Beyond The Fine Print: The Tech Law Podcast

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/ [https://themidlifementors.com/] The Midlife Mentors podcast - https://themidlifementors.com/podcast-2/ [https://themidlifementors.com/podcast-2/] RMOK Legal- https://www.rmoklegal.com/ [https://www.rmoklegal.com/] CONNECT Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ [https://www.linkedin.com/in/roryokeeffe/] LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 [https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35] Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 [https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926] YouTube - https://www.youtube.com/@BeyondTheFinePrint/ [https://www.youtube.com/@BeyondTheFinePrint/]

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 [https://books.google.co.uk/books/about/Corporate_Sociopath_Handbook.html?id=2-c3EQAAQBAJ] RMOK Legal- https://www.rmoklegal.com/ [https://www.rmoklegal.com/] CONNECT Jonathon Grantham on LinkedIn - https://www.linkedin.com/in/jonathongrantham/ [https://www.linkedin.com/in/jonathongrantham/] Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ [https://www.linkedin.com/in/roryokeeffe/] LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 [https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35] Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 [https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926] YouTube - https://www.youtube.com/@BeyondTheFinePrint/ [https://www.youtube.com/@BeyondTheFinePrint/]

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/ [https://obelisksupport.com/] RMOK Legal - https://www.rmoklegal.com/ [https://www.rmoklegal.com/] CONNECT Dana Denis-Smith OBE on LinkedIn - https://www.linkedin.com/in/ddenissmith/ [https://www.linkedin.com/in/ddenissmith/] Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ [https://www.linkedin.com/in/roryokeeffe/] LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 [https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35] Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 [https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926] YouTube - https://www.youtube.com/@BeyondTheFinePrint/ [https://www.youtube.com/@BeyondTheFinePrint/]

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: 1. How CEOs and CFOs evaluate risk. 2. What executives actually want to hear from legal teams. 3. The categories of legal risk that matter most to leadership. 4. Explaining legal issues without drowning executives in detail. 5. The questions in-house counsel should ask themselves before escalating an issue to the CEO. 6. When a “risk” isn’t actually a risk. 7. Where small risks can grow into major problems. 8. How AI is reshaping white-collar work. 9. 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/ [https://www.rmoklegal.com/] CONNECT Nick Jain on LinkedIn - https://www.linkedin.com/in/nickmjain [https://www.linkedin.com/in/nickmjain] Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ [https://www.linkedin.com/in/roryokeeffe/] LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 [https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35] Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 [https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926] YouTube - https://www.youtube.com/@BeyondTheFinePrint/ [https://www.youtube.com/@BeyondTheFinePrint/]

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: 1. What’s real about AI in 2026 and what’s pure fantasy. 2. The “plug and play” AI myth leading businesses into chaos. 3. Why AI collisions can be an even bigger risk than hallucinations. 4. What constraints companies should be placing on AI systems. 5. Defending AI-driven decisions in court. 6. Where to start with AI implementation. 7. Why legal teams need to care about brand as much as the marketing department. 8. When AI “time savings” aren’t really savings 9. 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 BXAIOD - https://bxaios.com/workflow-finder [https://bxaios.com/workflow-finder] RMOK Legal- https://www.rmoklegal.com/ [https://www.rmoklegal.com/] CONNECT Allen Martinez - https://www.linkedin.com/in/allenmartinez/ [https://www.linkedin.com/in/allenmartinez/] Rory O’Keeffe on LinkedIn - https://www.linkedin.com/in/roryokeeffe/ [https://www.linkedin.com/in/roryokeeffe/] LISTEN Spotify - https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35 [https://open.spotify.com/show/1gIj9v3yCsj5XNBbrS0byC?si=90ced509f70b4a35] Apple Podcasts - https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926 [https://podcasts.apple.com/us/podcast/beyond-the-fine-print/id1826498926] YouTube - https://www.youtube.com/@BeyondTheFinePrint/ [https://www.youtube.com/@BeyondTheFinePrint/]