Jamie Tso and Ray Sun, the founders of LegalQuants, discuss a fundamental shift in the legal profession: the transition from legal engineering to "legal quant" work. The conversation explores how technically fluent lawyers are using vibe coding, frontier AI models, and first-principles thinking to move beyond mere efficiency and toward the complete redesign of legal services.

Jamie and Ray share their backgrounds in Big Law and their journeys into building custom legal tech tools. They delve into the origins of the LegalQuants community—an exclusive, invitation-only network of "builders"—and discuss the future of the billable hour in an era where AI can automate routine intellectual labor.

Episode Highlights

• Jamie and Ray's origin stories: From annotating mutual fund prospectuses to early experiments with machine learning and TensorFlow.

• Ray's background as one of the world's first Legal Engineers and the creation of his Global AI Regulation Tracker.

• Defining the Legal Quant: How they differ from traditional Legal Engineers by seeking "alpha" and redesigning legal workflows from first principles.

• The growth of the LegalQuants community: From a small WhatsApp group to a global network of elite lawyer-builders.

• The "Unicorn Talent" gap: Why the next generation of elite legal work is defined by the operator, not the tool.

• The death of the friction-based pricing model and the future of value-based billing.

• Stress-testing Claude and Anthropic's Legal Plugin: Why the "ceiling" of AI utility is set by the lawyer's ability to design custom skills.

Things We Talk About in this Episode

• LegalQuants Substack: legalquants.substack.com – Weekly digests and deep dives into legal AI strategy.

• Global AI Regulation Tracker: techieray.com – Ray Sun's interactive map of worldwide AI laws and policies.

We welcome back Sabastian Niles, President and Chief Legal Officer at Salesforce, to discuss his recent "Open Letter to Law Firms." As the legal industry hits a critical inflection point, Sabastian argues that the era of "AI theater" and small-scale pilots is over.

The conversation dives deep into the Innovator's Dilemma facing law firms, the shift toward agentic AI, and how firms must reimagine their business models to remain competitive. Sabastian highlights that legal professionals are uniquely positioned to lead the charge in trusted AI transformation, provided they embrace transparency, data integration, and shared efficiency gains with their clients.

Specifically,  he offers four systems law firms and other service providers must establish if they want to succeed in the AI era: 

• System of Engagement: A unified digital interface that replaces fragmented tools with seamless, real-time collaboration between firms and clients.
• System of Agency: An ethically governed AI framework that scales firm capacity and reimagines service delivery while maintaining strict human oversight and compliance.
• System of Work: A trusted, enterprise-grade platform that integrates daily professional applications into a cohesive, high-performance workflow.
• System of Context: A secure "single source of truth" for client data that ensures strategic counsel is grounded in history while protecting attorney-client privilege.

Other Things We Talk About in this Episode

• The End of the Pilot Era: Moving beyond experimentation to integrated, unified AI platforms is no longer optional—it is a prerequisite for competitiveness.

• The Relationship Challenge: AI should be used to break down internal silos, allowing firms to bring their "tribal knowledge" and collective intelligence to every client engagement.

• System of Agency: A shift from manual workflows to "agentic" systems where AI agents handle triage, research, and routine queries (e.g., Salesforce's Outside Counsel Support Agent).

• Value-Based Evolution: Law firms must navigate the friction between the billable hour and AI-driven efficiency by focusing on superior outcomes and shared savings.

• Trust as Propulsion: In legal services, trust isn't just a guardrail; it's a growth lever. Mastering "Trusted Agentics" ensures human-aligned AI that respects privilege and confidentiality.

One of the most listened to episodes in 2025 featured a conversation with Andrea Muttoni, President of Story Protocol. The discussion explores how blockchain technology is being used as a foundational infrastructure for intellectual property (IP), aiming to simplify and modernize the process of registration, licensing, and monetization for creators and IP owners. Muttoni details his journey from a bedroom music producer to a product manager at Amazon and eventually to a leader in the blockchain industry, driven by a passion for the intersection of technology and creativity.

The conversation delves into the core problems Story Protocol aims to solve, particularly the complexities of copyright, fair use, and attribution in the age of AI-generated content. Muttoni introduces key concepts like the Programmable IP License (PIL), a customizable and on-chain license that makes IP rights more transparent and accessible. He also provides an overview of Poseidon, a new initiative that leverages the Story Protocol to create a marketplace for IP-safe, real-world data needed to train AI models, ensuring that data creators and owners are fairly compensated.

Key Takeaways

• Andrea's Background: From a bedroom hip-hop producer to a product manager at Amazon working on Kindle and Alexa, Muttoni shares his path to the world of crypto and blockchain.

• What is Story Protocol?: A deep dive into Story Protocol's mission to create an open IP blockchain. It's a way to register, license, and monetize IP in a more liquid and accessible way.

• The Programmable IP License (PIL): Explanation of how this universal, customizable, and on-chain license simplifies IP transactions and makes it easier for others to legally use a creator's work.

• Introducing Poseidon: Details on the new platform built on the Story Protocol to address the "data gold rush" for AI. Poseidon allows for the licensing of real-world, IP-cleared data to AI companies, ensuring fair compensation for contributors.

• Promoting Adoption: Discussion on how Story Protocol uses a web3 incentive model to encourage widespread adoption and create a network effect for its IP infrastructure.

• Why Story Protocol?: Muttoni explains what makes their platform uniquely suited for IP rights compared to other blockchains, emphasizing that the network was built from the ground up specifically for this use case.

Things We Talk About in this Episode

• Story Protocol: story.foundation

• Story Protocol IP Portal: portal.story.foundation

• Poseidon: psdn.ai

• Story Protocol Developer Docs: docs.story.foundation

• WIPO Report: A report on intangible assets, mentioned as a key indicator of the value of intellectual property.

 

Avaneesh Marwaha, the CEO of Litera, visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law.

The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company to its current role as a comprehensive legal tech ecosystem. Avaneesh highlights the company's strategic shift from acquiring to building new technologies. He also emphasizes the importance of Litera's strong partnership with Microsoft and the company's focus on enhancing law firms' productivity and client service.

Key Takeaways:

• Pivoting from Law to Business: Avaneesh's move from practicing IP law to an in-house role and eventually becoming a CEO was driven by his desire for a more active role in business decision-making. He saw lawyers as reactive to business decisions, and he wanted to be at the forefront of the action.

• The Value of a Law Degree in Business: Avaneesh shares his perspective on the value of a law degree for business professionals, highlighting the critical thinking and risk tolerance skills it provides. He notes that the corporate transaction course he took in law school was particularly beneficial, teaching him about corporate governance and fiduciary duties.

• Litera's Evolution: Avaneesh discusses how Litera has grown through strategic acquisitions and a recent focus on internal development. He explains how the company integrates various tools, like Kira and Foundation, to create a seamless ecosystem for lawyers within their daily workflows, primarily in Outlook and Word.

• The Impact of Generative AI: The discussion touches on the transformative impact of AI on the legal tech industry. Avaneesh explains how AI has enabled Litera to accelerate its product development and introduce features that proactively assist lawyers with tasks like document comparison and client relationship management.

• Build vs. Buy Strategy: Avaneesh outlines Litera's shift from a buy-heavy strategy to a more balanced build-and-invest approach. This change is largely due to the increased efficiency and speed of development enabled by AI tools.

• Future of Legal Tech: Avaneesh shares his vision for the future of Litera, which includes a focus on "maniacal client service" and helping law firms proactively grow their business. He believes that as automation handles routine tasks, lawyers will have more capacity for business development and client-centric work.

Things We Talk About

• Kira Systems - A company acquired by Litera specializing in AI-powered contract analysis.

• Foundation Software - A business acquired by Litera focused on knowledge management.

• Doxly - A document formatting and repair tool.

In one of the most popular episodes of the year, Legalbenchmarks.ai Founder Anna Guo discusses her organization's research that tests whether artificial intelligence custom-made for legal tasks better than general AI tools.

Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for colleagues quickly revealed a strong community interest in a systematic approach to evaluating legal AI tools. This led to the creation of Legalbenchmarks.AI, dedicated to finding out where the promise of humans plus AI is truly better than humans alone or AI alone.

The core of the research involves measuring the "delta," or the extent to which AI can elevate human performance. To date, Legalbenchmarks.ai conducted two major studies: one on information extraction from legal sources and a second on contract review and redlining.

Key Findings from the Studies:

• Accuracy vs. Qualitative Usefulness: The highest-performing general-purpose AI tools (like Gemini) were often found to be more accurate and consistent. However, the legal-specific AI tools often received higher marks in qualitative usefulness and helpfulness, as they align more closely with existing legal workflows.

• Methodology: The testing goes beyond simple accuracy. It includes a three-part assessment: Reliability (objective accuracy and legal adequacy), Usability (qualitative metrics like helpfulness and coherence for tasks such as brainstorming), and Platform Workflow Support (integration, citation checks, and other features).

• Human-AI Performance: In the contract analysis study, AI tools matched or exceeded the human baseline for reliability in producing first drafts. Crucially, the data demonstrated that the common belief that "human plus AI will always outperform AI alone" was false; the top-performing AI tool alone still had a higher accuracy rate than the human-plus-AI combo.

• Risk Analysis: A significant finding was that legal AI tools were better at flagging material risks, such as compliance or unenforceability issues in high-risk scenarios, that human lawyers missed entirely. This suggests AI can act as a crucial safety net.

• Strengths Comparison: AI excels at brainstorming, challenging human bias, and performing mass-scale routine tasks (e.g., mass contract review for simple terms). Humans retain a significant edge in ingesting nuanced context and making commercially reasonable decisions that AI's instruction-following can sometimes lack.

In the most listened to episode of 2025, author of "Systemology" and business systems expert, David Jenyns, discusses the importance of systemizing business processes, even in the nuanced field of law. Jenyns debunks the myth that legal work is too bespoke to be systemized, explaining how just like any other business, documenting legal workflows unlocks scalability and creativity. He shares his journey from digital SEO agency owner to becoming a systems expert and outlines the seven steps of his Systemology framework.

• Key Topics:

  • The importance of documenting processes in any business, including legal services.

  • How systemization can create space for creativity in legal work.

  • The Systemology framework and its seven steps: Define, Assign, Extract, Organize, Integrate, Scale, and Optimize.  

  • The role of a "systems champion" in implementing a systems culture.

  • Addressing common misconceptions about systemizing legal work.

  • Practical tips for getting started with systemizing processes.

• Resources Mentioned:

• Systemology book by David Jenyns

• System Hub software

• The E-Myth by Michael Gerber

• Systemology Podcast (Mentioned interview with Crow Estate Planning firm)

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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Meredith Kildow, President of Consilio discusses her career path from finance to leading global operations and delivery for one of the largest companies in the legal and eDiscovery space.

Meredith shares insights into building a revenue organization from the ground up and the shift to her current role overseeing operations and delivery for a highly acquisitive company. The conversation focuses on the practical, present-day applications of Artificial Intelligence (AI) in the legal industry, examining how it's moving beyond "innovation theater" to drive ROI, efficiency, and cost reduction in corporate legal departments.

Key Discussion Points:

• The Transition: Meredith's journey from finance to operations, tech, and ultimately, a leadership role at Consilio.

• Revenue Operations vs. Chief Revenue Officer (CRO): Defining the roles and how to build a robust revenue organization, particularly in an acquisitive company.

• Improving Delivery from a Revenue Background: The importance of client listening and how a revenue-centric mindset can enhance service delivery and collaboration between sales and operations teams.

• AI in Legal: Clients view AI as both a problem and a solution. Discussion covers where real adoption is happening today (e.g., contract review, eDiscovery review) and the internal pressures on corporate legal departments to show AI efficiency.

• The AI Skills Gap and Literacy: Addressing the need for AI literacy among legal professionals and how Consilio is adding value through guided expertise, innovation labs, and rapid prototyping.

• Consilio's AI Offerings: A look at tools like Aurora, ECI (Early Case Intelligence), and specialized AI suites for privilege identification (PrivGen), review, and investigations, emphasizing flexibility and a secure, private cloud environment.

This episode features a conversation with Cecilia Ziniti, Co-Founder and CEO of GC.AI. Cecilia traces her career from early the early days of the internet to founding an AI-driven legal platform for in-house counsel.

Cecilia shares her journey, starting as a paralegal at Yahoo in the early 2000s, working on nascent legal issues related to the internet. She discusses her time at Morrison & Foerster and her role at Amazon, where she was an early member of the Alexa team, gaining deep insight into AI's potential before the rise of modern large language models (LLMs).

The core discussion centers on the creation of GC AI, a legal AI tool specifically designed for in-house counsel. Cecilia explains why general LLMs like ChatGPT are insufficient for professional legal work—lacking proper citation, context, and security/privilege protections. She highlights the app's features, including enhanced document analysis (RAG implementation), a Word Add-in, and workflow-based playbooks to deliver accurate, client-forward legal analysis. The episode also touches on the current state of legal tech, the growing trend of bringing legal work in-house, and the potential for AI to shift the dynamics of the billable hour.

 

In this episode, Sabastian Niles, President and Chief Legal Officer at Salesforce, takes a deep dive into the intersection of corporate strategy, in-house legal careers, and the transformative power of Agentic AI.

Sabastian shares his unique career path from a near two-decade tenure at a prestigious law firm before joining Salesforce. This conversation is essential for anyone interested in the evolving role of the Chief Legal Officer and the practical application of cutting-edge technology in legal operations.

Things We Talk About in this Episode

• The In-House Career Journey: Sabastian's path highlights an early interest in the law and business connection and the role of the lawyer as a trusted advisor looking at the full lifecycle of a client's needs.

• Advice for Aspiring In-House Counsel: The importance of self-awareness, understanding your "why," and approaching your work with dedication and authenticity.

• Salesforce Legal as Customer Zero: How the Salesforce legal department uses the company's own technology, including building their outside counsel management platform on Salesforce and using internal AI agents in Slack channels for sales self-service.

• Understanding Agentic AI & Agentforce: An explanation of AI agents—systems that can reason and take actions on behalf of human direction—and Salesforce's focus on trusted agentics through the Agentforce Command Center.

• The Power of AI Guardrails: Sabastian explains that trust is an accelerant for innovation, not an obstacle. Guardrails define what an AI agent shouldn't do, ensuring responsible and ethical deployment, particularly around data access and defined roles.

• Legal Departments as an Accelerant, Not a Blocker: The vision for the optimized global legal department is one that is deeply embedded in product design, mitigating risk, and serving as a super connector across the entire organization.

• Regulation and Responsible Innovation in Artificial Intelligence: A discussion on the fast pace of tech innovation versus the speed of regulation, and why major tech companies must uphold high standards and embrace risk-based, interoperable approaches to drive responsible AI adoption.

Is artificial intelligence custom-made for legal tasks better than general AI tools like Google Gemini and ChatGPT? That is the topic of this episode featuring Legalbenchmarks.ai Founder Anna Guo. Anna is a former BigLaw lawyer who left the practice to become an entrepreneur and now focuses her energies on quantifying the utility of AI in the legal industry. Anna's initial anecdotal research for colleagues quickly revealed a strong community interest in a systematic approach to evaluating legal AI tools. This led to the creation of Legalbenchmarks.AI, dedicated to finding out where the promise of humans plus AI is truly better than humans alone or AI alone.

The core of the research involves measuring the "delta," or the extent to which AI can elevate human performance. To date, Legalbenchmarks.ai conducted two major studies: one on information extraction from legal sources and a second on contract review and redlining.

Key Findings from the Studies:

• Accuracy vs. Qualitative Usefulness: The highest-performing general-purpose AI tools (like Gemini) were often found to be more accurate and consistent. However, the legal-specific AI tools often received higher marks in qualitative usefulness and helpfulness, as they align more closely with existing legal workflows.

• Methodology: The testing goes beyond simple accuracy. It includes a three-part assessment: Reliability (objective accuracy and legal adequacy), Usability (qualitative metrics like helpfulness and coherence for tasks such as brainstorming), and Platform Workflow Support (integration, citation checks, and other features).

• Human-AI Performance: In the contract analysis study, AI tools matched or exceeded the human baseline for reliability in producing first drafts. Crucially, the data demonstrated that the common belief that "human plus AI will always outperform AI alone" was false; the top-performing AI tool alone still had a higher accuracy rate than the human-plus-AI combo.

• Risk Analysis: A significant finding was that legal AI tools were better at flagging material risks, such as compliance or unenforceability issues in high-risk scenarios, that human lawyers missed entirely. This suggests AI can act as a crucial safety net.

• Strengths Comparison: AI excels at brainstorming, challenging human bias, and performing mass-scale routine tasks (e.g., mass contract review for simple terms). Humans retain a significant edge in ingesting nuanced context and making commercially reasonable decisions that AI's instruction-following can sometimes lack.

Discussion Highlights:

• [0:00] – Introduction and background of Anna Guo and Legal Benchmarks AI.

• [4:30] – The impetus for starting systematic AI benchmarking.

• [6:00] – Explaining the concept of measuring the "delta" in performance.

• [9:00] – Detailed breakdown of the three-part AI assessment methodology.

• [15:00] – Discussion of the contrasting results: general LLM accuracy vs. legal AI qualitative value.

• [19:00] – Results on AI performance matching human reliability in contract drafting.

• [21:00] – Debunking the myth about Human + AI always outperforming AI alone.

• [23:00] – The finding that legal AI excels at surface material risks that lawyers miss.

• [27:00] – A SWOT analysis of when to use humans and when to use AI.

• [30:00] – Future roadmap for Legal Benchmarks AI research.

 

Justin Wales, Head of Legal for the Americas at Crypto.com, and author of The Crypto Legal Handbook visits the show to provide his unique perspective on pivoting from a career in Constitutional Law, including work on high-profile appellate cases like the Obergefell gay marriage decision, to becoming a trailblazer in crypto law and blockchain technology. 

He shares his serendipitous journey stemming from a law school article that launched his legal career and his subsequent deep dive into crypto, sparked by WikiLeaks accepting Bitcoin donations.

The discussion covers the evolution of his practice to one of the first successful crypto legal groups at a large law firm. Justin emphasizes the necessity for any lawyer in the space to use the technology and become a generalist to navigate the multi-jurisdictional and rapidly evolving industry. 

Finally, the conversation touches on the critical distinction between centralized finance (CeFi) and decentralized finance (DeFi), and his outlook that crypto's infrastructure will ultimately serve as the underpinning for future advancements like Artificial Intelligence (AI) and the Internet of Things (IoT).

Episode Highlights:

 * Justin's start in Constitutional Law, beginning with a law school paper on unconscionable cruise ship employment contracts that led to Supreme Court brief writing.

 * The shift to crypto law: WikiLeaks and Bitcoin's role in it introduced Justin to blockchain technology.

 * Building a pioneering crypto legal practice at a large firm in the early days (2013-2015).

 * Why the best in-house lawyers, especially in a cutting-edge field like crypto, need to be generalists, not hyper-specialized.

 * The inspiration and philosophy behind writing The Crypto Legal Handbook—creating an affordable, regularly updated, and candid resource for students and practitioners.

 * Advice for aspiring crypto lawyers today: the field is more mature and requires blending traditional financial regulatory expertise with an industry-wide approach.

 * The fundamental distinction between Centralized Finance (CeFi) and the legally complex, more innovative world of Decentralized Finance (DeFi).

 * Rule #1 for Crypto Lawyers: Why you must use the technology and the risks of lawyers who are frozen in time with their technical understanding.

 * High-level overview of US policy efforts to regulate crypto, including the GENIUS Act (Stablecoins) and the Clarity Act (Securities vs. Commodities regulation).

 * Justin's crystal ball: The long-term view that crypto infrastructure will eventually become an unseen layer beneath the rise of AI agents and IoT.

 

Things We Talk About in this Episode

 

 * Book: The Crypto Legal Handbook by Justin Wales

 * Book: Read Write Own by Chris Dixon

 * JustinWales.com (for more information on the book and author)

 

Ayana Dow, Senior Counsel at the DeFi Education Fund (DEF) shares her unique career trajectory from Big Law and Capitol Hill to the forefront of decentralized finance policy. The discussion centers on the critical need for regulatory clarity in crypto, the distinction between decentralized protocols and centralized entities, and the ongoing efforts to educate lawmakers on blockchain technology.

Key takeaways include an analysis of how current market structure bills might shift oversight to the CFTC and the importance of protecting software developers to ensure the continued innovation of DeFi systems.

Episode Highlights

• From Big Law to D.C. Policy: Dow discusses her transition from traditional M&A and regulatory work to policy-focused roles.

• Experience on the Hill: Insights from Dow's time as a policy fellow for Congressman Jim Clyburn and her internship at the CFTC.

• The Tennis Connection: How the real-time problem-solving skills learned as a collegiate tennis player apply to navigating shifting SEC guidance.

• The Crypto "Genesis Block": Why the potential for financial inclusion and "debanking" issues drew Dow to the crypto industry.

• Mission of the DeFi Education Fund: An overview of DEF's role as a nonpartisan advocacy group focused on sound policy and judicial education.

• Law Firm vs. In-House Policy: The structural challenges of conducting long-term policy work within the billable hour model of a traditional law firm.

• Why Focus on Developers?: Understanding why the DeFi Education Fund prioritizes the protection of software developers over specific tokens or protocols.

• Market Structure & Regulatory Harmonization: A breakdown of recent SEC and CFTC guidance and the future of congressional legislation.

• The Impact of Chevron Deference: Discussion on how the removal of Chevron deference changes how agencies and judges interpret financial laws.

 

 

Resources Mentioned

• DEF's Myth v. Fact Sheet on the BRCA (Link)

• A DEF blog post on the Promoting Innovation in Blockchain Development Act of 2026

• A DEF Letter to the SEC in response to Citadel Securities 

Avaneesh Marwaha, the CEO of Litera, visits the show to discuss his journey from IP lawyer to becoming a legal tech CEO and investor. He discusses the motivations behind his career pivot, including his desire to be a decision-maker and his passion for the business side of law.

The conversation delves into the evolution of Litera, from its origins as a document-focused migration software company to its current role as a comprehensive legal tech ecosystem. Avaneesh highlights the company's strategic shift from acquiring to building new technologies. He also emphasizes the importance of Litera's strong partnership with Microsoft and the company's focus on enhancing law firms' productivity and client service.

Key Takeaways:

• Pivoting from Law to Business: Avaneesh's move from practicing IP law to an in-house role and eventually becoming a CEO was driven by his desire for a more active role in business decision-making. He saw lawyers as reactive to business decisions, and he wanted to be at the forefront of the action.

• The Value of a Law Degree in Business: Avaneesh shares his perspective on the value of a law degree for business professionals, highlighting the critical thinking and risk tolerance skills it provides. He notes that the corporate transaction course he took in law school was particularly beneficial, teaching him about corporate governance and fiduciary duties.

• Litera's Evolution: Avaneesh discusses how Litera has grown through strategic acquisitions and a recent focus on internal development. He explains how the company integrates various tools, like Kira and Foundation, to create a seamless ecosystem for lawyers within their daily workflows, primarily in Outlook and Word.

• The Impact of Generative AI: The discussion touches on the transformative impact of AI on the legal tech industry. Avaneesh explains how AI has enabled Litera to accelerate its product development and introduce features that proactively assist lawyers with tasks like document comparison and client relationship management.

• Build vs. Buy Strategy: Avaneesh outlines Litera's shift from a buy-heavy strategy to a more balanced build-and-invest approach. This change is largely due to the increased efficiency and speed of development enabled by AI tools.

• Future of Legal Tech: Avaneesh shares his vision for the future of Litera, which includes a focus on "maniacal client service" and helping law firms proactively grow their business. He believes that as automation handles routine tasks, lawyers will have more capacity for business development and client-centric work.

Things We Talk About

• Kira Systems - A company acquired by Litera specializing in AI-powered contract analysis.

• Foundation Software - A business acquired by Litera focused on knowledge management.

• Doxly - A document formatting and repair tool.

 

A conversation with Ben Chiriboga, Chief Growth Officer at legal CRM company Nexl and host of the This Legal Life podcast. Ben shares his journey from a litigator to a legal tech innovator. He recounts how an early e-discovery tool using natural language processing completed in six hours what had taken him six months, leading to an epiphany about the power of legal technology.

The conversation delves into the legal industry's historical resistance to technology, prioritizing billable hours over efficiency, and how Ben leveraged his legal experience to transition into a new role in tech. Ben discusses the challenges of building a legal tech company and the critical distinction between a general CRM and one designed specifically for law firms. The episode concludes with a thought-provoking discussion on the impact of AI on the legal profession, focusing on what aspects of law are truly "fundamental" and what new roles and jobs AI will create.

Key Takeaways

• The Power of Tech: Legal tech tools can drastically improve efficiency, as demonstrated by an e-discovery tool that performed six months of work in just six hours.

• Transitioning Careers: A background in law can be a valuable asset in the legal tech sector, but success requires adapting to new skills like sales, marketing, and growth strategy.

• The "Why" Behind a Legal CRM: General CRMs are built for sales teams with built-in incentive structures, whereas a legal-specific CRM, like Nexle, is designed to passively collect and enrich data without requiring lawyers to manually input information.

• The Fundamentals of Law: The human element—relationship building, counseling, and strategic advisory—is the core function of a lawyer that AI cannot replicate.

• The Future of Legal Jobs: AI's true impact will not be in better-drafted motions, but in the creation of new "legal adjacent" roles and business models that merge legal expertise with technology and data.

We welcome back legal marketing expert Gyi Tsakalakis, President of AttorneySync and host of the Lunch Hour Legal Marketing podcast. Five years after Gyi's first appearance on Technically Legal, he discusses the dramatic shifts in digital marketing for law firms, driven largely by the rise of artificial intelligence.

Gyi highlights how AI is changing the landscape for lawyers, from automating back-office functions and data analysis to influencing content creation and search engine optimization (SEO). He explains why law firms must diversify their marketing channels beyond just Google to adapt to the new era of conversational search and AI overviews. Despite these technological advances, Gyi emphasizes that the human connection, including a simple handwritten note, remains the most powerful tool in an attorney's arsenal. He argues that as technology automates the mundane, it forces lawyers to focus on the relationships and empathy that truly differentiate their practice.

Key Takeaways:

• Diversify Marketing Channels: Law firms must move beyond a "one-trick pony" approach with platforms like Google and diversify their client acquisition strategies to include social media, email, and local events.

• The Problem with Client Intake: Gyi discusses the persistent issue of lawyers not responding to inquiries and how AI can help automate certain parts of the intake process, though the human touch is still crucial for building trust.

• Do What the Bots Cannot: Attorneys should leverage AI for tasks that can be automated (e.g., scheduling, data analysis) to free up time to focus on complex legal work and building meaningful client relationships.

• AI for Data Analysis: A powerful, overlooked use case for AI in a law firm is analyzing internal data, such as call transcripts and financial records, to identify blind spots and inform marketing strategies.

• The Future of SEO and Search: Gyi predicts that search will become more conversational and influenced by AI Overviews and that ad-based models will be integrated into all major AI platforms.

 

This episode features a conversation with Andrea Muttoni, President of Story Protocol. The discussion explores how blockchain technology is being used as a foundational infrastructure for intellectual property (IP), aiming to simplify and modernize the process of registration, licensing, and monetization for creators and IP owners. Muttoni details his journey from a bedroom music producer to a product manager at Amazon and eventually to a leader in the blockchain industry, driven by a passion for the intersection of technology and creativity.

The conversation delves into the core problems Story Protocol aims to solve, particularly the complexities of copyright, fair use, and attribution in the age of AI-generated content. Muttoni introduces key concepts like the Programmable IP License (PIL), a customizable and on-chain license that makes IP rights more transparent and accessible. He also provides an overview of Poseidon, a new initiative that leverages the Story Protocol to create a marketplace for IP-safe, real-world data needed to train AI models, ensuring that data creators and owners are fairly compensated.

Key Takeaways

• Andrea's Background: From a bedroom hip-hop producer to a product manager at Amazon working on Kindle and Alexa, Muttoni shares his path to the world of crypto and blockchain.

• What is Story Protocol?: A deep dive into Story Protocol's mission to create an open IP blockchain. It's a way to register, license, and monetize IP in a more liquid and accessible way.

• The Programmable IP License (PIL): Explanation of how this universal, customizable, and on-chain license simplifies IP transactions and makes it easier for others to legally use a creator's work.

• Introducing Poseidon: Details on the new platform built on the Story Protocol to address the "data gold rush" for AI. Poseidon allows for the licensing of real-world, IP-cleared data to AI companies, ensuring fair compensation for contributors.

• Promoting Adoption: Discussion on how Story Protocol uses a web3 incentive model to encourage widespread adoption and create a network effect for its IP infrastructure.

• Why Story Protocol?: Muttoni explains what makes their platform uniquely suited for IP rights compared to other blockchains, emphasizing that the network was built from the ground up specifically for this use case.

Things We Talk About in this Episode

• Story Protocol: story.foundation

• Story Protocol IP Portal: portal.story.foundation

• Poseidon: psdn.ai

• Story Protocol Developer Docs: docs.story.foundation

• WIPO Report: A report on intangible assets, mentioned as a key indicator of the value of intellectual property.

 

Crypto lawyer Nelson Rosario returns to the show to discuss the evolving landscape of decentralized AI and his role as General Counsel for the the Advanced AI Society (formerly known as the Decentralized AI Society), an association focused on engineering best practices, advocating for policy, fostering community, and enabling capital formation for decentralized AI startups

Nelson discusses the changing definition of decentralization, highlighting its origins in early crypto's focus on resilience and censorship resistance, and its current intersection with artificial intelligence. He explains the core reasons driving decentralized AI efforts: the potential for single service providers to control our access to AI models, computing power, and the data that underlies it all.

The conversation explores how decentralized AI aims to offer an alternative to large tech companies like Facebook, Microsoft, and OpenAI,  But Nelson also points out the challenges of competing with resource rich organizations and suggests that decentralized AI might complement existing systems by "chopping it up" into distributed components. 

The discussion also touches upon current players in the decentralized AI space, notably Bitensor and HyperCycle, and highlights the role of decentralized storage solutions like Filecoin and Arweave.

Nelson concludes by reflecting on the potentially profound societal impact of AI, likening it to other "tectonic technological revolutions" in human history. Drawing from the "Butlerian Jihad" concept in Frank Herbert's Dune, he cautions against blindly trusting AI and underscores the need for humans to remain intentional in their use of technology to prevent a decline in critical thinking and creativity.

Key Takeaways:

• Decentralization in AI aims to prevent single points of control over models, compute, and data, promoting censorship resistance.

• Decentralized AI faces challenges in competing with large, centralized tech companies due to their immense resources, but can serve as a complementary set of systems.

• DePIN (Decentralized Physical Infrastructure) is crucial for the robust existence of decentralized AI applications.

• Industry associations like the Advanced AI Society play a vital role in setting standards, advocating for policy, building community, and attracting capital for decentralized AI projects.

• AI represents a transformative technological shift, and intentional human engagement is critical to navigate its societal implications.

In this episode, Dave Siegfried discusses the company he heads, Official AI -- a company focused on helping its customers create and verify authentic AI content. Siegfried, a "recovering accountant" with a background in tech and media licensing, discusses his journey from co-founding Audiosocket, a music licensing platform, to addressing challenges in generative AI.

The conversation highlights the evolution of intellectual property protection in the digital age. Siegfried explains how Official AI empowers individuals and brands to create AI-generated images and videos with consent, credit, and compensation for the use of their name, image, likeness, and voice. He details Official AI's "vault technology," which creates a "blueprint" of a person's likeness from a small set of images, enabling authorized creation of synthetic media.

The discussion also delves into provenance technology and the Coalition for Content Provenance and Authenticity (C2PA) open-source standard, which Official AI leverages to track content origin and changes, ensuring authenticity. Siegfried touches on the challenges of verifying content on social media platforms and the future role of blockchain technology in creating immutable records of consent. The episode concludes with insights into Official AI's business model, customer base (including athletes and historic estates), and future roadmap.

Key Takeaways:

• Generative AI presents significant challenges and opportunities for intellectual property rights, particularly concerning name, image, likeness, and voice.

• Official AI aims to proactively address these challenges by providing a platform for consent-based AI content creation.

• Provenance technology, including C2PA, is crucial for verifying the authenticity and authorized use of AI-generated content.

• The legal landscape surrounding AI and publicity rights is rapidly evolving, requiring adaptable technological solutions.

Things We Talk About in this Episode

• Official AI Website: Visit theofficial.ai to learn more about their platform and services.

• Contact Dave Siegfried: Dave can be reached at dave@theofficial.ai.

• Content Authenticity Initiative (C2PA): Explore the open-source standard for content provenance and authenticity at c2pa.org.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

This episode is a conversation with Spellbook co-founder Scott Stevenson about intersection of technology and creativity. Spellbook is a AI contract co-pilot for transactional lawyers that plugs into Microsoft Word. Despite founding a legal technology company, Scott is not a lawyer but is computer engineer by training.

As a kid Scott was into video games and in fourth grade he talked his parents into getting him a computer because he wanted to figure out how to create them. By middle school he was building websites and eventually landed an internship at Electronic Arts.

Scott is also interested in electronic music and he launched his first start up, Mune, with a music professor, to create a whole new musical instrument that combined the power of digital music with an acoustic instrument. It was during his time at Mune that Scott started to think about building a legal tech company.

After he got his first legal bill he figured there might be a more efficient and less expensive way to do legal work. So he and lawyer buddy founded Rally, a document automation and templating engine for law firms which later begat Spellbook, but he funny thing about Spellbook, it was originally conceived as a marketing idea to generate leads for Rally.

 

Things We Talk About in This Episode

 

Mune (Scott's Digital Instrument Startup)

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

A conversation with Kelly Twigger, an E-Discovery veteran and founder of ESI Attorneys and Minerva26. Kelly shares her journey into E-Discovery, stemming from the first-ever ABA event on the topic in the early 2000s, and the rapid evolution of case law and technology that led her to develop E-Discovery Assistant which has now been rebranded Minerva 26.

The discussion delves into how Minerva 26, a strategic command center for E-Discovery, curates case law, rules, checklists, and offers on-demand education. Kelly explains the reasoning behind rebranding from "E-Discovery Assistant" to "Minerva 26," emphasizing the shift from data tools to knowledge and strategic insight. The conversation also explores the current challenges legal professionals face in adopting technology, the impact of AI on the legal industry, and the need for updated federal rules of civil procedure to address technological advancements.

Key Takeaways:

• Proactive E-Discovery: The importance of engaging with E-Discovery issues early in a case to save time and money, and to maximize the utility of electronically stored information (ESI).
• Technology's Transformative Power: ESI, unlike paper, offers immense opportunities to leverage technology for more efficient and effective legal analysis and fact-finding.
• Overcoming Fear and Expense: The primary barriers to technology adoption in the legal field are fear and perceived expense, which can be overcome through education and strategic planning.
• AI's Role in Legal: AI is not replacing lawyers but enhancing their capabilities by improving efficiency, accuracy, and providing valuable insights.
• The Need for Rule Updates: The rapidly changing technological landscape necessitates updates to the Federal Rules of Civil Procedure to provide clarity and consistency, especially concerning issues like control over personal devices and the use of advanced E-Discovery tools like Technology Assisted Review (TAR).

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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Studies determined that at least one litigant does not have a lawyer in 75% of civil cases in the United States. The number is even higher when it comes to family law, domestic violence, housing, and small claims matters.

But organizations like Oregon's Commons Law Center are doing something about it. On this episode, Kamron Graham, the Law Center's Executive Director, talks about the not for profit law firm's efforts to provide affordable legal assistance to people that make too much to qualify for legal aid, but don't make enough to hire a lawyer.

The Commons Law Center helps out people facing evictions, have family law issues or need help with wills and estate planning.

Kamron initially planned to pursue a career in finance but pretty quickly figured out that her empathy and concern for others probably might not jibe with a Wall Street career. After returning to Oregon after college in the Northeast, Kamron started her career working in group homes, homeless shelters and served a stint with the United Way.

These experiences made clear to her that a professional degree might help her have a greater impact on people's lives and give her even more of an opportunity to use her education to help others. So, in her 30s she decided to go to law school. 

After law school continued her career helping the underserved, including work for Legal Aid Services of Oregon and work as a public defender.

Eventually she landed at the Commons Law Center, starting as a tenant defense attorney and ascending to the role of executive director. 

The business model of the Commons Law Center is not free legal work, but charging a sliding scale fee based on a client's income. Currently 70% of the firm's budget comes from fees. The firm is working to become 100% self-sufficient, but in the meantime to fill the gap, the firm leverages tech to streamline their processes and keep costs down. It also relies on donors, foundations, and grants. 

Learn more about Kamron.

A conversation with Bim Dave, CEO of Helm 360, a consultancy focused on helping law firms optimize technology investments. Bim shares his experience in the legal tech space, tracing his journey from a technical support role at Elite (later acquired by Thomson Reuters) to leading a consultancy dedicated to improving law firm operations through strategic technology implementation. The discussion covers the critical aspects of data migration, the benefits smaller law firms can derive from technology, key factors for successful software implementation, and perspectives on hyped versus underutilized technologies in the legal field. Bim also offers a glimpse into the potential future of law firms, emphasizing the transformative role of AI.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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Kara Peterson and Richard DiBona, the husband-and-wife co-founding team behind Descrybe, discuss the legal research platform they built designed to "democratize access to the law." The discussion explores the unique dynamics of married cofounders and how they are leveraging Generative AI to disrupt a landscape long dominated by high-cost legacy providers.

Richard, a software engineer, and Kara, a marketing expert, share their journey from a personal legal issue to building a platform that processes over 100 billion tokens of legal data. They explain why they chose to build an AI-native system from the ground up rather than simply layering a "wrapper" over existing models—a decision that allows them to offer professional-grade tools at a fraction of the traditional cost.

In this episode, they discuss:

🔷 Why legacy legal research platforms have maintained such strong moats—and how AI changes that

🔷 The difference between "wrapper" AI tools and building a system from the ground up

🔷 How their structured, multi-step reasoning process improves accuracy and reduces hallucinations

🔷 What benchmarking against the Bar Exam reveals about legal AI performance

🔷 Where Descrybe is headed as they expand their toolkit

A conversation with Yelena Shkolnik, a partner at Jump Capital, a venture capital firm with growing interest in legal tech companies. Yelena shares her journey from investment banking and entertainment finance to the world of venture capital, highlighting her focus on identifying transformative technologies.

The conversation delves into Jump Capital's investment philosophy, particularly their thematic approach and focus on Series A and B funding rounds. Yelena articulates what makes a legal tech company attractive to Jump, emphasizing the importance of demonstrated traction, a strong team dynamic, and a deep understanding of the specific challenges and opportunities within the legal industry. 

Yelena provides a nuanced perspective on the billable hour model and the potential for technology, including AI, to reshape legal workflows and access to justice. She also shares her thoughts on the necessity of legal background for founders and whether legal tech will eventually just become "tech".

Key Takeaways:

• A deep understanding of the legal industry's nuances and specific problems is crucial for attracting legal tech investment.

• While AI presents significant opportunities, the entrenched nature of law firms and the complexities of legal workflows require thoughtful and targeted solutions.

• The rise of legal operations within enterprises is driving demand for technologies that enhance efficiency and manage risk.

• The consumer side of legal tech holds significant potential for expanding access to justice.

Amanda Tuminelli, Chief Legal Officer for the DeFI Education Fund, visited the podcast in September to discuss her crypto journey, her role with the organization and its objectives.

Since then, she was promoted and is now the Executive Director of DEF which is a nonpartisan research and advocacy group working to explain the benefits of DeFi, achieve regulatory clarity for the future of the global digital economy, and help realize the transformative potential of DeFi for everyone.

Amanda goes in depth into the DEF's areas of focus:

• Research and Advocacy

• Policymaker Education

• Messaging for Crypto Companies

• Research about Blockchain Issues and Regulations

• Providing "Legal Firepower" to Crypto Causes; and

• DeFi Project Best Practices

Amanda also discusses how lawyers can pursue a career in crypto and why that wasn't the case a few years ago. It's not only an option now because the industry is more mature, but also because of the openness of those in the crypto world and their desire for passionate individuals to join them. To get a job in crypto law, Amanda emphasizes the importance of understanding the technology and finding projects of interest. 

So how did Amanda get to the DEF? She started out as a securities and white collar crime lawyer, but a case came along that would change her career trajectory. She was working for Kobre and Kim, a law firm focused on disputes and investigations, when the firm was hired by a client accused of running an illegal crypto mining scheme. To get up to speed on the case and get her client out of jail, she had to dive deep into learning about blockchain technology and that is when she caught the bug. A few years later, a friend and former college friend contacted her about joining the legal team at the DeFI Education Fund and she took them up on it.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

In this episode, author of "Systemology" and business systems expert, David Jenyns, discusses the importance of systemizing business processes, even in the nuanced field of law. Jenyns debunks the myth that legal work is too bespoke to be systemized, explaining how just like any other business, documenting legal workflows unlocks scalability and creativity. He shares his journey from digital SEO agency owner to becoming a systems expert and outlines the seven steps of his Systemology framework.

• Key Topics:

• The importance of documenting processes in any business, including legal services.

• How systemization can create space for creativity in legal work.

• The Systemology framework and its seven steps: Define, Assign, Extract, Organize, Integrate, Scale, and Optimize.  

• The role of a "systems champion" in implementing a systems culture.

• Addressing common misconceptions about systemizing legal work.

• Practical tips for getting started with systemizing processes.

• Timestamps:

• [00:00:00] Introduction and guest introduction: David Jenyns

• [00:02:00] David Jenyns's background and journey to systemology

• [00:08:00] The importance of a systems culture

• [00:12:00] Addressing the question: Why systemize?

• [00:15:00] Systemizing bespoke work, specifically in the legal field

• [00:20:00] The seven steps of Systemology

• [00:21:00] Step 1: Define

• [00:28:00] Step 2: Assign

• [00:30:00] Step 3: Extract

• [00:33:00] Step 4: Organize

• [00:37:00] Step 5: Integrate

• [00:46:00] Step 6: Scale

• [00:50:00] Step 7: Optimize

• [00:54:00] Where to start with systemizing processes

• [00:56:00] Conclusion

• Resources Mentioned:

• Systemology by David Jenyns

• System Hub software (systemhub.com)

• The E-Myth by Michael Gerber

• Systemology Podcast (Mentioned interview with Crow Estate Planning firm

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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A conversation with Sean Fitzpatrick, CEO of LexisNexis, North America, UK, and Ireland. Fitzpatrick discusses how LexisNexis is integrating AI into its products to enhance legal practice. The discussion covers the company's approach to innovation, the role of AI in improving attorney efficiency and client outcomes, and the future of legal technology. Key topics include LexisNexis's AI assistant "Protégé," the company's philosophy on AI, and the impact of AI on the legal profession.

• [0:09-1:43] Introduction to Sean Fitzpatrick and LexisNexis's focus on AI in legal tech.
• [2:05-4:37] Fitzpatrick's career journey at LexisNexis and the evolution of the company's technology.
• [7:48-8:20] LexisNexis's philosophy on AI: to make attorneys more efficient and drive better outcomes.
• [8:20-10:24] Overview of LexisNexis's AI tools, including Protégé and its features (drafting, Vault, etc.).
• [11:46-12:45] LexisNexis's partnership with OpenAI and its benefits.
• [15:14-16:01] The importance of data in AI and LexisNexis's approach to ensuring reliability and combating hallucinations.
• [16:30-17:37] Explanation of agentic AI and its significance for the legal field.
• [19:05-19:31] The role of document management systems (DMS) and LexisNexis's integration with them, including the acquisition of Henchman.
• [24:17-25:39] Discussion on the impact of AI on legal jobs and the belief that AI will augment, not replace, lawyers.
• [27:30-28:27] Fitzpatrick's prediction on the rapid advancement and adoption of generative AI in the legal industry.

A conversation with Jaron Luttich, co-founder of Element Standard, a legal tech startup designed to bring transparency and organization to litigation. Jaron discusses how Element Standard's "CONTROLit" app and litigation cartography help litigators manage cases, improve client communication, and streamline internal processes. He highlights the disconnect between traditional legal practices and modern client expectations for transparency, drawing comparisons to consumer experiences like ride-sharing and package tracking. Jaron also addresses how the litigation management software can enhance associate training and provide valuable structured data for law firms. The company will be participating the ABA Techshow 2025 Startup Alley.

Things We Talk About in this Episode

• elementstandard.com

• Jaron Luttich's LinkedIn profile

• CONTROLit™ by Element Standard - Legaltech Hub

• Element Standard's LinkedIn page.

 

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

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This episode involves two people with very distinguished careers. Bridget M. McCormack who now heads the American Arbitration Association (AAA) and Colin Rule, the founder of ODR.com just acquired by The AAA.

Bridget has served in just about every role you can in the legal industry. She started her legal career in legal aid and as a public defender handling trials and appeals. She then moved to teaching law school, first at Yale and then Michigan.

After her stint as an educator, she decided she wanted to help foster even more change and won a seat on the Michigan Supreme Court where she ultimately ascended to the position of Chief Justice. Fast forward to 2023 and she took the helm of the AAA.

One of Bridget's biggest initiatives at AAA is bringing tech into the arbitration process and that is where Colin Rule comes in. He founded an online dispute resolution (ODR) company, about 15 years ago that ultimately became ODR.com which the AAA just announced it was acquiring.

To say that Colin is an ODR OG is an understatement. He literally wrote the book on ODR way back in the early days of the internet. Ebay brought him on board in the early 2000s where he headed up the company's ODR function.

In this episode Bridget and Colin discuss: 

• AAA's acquisition of ODR.com: The strategic partnership between AAA and odr.com to revolutionize dispute resolution.

• AI's transformative role in dispute resolution: How AAA is using AI internally and through external tools to improve efficiency and accessibility.

• The future of dispute resolution: A vision for a more accessible, efficient, and user-friendly system that leverages technology and data.

 

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

This episode features Daniel Rollingher, co-founder of Fabrica, a company leveraging blockchain technology to revolutionize real estate ownership. Rollingher discusses Fabrica's innovative approach to putting real estate titles on chain, creating a more transparent and efficient system for property transactions. He explains how Fabrica's platform uses NFTs to represent property ownership, simplifying the process of buying, selling, and managing real estate assets.

The conversation also explores the legal framework behind Fabrica's blockchain real estate platform, including the use of trusts and smart contracts to ensure secure and verifiable ownership. Additionally, Rollingher touches on the use of blockchain in real estate to address challenges in the traditional real estate market, such as title insurance and liquidity issues.

Key Takeaways:

• Fabrica uses NFTs to represent real estate ownership, streamlining transactions and property management.

• The platform employs a unique trust model to connect on-chain ownership with real-world legal frameworks.

• Fabrica aims to improve transparency and efficiency in real estate transactions through blockchain technology.

• The company is exploring the potential of blockchain and real estate to disrupt traditional processes, such as title insurance and recording deeds.

• Fabrica's platform offers solutions for unlocking liquidity in land assets and other real estate holdings.

• The company is actively working on expanding its blockchain real estate platform to new jurisdictions and asset classes.

Resources/Links:

• Fabrica website: fabrica.land

• Daniel Rollingher on Twitter: @notdroll

 

Jack Weinberger, co-founder of Ajax, a legal tech app that handles timekeeping for lawyers, shares his unconventional journey from finance to legal tech. Jack discusses his experiences in investment banking and private equity, and how those roles, while not directly related to law, sparked his interest in entrepreneurship and ultimately led him to the world of legal tech. He details the challenges of building a legal tech company, emphasizing the importance of understanding the specific needs of lawyers and addressing the critical concerns of data security. Jack also provides insight into Ajax's innovative approach to timekeeping, which uses AI to automate the process of generating time entries by analyzing a lawyer's activity on their computer. He explains how Ajax integrates with popular practice management software and highlights the significant time savings and increased accuracy that Ajax offers to legal professionals. Finally, Jack shares some exciting upcoming features that Ajax is developing, including capturing impromptu conversations and further streamlining the user experience.

Key Takeaways

• Career transitions from finance to legal tech are possible, highlighting the transferable skills and entrepreneurial spirit.

• Building successful legal tech solutions requires a deep understanding of lawyer workflows and pain points, with timekeeping being a major one.

• Data security is paramount in legal tech, and companies must prioritize client confidentiality.

• AI is transforming legal practice by automating tasks like timekeeping, allowing lawyers to focus on higher-value work.

Additional Information

• Ajax website: https://www.joinajax.com/

• Learn more about Jack. 

 

This episode features Tom Dunlop, founder of Summize, a contract lifecycle management (CLM) platform. Tom discusses his unique path to founding Summize, from his background as a professional athlete and lawyer to his passion for solving real-world problems with technology.

Key takeaways:

• The genesis of Summize: Tom explains how his experience reviewing hundreds of contracts manually led to the idea for Summize.

• Early challenges and the evolution of AI: Tom describes the initial challenges of summarizing contracts using AI in 2018 and how the advent of generative AI has revolutionized Summize's capabilities.

• Summize's unique approach: Summize differentiates itself by embedding its functionality within popular workplace tools like Slack, Teams, and Microsoft Word, allowing users to manage contracts without leaving their familiar workflows.

• How Summize works: Tom explains how Summize uses AI to curate contract data and provide summaries that are relevant and tailored to specific business needs.

• The future of Summize: Tom shares his vision for the future of Summize, including plans to further leverage AI, enhance native integrations, and incorporate validated content from the legal community. 

Resources and Links:

• Summize Website: summize.com

• Connect with Tom on LinkedIn

Keywords: legal tech, contract lifecycle management (CLM), AI, generative AI, contract summarization, legal technology, Summize, Tom Dunlop, Microsoft Word, Slack, Teams, Outlook, DocuSign

A conversation with Lucas Moskowitz, General Counsel for financial services company Robinhood. Launched in 2013, Robinhood's stated mission is to "democratize finance for all" by making it easy for investors to start investing with a few bucks rather than having to be a high roller. Key to this effort is the fact that Robinhood offers commission-free trading and also provides access to cryptocurrencies.

The discussion covers various topics, including:

• Robinhood's Mission: Lucas explains Robinhood's mission to democratize finance by breaking down barriers to investing and making it accessible to everyone, regardless of their financial background.

• Lucas's Career Path: Lucas shares his unique career journey, transitioning from big law to the SEC, Capitol Hill, and eventually Robinhood. He emphasizes the importance of diverse experiences in shaping his perspective.

• Regulation in the Financial Industry: Lucas advocates for a data-driven approach to regulation, striking a balance between investor protection and fostering innovation and access.

• Crypto & Blockchain: The potential of crypto and blockchain technology is explored, with Lucas highlighting their role in making financial markets more efficient.

• Education: The importance of educating investors about making sound investment decisions and also educating legal professionals about emerging technologies like blockchain and tokenization of assets.

Stay in the know:

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Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

The legal industry is not confronting a single disruption but a redistribution of work, capital, and regulation across a system under stress.

The boundaries of Unauthorized Practice of Law (UPL) in the near term may be defined more by what regulators must allow than what they restrict.

These are just a couple of conclusions from author and legal business strategist Ken Crutchfield in a recent trilogy of articles he penned about the pressure artificial intelligence is placing on legal service delivery and regulations barring the unauthorized practice of law. 

In this episode, Ken is joined by Indiana University Mauer School of Law Professor, Bill Hendersonand ethics attorney Jim Doppke to discuss how Generative AI and Large Language Models (LLMs) are disrupting the legal industry.

The conversation focuses on the shifting boundaries of UPL regulation and how technology is redistributing legal work from traditional law firms to consumers and Alternative Legal Service Providers (ALSPs).

The panel explores the "Uberization" of UPL rules—where technology precedes regulation—and the tension between protecting the public from "bad" AI advice and yet leveraging these tools to bridge the massive Access to Justice gap.

Things We Talk About in this Episode

• The ROI of AI: Significant investment in legal tech is driven by the potential to replace labor with technology, rather than just replacing older software.

• Defining the Line: Regulators are struggling to distinguish between providing "legal information" (permissible) and "legal advice" (restricted).

• The "Whole Product" Solution: While AI can generate drafts, it often lacks the "tacit knowledge" and human trust required to navigate the Byzantine court system.

• Regulatory Shift: Rather than banning LLMs, regulators are increasingly focused on holding individual lawyers accountable for the "wrong" use of technology (e.g., failing to verify AI-generated citations).

• Allied Legal Professionals (ALPs): Emerging roles, like those being piloted in Indiana, may serve as a human bridge between AI-driven tools and underserved populations.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

In this Best of 2024 episode, we revisit our conversation with Scott and Digby Leigh, founders of AltFee—a legal tech startup tackling one of the industry's biggest challenges: the billable hour.

Despite decades of debate, the billable hour still dominates legal billing. Enter AltFee. The app helps legal professionals scope, price, and manage projects using alternative fee arrangements (AFAs), offering clients more transparency and value.

Scott and Digby highlight why AFAs matter now more than ever: as AI reduces time spent on tasks, value-based pricing will become essential. AltFee provides a foundation for law firms to shift away from time-based billing, encouraging lawyers to focus on the actual value of their services—not just the clock. From scoping projects to auditing fees, this conversation explores the future of legal pricing and how AFAs can reshape client relationships for the better.

If you're curious about innovation in legal tech, or if you're tired of the constraints of hourly billing, this episode is a must-listen.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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What does it take to build a successful legal tech startup?   In this Best of 2024 episode, we revisit our conversation with Zach Posner, co-founder of the LegalTech Fund, an investment fund focused on supporting innovative legal technology companies.
Zach's unique perspective on legal tech investing is rooted in his broad experience, including building an education tech company acquired by McGraw Hill. During our conversation, he shares valuable insights into what makes startups thrive. From the importance of transparent investor updates to fostering frequent, meaningful customer interactions that guide product development.   We also explore the LegalTech Fund's investment focus:

• Tools leveraging contracting data for business insights
• Tech solutions expanding access to legal services

Whether you're an entrepreneur, an investor, or simply interested in the evolution of legal tech, this episode is full of practical advice and inspiring insights.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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In one of the most popular episodes of 2024, John Grant talks about how legal teams can adopt Agile and Kanban project management methodologies to optimize workflows, correct bottlenecks and increase client satisfaction. John is a lawyer and the founder of The Agile Attorney consultancy.

As John explains, the traditional project management method is waterfall. A technique often used by technology companies, involving a sequential approach where each stage is dependent on the completion of the previous one.

But John is a proponent of the newer, Agile methodology, which emerged from the software development community. It is a flexible approach where tasks are broken down into small increments with minimal planning, and processes are iterative. Agile is one of John's favorites because he believes it is well suited for legal work.

John also talks about the value of a Kanban board, a visual tool used to manage work at various stages of a process. It typically includes columns such as "To Do," "Doing," and "Done".

So why is he so into project management methodologies? Because despite coming from a long line of lawyers, before he went to law school, he first worked in tech.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

Conrad Everhard, founder of Flatiron Law Group discusses his career trajectory from Georgetown University to becoming a partner at Big Law firms Jones Day and Brian Cave. He explains why he left BigLaw to found Flatiron Law Group, to provide a more cost effective and efficient way to offer legal services to clients involved in mergers and acquisitions.

To do so, the firm leverages a multi-pronged model: flat fees, low overhead, general contract labor to assist with the more labor intensive parts of an M&A deal, and advanced technology, including the firm's own custom build Deal Driver software that provides the clients with data and other insight about the deals they are working on.

Conrad also talks about his work with Stanford's Codex project, where he is helping develop an AI based negotiation simulator to train young lawyers in M&A deals. He highlights the importance of capturing the decision-making process of senior lawyers to effectively guide the AI model.

Key Discussion Points & Timestamps:

Transition from Big Law to Entrepreneurship: [0:40 - 13:03]

The Flatiron Model: [14:16 - 26:48]

Work with Codex and AI in Legal Training: [26:48 - 33:00]

Resources & Links:

Flatiron Law website: flatiron.legal

Episode Credits

Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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This episode features Stan Shepard, General Counsel of Atlassian, a leading provider of team productivity and collaboration software. Stan discusses his unique career journey from a finance journalist to the current GC of Atlassian. He shares valuable insights into how Atlassian's legal department leverages the company's productivity software products and AI for maximum efficiency.

Episode Highlights:

[00:00:09]: Introduction and Stan's background - Learn about Stan's journey from finance journalist to lawyer at Charles Schwab, and eventually to his current role at Atlassian.

[00:04:00]: Why Stan transitioned from journalism to law - Discover his motivations for pursuing a legal career, including the desire for greater impact and client interaction.

[00:07:00]: The growth of Atlassian's legal department - Hear how the legal team has expanded significantly alongside the company's rapid growth, particularly during the pandemic.

[00:12:39]: How Atlassian's legal team uses their own products - Stan explains how Atlassian's legal department utilizes Jira, Confluence, and other tools to streamline workflows and improve collaboration.

[00:14:10]: AI routing of legal requests - Discover how AI automates the process of routing incoming legal requests to the appropriate specialists.

[00:17:02]: Atlassian's new AI product, Rovo - Learn about Rovo's search, chat, and agent capabilities, designed to enhance teamwork and efficiency.

[00:23:31]: Advice for legal departments adopting AI - Stan provides practical guidance on how legal teams can effectively integrate AI into their workflows.

[00:24:29]: Responsible AI implementation - Stan emphasizes the importance of approaching AI adoption with a focus on ethical considerations and mitigating potential biases.

[00:28:16]: Atlassian's involvement with BSA | The Software Alliance - Learn about Atlassian's advocacy work in the global software industry and their efforts to shape responsible tech policy.

Key Takeaways:

• Embrace continuous learning: Stan's career path underscores the importance of adaptability and a growth mindset.
• Leverage technology for efficiency: Atlassian's legal team exemplifies how technology can optimize legal workflows and improve collaboration.
• Adopt AI responsibly: Stan highlights the need for a thoughtful and ethical approach to AI implementation.

Resources Mentioned:

• Atlassian: www.atlassian.com
• Jira: Atlassian's project management software.
• Confluence: Atlassian's knowledge management software.
• Loom: Atlassian's asynchronous video messaging tool.
• Rovo: Atlassian's new AI product with search and chat functionality.
• Responsible Tech Review Template: A guide for responsible AI development. (Available on Atlassian's website)
• BSA | The Software Alliance: bsa.org

Connect with Stan Shepard:

LinkedIn: Stan Shepard

  Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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New Era ADR CEO Rich Lee makes a return appearance to Technically Legal to talk about the company's cutting-edge platform revolutionizing dispute resolution. Rich first came on the podcast in 2021 right as the company launched. Rich discusses the company's mission to provide a faster, more efficient, and cost-effective alternative to traditional litigation and arbitration, the company's growth and what he has learned from a few years in.

Key takeaways:

• New Era ADR offers a unique platform for resolving disputes in under 100 days, significantly faster than traditional methods.  

• The platform leverages technology to streamline processes, reduce costs, and enhance accessibility for all parties involved.  

• New Era ADR boasts a diverse pool of experienced and qualified neutrals, ensuring fair and impartial resolutions.  

• The company's commitment to innovation is evident in its use of data and technology to drive efficiency and transparency.

Timestamps:

• [00:00:00] Introduction and recap of New Era ADR

• [00:01:30] Discussion of the platform's features and benefits

• [00:05:00] How New Era ADR addresses common dispute resolution challenges

• [00:10:00] The importance of social proof in legal innovation

• [00:15:00] Attracting and recruiting qualified neutrals

• [00:20:00] The neutral selection process

• [00:25:00] Future developments and roadmap for New Era ADR

• [00:30:00] The impact of New Era ADR on various stakeholders

Resources and Links:

• New Era ADR website: https://www.neweraadr.com/

 

This episode features Matthew Rasmussen, Founder and CEO of ModeOne, which is an app that provides targeted smart phone data discovery. Matt discusses his journey from a psych major waiting tables to landing a job in eDiscovery in its earliest days-- a job that ultimately helped him land jobs in BigLaw for multiple firms running their litigation technology departments. It was when he was working for O'Melveny & Meyers when he had his "light bulb moment" that led to the creation of ModeOne, a solution addressing the challenges of efficient data collection from mobile devices.

Matt explains how ModeOne works, its benefits over traditional digital forensic collection methods, and how it addresses concerns about evidentiary defensibility. He also highlights the various use cases for ModeOne beyond litigation, including internal investigations, HR matters, and compliance. The conversation delves into ModeOne's development, its unique approach compared to competitors, and its future roadmap, including internationalization and integrations with other platforms like Relativity.

Learn more about Matt.

Key Discussion Points:

• [0:39] Matt's unconventional path to eDiscovery

• [3:35] The "light bulb moment" that sparked the idea for Mode One

• [9:02] How Mode One works and its advantages

• [11:36] Addressing evidentiary concerns and gaining credibility

• [19:19] Expanding use cases beyond litigation

• [22:48] iOS and Android certification process

• [23:31] Apps and data supported by Mode One

• [25:18] Mode One's built-in review tool and Relativity integration

• [28:04] Future roadmap and upcoming features

 

Jason Heinze originally wanted to be an architect but got into disability law after taking over his father in law's practice. To establish his client's disability claims, he would have them manually enter daily notes into a pain journal, but he often had difficulty getting clients to consistently maintain the journals because they might forget and it was a completely manual process.

He thought to himself, there has to be an app for that, but when he looked, he found some that were close, but not exactly what he needed. So, he created his own and called it ClaimData. By using the app, disability claimants can now make pain journal entries via a web app and it will also remind them to enter it. 

ClaimData uses a progressive web app model for efficiency and cost-effectiveness. ClaimData integrates with case management systems and plans to expand into personal injury and workers' compensation. The app aims to simplify the evidence-gathering process for attorneys, making it easier to prove disability cases.

 

Amanda Tuminelli, Chief Legal Officer for the DeFI Education Fund, visits the podcast to discuss her role with the organization and its objectives. (What is DeFi? It is shorthand for Decentralized Finance and the backbone of DeFi is blockchain technology and smart contracts.)

The DeFi Education Fund is a nonpartisan research and advocacy group working to explain the benefits of DeFi, achieve regulatory clarity for the future of the global digital economy, and help realize the transformative potential of DeFi for everyone.

Amanda goes in depth into the DEF's areas of focus:

• Research and Advocacy

• Policymaker Education

• Messaging for Crypto Companies

• Research about Blockchain Issues and Regulations

• Providing "Legal Firepower" to Crypto Causes; and

• DeFi Project Best Practices

Amanda also discusses how lawyers can pursue a career in crypto and why that wasn't the case a few years ago. It's not only an option now because the industry is more mature, but also because of the openness of those in the crypto world and their desire for passionate individuals to join them. To get a job in crypto law, Amanda emphasizes the importance of understanding the technology and finding projects of interest. 

So how did Amanda get to the DEF? She started out as a securities and white collar crime lawyer, but a case came along that would change her career trajectory. She was working for Kobre and Kim, a law firm focused on disputes and investigations, when the firm was hired by a client accused of running an illegal crypto mining scheme. To get up to speed on the case and get her client out of jail, she had to dive deep into learning about blockchain technology and that is when she caught the bug. A few years later, a friend and former college friend contacted her about joining the legal team at the DeFI Education Fund and she took them up on it.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

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AffiniPay is historically a fintech company with a big presence in legal. Their flagship product is LawPay used by law firms to bill clients and accept payments. Dru joined the company in 2021 and right around that time, the company ventured beyond the world of payment software and acquired MyCase, which is law practice management software used by law firms to keep all case details and documents in a single location, keep track of tasks and streamline client communications.

Growing up, Dru wanted to be a lawyer because she comes from family of lawyers, including her father. She studied law at the University of Chicago, but after a couple of gigs with law firms, she figured out that maybe the law wasn't for her.

So, she finished her MBA and went to work for Boston Consulting. After a few years as a consultant, she needed a break, and, being somewhat of a foodie, she went to work in the kitchens of some of New York's finest dining establishments.

She took lessons learned from the kitchen into her later work as a co-founder of a baby monitor start-up and ultimately roles as CEO of the property management company Grace Hill and now AffiniPay.

In this episode, Dru talks about:

• Joining AffiniPay and its mission

• The company's acquisition of MyCase and expansion into practice management software

• Affirm, AffiniPay's Buy now, pay later product and its impact

• The company's AI plans and integration within the platform

• Core responsibilities of a CEO and what has surprised her in her role as a CEO

 

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Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

 

Donald Beshada, former litigator turned legal tech entrepreneur and CEO of Covalynt shares his journey from big-law to the forefront of using data science in litigation. Specifically, to address systemic fraud in class action settlements.

The conversation explores the evolution of claims administration—from the traditional "People Magazine" notice era to the current digital landscape dominated by targeted advertising and sophisticated fraud bots. Donald explains how his company uses data science and identity resolution to bring "scientific rigor" to ensure class action settlements reach legitimate claimants while filtering out fraudulent activity.

Key Takeaways:

• The Shift in Fraud: How class action fraud evolved from "couponing" websites to sophisticated, non-US-based bot attacks.

• Defensible Clarity: Why "gut feelings" about fraud don't hold up in court, and the necessity of providing an evidentiary framework for disqualifying claims.

• Data Science vs. Traditional Settlement Administration: A look at how the Apple Antitrust case served as an inflection point, proving that old-school matching methods are no longer sufficient for class certification or ascertainability.

• The Future of Notice: Moving toward a world where data science can connect retail purchases directly to individuals, potentially eliminating the need for expensive, broad-market advertising.

 

A conversation with Lucas Moskowitz, General Counsel for financial services company Robinhood. Launched in 2013, Robinhood's stated mission is to "democratize finance for all" by making it easy for investors to start investing with a few bucks rather than having to be a high roller. Key to this effort is the fact that Robinhood offers commission-free trading and also provides access to cryptocurrencies.

The discussion covers various topics, including:

• Robinhood's Mission: Lucas explains Robinhood's mission to democratize finance by breaking down barriers to investing and making it accessible to everyone, regardless of their financial background.

• Lucas's Career Path: Lucas shares his unique career journey, transitioning from big law to the SEC, Capitol Hill, and eventually Robinhood. He emphasizes the importance of diverse experiences in shaping his perspective.

• Regulation in the Financial Industry: Lucas advocates for a data-driven approach to regulation, striking a balance between investor protection and fostering innovation and access.

• Crypto & Blockchain: The potential of crypto and blockchain technology is explored, with Lucas highlighting their role in making financial markets more efficient.

• Education: The importance of educating investors about making sound investment decisions and also educating legal professionals about emerging technologies like blockchain and tokenization of assets.

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A conversation with Matthew Veale, a European Patent Attorney and UPC Representative at PatSnap, an app that provides users with a comprehensive and user-friendly platform to conduct patent searches. Matthew discusses his experiences from work as an attorney in private practice and a stint at the UK Patent Office before joining PatSnap.

Matthew will discuss:

• The future of AI in patent searches: How PatSnap's new AI component is transforming years of knowledge into a 10-second search.

• AI's capabilities in analyzing and classifying images: Why AI can outperform humans in these tasks.

• The impact of AI on legal practice: Assisting attorneys in understanding patent data and improving client communication.

• The role of AI in due diligence: Enhancing efficiency without replacing human expertise.

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This episode involves two people with very distinguished careers. Bridget M. McCormack who now heads the American Arbitration Association (AAA) and Colin Rule, the founder of ODR.com just acquired by The AAA.

Bridget has served in just about every role you can in the legal industry. She started her legal career in legal aid and as a public defender handling trials and appeals. She then moved to teaching law school, first at Yale and then Michigan.

After her stint as an educator, she decided she wanted to help foster even more change and won a seat on the Michigan Supreme Court where she ultimately ascended to the position of Chief Justice. Fast forward to 2023 and she took the helm of the AAA.

One of Bridget's biggest initiatives at AAA is bringing tech into the arbitration process and that is where Colin Rule comes in. He founded an online dispute resolution (ODR) company, about 15 years ago that ultimately became ODR.com which the AAA just announced it was acquiring.

To say that Colin is an ODR OG is an understatement. He literally wrote the book on ODR way back in the early days of the internet. Ebay brought him on board in the early 2000s where he headed up the company's ODR function.

In this episode Bridget and Colin discuss: 

• AAA's acquisition of odr.com: The strategic partnership between AAA and ODR.com to revolutionize dispute resolution.

• AI's transformative role in dispute resolution: How AAA is using AI internally and through external tools to improve efficiency and accessibility.

• The future of dispute resolution: A vision for a more accessible, efficient, and user-friendly system that leverages technology and data.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI

Dr. Heidi Gardner of the Harvard Business and Law Schools joins the podcast to talk about about latest book Smarter Collaboration and the importance of collaboration in legal teams and in all organizations generally.

Smarter Collaboration is Dr. Gardner's second book and a follow up to Smart Collaboration: How Professionals and Their Firms Succeed by Breaking Down Silos. Both books are helpful to those in law because much of Dr. Gardner's research is based on the many years she studied collaboration in professional service firms, including many law firms.

Why is collaboration across different disciplines and business units important? As Dr. Gardner explains, most importantly, it creates better client outcomes which improve revenues and profits. But collaboration doesn't just help make clients happy and improve the bottom line, it also fosters diversity and reduces enterprise risk.

Dr. Gardner has cold hard data that supports her conclusions: Back in the 1970s, 60% of US patents were awarded to individual inventors. Nowadays, that numbers has reversed. The vast majority of patents are issued to teams and the more diverse the backgrounds of those teams, the more successful their innovation.

Episode Credits

Editing and Production: Grant Blackstock

Theme Music: Home Base (Instrumental Version) by TA2MI