Zach Abramowitz is Legally Disrupted

What does it mean to be a valuable lawyer in the age of AI? In this episode, Zach sits down with litigator, technologist, and AI evangelist Damien Riehl to explore how legal expertise evolves, not disappears, in a world of generative models and automation. From his unique path as both a practicing attorney and self-taught coder to his widely discussed “All the Music” project, Damien argues that the future belongs to lawyers who und...

• Why Ivo scrapped its original product to go all-in on LLMs
• The “innovator’s dilemma” facing legacy CLM vendors
• Why in-house lega...

Zach checks in with second-time guest, Spellbook CEO, Scott Stevenson for a wide ranging conversation on some of the hottest topics of the day:

• Why positioning AI for Legal as a two horse race is deeply flawed

• The benefits of selling direct to lawyers as opposed to Chief Innovation Officers

• In-house legal buyers versus law firms

• BigLaw versus small and medium size law firms

• How AI Startups will need to contend with t...

Zach announces that, for the first time since ChatGPT launched, he's investing in a legal AI startup. In this episode, he's joined by Nick Fleisher, CEO of Sandstone, to unpack why in-house legal teams, not law firms, may be the biggest winners of the AI era. Drawing on Nick's background at McKinsey where he advised law firms on AI, the conversation explores why legacy tools are failing lawyers and how AI can solve a problem that...

Zach speaks with Cecilia Ziniti, founder and CEO of GC AI, about why in-house legal teams are often ahead of law firms when it comes to adopting AI - and what that signals for the future of the profession. Drawing on her experience as a former general counsel and AI leader, Cecilia explains why legal AI must be purpose-built for real workflows, how trust and precision shape adoption, and why lawyers who learn to work with AI will ...

Zach sits down with NetDocuments Chief Product Officer Dan Hauck to unpack how AI is truly being used inside law firms and in-house legal teams today - from large-scale document profiling to agentic assistants that search, summarize, and edit directly within the DMS. Recorded live at ND Inspire conference, Dan explains why lightweight models are unlocking new automation, how in-house teams are often leading on adoption, and why th...

Zach talks with Jen Berrent, former WeWork executive and founder of Covenant, an AI-first law firm reimagining how deals get done. They dive deep into what it means to build a law firm from the ground up around artificial intelligence — not as a tool, but as the foundation. Jen shares her perspective on why too much work still runs through Big Law, how AI is transforming the middle tier of legal work, and what it takes to balance h...

• The origin story of Harvey and how it became the “Dallas Cowboys of Legal Tech”

• Lessons from the early days of AI at Google Brain and DeepMind

• Why the real opportunity isn...

• Robin AI's Struggles 
• Personal Connections and Reflections 
• Sp...

• Understanding Centari's Vision 
• Unique Market Insights and Adoption
• Challenges and Opportuniti...

• Non-Lawyer Ownership of Law Firms 
• AI in Transactional Work 
• The Business Model of AI-First Law Firms
• Measurable ROI in Legal Tech
• The IKEA Catalog Scenario 
• AI-First Firms vs. Incumbents
• Market S...

In this episode, Zach interviews Tara Waters, founder of TLW Consulting and former Chief Digital Officer at Ashurst, who led the firm’s rollout of Harvey. They discuss Harvey’s meteoric rise in legal AI, Tara’s firsthand experiences adopting Harvey within a global firm, and how legal teams evaluate AI tools. The conversation explores why lawyers initially gasped at Harvey’s capabilities, how expectations have mature...

• AI and Contracts: A Boring Use Case
• The Adoption Curve of AI in Legal 
• The Story of Law Insider 
• The Birth of One NDA 
• The Future of AI and Contracting 
• Legacy Product Overview 
• AI Capabilities and New SKU 
• User Growth and Market Excitement 
• Product Distribution and Democratization...