Aditya Shivkumar on Why Legal AI Needs Empathy

Matt Basile on why Customers love AI Native Law Firms. The age of Legal AI is here.

Salvador Carranza sits down with Matthew Basile, founder and CEO of Naya Software and Naya Law, to unpack what an AI-native law firm actually looks like when a real estate lawyer builds one himself. They get into why selling legal AI tools to law firms has failed for a decade, why Naya pivoted to sell outcomes directly to mortgage lenders, and what a Management Services Organization model unlocks when a firm stops protecting the billable hour. Matt lays out exactly how a curious builder becomes a legal AI expert in 2026: not by reading, but by trying. Watch the full conversation for the playbook on full-stack AI law firms from someone shipping them today. CHAPTERS 00:00 Introduction to Matt Basile's Journey03:32 Parenting and Entrepreneurial Mindset06:19 The Importance of Travel in Shaping Perspectives10:10 Transitioning from Software to Law13:58 Navigating Change in the Legal Industry18:12 Embracing Iteration and Learning from Failure22:05 Building Naya: A Solution for Legal Challenges27:49 The Shift to Full Stack Law Firms32:13 Navigating Competition in Legal Tech36:17 Curiosity and Learning in Legal Practice42:15 Understanding Naya's Role in Legal Tech46:18 Future Strategies for Naya and Legal Partnerships Takeaways * The only way to get good at legal AI is to stop reading and start trying. Curiosity and iteration beat credentials. * LLMs are a programming language inside a software stack, not a feature you paste on top of a legacy workflow. * Selling AI tools to law firms failed for a decade because clients buy outcomes, not productivity gains. * Naya pivoted from selling to lawyers to selling to the mortgage lenders who actually stand to benefit from faster closings. * The Management Services Organization model lets an AI-native firm scale legal capacity without traditional partnership drag. * Clients are ready to cannibalize the billable hour; most partners five years from retirement are not. * The right hire for a tech-first law firm is a builder who wants to sell the new model, not a lawyer who wants billable stability. * Legal work product still has to be 100 percent right. The tools you build to get there can ship at 80 percent and iterate. * Document automation has been viable technology for 10 years. The reason it did not stick is incentive structure, not capability. * Enterprise systems that teams already work in every day are defensible in a way point AI tools are not. 👤 Guest BioMatthew Basile is the founder and CEO of Naya Software and Naya Law, based in the Greater Tampa Bay Area. He earned his JD at Fordham University School of Law, where he served on the Fordham Urban Law Journal, and practiced real estate law before leaving to build Naya full-time. Naya is an AI-powered enterprise platform for commercial real estate mortgage originations; its users have closed 1,319 transactions totaling $35.2 billion, running on Microsoft Azure with SOC 2 Type II certification. Matt writes the "Technology for Real Estate Transactions Newsletter" on LinkedIn, where he focuses on AI-native law firm design, Alternative Business Structure and Management Services Organization models, and real estate transaction technology. In his free time he is raising four boys, traveling with his family, and hiking and skiing with them whenever possible.🔗 Connect With Matt• LinkedIn: https://www.linkedin.com/in/matthewjbasile/• Naya Software: https://www.nayasoftware.com🔗 More From SalvadorPossibLaw: https://www.possiblaw.comFull podcast library, essays, and tools for legal professionals who are done watching from the sidelines.LinkedIn: https://www.linkedin.com/in/salvadorcarranza This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.possiblaw.com [https://www.possiblaw.com?utm_medium=podcast&utm_campaign=CTA_1]

Aditya Shivkumar on Why Legal AI Needs Empathy

Salvador Carranza sits down with Aditya Shivkumar, founder of RDO (Resolve Disputes Online), to unpack how an AI-native online dispute resolution platform gets built from inside a court system instead of around it. They go deep on the access-to-justice problem, why legal AI still has to sit next to the empathy of a human judge rather than replace it, and the Tyler Technologies partnership that puts RDO in reach of more than 45% of US state courts. Aditya breaks down the AI negotiator RDO trained for sub-$100K monetary disputes, why founder resilience is the real moat in legal tech, and how a two-month ICU stay reset his view of time and purpose. Watch the full conversation for a grounded look at what legal AI looks like when it is designed to enable the judiciary, not replace it.CHAPTERS00:00 Introduction00:57 Life beyond the hustle: wildlife, sports, and law04:47 Safari lessons on perseverance09:09 Becoming a sports administrator13:52 Premier Futsal and sports law in action18:42 Law, politics, business, and the rise of AI22:15 AI as a bull in a china shop or a focused Malinois23:27 Cardiff, mediation, and a first startup failure28:46 What failure teaches entrepreneurs34:56 India, resilience, and original thinking39:59 Access to justice and the role of AI44:40 RDO and the Tyler Technologies partnership51:15 How online dispute resolution actually works54:29 An AI negotiator for small-claim disputes58:23 COVID, the ICU, and finding purpose01:01:22 Where to find AdityaTakeawaysAccess to justice is a global problem UN Sustainable Development Goal 16.3 names but most systems still do not operationalize.Legal AI should enable dispute resolution, not replace the empathy a human judge brings to a contested case.Courts, not lawyers, are the real customer for B2B legal AI in dispute resolution because the judiciary controls the workflow.Roughly two-thirds of US court disputes are under $100,000 and are strong candidates for asynchronous AI-assisted settlement.An AI negotiator trained on dispute history can bring two parties into a settlement zone without a human in the loop.First attempts fail. The B2C version of RDO failed before the B2B court-integrated version that now ships.Resilience compounds. Safari after safari with zero sightings teaches the same lesson a failed startup does.The Tyler Technologies partnership expands RDO's reach to more than 45% of US state courts through existing case-management integrations.Purpose is easier to find after a forced reset. Aditya's two-month ICU stay clarified how he invests his next few decades.Indian entrepreneurship is shaped by policy (tax breaks, self-reliance framing) plus a cultural default of adaptability.👤 Guest BioAditya Shivkumar is the founder of RDO (Resolve Disputes Online), a B2B online dispute resolution platform that integrates with court case-management systems to let litigants, lawyers, judges, and mediators resolve disputes asynchronously. RDO operates across four to five US states and recently announced a partnership with Tyler Technologies that makes it the preferred ODR supplier across North America and Canada, reaching more than 45% of US state courts. Aditya earned his law degree at Cardiff University and began his career as a sports lawyer, including work on the launch of India's Premier Futsal League with players like Luis Figo, Paul Scholes, and Deco. He sits on the committee of the Madras Motorsports Club, the oldest motorsports club in India, and frames his work through the lens of resilience and original thinking after recovering from a severe case of COVID in 2021 that left him in the ICU for two months.🔗 Connect With Aditya• LinkedIn: https://www.linkedin.com/in/aditya-shivkumar-5b40837/• RDO: https://resolvedisputes.online🔗 More From SalvadorPossibLaw: https://www.possiblaw.comFull podcast library, essays, and tools for legal professionals who are done watching from the sidelines.LinkedIn: https://www.linkedin.com/in/salvadorcarranza👉 If you are a lawyer, GC, or legal leader who wants to stop waiting for vendors to package the future and start architecting it yourself, subscribe and tap the bell. New conversations with builders every week. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.possiblaw.com [https://www.possiblaw.com?utm_medium=podcast&utm_campaign=CTA_1]

Owning Your Future: Travis West on Service, Entrepreneurship, and Legal Innovation

In this conversation, Salvador Carranza and Travis West explore what it really means to “own your future” through service, entrepreneurship, and legal innovation. Travis shares his non-linear journey—from political work to volunteering for the Ranger Regiment—and how that experience shaped his leadership style, emotional intelligence, and commitment to transparency, community, and purpose. They also dive into what’s changing inside the legal industry right now: sharper risk assessment, better business decisions, and how technology, automation, and legal tech are reshaping how firms operate. Travis breaks down what responsible experimentation with artificial intelligence and deep learning looks like in a real firm—how to evaluate vendors, avoid hype, and build a culture of curiosity and adaptability (without sticking your head in the sand). Along the way, they touch on parenting, relationships, and the success habits that compound over time—especially for lawyers and legal professionals who want self development, self help, and self improvement that actually works. Listen to the entire podcast and learn even more! Takeaways • Success is usually non-linear—your journey matters as much as your destination. • Community is built through shared challenge, not transactional networking. • Relationship-building beats “used car salesman” energy every time. • Being an entrepreneur is a mindset, not just starting a startup. • Build your career with intention: work backward from where you want to land. • Firms are businesses—understand overhead, margins, and what “success” means. • Tech adoption requires curiosity + governance (especially with confidential data). • Legal AI is powerful, but data sources + nuance still matter more than hype. • Practice areas with repetition will see faster automation and consolidation. • Domain expertise + creativity remain differentiators in complex legal work. 👤 Guest Bio Travis West is a veteran, attorney, and entrepreneur focused on service-driven work, building community, and helping teams adapt to change. His career blends law, leadership, and technology-minded thinking—grounded in real-world life lessons and a commitment to doing hard things. 🔗 Connect With Travis • LinkedIn: https://www.linkedin.com/in/travisjameswest/ [https://www.linkedin.com/in/travisjameswest/] 🔗 More From Salvador Carranza • PossibLaw: www.possiblaw.com [http://www.possiblaw.com] • LinkedIn: https://www.linkedin.com/in/salvadorcarranza/ [https://www.linkedin.com/in/salvadorcarranza/] 👉 Subscribe to PossibLaw. We’re ReCoding the Vibe in the legal industry by empowering creativity. Our mission is to be your guide to the future of legal by identifying and analyzing Builders—individuals who don’t merely inhabit an industry, but actively construct new systems, workflows, and paradigms within it. We aim to prove that anything is possible. Subscribe, pull up a chair, and let’s invent what’s next, together. ⏱️ Chapters 00:00 – Welcome to PossibLaw (possiblaw) + why success is non-linear 01:00 – Travel, family, parenting, and perspective 06:15 – Why Travis chose military service (before 9/11) 10:00 – The Ranger path: challenge, identity, and purpose 22:00 – Community, camaraderie, and what “earned your seat” means 33:00 – Networking that isn’t transactional: how relationships actually work 42:00 – Starting a firm: the founder journey, risk, and real-world lessons 58:00 – Tech stack choices, remote work, and experimenting with AI tools 01:13:00 – Where law is going: ownership rules, consolidation, and innovation 01:21:45 – Actionable advice: curiosity + entrepreneurial mindset 01:26:00 – Closing thoughts This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.possiblaw.com [https://www.possiblaw.com?utm_medium=podcast&utm_campaign=CTA_1]

Legal Ops, AI, and High Agency. Why Legal Professionals Who Learn AI Win with Gabriel Saunders

Episode Summary What does it look like when a lifelong builder brings entrepreneurial thinking into legal operations? In this episode of PossibLaw, host Salvador Carranza sits down with Gabriel Saunders, Director of Legal Operations at EXOS, to explore how curiosity, technical fluency, and high agency can transform not just a career—but an entire organization. From building gaming PCs and startups, to uncovering systemic failures in criminal discovery, to automating legal workflows with AI, Gabriel shares a rare, inside look at how real innovation happens. Not through hype, but through persistence, systems thinking, and a willingness to learn faster than everyone else. This is a must-listen for lawyers, legal ops professionals, and anyone navigating the intersection of AI, law, and modern work. Key Takeaways ●      Why AI rewards builders, not passive users ●      How legal ops can become a force multiplier across the business ●      What most companies get wrong about AI tools and vendors ●      A practical framework for prompting, automation, and learning loops ●      Why “waiting to see” is the riskiest strategy right now ⏱️ Episode Highlights & Timestamps ●      00:00 – Welcome to PossibLaw ●      01:00 – Gaming, DIY, and the psychology of builders ●      07:00 – Raising kids with technology without outsourcing thinking ●      10:00 – Health, biofeedback, and using AI for personal optimization ●      15:00 – Entrepreneurial mindset and first-principles learning ●      23:00 – Founding a legal tech company and uncovering systemic failures ●      35:00 – Why CaseKey didn’t survive—and what it taught instead ●      42:00 – Returning to legal through legal operations ●      51:00 – Becoming an intrapreneur inside EXOS ●      58:00 – How Gabriel evaluates AI vendors (and why most fail) ●      1:05:00 – Prompting frameworks and AI literacy for lawyers ●      1:15:00 – The future of legal work and why learning now matters ●      1:19:00 – One actionable habit every listener should adopt This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.possiblaw.com [https://www.possiblaw.com?utm_medium=podcast&utm_campaign=CTA_1]

Mindset Over Mayhem: Shift Your Perspective, Elevate Your Decisions

Chapters 00:00 Introduction to Entrepreneurship Mindset 04:16 Personal Background and Interests 07:02 The Immigrant Perspective on Risk and Grit 10:02 Navigating the Entrepreneurial Journey 12:54 Understanding Risk Tolerance 15:39 The Importance of First Principles 18:21 Taking Small Steps to Build Confidence 20:58 The Role of Empathy in Leadership 23:33 Navigating Hard Times as an Entrepreneur 36:46 Integrating Grounding Techniques in Legal Practice 38:47 The Importance of Perspective in Legal Challenges 41:12 Continuous Learning and Multidisciplinary Approaches 47:41 Staying Close to Customers in Business 52:54 Building Community and Authentic Connections 01:00:56 Navigating Entrepreneurial Decisions and Opportunities This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.possiblaw.com [https://www.possiblaw.com?utm_medium=podcast&utm_campaign=CTA_1]