Entertainment. Business Law. AI Model Training.
Executive-level counsel and AI advisory for businesses, founders, and creative enterprises—grounded in nearly 25 years of legal and operational leadership.
Senior Counsel. Operator’s Perspective.
Former Executive Vice President and General Counsel of Five Below, Inc. Ron Masciantonio brings nearly 25 years of legal, executive, and boardroom experience to every engagement—translating complex issues into practical decisions.
Counsel for What Comes Next
BUSINESS & OUTSIDE GENERAL COUNSEL
Commercial agreements, retail and office leasing, governance, risk management, and executive decision support.
ENTERTAINMENT & CREATOR COUNSEL
Recording, talent, management, licensing, brand, and commercialization agreements informed by real industry experience.
AI TRAINING & ADVISORY
Professional training, reliable workflows, model-output evaluation, governance, confidentiality, verification, and accountable adoption.
The Hardest Thing to Teach AI Is Judgment.
Ron trains and evaluates frontier AI systems, develops rigorous rubrics and escalation standards, and helps professionals build workflows that combine speed with verification, confidentiality, and human accountability.