How this ex GC's frustration with legal software turned into a startup

How this ex GC's frustration with legal software turned into a startup

Guest: Brent FareseRole: CEO and Co-Founder, AlineWebsite: aline.co This episode is brought to you by Aline. Try Aline’s trusted and verified legal AI today for free. [https://www.aline.co/legal-ai] I spoke with Brent Farese, CEO and co-founder of Aline, an agentic legal AI platform built exclusively for in-house teams. Brent trained as an IP attorney with a mechanical engineering and computer science background, then worked as Assistant General Counsel one of the world’s leading enterprise blockchain companies. We discussed: → The three tiers of document search (keyword, semantic, agentic) and why getting this right is the hard engineering problem nobody talks about→ Why legal AI is roughly two years behind agentic coding — and what infrastructure still needs to be built before it catches up→ Why frontier model providers entering legal is actually a tailwind for specialist platforms→Why making legal work cheaper and faster is likely to produce more legal work, not less→ Why “building the GitHub for law”, with proper version control, is needed in 2026. I hope you enjoy listening just as much as I did recording it. Want to feature in the next Best Practice podcast? Email george@georgehannah.com [george@georgehannah.com] This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit bestpracticeai.substack.com [https://bestpracticeai.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Is owning the data still the moat in Legal AI? Sean Fitzpatrick, CEO of LexisNexis Legal

Is owning the data still the moat in legal AI?I spoke to Sean Fitzpatrick, a senior leader at LexisNexis - one of the largest legal AI companies in the world.Sean Fitzpatrick is CEO of the Global Legal Business at LexisNexis. He has been there for 21 years, growing up through the shifts from digital to cloud to AI, after starting out as a consultant at McKinsey.We discussed:→ Whether 200 billion proprietary documents are still a defining asset - or whether the nature of the moat has changed.→ Why "probably right" is the standard for frontier models, and why that standard fails in law.→ How their partnership with Harvey actually works.→ Sean's thoughts on hallucinations in legal AI.→ What happens to the junior lawyer apprenticeship model when the grunt work that builds judgment disappears.Sean has watched every major technology shift in legal over two decades, and makes the case for why content plus technology is far harder to displace than either alone. It was an honour to speak to Sean, and I hope you take something useful away from this. Know someone, or want to feature on the Best Practise Podcast? Email george@georgehannah.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit bestpracticeai.substack.com [https://bestpracticeai.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Andrew Thompson on What Legal AI Can Learn From Software Engineering

Guest: Andrew Thompson Role: CTO, Orbital LinkedIn: https://www.linkedin.com/in/andrewmatthewthompson/ [https://www.linkedin.com/in/andrewmatthewthompson/] Website: www.orbital.tech [http://www.orbital.tech] (company) | www.andrewthompson.co [http://www.andrewthompson.co] (personal blog) This AI platform powered over 200,000 property transactions last year and raised $60M in January to expand even further. I spoke with Andrew Thompson, CTO at Orbital. Andrew previously built the Caffè Nero app, ran product and tech at Appear Here, founded his own AI company, and now leads engineering, product and a team of in-house real estate lawyers at Orbital. We discussed: → How Orbital mix both generalist LLM’s and their own classical ML into one product. → Why legal is roughly 12-18 months behind software engineering, and how to use that lag. → What “ship early and often” actually looks like inside a regulated industry. → Andrew’s tips and advice for Andrew is an absolute genius in everything LLM’s and how to make the most of it in the physical space around us. I really hope you take away something useful from this. Want to feature in the Best Practice podcast? Email george@georgehannah.com [george@georgehannah.com] Sources mentioned in the episode: * Orbital’s $60M Series B (Jan 2026, led by Brighton Park Capital): https://tech.orbitalwitness.com/posts/2026-01-23-series-b-announcement/ [https://tech.orbitalwitness.com/posts/2026-01-23-series-b-announcement/] * Caffè Nero (Andrew’s previous build): https://caffenero.com * Appear Here (Andrew’s previous build): https://www.appearhere.co.uk * Seedcamp (where Andrew was a startup mentor): https://seedcamp.com * ElevenLabs (referenced re: agentic insurance): https://elevenlabs.io * Legalweek New York 2026 (referenced throughout) * McKinsey research on automatable legal work (referenced) * OpenAI ChatGPT and GPT-4 (referenced as the inflection point) * Anthropic Claude (referenced) * Google BERT and T5 (Orbital’s pre-LLM stack) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit bestpracticeai.substack.com [https://bestpracticeai.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Meet The Startup Building AI For The Messiest Part of Law

“Crack the chronology, crack the case.” That’s what Gregory Mostyn‘s [https://www.linkedin.com/in/gregory-mostyn-9b3a89b8/] father - a barrister, then judge for 42 years - was told on his first day in chambers. Decades later, it’s the founding insight behind Wexler. I spoke with Gregory Mostyn, co-founder and CEO of Wexler, the fact intelligence platform now used by huge massive circle firms in their litigation teams. Greg isn’t a lawyer. He grew up watching his father - who handled some of the highest-profile family cases in England - come home with ten ring binders to read before court the next morning. That image, plus a stint at Entrepreneur First, became Wexler. The company has 20x’d ARR since pre-seed and just raised $5.3m led by Pear VC. We discussed: → Why Wexler went deep on litigation when every other legal AI startup was going broad → The “verification tax” and where fully agentic legal AI actually breaks down → Why consumption pricing beats per-seat for litigation work (and how they structure it) → How his 67-year-old father is now vibe-coding apps for his tennis club → What it takes to close a Big Law deal in a week I absolutely loved recording this episode and I hope you enjoy listening to it just as much as I did. Know someone that might want to come on the Best Practice Podcast? Email me at george@georgehannah.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit bestpracticeai.substack.com [https://bestpracticeai.substack.com?utm_medium=podcast&utm_campaign=CTA_1]

Meet the Startup Building the Matter Management Layer Legal AI Forgot About

I keep hearing about legal AI tools that do the work better. What I haven’t heard, until now, is anyone building the tool that remembers what the work is actually for. In this episode I chat with Dillon Hirandiran, founder and CEO of Counsel (gc.inc) Dillon previously worked in investment banking, then built his first startup during Covid. The experience of navigating legal work as a founder - seed rounds, Delaware flips, cap tables - is what first drew him to the problem Counsel is now solving. Counsel is an autonomous matter management system for law firms - reading every email, every message, and maintaining a persistent context layer across everything a firm has going on. We discussed: → Why the hardest problem in legal AI has never really been document generation, but instead it’s CONTEXT retention across matters. → Why clients can’t always evaluate the quality of legal work, only its responsiveness → What a “10x attorney” actually looks like when AI handles the document layer, and why being a workhorse is the worst thing a junior lawyer can be right now → Why the biggest risk to Big Law isn’t pricing pressure from in-house or AI, but is actually their own talent leaving. Want to sponsor or feature on the Best Practice Podcast? Email george@georgehannah.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit bestpracticeai.substack.com [https://bestpracticeai.substack.com?utm_medium=podcast&utm_campaign=CTA_1]