Podcast
LawNext
Hosted by Populus Radio, Robert Ambrogi · EN
LawNext is a weekly podcast hosted by Bob Ambrogi, who is internationally known for his writing and speaking on legal technology and innovation. Each week, Bob interviews the innovators and entrepreneurs who are driving what's next in the legal industry. From legal technology startups to new law firm business models to enhancing access to justice, Bob and his guests explore the future of law and legal practice.
28episodes
Episodes
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How AI Is Transforming the Way Law Firms Win Business, with Ikaun President Jason Noble
3w ago00:40:41Tap to summarizeLaw firms sell experience — but for decades, harnessing and operationalizing that experience has been a largely manual, chaotic process. In this episode, recorded live at the Legal Marketing Association annual conference in New Orleans, host Bob Ambrogi sits down with Jason Noble, president and chief of product strategy at Ikaun, to talk about how his company is changing that. Ikaun is a managed service and technology platform that helps law firms streamline the proposal and RFP response process — from capturing and organizing matter experience data to using AI to assemble and draft competitive pitches. Jason explains how the platform works, how the arrival of generative AI transformed what was previously possible, and why Ikaun positions itself as a managed service rather than a self-serve SaaS tool. Jason and Bob also get into the bigger picture of how law firms are responding to AI-driven changes in the competitive landscape, whether the billable hour can survive in an AI-augmented world, and whether the RFP process itself will look the same in the years ahead — or whether we're moving toward a future where agents are submitting and responding to proposals with minimal human involvement. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Chapters (00:00) Introduction to Ikaun and Legal Tech Innovations (02:30) Jason Noble's Journey and Background (05:20) The Evolution of Ikaun and Its Focus (07:09) Experience Management in Legal Firms (10:30) Gathering Experience Data in Litigation (11:48) How Ikaun's Platform Works (14:05) The Impact of AI on Proposal Processes (18:07) Current Landscape of RFP Responses (20:31) Differentiating Ikaun from Competitors (22:45) Knowledge Management vs. Experience Management (24:01) Tailoring Solutions for Law Firms (25:49) Qualities of Successful Law Firms (27:24) Law Firms' Response to AI Integration (29:54) Pricing Strategies in RFP Responses (31:21) Competitive Landscape and AI's Influence (33:27) The Future of Billable Hours (35:50) The Future of RFPs and AI's Role (39:33) Client Satisfaction and Future Directions If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →Legal Marketing Association President Rachel Shields Williams On AI, Innovation, and Why People Still Come First
Apr 2700:44:31Tap to summarizeRecorded live at the annual meeting of the Legal Marketing Association in New Orleans, this episode features a conversation with Rachel Shields Williams, president of the LMA and director of client intelligence at Sidley Austin, where she has spent 17 years building out roles at the intersection of marketing, business development, knowledge management and data. Earlier this year, Rachel was named a recipient of ALM's Monica Bay Women in Legal Tech Award. Rachel and host Bob Ambrogi discuss how AI is reshaping the work of legal marketers, and why she believes the marketing community is uniquely positioned to help law firms move past the "I'm curious, I want to click the buttons" stage of AI adoption to sustained, repeatable value. They get into the state of innovation in big law — including Rachel's view that firms cannot use AI or money to "skip the canyon of despair" in change management — and why she thinks meaningful innovation often looks less like a headline and more like getting one percent better every week. The conversation also covers the changing competitive landscape facing traditional firms, from AI-native entrants like Norm AI to MSOs and a resurgent ALSP market; the long-running debate over the billable hour; the four interrelated elements Rachel sees at the heart of every law firm's data — documents, clients, matters, and people; and what firm leaders should be doing right now to stay competitive over the next decade. Throughout, Rachel returns to a theme about which she calls herself an "unapologetic humanist" — technology and process will keep changing, but the firms that win will be the ones that put the right people in the room first. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
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Built on a Weekend: Damien Riehl and Mike Bommarito Show What Vibe Coding Can Really Do
Apr 1501:01:31Tap to summarizeWe don't usually say this, but for today's LawNext, you're going to want to watch the video version, if you can. The audio will be good, but the video will be great. You can find it on YouTube. Why? Because we're going to be talking today about vibe coding, and you're going to want to see what our guests are showing today, not just hear them tell about it. Those guests are Damien Riehl and Michael Bommarito. By day, Damien works on AI products at Clio and Mike is CEO of 273 Ventures, a company that provides AI strategy and services for law firms and legal professionals. But outside their day jobs, they are also founders of the ALEA Institute, the Institute for the Advancement of Legal and Ethical AI, where a central focus of theirs is the FOLIO Project, which is seeking to develop and maintain open legal standards and a comprehensive ontology to enable different legal systems to communicate with each other. FOLIO is an outgrowth of the SALI Alliance, whose ontology was largely developed by Damien. So what does any of this have to do with vibe coding? Well, in connection with their FOLIO project, Damien and Mike have been building an array of tools for tagging and enriching legal documents (FOLIO Enrich), for mapping law firm taxonomies (FOLIO Mapper), for browsing and editing legal ontologies (FOLIO Ontology Explorer), and much more. (See the full list of FOLIO resources.) And they've built all of it by vibe coding. Not over months, not with a team of developers, but on their own, often in a single weekend day, using AI coding tools. When Damien first showed LawNext host Bob Ambrogi what he and Mike were developing, Bob thought, "It's not enough for me to just write about this. It really has to be seen, in action." So he asked Damien and Mike to come on LawNext, share their screens, walk us through what they've been building, and show us what vibe coding actually looks like in action when it's applied to serious legal technology problems. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →Learned Hand's Shlomo Klapper on Why Courts Are the Next Frontier for Legal AI
Apr 701:06:36Tap to summarizeAre courts the next frontier for legal AI? Shlomo Klapper, founder and CEO of the AI-driven judicial case-preparation platofrm Learned Hand, believes they are. A former litigator at Quinn Emanuel and law clerk for the 2nd U.S. Circuit Court of Appeals, Klapper is building what he calls a "reasoning engine" for judges — AI tools designed to help them manage crushing caseloads by organizing case materials, flagging when lawyers bend the truth, and drafting bench memos and orders. LawNext host Bob Ambrogi interviews Klapper on the heels of significant news: Learned Hand just announced a partnership with the Superior Court of Los Angeles County, the largest trial court in the nation, to explore how AI can support judicial officers across the full arc of a case — from filing through drafting. The company's technology — the only AI built exclusively for the judiciary — is also used by the Michigan Supreme Court and trial courts in 10 states. In today's conversation, Klapper discusses why courts are the next frontier for legal AI, what it takes to earn the trust of judges, and how Jevons Paradox — the idea that as legal services get cheaper, demand will explode — is reshaping the justice system. They also dig into the difficult questions around how Learned Hand addresses concerns about bias and hallucinations, and how it can overcome judges' skepticism about AI and achieve broad judicial adoption. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →Mary Technology Wants to Solve Litigation's 'Fact Chaos' Problem
Mar 3100:43:57Tap to summarizeE-discovery platforms have gotten great at narrowing millions of documents down to manageable sets. But what happens next — the grueling work of extracting facts, organizing them, and building a reliable case narrative — has remained largely manual. In this episode of LawNext, host Bob Ambrogi talks with Daniel Lord-Doyle, cofounder and CEO of Mary Technology, about the Australian startup's bet that "fact management" is the missing layer in litigation technology. Mary's approach is distinct from the large AI platforms that store documents as embeddings in vector databases. Instead, the company extracts every individual fact, enriches it with metadata, and links it directly back to its source — creating what Lord-Doyle calls a verifiable chain from work product to evidence. He makes a compelling case that in litigation, where fault tolerance is low and the stakes are high, the nuance lost by compression-based AI systems is exactly what matters most. The company just closed a $7 million (Australian) seed round led by OIF Ventures and is expanding into the U.S. with a new San Francisco office and a new self-serve platform that lets smaller firms try it without a sales process. Lord-Doyle also talks about the concept of "productive friction" — why Mary deliberately won't let lawyers skip the verification step — and what he's learned about bringing an Australian legal tech product to the American market. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →LawNext on Location: Visiting Everlaw's Headquarters For A Conversation with AJ Shankar, Founder and CEO
Mar 1900:39:41Tap to summarizeFor the final installment of our LawNext on Location series, Bob heads across the bay, from San Francisco to Oakland, to the headquarters of e-discovery company Everlaw, where he sits down with founder and CEO AJ Shankar for a conversation about technology, AI and being in it for the long game. AJ grew up in Connecticut, came west in 2002 for a computer science PhD at UC Berkeley, and has lived within a few blocks of the Berkeley campus ever since. He stumbled into the legal industry almost by accident — recruited to serve as a technical expert in litigation involving how the internet worked — and quickly realized that the legal world was home to some of the most technically fascinating and underserved problems he'd ever encountered. He never left. AJ had a prior startup, a computer vision company that was acquired, before launching Everlaw in 2011. The company was cloud-native and ML-infused from the start, built on the conviction, AJ says, that there's no single way to find the needle in a discovery haystack, and that building a genuinely useful litigation platform requires solving for collaboration, ease of use and scalability all at once. The bulk of the conversation focuses on generative AI, and how Everlaw has approached it differently than much of the market. Rather than bolting on a chatbot, AJ says, Everlaw embedded AI deliberately throughout the platform — document summarization, coding suggestions, deposition analysis, fact extraction — always grounding responses in the actual documents at hand and citing sources so users can verify the work. The December launch of Deep Dive, which lets litigators pose a question and get a synthesized, cited answer drawn from an entire document corpus in about a minute, is the feature AJ calls a "new era" for discovery — one he genuinely believes represents a categorical shift. As Everlaw continues to grow, it also remains independent, with no private equity and no outside majority owners. As for AJ, he says he is in it for the long game, and has never included an exit slide in a fundraising deck. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Chapters 00:00 Introduction and Setting the Scene 03:23 The Journey to Founding Everlaw 08:36 The Evolution of Everlaw's Technology 11:06 Incorporating Generative AI into Legal Processes 14:04 Deep Dive: A New Era in Discovery 19:17 Transformative Experiences in Legal Discovery 22:27 Previewing Innovations at Legal Week 25:03 Understanding AI's Limitations in Legal Contexts 28:11 Navigating Hype in Legal Technology 30:47 The Impact of Foundation Models on Legal Software 34:36 Future Vision for Everlaw and Legal Tech 38:13 Closing Thoughts and Company Philosophy If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →LawNext on Location: At A Sonoma Winery, A Conversation with Briefpoint CEO Nathan Walter about Discovery, Disruption and, Of Course, Wine
Mar 500:50:48Tap to summarizeContinuing his on-location interview tour of San Francisco, Bob heads an hour north to Santa Rosa to sit down with Nathan Walter, cofounder and CEO of Briefpoint, over a bottle of red wine at Paradise Ridge Winery, a spot literally around the corner from Nathan's house, sitting on the edge of the Mayacamas Mountain Range that divides Sonoma and Napa counties. It is a fitting setting for a founder who grew up in Sonoma wine country, where wine is less a luxury than a way of life, and where his family's most treasured heirloom was a bottle from the year he was born. Nathan's path to founding Briefpoint is an origin story rooted in genuine frustration with the legal system. A U.C. Santa Barbara philosophy major who drifted into law school for lack of better options, he ultimately landed in civil litigation – and grew increasingly disillusioned with how discovery was weaponized to bleed defendants dry financially, even when they had done nothing wrong. After a particularly infuriating mediation where opposing counsel openly admitted the shakedown strategy, Nathan decided to do something about it. He taught himself to code from YouTube videos, built vaporware prototypes, cold-called attorneys to test demand, and eventually found his technical cofounder through a Discord gaming community he had created to build a social life after moving to Orange County. What followed was a years-long grind – including an 18-month stretch working days as an entry-level sales rep at another legal tech company and nights building Briefpoint, until a close acquaintance invested $100,000 of her own money so he could focus full time. Briefpoint launched in June 2022, before the ChatGPT wave, focusing narrowly on automating discovery responses – drafting objections, pulling relevant documents and generating formatted Word documents ready to sign. Nathan talks about the company's deliberate "go deep, not wide" strategy: rather than expanding into motions or other legal workflows to chase the AI hype cycle, Briefpoint is doubling down on doing discovery so exceptionally well that firms will pay for it alongside broader AI platforms, the way teams use Slack alongside the full Microsoft suite. The conversation also covers the threat to legal tech companies posed by foundation models such as Claude and GPT, the psychology behind why attorneys are resistant to automation (Nathan has a theory about "superstitious control" and lucky jerseys), the parallels between winemaking and product development, and the advice he'd give an aspiring founder: burn the ships, go full time and put yourself in a corner with no way out but forward. As for what varietal Briefpoint would be? A Russian River Pinot Noir – not a life-changing Cab, but reliably excellent at exactly what it promises. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City. If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →LawNext on Location: The View from Tiburon – A Conversation with Pablo Arredondo, Casetext Cofounder
Feb 2400:46:18Tap to summarizeAs Bob continues his LawNext on Location series – all recorded live in the San Francisco area at locations of each guest's choosing – he sits down with Pablo Arredondo at his home in Tiburon, a quaint Marin County town with a history stretching from Mexican land grants to naval outposts to a southern railway terminus. From Pablo's home office, the view looks out over Richardson Bay towards Sausalito and, if you look carefully, the Golden Gate Bridge can be seen in the distance. It is a setting that is entirely fitting for a conversation with someone who helped shape one of the more remarkable journeys in the annals of legal technology. Pablo was cofounder of Casetext, the once-scrappy startup that spent a decade iterating, pivoting and persisting before striking gold with CoCounsel, the first GPT-4-powered AI legal assistant, unveiled on the nationally televised Morning Joe show on March 1, 2023. Just four months later, Thomson Reuters acquired Casetext for $650 million in cash. Now, 2.5 years later, Pablo recently left TR, where he is, as he puts it, building a Lego Death Star with his daughter and finally paying attention to his well-being after 16 years of nonstop pursuit. In this wide-ranging conversation, Pablo reflects on the long road to CoCounsel – from a failed crowdsourcing experiment to CARA's brief analysis tool to the pivotal moment when Casetext signed a $20,000 innovation license with OpenAI and got early access to GPT-4, 10 weeks before ChatGPT's public launch. He describes the surreal experience of those first 48 hours after CoCounsel's debut, when he and cofounder Jake Heller identified 74 distinct legal use cases the tool could handle – any one of which, he says, "would have been a company in the old world." Pablo and Bob also dig into the bigger questions surrounding legal AI, including whether the field is advancing as fast as he expected; what the foundation models from Anthropic, OpenAI and Google mean for legal-specific AI companies such as Harvey; and why he believes reasoning models and agentic AI represent the next genuinely profound leap beyond GPT-4. Pablo also candidly reflects on the TR acquisition and his work while at TR, and he offers hints on what may lie ahead for him – at least once that Death Star model is done. It is a conversation that is part memoir, part technology seminar and part meditation on what it means to have built something that changed a profession – and his life – all recorded with a sweeping, albeit cloudy, view of the majesty of San Francisco Bay. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City. If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →LawNext on Location: Lunch with Alex Su of Latitude Legal In Alameda, Calif.
Feb 1800:44:12Tap to summarizeThis episode is recorded live, and is best enjoyed on YouTube. Watch the episode here. While Bob is visiting San Francisco for two weeks, he is sitting down for conversations with legal tech innovators and entrepreneurs "in their natural habitats" – places in the Bay Area they consider special. Today, in the first in this series, Bob sits down for lunch with Alex Su, chief revenue officer at Latitude Legal, over Thai iced tea and tofu dishes at Phnom Penh House, a Cambodian restaurant in Alameda that Alex considers something of a personal institution, frequenting it for both family meals and business meetings. Alex's career path is anything but linear. He started as an associate at Sullivan & Cromwell in New York, clerked for a federal judge in Chicago, then drifted through a plaintiff's firm, a brief solo practice, and ultimately a leap of faith into legal tech sales – joining e-discovery company Logikcull in 2016. From there, he moved to Everlaw, then to Ironclad, where he served as head of community development, building a reputation that spread well beyond any job title. That reputation was shaped in large part by TikTok, where Alex's comedic, self-effacing videos skewering law firm culture – partners, associates, privilege logs and the absurdities of BigLaw – earned him more than 100,000 followers, got shared inside Ironclad's internal Slack, and ultimately helped land him his next job. It's a story of accidental virality and deliberate reinvention that mirrors the broader shifts he sees in the legal profession. Now at Latitude Legal, an ALSP providing on-demand legal talent to law firms and corporate legal departments, Alex represents a kind of poetic symmetry: a lawyer known for championing "alternative careers" working at an "alternative legal services provider" — a label he thinks has outlived its usefulness, given how mainstream flexible legal talent has become. Bob and Alex also dig into the current state of legal AI – what's overhyped, what's underhyped, and why the pandemic was arguably a bigger inflection point for legal tech adoption than generative AI. Plus, Alex and Bob reflect on Bob's three decades of covering legal innovation, the stubborn persistence of the billable hour, and why the justice gap remains stubbornly wide despite all the talk of disruption. It is a wide-ranging and candid conversation – one you may want to watch on video instead of just listening to the audio. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City. If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts. Chapters 00:00 Intro to Today's Lunch: A Special In-Person Series 04:45 Career Transitions: From Law to Legal Tech 23:27 Going Viral: The TikTok Journey 25:10 Balancing Humor and Professional Identity 26:54 Redefining Career Paths for Lawyers 28:39 The Evolution of Legal Careers 30:35 Innovation in Legal Practice 34:07 The Impact of the Pandemic on Legal Technology 34:28 The Future of Legal Technology and AI 38:10 Navigating Uncertainty in Legal Services 40:18 The Ongoing Relevance of Traditional Legal Models 42:11 Personal Reflections and Future Outlook
Transcribe →From Customer to Acquirer: Filevine's Ryan Anderson and Pincites' Sona Sulakian on Building AI Contract Intelligence
Jan 2800:36:40Tap to summarizeIn this episode of LawNext, we talk with Ryan Anderson, co-founder and CEO of Filevine, and Sona Sulakian, former CEO and co-founder of Pincites, about Filevine's acquisition of the AI-powered contract redlining company. The deal, which closed in December, marks Filevine's second major AI acquisition of the year. Even more notably for this traditionally litigation-focused company, it represents a significant strategic expansion into the corporate and transactional legal market — a segment where Filevine saw 120% growth in 2025. What makes this acquisition particularly compelling is its origin story: Filevine was actually a customer of Pincites before acquiring the company. After Filevine's legal team became early adopters and enthusiastic users of the product, Anderson and his team recognized that Pincites' Word-native contract intelligence platform filled a critical gap in their offerings. The acquisition brings aboard sister co-founders Sona and Mariam Sulakian and their team, who will continue developing what Filevine now calls "LOIS for Word" — a drafting and redlining tool integrated directly into Microsoft Word. Along with host Bob Ambrogi, they discuss how the Sulakian sisters identified the market gap that led them to build Pincites, why they chose to build directly into Word rather than create a standalone platform, and what attracted them to Filevine among multiple suitors. Anderson shares his vision for building a comprehensive Legal Operating Intelligence System (LOIS) that connects contracts, depositions and all legal work into a single unified platform. They also explore the broader implications of AI for legal practice and access to justice, and how tools like Pincites and Filevine are transforming the way legal work gets done. Thank You To Our Sponsors This episode of LawNext is generously made possible by our sponsors. We appreciate their support and hope you will check them out. Paradigm, home to the practice management platforms PracticePanther, Bill4Time, MerusCase and LollyLaw; the e-payments platform Headnote; and the legal accounting software TrustBooks. Briefpoint, eliminating routine discovery response and request drafting tasks so you can focus on drafting what matters (or just make it home for dinner). Legalweek, March 9-12, North Javits Center, New York City. If you enjoy listening to LawNext, please leave us a review wherever you listen to podcasts.
Transcribe →