mute it, or ad-block it. Out-of-home advertising is evolving quickly, with head-turning billboards, bus stops and spectacular stunts taking over headlines, as organisations seek to stand out in a crowded marketplace. But the legal questions behind those dazzling digital displays are just as complex as the technology powering them. In this episode, I’m joined by Yvonne Fer...
Are We Training The Lawyers of the Future or Programming Compliance Bots? 06.11.2025 1:00:19
Are we preparing the next generation of lawyers for the world that’s coming, or the one that’s already been and gone? In this episode, we’re joined by Professor Richard Ashcroft, Executive Dean at City Law School, City St George's, University of London, a bioethicist, and former Alan Turing Fellow. Richard has spent his career navigating the crossroads of law, ethics, and technology, and now he’s...
A Lawyer’s Guide To Finding Your Identity & Reinventing Yourself 23.10.2025 44:41
What happens when the job title you’ve built your identity around suddenly disappears? For many lawyers, redundancy (or other kinds of career shifts) can feel like losing a part of yourself. But leadership coach, Daryl Seager, who joins me on this episode tells a different story. Daryl has helped over 2500 leaders across 20 countries reclaim their confidence, clarity and voice. And he brings us a...
How To Build The Right Legal Tech Stack On A Budget with Jon Bartman 09.10.2025 49:41
With thousands of legal tech options on the market (and more popping up every day), deciding what’s right for your in-house legal team can be overwhelming. In-house teams are facing a compliance crunch with AML reforms, AI regulations, ESG mandates and more, and piling on a plethora of platforms to peruse (and finding one that’s within budget), is a mighty task in itself. That’s why, in this episo...
Where AI Fits Into The Legal World - The Risks, Rewards & Opportunities - with Ravi Tandon and Henry Goodwin 25.09.2025 46:14
Over 40% of UK lawyers are already using AI right now, and almost every legal team either has AI in play or is planning for it. And for in-house legal teams that aren’t using AI, the challenge generally isn’t around resistance, it’s time, budgets and knowing where to begin. That’s why in this episode of Beyond The Fine Print, I’m joined by Henry Goodwin, Partner at Leo Capital, and Ravi Tandon, Co...
From Council Estate to Council Chambers: Stephanie Boyce on Equity and AI 11.09.2025 44:00
AI is reshaping the legal world, but if we don’t fix equity first, are we just building systems that repeat the same old biases? In this episode, I sit down with the 177th President of the Law Society of England and Wales and the first person of colour to take on the role. Stephanie Boyce grew up on a council estate in England, then moved to the US, before moving back to the UK to study law. And s...
How Lawyers Can Keep the Human Connection in an AI World - with Patricia Gannon 28.08.2025 37:39
With AI tools moving in to replace all sorts of elements of a lawyer's role, how do we keep real human connection alive? The relationships and trust that make legal work effective are built on making connections. And that’s why we’ve invited Patricia Gannon onto this episode. Patricia is the Founder & CEO at Platforum9, a tech platform that connects legal minds through audio conversations. Pat...
Taming The 5 Beasts of an In-house Lawyer with Tom Fleuriot 14.08.2025 58:59
What do legal operations and a trek through the African savannah have in common? According to our guest in this episode, more than you might think. Legal ops whisperer, Tom Fleuriot, joins us to decode the Five "Beasts" that in-house lawyer must tame in order to thrive in today's complex legal and business environments. Tom is the founder of Flocsam, and brings a huge amount of tactical insi...
What Lawyers Need To Know About Quantum Computing TODAY 31.07.2025 41:52
What comes to mind when you hear the term ‘quantum computing’? A caped crusader defending the multiverse? Or maybe just a really expensive calculator that no one actually understands? If you're not up to scratch on all things quantum - you’d better listen to this episode… Our guest is Rebecca Keating, Barrister at 4 Pump Court and co-author of The Law of Quantum Computing. She unpacks what quantum...
Beyond The Fine Print: START HERE! 10.07.2025 1:01
Overworked, under-resourced, juggling complex legal challenges? If this sounds familiar, Beyond The Fine Print is the podcast for you. Managing high-stakes decisions on tight deadlines leads to stress and burnout, and keeping up with what’s coming next in law and the world of tech can feel like a full-time job in itself. Beyond The Fine Print cuts through the noise, delivering digestible ins...
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