The Future of Law Is Today

Ceschino | The Legal Tech Guide

Straight talk on law, legal tech, and the future of the profession with experts on the practice of law, AI and other technology, legal operations, and education. Hosted by Ceschino Brooks_de_Vita, Harvard Law grad, ex-BigLaw attorney, legal tech / AI expert, and founder of The Legal Tech Guide. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).

  1. The Legal OS and Reshaping the Practice of Law, ft. 9to5 Founder Marla Calvert Miller and Legal Futurist Anastasia Boyko | The Future of Law Is Today, Ep. 17

    2d ago

    The Legal OS and Reshaping the Practice of Law, ft. 9to5 Founder Marla Calvert Miller and Legal Futurist Anastasia Boyko | The Future of Law Is Today, Ep. 17

    Summary This episode explores an emerging concept in legal tech and AI: the legal operating system. 9to5 Legal Docs founder Marla Calvert Miller and legal futurist Anastasia Boyko share insights earned over a varied pair of careers in legal practice, legal tech, and legal education and training. They join Ceschino to discuss how AI and the concept of the legal OS are giving lawyers a chance to reshape legal services and rethink what they want their careers as lawyers to be. The discussion also addresses the importance of a systems-based approach to tech and legal operations, and strategies for managing change in legal practices. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com). Takeaways AI gives us a chance to rethink legal service delivery as a profession 9to5 is building a legal operating system for transactional law The legal OS needs to do more than just handle documents, matters, and intake Different types of practice need their own tailored operating systems Empathy and human connection are core competencies in legal tech and legal practice, now more than ever Lawyers should reflect on their career goals and personal values when making decisions, from adopting new tech to choosing career paths Lawyers must prioritize security and privacy in legal AI implementations Practice managers need to engage with clients to understand their needs and preferences Leaders should develop a North Star to guide change management in legal practices Chapters 00:00 Introduction to Marla’s and Anastasia’s Legal Journeys 04:10 Shaping Legal Careers 09:00 Reimagining Legal Services With AI 14:20 The Legal Operating System Concept 17:10 Putting Lawyers’ Clients Front and Center in Legal Tech 20:11 Reacting to Claude for Legal 24:38 Substance in Legal AI Marketing: What Do The Tools Really Do? 27:19 Navigating Security When Trying Legal AI 30:12 Business of Law: Shifting to Alternative Billing Arrangements 35:23 Nobody Wants to Talk to Your AI Bot 37:44 Fixing the Empathy Blind Spot in Legal Services 39:57 Defining Your Team's North Star to Guide Tech Adoption 42:59 Keeping It Human: Keep It Weird Keywords Legal Tech, AI, Legal Innovation, Legal Practice, Legal Operating System, Legal Careers, Legal Tech Adoption, Legal AI Tools

    47 min
  2. Staying Composed Even With Ambitious Goals, ft. Paragon Tech Founder Jay McAllister | The Future of Law Is Today, Ep. 16

    May 15

    Staying Composed Even With Ambitious Goals, ft. Paragon Tech Founder Jay McAllister | The Future of Law Is Today, Ep. 16

    Summary Jay McAllister joins Ceschino to share his experience working in high-pressure environments of his own creation, and how he maintains focus and composure while targeting ambitious goals. Jay discusses the inspiration behind and results of his 100x social experiment. The conversation also explores the psychology of personal motivation, pressure, and the desire for achievement, and how to balance goal-oriented ambition with a productive level of appreciation for the progress that’s already been made. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com). Takeaways Before starting a new business initiative, it’s crucial to define parameters for success Business initiatives should focus on eliminating the largest constraints, not pet projects The best way to elevate performance is with consistent processes and systems Jay challenged himself to 100x his output on social media to source new clients He established accountability and set up systems and support to make scaling possible Self-assessment is often overly negative — it’s important to acknowledge the gains made as well as remaining goals Mindset matters: believing you can do something new is a prerequisite to doing it Taking on greater responsibility can force people to become more productive in general Chapters 00:00 Jay’s Focus as an Entrepreneur and Advisor to Attorneys 05:45 Defining Success in Business Initiatives 10:56 Elevating Performance With Consistent Processes and Systems 11:54 The 100x Social Experiment: Inspiration 16:02 Purpose and Structure of the 100x Experiment 19:42 The Gap Versus the Gain: Learning to Reframe Self-Assessment 24:40 Desire as a Personal Contract to Be Unhappy 26:33 Never Say “Can’t” 29:43 Setting Up the 100x Experiment 35:16 Productivity Hack: Take on More Work 38:07 Results of the 100x Experiment 43:06 Keeping It Human: Fun Economics and Science Facts Keywords Law, legal tech, AI, productivity, motivation, inspiration, scaling, discipline, business operations, legal operations, systems thinking, process improvement

    48 min
  3. What Is AI, Anyway? A Primer for Lawyers, ft. 2nd Chair Co-Founder Austin Brittenham | The Future of Law Is Today, Ep. 15

    May 1

    What Is AI, Anyway? A Primer for Lawyers, ft. 2nd Chair Co-Founder Austin Brittenham | The Future of Law Is Today, Ep. 15

    Summary Austin Brittenham, a lawyer and legal tech founder who started his legal AI company while still in law school, provides a thorough overview of AI – what it is, how the tech has evolved, and where it’s going. He dives into the implications of AI for lawyers and the practice of law, from everyday document automation to fabricated images presented as evidence in court. Ceschino and Austin also examine what people building AI for lawyers need to keep in mind, whether as tech vendors or in-house within legal practices. The conversation concludes with a reflection on how reinforcing critical thought can help future generations maintain their mental acuity in the age of AI. Takeaways The arc of AI has progressed from if-then logic to machine learning to generative AI AI has recently evolved from small language models developed by machine learning startups to large language models powering generative AI applications Large language models may be plateauing in terms of the information that can be gained from web scraping, but alternative teaching methods such as reinforcement learning may lead to future advancements Legal tech may be moving toward broad platforms that host specialized add-on solutions, or toward a future where legal practices bring in engineering talent to build bespoke solutions AI and vibe coding raise the risk of people reinventing the wheel with custom apps Whether building legal AI as a tech vendor or in-house, you need to stay plugged in with the people who will use it every day Chapters 00:00 Introduction to Austin and His Legal AI Journey 03:35 Navigating Legal AI as an Entrepreneur 06:55 The Types of AI Lawyers Should Know About 13:09 Practical Applications of Generative AI 22:10 The Platformization of Legal Tech 23:46 Alternative Future: Building In-House Tech Capabilities 28:07 Reinventing the Wheel With AI and Vibe Coding 32:28 The Importance of Legal Expertise When Building Legal Tech 38:05 The Need to Stay Plugged In With End Users When Building Tech 42:51 What’s Next, Beyond LLMs and Gen AI? 48:38 Keeping It Human: Developing Critical Thought Through Debate Keywords Generative AI, large language models, machine learning, small language models, legal tech, law, litigation, tech procurement, cybersecurity, ethics, compliance, vibe coding, critical thinking

    54 min
  4. Automation vs. AI for Lawyers, ft. Director of Automation Elisa Silverglade | The Future of Law Is Today, Ep. 14

    Apr 15

    Automation vs. AI for Lawyers, ft. Director of Automation Elisa Silverglade | The Future of Law Is Today, Ep. 14

    Summary Elisa Silverglade discusses her journey in legal automation, emphasizing the importance for lawyers of client relationships over simply getting paperwork done. She distinguishes between AI and automation, explaining how automation can enhance efficiency in law firms. The discussion also covers the significance of change management in implementing automation, the deterministic nature of robotic process automation as opposed to the probabilistic nature of generative AI, and the evolving roles of employees in the legal field. The conversation concludes with a focus on the human element in automation and the potential for technology to create more fulfilling work environments. Takeaways Automation can significantly reduce repetitive tasks in law firms. The core value in law is the client relationship, not just paperwork. AI mimics human thought, while automation replicates human behavior. Deterministic applications ensure consistent execution and accuracy. Change management is crucial for successful automation implementation. Automation can enhance job satisfaction by reducing grunt work. Younger employees will need to adapt to new roles as automation increases. The legal profession must focus on client relationships to provide value. Technology should augment human work, not replace it. Chapters 00:00 Introduction to Legal Automation and AI 04:58 The Difference Between Automation and AI 07:00 The Role of Automation in Legal Processes 16:29 Deterministic Vs. Probabilistic Applications 22:03 The Impact of AI on Work Quality and Customer Experience 27:10 Automation: Enhancing Work, Not Replacing It 34:34 Transforming Junior Roles in the Workforce 40:11 Keeping It Human: The Most Statistically Complex Game in History Keywords legal automation, AI, robotic process automation, law firms, change management, deterministic applications, client relationships, technology in law, future of work, human element

    43 min
  5. How Does Legal AI Really “Think?” ft. Opine Law Co-Founders Grant Taylor and Scott Tandoi | The Future of Law Is Today, Ep. 13

    Apr 2

    How Does Legal AI Really “Think?” ft. Opine Law Co-Founders Grant Taylor and Scott Tandoi | The Future of Law Is Today, Ep. 13

    Summary Grant Taylor and Scott Tandoi discuss their journey into legal tech, focusing on the integration of large language models in law. They explore the limitations of LLMs, the importance of context engineering, and how AI can augment human expertise rather than replace it. The discussion also touches on the future of AI in legal work, and personal insights into parenthood and including your children in what you do. Takeaways Large language models can process legal language but can’t analyze it. Context engineering is crucial for effective AI use in law. AI should augment human expertise, not replace it. The role of AI in legal work is to assist, not to take over. Prompt engineering is different from context engineering. AI can help with mundane tasks, freeing up human time. The future of AI in law involves more workflow automation. Understanding the limitations of LLMs is essential for legal professionals. Personal interests and experiences shape professional journeys. Chapters 00:00 The Genesis of Legal Tech Collaboration at Opine 03:42 Parsing the First Legal Case With AI: Hanson Brothers 05:11 Understanding LLMs: Parsing New Information vs. Built-In “Knowledge” 08:18 The Reliability of LLMs in Legal Contexts 10:13 Probabilistic vs. Deterministic Applications 12:50 Context Engineering: Enhancing AI Accuracy 17:03 The Importance of Backend Prompt Structure in AI Applications 20:30 Legal-Specific AI vs. General Purpose AI 22:43 Shepardization and Its Role in Legal AI 27:10 Finding the Balance: AI and Human Collaboration 39:46 The Shift to AI in Workflows 44:56 Keeping It Human: Sharing Sports, Work, and Interests With Kids Keywords legal tech, large language models, AI in law, context engineering, prompt engineering, legal work, AI limitations, generative AI, augmented intelligence

    53 min
  6. Why Is Buying Legal AI So Painful? ft. Legal Benchmarks Founder Anna Guo | The Future of Law Is Today, Ep. 12

    Mar 15

    Why Is Buying Legal AI So Painful? ft. Legal Benchmarks Founder Anna Guo | The Future of Law Is Today, Ep. 12

    Summary Anna Guo shares her journey from law to legal tech and AI, discussing the challenges faced in legal tech sales cycles, particularly the lengthy and complex demo processes. She emphasizes the disconnect between sales teams and the actual user experience, advocating for more user-friendly products and better education for legal professionals. The discussion also touches on the importance of benchmarking and differentiating legal tech solutions, as well as the need for more engaging marketing strategies in the legal tech space. Takeaways Anna Guo emphasizes the importance of sharing ideas and thoughts in the legal tech space. The sales cycle for legal tech can be painful, especially for smaller teams. There is often a disconnect between the internal champion and the rest of the legal team. User-friendly design is crucial for the adoption of legal tech products. Benchmarking can help differentiate legal tech solutions in a crowded market. Legal tech marketing often lacks engagement and distinctiveness. Vulnerability in marketing can build trust with potential clients. Education and training are essential for successful product adoption. Legal professionals are aware of the limitations of benchmarking studies. Engaging and humorous marketing can be effective in the legal tech space. Chapters 00:00 Anna Guo's Journey in Law and AI 6:19 The Disconnect in B2B Sales Processes 15:49 Navigating Product Demos as a Lawyer 20:21 The Importance of User-Friendly Design to Drive Product Adoption 23:02 The Era of Lawyer AI Upskilling 24:40 Building Trust: Acknowledging the Legal Tech Ecosystem 30:26 Legal AI Vendors Sound a Lot Alike — Are They Really? 35:34 The Need for Distinctive Marketing in Legal Tech 42:42 Keeping It Human: Board Game Obsession Keywords legal tech, AI governance, sales cycles, legal marketing, user experience, product demos, legal solutions, benchmarking, legal industry, technology adoption

    45 min
  7. Startup Lessons From a Litigator ft. Legion Founder Arthur Rothrock | The Future of Law Is Today, Ep. 11

    Mar 1

    Startup Lessons From a Litigator ft. Legion Founder Arthur Rothrock | The Future of Law Is Today, Ep. 11

    Summary Arthur Rothrock shares his journey from being a litigator to founding a legal tech company, Legion. He discusses the transformative impact of AI in legal practices, the challenges of selling to lawyers, and the importance of building trust in the legal tech ecosystem. Arthur emphasizes the need for transparency, respect for clients' time, and the significance of having legal expertise within tech teams. He also explores the complexities of targeting enterprise clients and the balance between risk and innovation in legal tech startups. Takeaways Arthur's journey from litigator to legal tech founder began with the advent of generative AI. Using AI, he was able to draft legal documents much faster than traditional methods. Building trust with lawyers requires transparency and respect for their time. Targeting enterprise clients requires meeting high security and compliance standards. Starting with small to mid-size firms allows for more flexibility and learning. Having legal experts on legal tech teams is crucial for product development and marketing. Risk management in startups is about balancing innovation with compliance. The importance of clear communication between legal and tech teams cannot be overstated. Respecting clients' time is essential for building long-term relationships. Chapters 00:00 From Litigator to Legal Tech Innovator 06:38 Navigating the Adversarial Nature of Law Through Legal Tech 10:05 The Importance of Transparency in Legal Tech 16:24 Starting Small: The Path to Enterprise 22:15 The Role of Subject Matter Experts in Legal Tech 35:08 Leaders Shape the Character of Their Organizations 42:03 Balancing Risk and Innovation in Legal Tech 44:33 Building Trust in Legal Tech 55:55 Keeping It Human: Everybody Was Kung Fu Fighting Keywords legal tech, litigation, AI, trust, enterprise clients, legal expertise, risk management, customer experience, innovation, startups

    1h 2m
  8. Designing a Better Legal Profession (and AI) ft. Legal Design Consultant Laura Hartnett | The Future of Law Is Today, Ep. 10

    Feb 15

    Designing a Better Legal Profession (and AI) ft. Legal Design Consultant Laura Hartnett | The Future of Law Is Today, Ep. 10

    Summary Laura Hartnett shares her journey into legal design, emphasizing the importance of a human-first approach and design thinking in legal operations. The discussion highlights her experience at the recent Women + AI Summit, focusing on the need for inclusive communities and the role of women in shaping AI in the legal profession and beyond. Key themes from the summit include the necessity of creating safe spaces for experimentation, the importance of human involvement in AI, and the ongoing challenges of bias in technology. Laura also shares her experiences living abroad and how they inform her perspective. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com). Takeaways Laura's journey from law and management consulting to legal design. The significance of design thinking in legal operations. The need for women to have a seat at the table in AI discussions. Creating inclusive communities is essential for innovation. The importance of safe spaces for experimentation with AI. AI should enhance human capabilities, not replace them. Bias in AI stems from human decisions, not algorithms. The role of the humanities in developing critical thinking skills. Legal tech must address real human experiences in the practice of law. Chapters 00:00 Laura's Journey into Legal Design 03:47 Understanding Design Thinking in Legal Practice 09:19 Redesigning Legal Work for Inclusivity 10:58 Women + AI Summit Overview 13:15 Building Inclusive Communities in Law, AI, and Legal Tech 20:32 Storytelling as a Tool for Change 24:05 Innovative Conference Design and Engagement 29:32 Creating Safe Spaces for Innovation 36:47 Balancing AI and Human Roles 37:50 The Importance of Critical Thinking in the Age of AI 44:29 Keeping It Human: A Year in Spain Keywords legal tech, design thinking, women in AI, legal operations, community building, AI ethics, burnout, human experience, innovation, legal industry

    47 min
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About

Straight talk on law, legal tech, and the future of the profession with experts on the practice of law, AI and other technology, legal operations, and education. Hosted by Ceschino Brooks_de_Vita, Harvard Law grad, ex-BigLaw attorney, legal tech / AI expert, and founder of The Legal Tech Guide. The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).

Information

  • Creator
    Ceschino | The Legal Tech Guide
  • Years Active
    2025 - 2026
  • Episodes
    17
  • Rating
    Explicit
  • Copyright
    © Ceschino | The Legal Tech Guide
  • Show Website
    The Future of Law Is Today