From Corporate Counsel to AI Mentor: A Legal Career Pivot

Masciantonio, who spent seven years as executive vice president and general counsel at the retail giant Five Below, now balances his boutique practice for entertainers and small businesses with 20 to 30 hours of AI training each week. Working through the platform Micro1, he treats the technology not as a threat to his livelihood, but as a mentee in need of nuanced guidance. His daily workflow involves creating complex contract scenarios, establishing rubrics for negotiation, and coaching AI systems to distinguish between minor technicalities and genuine "red line" issues.

The compensation model relies on a mix of hourly rates—sometimes reaching $200—and task-based multipliers that reward efficiency. Beyond the financial incentive, Masciantonio argues that the shift has regrounded him in the fundamentals of law. While he acknowledges the industry-wide anxiety regarding AI replacing rote legal work, he maintains that lawyers have an ethical mandate to shape these tools. By refining the decision-making logic of AI, he believes the profession can move away from repetitive, low-level tasks toward more impactful, high-level advocacy.