Beyond The Fine Print: The Tech Law Podcast

A Lawyer’s Guide To Building A Successful Legal Tech Company with Wanne Pemmelaar

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 Lawstronaut. What started as a legal challenge for Wanne, has now grown into a company that serves more than 3000 organisations worldwide, by ensuring they’re up to date with the latest data retention rules. But this conversation isn't all about retention schedules. It's about spotting opportunities where everyone else sees admin. It's about building trust in legal tech and understanding why some legal tech products succeed while others fail. And it’s about the lessons Wanne learned turning a spreadsheet and an idea into a global legal tech business. Covered in this episode: * Uncovering the legal challenges that are ripe for a more substantial solution. * Why data retention is far more important than most organisations realise. * The three biggest retention problems companies face. * How Wanne built trust in a platform covering jurisdictions worldwide. * The journey from lawyer to legal tech founder. * Why some legal tech products succeed while others fail. * How AI is doing what GDPR was supposed to do. * Lessons for lawyers considering entrepreneurship. * 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 filerskeepers - https://www.filerskeepers.co/ [https://www.filerskeepers.co/] RMOK Legal - https://www.rmoklegal.com/ [https://www.rmoklegal.com/] CONNECT Wanne Pemmelaar on LinkedIn - https://www.linkedin.com/in/wannepemmelaar/ [https://www.linkedin.com/in/wannepemmelaar/] 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/]

Will AI Tear Down The Velvet Curtain? The Future Of Law with Stephanie Sylvestre

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 The Children's Trust. Stephanie is now helping organisations build AI-powered digital twins and responsible AI systems designed to make legal expertise available not just to those who already have everything. As someone outside the legal profession, Stephanie brings a fresh perspective to some of the biggest questions facing lawyers today. We explore how AI is changing legal work, where the opportunities lie and who the future belongs to in the legal profession. Whether you're excited by AI, sceptical of it or simply trying to work out what’s worth paying attention to and what’s not, this episode is for you. Covered in this episode: * How AI is changing the legal profession and what remains uniquely human. * Why AI is removing traditional barriers to legal knowledge. * The difference between bespoke AI solutions and generic LLMs. * How much trust lawyers should place in AI-generated responses. * What responsible AI actually looks like in practice. * The opportunities and risks presented by agentic AI. * Who is accountable when an AI system gets something wrong. * How digital twins are being used in professional services. * How AI affects legal pricing models. * When organisations should avoid implementing agentic AI. * The future role of lawyers in an AI world. 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 Avatar Buddy - https://avatarbuddy.co/ [https://avatarbuddy.co/] RMOK Legal- https://www.rmoklegal.com/ [https://www.rmoklegal.com/] CONNECT Stephanie Sylvestre on LinkedIn - https://www.linkedin.com/in/stephanie-a-sylvestre/ [https://www.linkedin.com/in/stephanie-a-sylvestre/] 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/]

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/]