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. 1d ago

    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

  2. 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

  3. 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

  4. 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

  5. Jul 15

    Episode 141: Ian O'Brien and Dory Lord - CounselPro Founders

    “And so.. we wanted to essentially be able to provide this same level of capability that people would’ve paid thousands and thousands of dollars for a forensic analyst.” - Dory Lord Anyone who has been divorced understands how strenuous it is to sift through years of financial documents, as if the divorce itself wasn’t mentally taxing (pun intended). It’s the last thing people want to deal with, and now it’s a process that lawyers and forensic accountants can expedite! CounselPro co-founders Ian O’Brien (CEO) and Dory Lord (CRO) share their story behind expediting forensic financial processes. After experiencing this exact issue himself, Ian looked for a simpler way to deal with his financial statements and couldn’t find anything satisfactory. Through market research, he discovered a need to automate financial evaluation for family law and bankruptcy attorneys. With Dory’s marketing operations and legal tech background, and Ian’s engineering and marketing expertise, they joined forces to create CounselPro. In Ian’s words, “CounselPro is so easy, even a lawyer can use it.” With its “drag, drop, done” interface, CounselPro’s platform ingests thousands of pages of financial documents. It'll organize PDFs, categorize every transaction, flag missing statement ranges, and allow attorneys to search and filter by merchant, date, account, and more. The output can withstand scrutiny, making it court-ready by design. This episode covers Ian and Dory’s path to entrepreneurship, why they’re targeting solo practitioners and small law firms, the industries they want to reach next, and their vision for CounselPro’s future. More about Ian and Dory: * Ian O’Brien on LinkedIn * Dory Lord on LinkedIn * CounselPro Website * CounselPro 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

  6. Jul 8

    Episode 140: Dorna Moini - Gavel CEO & Founder

    We are ecstatic to welcome back our first returning guest since LegalTechLIVE’s revival, Dorna Moini, CEO and Founder of Gavel! Last time she was on the show (Episode 49), Gavel was known as Documate. The company has come a long way since then, so much so that it was recently acquired by Relativity! Stay with us until the end for Dorna’s inside scoop on this VERY newsworthy event. Her journey began in Big Law at Sidley Austin, where she worked on pro bono cases for domestic violence survivors as a litigator. Her time there sparked the idea for a document automation platform, which was later known as Documate. So, despite the risks of leaving a secure full-time job, she bet on herself and quit to pursue entrepreneurship. Not long after launching Documate, she realized early on that the legal tech industry was headed toward an AI-centered direction. With the help of her team, investors, and a CTO with deep AI knowledge, Documate was rebranded to Gavel. The rebrand was a necessary move to encompass the added AI-native products that complement the original document automation service. And for those of you who know Dorna, you may have even participated in suggesting a name for the rebrand! All the decisions she’s made as a founder have paid off, and Gavel is now part of the legal AI platform, Relativity. Hear from Dorna herself about how understanding her customers has helped her business grow, the benefits of staying agile, the hardest decisions she’s had to make as a founder, and her thoughts on the recent acquisition. More about Dorna: * Dorna on LinkedIn * Dorna on Substack * Gavel Website * Gavel on LinkedIn * Gavel Acquisition Announcement 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. Jun 24

    Episode 139: Erich Dylus - CamoText Founder

    You know the headlines where attorneys use mainstream AI tools for their legal work and inadvertently violate client-attorney privilege? Those are unfortunate stories and even more unfortunate realities. Clearly, not all AI is created equal. But what if there were a tool that anonymizes identifiable information that can be used anywhere at any time? Oh wait, there is! It’s called CamoText, and this episode features its founder, Erich Dylus. As a solo-practice lawyer, Erich underwent the mind-numbingly mundane task of manually removing private data in his legal work. He noticed that the labor of wiping metadata and copy-pasting clean text into AI chats was the kind of friction that causes lawyers to ignore privacy steps. Erich wanted a way to expedite and preserve confidentiality. Luckily for him, he’s also a programmer. The Python script he wrote became CamoText, a fully offline document app that detects and replaces PII (personally identifiable information) with placeholders. Names, email addresses, UUIDs, locations, finances, and other private information are camouflaged. And the best part? You can paste the sanitized version from CamoText into your AI tool of choice, with human review, of course. Tune in to learn about less obvious privacy vectors, how CamoText also serves non-legal industries, and why offline apps offer security by simplicity. More about Erich: * Erich Dylus on LinkedIn * CamoText Website * CamoText on LinkedIn * Varia Law Website * Varia Law 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. Jun 17

    Episode 138: Cheyenne Moseley - Rasa Legal Ops Director

    “What are legal operations?” “Is it different from business operations?” “How can non-profit legal tech companies build scalable processes?” Rasa’s Legal Operations Director, Cheyenne Moseley, describes her day-to-day responsibilities, the rewarding yet complex nature of expungement work, the tools that help her do her job, and why she traded the corporate life for deeply human work. Cheyenne spent 21 years at LegalZoom before joining Rasa. She started in customer service roles and worked her way up to director of an entire division. Within that time, she saw legal tech scale from Manila folders and FileNet to Salesforce and AI tools. After meeting her boss and the founder of Rasa, Noella Sudbury, she decided to leave her corporate job for a mission she couldn’t refuse. Rasa’s goal is to help people expunge their criminal records, which is different from LegalZoom’s high-volume business formation. As Legal Operations Director, she navigates multiple counties across multiple states whose courts have different timelines and processes (that’s if they have a process). Her role brings about additional nuances compared to business operations, as people’s freedom is the service Rasa offers. What remains the same is how Cheyenne applies the same operational skills she learned in corporate to a public benefit corporation setting. Get to know Cheyenne, understand legal operations and Rasa’s mission on a deeper level, and discover how she creates repeatable processes in this episode. More about Cheyenne Moseley: * Cheyenne Moseley on LinkedIn * Rasa Website * Rasa 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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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
    144
  • Rating
    Clean
  • Copyright
    © Nick Rishwain
  • Show Website
    LegalTechLIVE

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