From BigLaw to Solo Practice: Demystifying What it Means to Launch an AI-Native Law Firm

Dan Sito, former federal tax partner and AI innovation partner at Perkins Coie, joins VersionUp to discuss why he left Big Law to launch Sito PC, an AI-native law firm.

Our conversation reveals that going "AI-native" does not mean building a tech company, chasing high-volume/low-value work, or rebuilding a practice from scratch — it means a specialist lawyer using agentic tools to deliver premium work on his own terms.

The conversation covers how democratized access to agent harnesses like Claude Code and Codex has erased much of the resource advantage that kept top performers inside large firms, and why enterprise legal AI platforms (Harvey, Legora, Microsoft Copilot) solve for scale that a solo practitioner simply doesn't need. Sito explains how AI powers his legal practice and maps his work — client intake, legal research, drafting, risk allocation — into stages where agents add leverage while the lawyer keeps judgment and verification.

He also addresses the questions every lawyer thinking about going solo is asking: competitive advantage versus Big Law, the risk of clients insourcing AI, law firm pricing and whether AI-native means cheaper (he argues for expanding value, not just cutting cost), and business development as a solo. On the tech stack, Sito details running a local open model to keep confidential client data under his own control — converting confidential information to generalized inputs for frontier models — and why data autonomy and subscription pricing matter for a bootstrapped practice. A level-headed, practitioner's view of how AI changes the practice and business of law without disruption mythology.

At a time of AI-induced anxiety and fear in the profession, I think lawyers practicing at law firms will find Dan’s experience inspiring and hopeful. In-house lawyers practicing at corporate legal departments will find comfort and familiarity with the transition that Dan’s practice offers when compared to AI-native law firm start-ups, legaltech vendors, and general purpose LLM solutions claiming to be able to fulfill their legal needs.

Most importantly, Dan’s experience shows that lawyers are not predestined to be victims to AI disruption to the legal market. They are actors can choose to act. Individually, boot-strapped, and without having to restart their legal practice from scratch.

https://www.linkedin.com/in/daniel-sito/

https://www.linkedin.com/company/sito-pc/

https://sitopc.com/

ALL VIEWS EXPRESSED OUR OWN

* * *

Version Up Members is a free, invitation-only community for lawyers and legal professionals putting AI to work at law firms and legal departments. Request an invitation: versionup.ai/members