Beyond The Fine Print: The Tech Law Podcast

Rory O'Keeffe

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 is the tech law podcast designed for in-house legal counsel in tech and commercial sectors, bringing you clarity on UK and European regulations, helping you feel more informed, effective and just a bit less stressed. This isn’t a legal seminar. If you want to gain real value without falling asleep, subscribe to Beyond The Fine Print on your favourite podcast platform now. Beyond The Fine Print ® 2024.

  1. 6H AGO

    You Built the Career… So Why Doesn’t It Feel Right? with The Midlife Mentors

    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 it a crisis… In this episode, we’re joined by James and Claire Davis, co-founders of The Midlife Mentors. They’re married, run a business together, host a top 1.5% global podcast, and work with organisations on wellbeing, resilience and performance. Together, they help people navigate what they call “midlife contemplation” - the conversations that high performers often avoid having with themselves. We dive deep into why so many legal professionals feel disconnected from the life they built. If this sounds like you, this conversation will help you begin to think about how to reconnect with who you want to be. Covered in this episode: The “midlife contemplation” and how it affects people.The lie people are often sold about success.Why so many lawyers feel unfulfilled despite having it all on paper.Retraining the “negative first” instinct that we need to build in the legal profession, without losing your edge.Protecting your energy and setting boundaries.How hormonal changes show up in work and life.The dopamine trap and how to avoid it.How to recognise when you’re wearing a mask.Avoiding the self-pity trap that keeps people stuck.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE The Midlife Mentors - https://themidlifementors.com/ The Midlife Mentors podcast - https://themidlifementors.com/podcast-2/ RMOK Legal- https://www.rmoklegal.com/ CONNECT Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    47 min

  2. APR 30

    The “Dark 5 Traits”: How Corporate Sociopaths Make It To The Top with Jonathon Grantham

    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 people rise quickly inside large organisations. Jonathon brings a perspective on what actually gets rewarded behind the scenes and what it means for those trying to operate with integrity. We unpack the dark five traits - narcissism, Machiavellianism, sociopathy, sadism, and spitefulness - and how they show up in leadership and negotiations. We also dive into how to recognise these behaviours and protect your career (and your values). If you’ve ever left a negotiation or meeting feeling like you were played, this conversation will help you understand why. Covered in this episode: The “dark five traits” and how they show up in organisations.Which traits are most dangerous and which can be useful.Why certain behaviours are rewarded in large companies.How to spot manipulation in your contract negotiations.The line between smart leverage and unethical behaviour.The one trait every lawyer needs to develop.How to succeed without losing your integrity.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE Corporate Sociopath Handbook - https://books.google.co.uk/books/about/Corporate_Sociopath_Handbook.html?id=2-c3EQAAQBAJ RMOK Legal- https://www.rmoklegal.com/ CONNECT Jonathon Grantham on LinkedIn - https://www.linkedin.com/in/jonathongrantham/ Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    1h 1m

  3. APR 9

    Are We In A Bubble? What Needs To Change In The Legal Profession with Dana Denis-Smith OBE

    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 profession and she’s not afraid to ask the questions others avoid. We dive deep into whether the legal profession has really changed, or whether it’s just become better at talking about change. We speak about the inequalities that still exist in law and how lawyers are valued in an AI-driven world. If you ever feel like the legal profession is evolving but not fast enough, or not in the right ways, this conversation will challenge how you see its future. Covered in this episode: How the legal profession is trapped within a bubble.Where real progress is happening for women in law and where it isn’t.Whether the profession values its people or just says it does.The shift towards “do we even need a lawyer?” in an AI world.AI hallucinations and the risks appearing in legal work.Why “the future of law is female”.Whether the hourly billing model still makes sense in an AI world.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE Obelisk Support - https://obelisksupport.com/ RMOK Legal - https://www.rmoklegal.com/ CONNECT Dana Denis-Smith OBE on LinkedIn - https://www.linkedin.com/in/ddenissmith/ Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    52 min

  4. MAR 19

    What CEOs Really Think About Legal Risk (And How To Communicate It) with Nick Jain

    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 $100M+ operator who has spent years scaling companies, working directly with leadership teams and seeing first hand how legal advice lands in the laps of leaders. We unpack how CEOs and CFOs triage risk, how lawyers can communicate in numbers and choices rather than legal language and the habits that help legal professionals build credibility with leadership. If you’ve ever wondered how to get your advice heard (not just delivered) this conversation offers a view from the other side of the table. Covered in this episode: How CEOs and CFOs evaluate risk.What executives actually want to hear from legal teams.The categories of legal risk that matter most to leadership.Explaining legal issues without drowning executives in detail.The questions in-house counsel should ask themselves before escalating an issue to the CEO.When a “risk” isn’t actually a risk.Where small risks can grow into major problems.How AI is reshaping white-collar work.And more... If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/ CONNECT Nick Jain on LinkedIn - https://www.linkedin.com/in/nickmjain Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    40 min

  5. MAR 5

    The Legal Guardrails We Need To Prevent An AI Disaster with Allen Martinez

    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 division to helping scale a Shark Tank-funded company to a $300m exit, Allen now designs AI governance frameworks that stop AI systems from improvising their own dialogue and potentially destroying your brand in the process. We separate reality from fantasy when it comes to AI heading into 2026 and discuss how legal teams can build guardrails that protect both business growth and their brand trust. If you want to know how to make AI work for organisations while minimising the risk and legal headaches, this episode is for you (and you don’t need a computer science degree to follow along). Covered in this episode: What’s real about AI in 2026 and what’s pure fantasy.The “plug and play” AI myth leading businesses into chaos.Why AI collisions can be an even bigger risk than hallucinations.What constraints companies should be placing on AI systems.Defending AI-driven decisions in court.Where to start with AI implementation.Why legal teams need to care about brand as much as the marketing department.When AI “time savings” aren’t really savingsAnd more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE BXAIOD - https://bxaios.com/workflow-finder RMOK Legal- https://www.rmoklegal.com/ CONNECT Allen Martinez - https://www.linkedin.com/in/allenmartinez/ Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    48 min

  6. FEB 19

    Is The Law Ready For The Impending AI Identity Crisis? With Dina Ovsepian

    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 Ovsepian, Senior Associate at Gavrilov & Brooks and a leading business litigator working on deepfake cases in Los Angeles. Dina is helping clients protect their likeness and their careers. We unpack how deepfakes have evolved and the risks that they now pose, not just to celebrities, but to just about anyone. We take a look at the real-world harm already happening, and the legal landscape across the US, UK, and EU. This conversation explores what lawyers and in-house legal teams need to do to prepare for these challenges in 2026 and beyond. Covered in this episode: The explosion of deepfakes in recent years.Why modern deepfakes are more dangerous.How scammers are using deepfakes in new ways which you might never expect.The legal protections under review and the gaps that still exist.Can the law keep up with AI’s rapid expansion?What lawyers and in-house teams must prepare for in 2026.Finding opportunity inside the emerging AI risks.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/ CONNECT Dina Ovsepian - https://www.linkedin.com/in/dina-ovsepian-b8b7134a/ Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    50 min

  7. JAN 29

    The Biggest Cyber Security Risk And How To Fix It With Robert Siciliano

    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 recognisable educators in personal and corporate cyber security protection. Robert has appeared on CNN, MSNBC, Fox News, CNBC, The Today Show, and is quoted in outlets like USA Today and Forbes. He also delivers security awareness training to organisations to help them to get their people to care about security. We explore why typical workplace security training often fails, how to build what Robert calls a “strategic human firewall” and how to move employees from reluctant compliance to personal investment. If you want to protect your own and build a culture that protects the people who you work with and your operations, this episode is essential. Covered in this episode: The biggest risk to cyber security.Why most cyber security training doesn’t stick.What needs to change to get employees to care about cyber security.The risks AI introduces to organisational security.Why companies resist investing in security training.The one security habit everyone needs.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE RMOK Legal- https://www.rmoklegal.com/ CONNECT Robert Siciliano on LinkedIn - https://www.linkedin.com/in/robertsiciliano/ Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    49 min

  8. JAN 1

    Stop Wasting Money on Legal Tech! How to Get Rollouts Right with Merlin Beyts

    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 unpack the real reason why so many digital transformations fail, and how to ensure your tech implementations aren’t a wasted endeavour. Merlin uncovers the hidden signals that a team isn’t ready for more tech and the specific questions every legal leader should ask before rolling out AI. If you're about to pull the trigger on another tool, listen to this first - it might just save you a lot of time and money. Covered in this episode: How to avoid ‘shiny object syndrome’.When not to implement new tech.What sets successful tech rollouts apart from the flops.How to actually get ROI from a digital transformation.Why in-house teams experience buyers’ remorse after implementing tech solutions.The questions legal teams must answer before adopting AI.The truth about whether AI is coming for legal jobs.And more… If you got value from this episode of Beyond The Fine Print, subscribe on your favourite podcast platform so you don’t miss the next one. LEARN MORE LegalTechTalk - https://www.legaltech-talk.com/  RMOK Legal- https://www.rmoklegal.com/  CONNECT Merlin Beyts on LinkedIn - https://www.linkedin.com/in/merlin-beyts-652ab0168/  Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/  LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35  Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926  YouTube - https://www.youtube.com/@BeyondTheFinePrint/

    53 min
See All (20)

Trailer

Ratings & Reviews

About

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 is the tech law podcast designed for in-house legal counsel in tech and commercial sectors, bringing you clarity on UK and European regulations, helping you feel more informed, effective and just a bit less stressed. This isn’t a legal seminar. If you want to gain real value without falling asleep, subscribe to Beyond The Fine Print on your favourite podcast platform now. Beyond The Fine Print ® 2024.

Information

You Might Also Like