LegalTechLIVE

Nick Rishwain
  • 5.0 (9)
  • Technology
  • Updated Weekly

LegalTechLIVE is your front-row seat to the future of law and technology. Hosted by Nick Rishwain and Hana Zumout, this show features the innovators, tools, and ideas reshaping the legal industry, from SaaS breakthroughs to the rise of AI. www.legaltechlive.com

  1. 2d ago

    Episode 149: Josh Lokko - Statera CEO

    A highly recommended guest is the star of this episode! Joining Nick and Hana is Josh Lokko, CEO of Statera (That’s S-T-A-T-E-R-A, not to be confused with the US ADHD medication, Strattera. We felt the need to clarify that). ANYWAYS, Statera is an AI-powered legal tech startup catered to the capital markets practice, built by a capital markets lawyer. Since childhood, Josh knew he wanted to be a lawyer. After working at Shearman & Sterling in the capital markets practice, he grew frustrated with the manual “circle up” processes and late-night pricing supplements. Josh compared capital markets lawyers to sculptors, but instead of chiseling the marble, they spend half their day mining for it. Verifying hundreds of facts across prospectuses created unnecessary risk and consumed billable hours. The solution to this problem is Statera. Inspired by his self-built Excel VBA tool, Statera’s platform automates the grueling “circle up” process, cutting due diligence time by 80%! Rather than implementing pure agentic workflows, its self-deterministic AI foundations eliminate hallucination risks. Statera assists junior associates with tedious tasks unique to the capital markets industry, so they can focus on the work that seals the deals. Josh’s insight on the identity shifts leaving BigLaw, his goals for Statera, and his take on the legal tech industry are now available in Episode 149. More about Josh Lokko: * Josh Lokko on LinkedIn * Statera Website * Statera on LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  2. Sep 9

    Episode 148: Nam Nguyen - truthsystems COO and Co-Founder

    As everyone’s racing to adopt AI tools, how do law firms govern their use before it becomes a risk? This is what Nick uncovers in his interview with Nam Nguyen, COO of truthsystems - a YC-backed company building AI governance infrastructure specifically for law firms. If you don’t know him already, here’s Nam’s story and how truthsystems came to life. After growing up in Vietnam, Nam moved to the United States to study the intersection of linguistics and computer science at UCLA. He then did NLP research, worked in Southeast Asian fintech, and studied at Stanford Law with Dr. Megan Ma, researching supervisory AI agents. Through this research, he discovered an urgent market need: truthsystems. truthsystems is a software startup that flags noncompliant AI use in regulated industries. Nam and co-founder Anh (Alex) Mac decided to target law firms first because governance in legal can’t be a generic solution. Every matter has its own rules from outside counsel, emphasizing the importance of matter-level context. Coming from a tech background with a deep understanding of AI, their goal is to show legal professionals how to leverage AI to be more efficient while mitigating risk. For example, Charter is their browser extension and desktop app that monitors every prompt sent to Harvey, Claude, and Legora. It proactively redirects attorneys before sensitive information lands in the wrong place. Nam opens up about what’s next for truthsystems (a new product perhaps?), how data infrastructure beats model selection, and the cultural differences behind building tech in Episode 148. More about Nam Nguyen: * Nam Nguyen on LinkedIn * truthsystems Website * truthsystems on LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  3. Aug 26

    Episode 147: Jasmine Singh - Ironclad General Counsel

    Legal tech companies aren’t just selling products to firms; they’re selling to companies in their own industry. As someone who has implemented four contract lifecycle management (CLM) systems, twice with Ironclad, our next guest has buckets of information to share about in-house teams and what they actually need from tech. In arguably the most meta episode yet, meet Jasmine Singh, General Counsel at Ironclad! Jasmine started her career as a complex commercial litigator for Kirkland & Ellis and realized she wanted to use her “superpowers” of charisma, wit, and people-first instincts every day rather than waiting for the right strategic moment. Courageously leaving without a plan, she became a spin class instructor (which she loved!) and eventually landed roles at 24 Hour Fitness, Pinterest, Patreon, and her first GC position at Binti. As Ironclad’s GC, Jasmine’s is the primary legal advisor for the company and responsible for leading the legal team. For her, finding the right tools is about choosing the right partner, integration planning needs to account for the times things work and break, and AI is a sparring partner that pressure-tests her own work. Lawyers are always in the driver’s seat of what they produce, but embracing tech competently breeds an efficient in-house team, a quality that’s the opposite of a “cost center” stereotype! Jasmine names the problem no one’s solved yet, details what kills deals with vendors fast, shares where she trusts AI in legal work, and reveals the most underrated skill for running an in-house team in this episode. More about Jasmine: * Jasmine Singh on LinkedIn * Ironclad Website * Ironclad on LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  4. Aug 20

    Episode 146: Tom Martin - American Legal Technology Awards Co-Founder

    When: Sunday, October 25, 2026 Where: Suffolk Law School (Boston, MA) Pricing: $150 - Early Bird Discount / $250 - Standard Tom Martin, CEO of LawDroid, adjunct professor at Suffolk Law, and co-founder of the American Legal Technology Awards, talks to Nick and Hana about the seventh annual awards ceremony happening this October in Boston. Highlighting what makes our small but powerful industry so great, we finally get the origin story of the awards show we all know and love! A nomination for the British Legal Technology Awards in London inspired the American Legal Technology Awards, because the US legal tech community also deserved a spotlight. The collaboration that started with Tom, Patrick Palac, and Cat Moon grew into what many now call “Law Prom.” This black-tie event creates a virtuous cycle of recognizing innovators who do good, real, and purposeful work that inspires others to do the same. Tom shares how nominees are chosen, the judging process, and the moments that make the event unforgettable. And last but not least, Tom thanks sponsors such as Clio, ARAG Legal Insurance, ADM, and Practising Law Institute for their support of the American Legal Technology Awards. For more details, heartfelt memories, and potential category ideas for the future (perhaps an “Up-and-Comer” or “Newbie” award??), tune in to this episode. And buy your ticket while the Early Bird Discount is available! More about the American Legal Technology Awards: * American Legal Technology Website * American Legal Technology Awards LinkedIn More about Tom Martin: * Tom Martin on LinkedIn * Tom Martin on X * LawDroid Manifesto This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  5. Aug 12

    Episode 145: Horace Wu - Syntheia Founder

    You may know our guest as co-host of Further Comments and accidental (yes, accidental - we’ll get into that later) founder of Syntheia. Horace Wu makes his inaugural appearance on LegalTechLIVE and has plenty of stories that grab your attention. Hana couldn’t be a part of this great conversation, but here’s a snippet of what Nick and Horace covered. After nearly 15 years as an M&A lawyer across Australia and New York, he left law to build an events discovery app, only to fold 6 months later when Facebook and Google launched. Call it fate or divine intervention, an encounter with a German NLP company that had won a contract to review 10,000 leases with no lawyers on the team sparked a conversation about what became Syntheia (pronounced “Cynthia”). Using fixed rules and outputs, Syntheia deterministically extracts and structures transactional legal documents, breaking them into clauses, subclauses, and definitions. It offers multi-document comparison that surfaces differences and risk across a set of documents. Syntheia is a bootstrapped and profitable company, but it’s exploring the idea of being acquired or going through a first funding round. Watch Episode 145 to hear Horace’s founder origin story, how Syntheia helps transactional lawyers, and his prediction on how a market correction is coming to legal AI. More about Horace Wu: * Horace Wu on LinkedIn * Syntheia Website * Syntheia on LinkedIn * Further Comments Podcast (Apple Podcasts) This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  6. Aug 5

    Episode 144: Jonathan Watson - Clio CTO

    We bring you this episode at the request of Nick’s rampant and admirable curiosity to tie legal technology to national security happenings (see his LinkedIn post)! After a few X messages and email exchanges, we’re ecstatic to have Jonathan Watson, Chief Technology Officer at Clio, on the podcast! As Hana starts her new job at the time of this recording, Nick and Jonathan talk about all things cybersecurity and what that means for law firms and start-ups. Before Jonathan became the CTO of a leading legal tech powerhouse, he worked as a carpenter, internet cafe owner, and professional gamer! But to stay on topic here, he served in leadership roles at Shopify and Zynga, which helps him in his current position at Clio. Jonathan brings a unique perspective to an evolving topic: how large language models (LLMs) are changing the nature of cyberattacks. The conversation started with the NSA/Cyber Command’s testimony suggesting adversaries can compromise systems in hours, rather than weeks. So how does this happen? How should law firms and companies like Clio defend themselves? To put it simply, as the true insight is in the episode, Jonathan implores law firms to implement best practices like multi-factor authentication, no shared logins, and choosing vendors with real security investment. For startups, good development hygiene is paramount from day 1. Password vaults, data segmentation, and early investment in observability will set them up for success. As for Clio, a “breach-first” mindset helps Jonathan stay ahead of the vulnerabilities to monitor and protect company and client data. Jonathan dives deeper into the topics briefly mentioned in this description, so watch or listen to learn about vulnerabilities, prompt injections, what attackers actually want, and how to limit risk. More about Jonathan Watson: * Jonathan Watson on LinkedIn * Clio Website * Clio on LinkedIn * Clio for Enterprise on LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  7. Jul 29

    Episode 143: Jennifer Waite - Arnall Golden Gregory LLP CKIO

    If you’re a frequent listener of LegalTechLIVE, you might remember advice from a previous episode about knowing your audience and understanding who is making the buying decisions. For the founders out there, here’s a goldmine of an episode for you! As Hana settles into her first week at her new job, Nick Rishwain is joined by Jennifer Waite, Chief Knowledge & Innovation Officer at Arnall Golden Gregory LLP. And trust us, the best advice, especially for securing enterprise customers, comes from people who give it to you straight. Jennifer started her career as a law librarian. She briefly practiced law afterwards and now leads AI and innovation strategy at an Am Law 200 firm. Despite the seemingly unconventional path, she argues the opposite: librarians are well suited to knowledge management roles, as they’re trained in taxonomies, data organization, and customer service. In her seven years working for AGG, she treats AI strategy as a “living framework” that’s reviewed quarterly and looks for tools that fit her firm's needs. So, what does this mean for vendors looking to have firms like AGG as a client? We won’t spoil that part of the episode, but Jennifer shares several examples of do’s and don’ts for vendor pitches and what she values most when evaluating and retaining tools. The “AI creates less work” sentiment is the antithesis for people like Jennifer. As a vendor, it’s in your best interest to approach Jennifer with all the information at the ready. Whatever you do, DON’T cold call or email her. Jennifer’s insight is now available in Episode 143, so watch or listen to stories about vendor relationship experiences, her role in knowledge management, and tools she’s looking for now. More on Jennifer Waite: * Jennifer Waite on LinkedIn * Arnall Golden Gregory LLP Website * Arnall Golden Gregory LLP on LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

  8. Jul 22

    Episode 142: Gordon Cassie - Eno PDF Founder

    For our viewers in the legal technology space, you may have heard of Gordon Cassie, whose company, Closing Folders, was acquired by iManage in 2020. Now that he knows what it takes to build legal tech that gets adopted and acquired, he’s back with Eno PDF (Eno). Eno is an offline application that takes a different approach to AI-assisted document review, and a product Nick wished he had for his master’s classes. Anyways… here’s what we discussed. Most AI tools answer your questions with a generated summary and vague citations, but Eno is what Gordon calls “evidence-based AI.” It’s a zero-retention desktop app that surfaces the actual document snippets on screen so you can find what you’re looking for in your source material at 10x speed. Think of it as a “fuzzy Control F.” Because attorneys can’t afford to communicate paraphrases of the law to a client, this distinction is critical. Gordon’s time building Eno vastly differs from his Closing Folders days. Closing Folders’ audience was strictly for legal professionals, but anyone who uses PDFs can use Eno. He deliberately avoids taking VC money this time around and now views marketing as a valuable strategy to reach a wide range of professionals. Watch the episode to get detailed information about Gordon, Eno, and why locally run apps are becoming legal tech’s latest trend. More on Gordon Cassie: * Gordon Cassie on LinkedIn * Gordon Cassie on X * Eno Website * Eno on LinkedIn This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit www.legaltechlive.com

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5
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About

LegalTechLIVE is your front-row seat to the future of law and technology. Hosted by Nick Rishwain and Hana Zumout, this show features the innovators, tools, and ideas reshaping the legal industry, from SaaS breakthroughs to the rise of AI. www.legaltechlive.com

Information

  • Creator
    Nick Rishwain
  • Years Active
    2019 - 2026
  • Episodes
    148
  • Rating
    Clean
  • Copyright
    © Nick Rishwain
  • Show Website
    LegalTechLIVE