Ceschino | The Legal Tech Guide

The Future of Law Is Today

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).

Author

Ceschino | The Legal Tech Guide

Category

Technology

Podcast website

thelegaltechguide.com

Latest episode

Jul 1, 2026

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Episodes

An In-House Lawyer’s Perspective on Buying AI, ft. In-House Counsel Travis Zollner | The Future of Law Is Today, Ep. 19 01.07.2026

Summary Travis Zollner joins Ceschino to discuss the frustration of navigating the legal AI world as a practicing lawyer looking for reliable solutions and clear information about what any given solution does and doesn’t do. Travis discusses the challenges and opportunities of integrating AI into legal workflows, emphasizing the importance of accuracy and the need for human oversight. The conversa...

AI Negotiation Agents and the New Law Career, ft. Ozeki Founder Kenneth Carter | The Future of Law Is Today, Ep. 18 15.06.2026

Summary Kenneth Carter shares his journey from being a lawyer to founding Ozeki, a legal tech company focused on automating and enhancing negotiation processes. He discusses the limitations of generative AI in legal contexts and introduces the concept of “artificial discretion” as a more effective approach. The conversation explores the nuances of negotiation strategies, the role of trust in negot...

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 01.06.2026

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 res...

Staying Composed Even With Ambitious Goals, ft. Paragon Tech Founder Jay McAllister | The Future of Law Is Today, Ep. 16 15.05.2026

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 ba...

What Is AI, Anyway? A Primer for Lawyers, ft. 2nd Chair Co-Founder Austin Brittenham | The Future of Law Is Today, Ep. 15 01.05.2026

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 als...

Automation vs. AI for Lawyers, ft. Director of Automation Elisa Silverglade | The Future of Law Is Today, Ep. 14 15.04.2026

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 rob...

How Does Legal AI Really “Think?” ft. Opine Law Co-Founders Grant Taylor and Scott Tandoi | The Future of Law Is Today, Ep. 13 02.04.2026

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 ch...

Why Is Buying Legal AI So Painful? ft. Legal Benchmarks Founder Anna Guo | The Future of Law Is Today, Ep. 12 15.03.2026

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...

Startup Lessons From a Litigator ft. Legion Founder Arthur Rothrock | The Future of Law Is Today, Ep. 11 01.03.2026

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...

Designing a Better Legal Profession (and AI) ft. Legal Design Consultant Laura Hartnett | The Future of Law Is Today, Ep. 10 15.02.2026

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...

Is the Billable Hour Really Dying? ft. Billables AI Founder Nancy Jeng | The Future of Law Is Today, Ep. 9 01.02.2026

Summary Nancy 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 emph...

Taking the Initiative in Legal Ops, ft. Legal Ops Strategist Gabriel Saunders | The Future of Law Is Today, Ep. 8 15.01.2026

The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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...

Cutting Through the Legal Tech Noise, ft. Legau Founder Luís Alves Dias | The Future of Law Is Today, Ep. 7 01.01.2026

Description The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary We’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 r...

Meeting Lawyers Where They Are, ft. JuristAI Founder Ali Mohammed | The Future of Law Is Today, Ep. 6 16.12.2025

Description The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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...

Bridging the Trust Gap in Legal Tech, ft. TeareOne Founder James Teare | The Future of Law Is Today, Ep. 5 01.12.2025

The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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 a...

Legal Tech Marketing Is Broken, ft. Reality Brief Author Robert Forte Jr. | The Future of Law Is Today, Ep. 4 16.11.2025

The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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 transpar...

When to Build vs. Buy Legal Tech, ft. Talking Tree Founder Cecilia Wang | The Future of Law Is Today, Ep. 3 01.11.2025

The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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 opportuniti...

AI Rottweilers Are Coming for Lawyers? ft. Legalito Founder Peter Ambrose | The Future of Law Is Today, Ep. 2 01.11.2025

The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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 p...

How to Choose Legal Tech Your Team Will Actually Use, ft. BetterWiser Founder Lynette Ooi | The Future of Law Is Today, Ep. 1 01.11.2025

The Future of Law Is Today is the official podcast of The Legal Tech Guide ( thelegaltechguide.com ). Summary In 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 b...

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