Shows
The Future of Law Is TodayThe 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. 17SummaryThis 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...
2026-06-0247 min
The Future of Law Is TodayStaying Composed Even With Ambitious Goals, ft. Paragon Tech Founder Jay McAllister | The Future of Law Is Today, Ep. 16SummaryJay 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)....
2026-05-1547 min
This Legal Life: Lessons Learned from a Life in LegalBridging the Gap: Why Legal Tech Still Isn’t Reaching Lawyers (and How to Fix It)In this episode of This Legal Life, Ben Chiriboga sits down with Ceschino Brooks, founder of The Legal Tech Guide and host of Future of Law Today, to unpack one of the biggest challenges in the industry: why legal tech still struggles to connect with the people it’s built for. Drawing from his journey from Big Law to marketing and legal tech, Ceschino explores the disconnect between innovation and adoption, the rise of the “legal operating system,” and why better information—not more noise—is what the industry truly needs.
2026-05-0744 min
The Future of Law Is TodayWhat Is AI, Anyway? A Primer for Lawyers, ft. 2nd Chair Co-Founder Austin Brittenham | The Future of Law Is Today, Ep. 15SummaryAustin 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...
2026-05-0153 min
The Future of Law Is TodayAutomation vs. AI for Lawyers, ft. Director of Automation Elisa Silverglade | The Future of Law Is Today, Ep. 14SummaryElisa 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...
2026-04-1543 min
The Future of Law Is TodayHow Does Legal AI Really “Think?” ft. Opine Law Co-Founders Grant Taylor and Scott Tandoi | The Future of Law Is Today, Ep. 13SummaryGrant 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.TakeawaysLarge language models can process legal language but can’t analyze it.Context engineering is crucial for effective AI...
2026-04-0253 min
The Future of Law Is TodayWhy Is Buying Legal AI So Painful? ft. Legal Benchmarks Founder Anna Guo | The Future of Law Is Today, Ep. 12SummaryAnna 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.TakeawaysAnna Guo emphasizes the importance of sharing ideas...
2026-03-1545 min
The Future of Law Is TodayStartup Lessons From a Litigator ft. Legion Founder Arthur Rothrock | The Future of Law Is Today, Ep. 11SummaryArthur 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.TakeawaysArthur's journey from litigator to...
2026-03-011h 01
The Future of Law Is TodayDesigning a Better Legal Profession (and AI) ft. Legal Design Consultant Laura Hartnett | The Future of Law Is Today, Ep. 10SummaryLaura 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.
2026-02-1546 min
The Future of Law Is TodayIs the Billable Hour Really Dying? ft. Billables AI Founder Nancy Jeng | The Future of Law Is Today, Ep. 9SummaryNancy Jeng, co-founder of Billables AI, joins Ceschino to discuss the challenges of timekeeping in the legal profession and how her company aims to alleviate these pain points through innovative technology. She shares insights on the importance of user experience in billing software, the evolving landscape of billing models, and the role of AI in transforming time tracking. Nancy also emphasizes the need for transparency in client communications, and we even get to learn about the cultural preservation work she does through her personal projects.The Future of Law Is Today...
2026-02-0136 min
The Future of Law Is TodayTaking the Initiative in Legal Ops, ft. Legal Ops Strategist Gabriel Saunders | The Future of Law Is Today, Ep. 8The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this engaging, wide-ranging conversation, legal ops strategist Gabriel Saunders joins Ceschino Brooks_de_Vita to discuss all things legal tech and legal ops, from vibe coding to tech procurement to career advancement. Through it all, Gabriel emphasizes the importance of proactivity and curiosity to success in the field.TakeawaysVibe coding is a learned skill that requires the ability to articulate needs preciselyAI...
2026-01-1555 min
The Future of Law Is TodayCutting Through the Legal Tech Noise, ft. Legau Founder Luís Alves Dias | The Future of Law Is Today, Ep. 7DescriptionThe Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryWe’re starting 2026 with a conversation that explores the noise around legal tech and AI. Legau founder Luís Alves Dias joins host Ceschino Brooks_de_Vita to discuss how to cut through that noise with transparency and real value — and the conversation turns to some thoughtful reflection on what community building and paying it forward looks like, even outside of law and tech.TakeawaysThe...
2026-01-0140 min
The Future of Law Is TodayMeeting Lawyers Where They Are, ft. JuristAI Founder Ali Mohammed | The Future of Law Is Today, Ep. 6DescriptionThe Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this conversation, Ali Mohammed discusses his journey into legal tech, emphasizing the importance of understanding user needs and creating solutions that integrate seamlessly into lawyers' existing workflows. He highlights the challenges of developing legal software that meets the high standards of accuracy and reliability required in the legal profession. The discussion also covers the significance of feedback and iteration in product development, the role of AI in legal tech, and...
2025-12-1640 min
The Future of Law Is TodayBridging the Trust Gap in Legal Tech, ft. TeareOne Founder James Teare | The Future of Law Is Today, Ep. 5The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this conversation, James Teare shares his extensive experience in legal tech and discusses the critical trust gap between legal tech vendors and legal teams. He emphasizes the importance of reliability, user-centric design, and clear communication of value propositions. The discussion also covers the benefits of niche solutions, the need for technology to augment human work, and strategies to bridge the trust gap through transparency and compliance. Client success stories illustrate the significance of...
2025-12-0245 min
The Future of Law Is TodayLegal Tech Marketing Is Broken, ft. Reality Brief Author Robert Forte Jr. | The Future of Law Is Today, Ep. 4The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this conversation, Robert Forte shares his unique journey as both a lawyer and a pastor, discussing how his dual background informs his insights into the legal tech industry. He emphasizes the importance of honest communication between legal tech vendors and users, the need for transparency in marketing, and the balance between technology and legal practice. The discussion also touches on the challenges of adopting legal tech, the role of AI in legal practice...
2025-11-1649 min
Lawyers on FireEpisode 5: Legal tech marketing and the legal tech market – what is broken and how can it be fixed?Today's episode is presented by Corvel (www.corvel.de)KeywordsLegal tech, future of law, AI in law, legal tech guide, big law firms, BigLaw, BigTech, interdisciplinarity, creativity, legal profession, challenges, transformation, skillsSummaryIn this episode, we talk to Ceschino about his career path from young age to law and finally to legal tech. He shares his experiences and insights on the challenges in the legal tech world, the future of legal professions in the context of AI, clients‘ changing preferences and the transformation of...
2025-11-1441 min
The Future of Law Is TodayWhen to Build vs. Buy Legal Tech, ft. Talking Tree Founder Cecilia Wang | The Future of Law Is Today, Ep. 3The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this conversation, Ceschino welcomes Cecilia Wang, founder of TalkingTree.app, who shares her journey in law and legal tech, emphasizing the importance of access to justice and the evolution of legal technology from traditional methods to AI. She discusses the challenges and opportunities in the legal tech landscape, including the decision to build or buy tools, and the skills needed for effective legal tech adoption. The conversation highlights the collaborative nature of building...
2025-11-0132 min
The Future of Law Is TodayAI Rottweilers Are Coming for Lawyers? ft. Legalito Founder Peter Ambrose | The Future of Law Is Today, Ep. 2The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this conversation, Peter Ambrose joins Ceschino to share his unique journey from a technology background to running a law firm and a legal tech startup, Legalito. He discusses the current applications of AI in legal practice, the limitations of existing AI tools, and the importance of prompt engineering. Peter emphasizes the need for lawyers to embrace AI, the risks of clients using AI against them, and the necessity of having comprehensive data solutions...
2025-11-0130 min
The Future of Law Is TodayHow to Choose Legal Tech Your Team Will Actually Use, ft. BetterWiser Founder Lynette Ooi | The Future of Law Is Today, Ep. 1The Future of Law Is Today is the official podcast of The Legal Tech Guide (thelegaltechguide.com).SummaryIn this engaging podcast episode, Ceschino welcomes Lynette Ooi, founder and CEO of BetterWiser, to discuss the evolving landscape of legal tech. They explore the challenges of technology adoption in law firms, emphasizing the importance of change management and trust between vendors and buyers. Lynette shares insights on building capabilities, the significance of understanding the 'why' behind tech adoption, and the need for realistic expectations regarding AI's impact. The conversation also touches on parenting...
2025-11-0136 min