On this episode of The AI Native Advisor, Mike sits down with Nisiar Smith, founder and CEO of Courtside Wealth, for a conversation that speaks directly to what every founder-led RIA is grappling with: how to build trust at scale, serve a high-profile client base, and design a tech-enabled firm without losing the human edge.

Nisiar shares his journey from the traditional banking world to launching a modern RIA focused on athletes, entertainers, coaches, and entrepreneurs. These are clients with demanding schedules, complex needs, and no time for fluff. He breaks down what it takes to stand out in one of the most competitive advisory markets in the country, where trust isn't given and has to be earned through consistency and presence.

The conversation dives into how Courtside is using AI today, including onboarding, meeting prep, client communication, and internal workflows. Nisiar also lays out his vision for what comes next, including fully integrated systems, AI co-pilots that understand firm philosophy, and a model where the back office runs efficiently so the advisor can focus on relationships.

This is a tactical and thoughtful look at what it means to build a high-touch firm that uses AI as leverage rather than replacement. For any advisor thinking about trust, growth, and how to scale the unscalable, this one is worth a listen.