Salvador Carranza sits down with Matthew Basile, founder and CEO of Naya Software and Naya Law, to unpack what an AI-native law firm actually looks like when a real estate lawyer builds one himself. They get into why selling legal AI tools to law firms has failed for a decade, why Naya pivoted to sell outcomes directly to mortgage lenders, and what a Management Services Organization model unlocks when a firm stops protecting the billable hour. Matt lays out exactly how a curious builder becomes a legal AI expert in 2026: not by reading, but by trying. Watch the full conversation for the playbook on full-stack AI law firms from someone shipping them today.
CHAPTERS
00:00 Introduction to Matt Basile's Journey
03:32 Parenting and Entrepreneurial Mindset
06:19 The Importance of Travel in Shaping Perspectives
10:10 Transitioning from Software to Law
13:58 Navigating Change in the Legal Industry
18:12 Embracing Iteration and Learning from Failure
22:05 Building Naya: A Solution for Legal Challenges
27:49 The Shift to Full Stack Law Firms
32:13 Navigating Competition in Legal Tech
36:17 Curiosity and Learning in Legal Practice
42:15 Understanding Naya's Role in Legal Tech
46:18 Future Strategies for Naya and Legal Partnerships
Takeaways
The only way to get good at legal AI is to stop reading and start trying. Curiosity and iteration beat credentials.
LLMs are a programming language inside a software stack, not a feature you paste on top of a legacy workflow.
Selling AI tools to law firms failed for a decade because clients buy outcomes, not productivity gains.
Naya pivoted from selling to lawyers to selling to the mortgage lenders who actually stand to benefit from faster closings.
The Management Services Organization model lets an AI-native firm scale legal capacity without traditional partnership drag.
Clients are ready to cannibalize the billable hour; most partners five years from retirement are not.
The right hire for a tech-first law firm is a builder who wants to sell the new model, not a lawyer who wants billable stability.
Legal work product still has to be 100 percent right. The tools you build to get there can ship at 80 percent and iterate.
Document automation has been viable technology for 10 years. The reason it did not stick is incentive structure, not capability.
Enterprise systems that teams already work in every day are defensible in a way point AI tools are not.
👤 Guest Bio
Matthew Basile is the founder and CEO of Naya Software and Naya Law, based in the Greater Tampa Bay Area. He earned his JD at Fordham University School of Law, where he served on the Fordham Urban Law Journal, and practiced real estate law before leaving to build Naya full-time. Naya is an AI-powered enterprise platform for commercial real estate mortgage originations; its users have closed 1,319 transactions totaling $35.2 billion, running on Microsoft Azure with SOC 2 Type II certification. Matt writes the "Technology for Real Estate Transactions Newsletter" on LinkedIn, where he focuses on AI-native law firm design, Alternative Business Structure and Management Services Organization models, and real estate transaction technology. In his free time he is raising four boys, traveling with his family, and hiking and skiing with them whenever possible.
🔗 Connect With Matt
• LinkedIn: https://www.linkedin.com/in/matthewjbasile/
• Naya Software: https://www.nayasoftware.com
🔗 More From Salvador
PossibLaw: https://www.possiblaw.com
Full podcast library, essays, and tools for legal professionals who are done watching from the sidelines.
LinkedIn: https://www.linkedin.com/in/salvadorcarranza
