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.

On this episode of The AI Native Advisor, Mike sits down with David Rath, Partner and CIO at Continuum Wealth Advisors, for a conversation that hits right at the center of what every growing RIA is wrestling with right now: scale, succession, and the real role of AI in the next chapter of firm building.

David shares his path from Northwestern Mutual and Goldman to joining Continuum as the long-term successor to a 35-year rainmaker adviser. The two dig into what it actually looks like when decades of client knowledge lives inside one advisor’s head, and how to thoughtfully pull that institutional memory into systems that can support hypergrowth.

They get into the early wins with AI like note takers, but also the real constraints: fragmented data, messy CRM habits, legacy processes, and the tension between efficiency and keeping the human relationship intact. David lays out his vision for a future where an advisor can speak to an interface that updates plans, triggers trades, and pulls from a unified data layer, without ever losing the personal touch clients rely on.

It’s a grounded look at AI strategy from someone scaling an RIA in real time, navigating rapid growth, succession planning, and the next wave of advisor technology. If you’re building a firm for the long game, this one hits home.

In this episode, Mike and Danny dig into what it really means to scale relationships in the age of AI.

For decades, the advisor’s edge has come from trust. The ability to remember the details that matter most: a client’s dog’s name, a birthday, a question asked three months ago. But with books of 400 or 500 relationships, keeping that personal touch has become harder than ever.

That’s where Relationship Intelligence comes in. Mike and Danny share how Impruve is building Relationship IQ, a system that catalogs rapport, key dates, and past questions so AI can surface the right touchpoints at the right time. The goal is not to replace human connection. It is to strengthen it.

From designing trust-earning moments to filtering signal from noise, this episode pulls back the curtain on how AI can help advisors cast wider nets, stay personal at scale, and build stronger relationships that last.

Advisors have always worn the hat of educator -- sharing insights, breaking down complex topics, and guiding clients through change. But in an AI-saturated world, how do you separate genuine thought leadership from content noise?

In this episode, Mike and Danny unpack the tension between authentic creativity and AI-generated writing. The conversation explores how advisors can use AI to compound context, scale their impact, and stay differentiated, without falling into the trap of AI garbage flooding inboxes.

If you have ever felt torn between writing from scratch and letting AI do the heavy lifting, this one is for you.

Mike sits down with Danny to dig into one of the most requested workflows from advisors right now: making email actually work. They walk through how an AI-native operating system ties into Gmail and Outlook, listens in real time, and pulls the right signals out of the noise so nothing slips. From detecting money-movement requests to spotting “I’ll send the invite” promises, they show how an agent can track the follow-through across calendars, CRMs, and meetings, then close the loop without piling up more alerts. They also unpack the hardest part of AI-drafted replies, which is tone. You’ll hear how they model a sender’s voice from sent mail, bring just-enough context into the prompt, and keep a human in the loop so replies feel personal, not robotic.

For RIAs and ops leaders who want signal over noise, this is a clear look under the hood at how Impruve is turning inbox chaos into accountable workflows.

Everyone’s talking about AI note-takers. But the real question is what happens next.

In this episode, Mike and Danny pull back the curtain on integrations, the quiet but critical infrastructure that makes an AI operating system actually work for advisors. From APIs that act like drawers you can only open if you’ve earned trust, to security audits with Google and Zoom, to the “rat’s nest” of data in Salesforce, they unpack what it really takes to turn unstructured chaos into structured signal.

This episode is for advisors and RIA leaders who are ready to turn scattered data into usable intelligence, reduce time wasted in messy CRMs, and understand some of the technical foundation needed to scale with AI.

Every advisor has heard the buzz about AI notetakers. Game-changing at first, but quickly on their way to being just another commodity. The real question for advisors isn’t “who’s taking my notes?” It’s “how do I turn every client interaction into context that compounds over time?”
In this episode, Mike Shannon (CEO) and Danny Shannon (CTO) break down:

• Why the AI notetaker is today’s “light bulb” moment, but not the endgame
• How advisors should think about transcripts as raw inputs, not finished products
• What it takes to transform meeting notes into an operating system that actually scales trust and efficiency

If you’re an RIA leader, a financial advisor building for the future, or simply curious about how AI will reshape advisory workflows, this episode is for you.