AI – Legally Speaking Podcast

Season 10

From Tinder to Legal AI: How Ruben Miessen’s LEGALFLY Reinvents In-House Legal Teams – S10E31

On today’s Legally Speaking Podcast, I am delighted to be joined by Ruben Miessen. Ruben is the CEO and Co-Founder of LEGALFLY, a European enterprise legal AI company, building a secure, governed legal operating system for in-house teams in regulated industries. Before founding LEGALFLY, Ruben worked as a senior product manager at Tinder, where he led initiatives and built a team that would later become the founding team behind LEGALFLY. With his co-founders, Ruben identified how legal bottlenecks could

August 10, 2026

Blog

Stop Asking If Legal AI Is Accurate. Start Asking If It’s Reproducible.

Run the same contract through the same AI system 20 times. Should a lawyer expect the same legal findings 20 times? In a reproducibility stress test from my research published at ICCS 2026, 15 documents were each analyzed 20 times. The pure large-language-model baseline produced an average of 18.3 distinct output sets per document across those 20 identical re-runs. The deterministic hybrid architecture produced one. That gap points to a question legal teams should be asking AI vendors far more

August 8, 2026

Season 10

How Olliers Solicitors Quadrupled Turnover by Rethinking Criminal Law – Matthew Claughton – S10E30

On today’s Legally Speaking Podcast, I am delighted to be joined by Matthew Claughton. Matthew is the Managing Director of Olliers Solicitors, one of the UK’s leading criminal defence firms. Since taking full control of the business in 2018, he has helped steer Olliers through a major period of growth, quadrupling turnover, strengthening its reputation in privately funded criminal defence, and building a firm widely recognised for its expertise in pre-charge engagement, serious crime, fraud, regulatory work and crisis

August 3, 2026

Season 10

Premier League to Legal Pioneer: How Neil Heaney Turned a Legal Disaster into a Global Goal – S10E29

On today’s Legally Speaking Podcast, I am delighted to be joined by Neil Heaney. Neil is the CEO and founder of Judicare Law International, a specialist UK law firm focused on international legal matters. He founded the business after being frustrated by the quality of legal advice he received when he himself purchased property abroad. Today, Judicare handles matters across Europe, Asia, Africa and the Middle East. Before building Judicare, Neil was also a professional footballer, coming through Arsenal

July 27, 2026

Season 10

Skill Over Salary | Fighting Bullies: The Case for a Career in Plaintiffs’ Law – Bill Reid – S10E28

On today’s Legally Speaking Podcast, I am delighted to be joined by Bill Reid. Bill is the senior founding partner of Reid Collins, a former federal prosecutor, a two-time Benchmark Litigation U.S. Plaintiff Litigator of the Year, an adjunct professor atthe University of Texas School of Law, and the author of Fighting Bullies: The Case for a Career in Plaintiffs’ Law. Over the course of his career, he has prosecuted precedent-setting cases and recovered billions of dollars in complex

July 20, 2026

Season 10

Patrick McCann: Authentic Leadership, Social Mobility & Building the Law Firm of the Future – S10E27

On today’s Legally Speaking Podcast, I am delighted to be joined by Patrick McCann. Patrick is the Chief Executive of the City of London Law Society, representing more than 21,000 solicitors and some of the largest law firms in the world. With more than 30 years of experience across legal practice, learning, development and talent strategy, Patrick has become one of the most influential voices shaping the legal profession. Before joining the London Law Society, Patrick served as the

July 13, 2026

Season 10

CILEX to New York Bar: How InHouseW’s Madeleine Weber is Helping Law Students Pass the SQE – S10E26

On today’s Legally Speaking Podcast, I am delighted to be joined by Madeleine Weber. Madeleine is Senior Counsel, EMEA at Sitetracker. She has had an unconventional route into the legal profession, studying-CILEx, New York Bar, QLTS and SQE2. Madeleine also runs inhousew, an education platform helping aspiring solicitors prepare for SQE2 through different resources. She is committed to supporting the next generation of solicitors, having helped 2,000 students over the past 3 years. So why should you be

July 6, 2026

Season 10

Winning Cases with Wexler AI: Gregory Mostyn on Why The Future of Litigation Starts Here – S10E25

On today’s Legally Speaking Podcast, I am delighted to be joined by Gregory Mostyn. Gregory is the Co-Founder and CEO of Wexler. Wexler offers advanced AI-driven solutions for eDiscovery, document review and litigation services. With clients including Clifford Chance, Herbert Smith Freehills Kramer and Burges Salmon, Wexler is ‘on a mission to solve the most complex cases. So why should you be listening in? You can hear Rob and Gregory discussing: – Marketing Yourself In Every Possible Situation

June 29, 2026

Season 10

You Never Know Where Clients Will Find You: How Colleen Joyce Pioneered Lawyer.com – S10E24

On today’s Legally Speaking Podcast, I am delighted to be joined by Colleen Joyce. Colleen is the CEO of Lawyer.com. She has experience hosting marketing courses for lawyers and helping launch new products. Colleen started her entrepreneurial journey at Popstar.com, a trusted celebrity online resource. Colleen is also the Founder of the Lawyer Growth Summit. So why should you be listening in? You can hear Rob and Colleen discussing: – Community drives growth – Visibility matters more than

June 22, 2026

Season 10

Laurence Lieberman on Legal Careers, Music & Why Lawyers Should Be More Human – S10E23

On today’s Legally Speaking Podcast, I am delighted to be joined by Laurence Lieberman. Laurence is a Partner in the London office of Pillsbury, where he specialises in complex, high-value and often cross-border business disputes, resolved through court litigation and international arbitration. He has more than 25 years of experience, with deep expertise across technology, life sciences and financial services, as well as longstanding work connected to India and Israel. Alongside all of that, Laurence also has a creative

June 15, 2026