Want to be a Crypto Lawyer? Rule # 1: Use the Technology. Rule #2: Beware of Hyper-Specialization (Justin Wales-Head of Legal, Crypto.com & Author of Crypto Legal Handbook)
Technically Legal - A Legal Technology and Innovation Podcast
Release Date: 10/09/2025
Best of 2025 - From IP Lawyer to Investor to CEO to Legal Ecosystem Builder (Avaneesh Marwaha, Litera CEO)
Technically Legal - A Legal Technology and Innovation Podcast
Avaneesh Marwaha, the CEO of , 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...
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Best of 2025 - Benchmarking Legal AI: Measuring the Delta Between Man and Machine (Anna Guo Legalbenchmarks.ai)
Technically Legal - A Legal Technology and Innovation Podcast
In one of the most popular episodes of the year, Founder 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...
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Best of 2025: The Future of Real Estate is Here (and It's on Blockchain) -Daniel Rollingher (GC Fabrica)
Technically Legal - A Legal Technology and Innovation Podcast
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Best of 2025: Building and Documenting Better Legal Workflows: Insights from Systemology Author David Jenyns
Technically Legal - A Legal Technology and Innovation Podcast
In the most listened to episode of 2025, author of "" and business systems expert, , 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. ...
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Future-Proofing Legal Ops: AI Literacy, Innovation and Augmentation (Meredith Kildow, President Consilio)
Technically Legal - A Legal Technology and Innovation Podcast
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...
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Technically Legal - A Legal Technology and Innovation Podcast
This episode features a conversation with , Co-Founder and CEO of . 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...
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From 'No' to 'Go': How AI Guardrails Drive Trust, Enabling Legal to be a Business Accelerant, Not Blocker (Sabastian Niles, Salesforce President & CLO)
Technically Legal - A Legal Technology and Innovation Podcast
In this episode, , President and Chief Legal Officer at , 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...
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Benchmarking Legal AI: Measuring the Delta Between Man and Machine (Anna Guo Legalbenchmarks.ai)
Technically Legal - A Legal Technology and Innovation Podcast
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 Founder . 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...
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Want to be a Crypto Lawyer? Rule # 1: Use the Technology. Rule #2: Beware of Hyper-Specialization (Justin Wales-Head of Legal, Crypto.com & Author of Crypto Legal Handbook)
Technically Legal - A Legal Technology and Innovation Podcast
, Head of Legal for the Americas at Crypto.com, and author of 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...
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The Business of Law: From IP Lawyer to Investor to CEO to Legal Tech Ecosystem Builder (Avaneesh Marwaha, Litera CEO)
Technically Legal - A Legal Technology and Innovation Podcast
Avaneesh Marwaha, the CEO of , 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...
info_outlineJustin 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)