Beyond The Fine Print: The Tech Law Podcast

Rory O'Keeffe
  • 5.0 (1)
  • BUSINESS
  • UPDATED BIWEEKLY

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. 3D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 12/18/2025

    How To Stop Being The “Department of NO” And Earn Trust At The Leadership Table with Dr. Heidi Gardner

    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. Heidi is a Distinguished Fellow at Harvard Law School and CEO of research/advisory firm, Gardner & Co. Heidi also has had two Washington Post best sellers, just to name a few things that make this conversation not to be missed… When it comes to understanding how professionals can stop tripping over silos and start working smarter, together, Heidi is the real deal. So if you want to step into the role of strategic collaborator, who shapes the direction of the business, don’t miss this episode. Covered in this episode: How in-house lawyers can flip the narrative and become growth enablers.The causes behind mistrust between legal departments and the rest of the business.Turning “no” into a tool for alignment rather than friction.Communicating legal advice in a way that influences decisions.Translating legal risks into strategic value.Building trust across departments.Future-proofing legal teams.The surprising way AI can strengthen collaboration inside legal teams.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 Dr. Heidi Gardner on LinkedIn - https://www.linkedin.com/in/heidi-k-gardner-ab5b825  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/

    51 min

  7. 12/04/2025

    Every Lawyer Needs To Do THIS. We Cut Contract Cycle Time By 40%! with Sarah Derbyshire

    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 than a game of snakes and ladders, and that’s part of what makes her so effective. We dig deep into how Sarah was able to cut contract cycle time by 40% in her first year at Baringa, the approach she uses to turn resistance into applause, and the key to implementing change without causing chaos. This is for anyone working within a legal department who wants to have more of an impact and keep up, without burning out. Covered in this episode: How Sarah reduced contract cycle time at Baringa by 40%.How to implement change in a way that creates minimum chaos.The one thing every lawyer needs to do with regards to AI.Understanding needs vs wants with AI.The benefits of a squiggly career.How Sarah went from hating networking to co-founding a thriving network.What makes a leader in modern legal teams?Why compliance isn’t only legal’s responsibility.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 Sarah Derbyshire on LinkedIn - https://www.linkedin.com/in/sarah-derbyshire-aa4a5684/  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/

    39 min

  8. 11/20/2025

    Inside the Legal Strategy Powering the World’s Boldest Ads

    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 Fern, General Counsel at Talon, who’s steering legal strategy in one of the most dynamic corners of advertising. With experience at BBC and Deutsche Telekom, Yvonne brings a sharp legal and commercial lens to everything from AI liability to ESG compliance. For in-house lawyers, this conversation is packed with insight on balancing priorities, building boundaries and keeping pace with a rapidly changing industry. Covered in this episode: The legal and ethical challenges in ad tech and out-of-home advertising.Navigating AI liability.The rise of ESG compliance and how critical it will become.Setting boundaries as an in-house lawyer.The secret to smoother negotiations.Is AI a legal lifeline or a liability?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 Yvonne Fern - https://www.linkedin.com/in/yfern/  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/

    41 min
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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.

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