On this episode of The AI Native Advisor, Mike Shannon sits down with Brett Wysopal, Founder and CEO of Wysopal Wealth Planning, for a candid conversation about where AI is actually delivering value in financial advice, and where it’s still falling short.

Brett works with equity-compensated tech professionals navigating complex stock options, tax decisions, and liquidity events. In an industry flooded with new tools, he shares a grounded perspective: the problem isn’t a lack of technology. It’s that none of it truly talks to each other.

They unpack:
• Why data fragmentation is the biggest bottleneck in advisory tech
• How AI is helping streamline meeting prep and scenario analysis
• The realities of serving busy, tech-native clients
• Where AI meaningfully saves time and where expertise still matters most
• What the next evolution of AI in wealth management could look like

This episode is a practical look at AI from someone building on the front lines, balancing complexity, client expectations, and an increasingly crowded tech stack.

If you’re an advisor, founder, or operator thinking about how AI fits into your workflow, this conversation is for you.

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On this episode of The AI Native Advisor, Mike sits down with Joel Miller, Founder and Senior Financial Planner at Flames Financial Planning, for a conversation that gets to the heart of how AI is reshaping the economics and the human side of modern financial advice.

Joel shares his journey from working inside traditional advisory models to launching a flat-fee planning firm designed to serve clients more holistically. The two explore why tying revenue solely to assets under management is becoming less aligned with the real value advisors provide, and how technology is making new business models possible.

They dig into the practical realities of using AI day-to-day: from automating meeting notes and follow-ups to freeing solo founders from administrative work. But the conversation goes deeper than productivity gains. Joel explains why the next wave of AI won’t just make advisors faster, it will help them become more proactive by surfacing insights, tracking life events, and strengthening client relationships over time.

It’s a grounded look at how AI is enabling a new generation of advisory firms: smaller, more agile, and deeply relationship-focused. If you’re thinking about the future of wealth management, entrepreneurship, or how AI changes the way professionals serve clients, this conversation is a must-listen.

In this episode of The AI Native Advisor, Mike Shannon sits down with Aditi Kapadia, Founder & CEO of Wealth IQ, to explore how AI is reshaping the future of financial advice.

Aditi shares her unconventional journey from wealth advisor to AI builder — teaching herself to code and developing a proprietary “money mindset” assessment tool to better understand how clients think about financial decisions.

The conversation dives into how AI can strengthen—not replace—the human advisor relationship, and why the future of wealth management will belong to hybrid professionals who combine empathy, behavioral insight, and technology.

In this episode, you’ll learn:
• Why traditional wealth advice often fails to serve mid-level high earners
• How Aditi built her own AI tool from scratch with no technical background
• The role of behavioral psychology in financial decision-making
• Why AI should act as an assistant, not an author
• How AI can enhance client relationships between meetings

If you’re an advisor, founder, or leader curious about how AI will transform professional services, this conversation offers a practical look at what’s coming next.

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The conversation delves into the intersection of music and finance, the writing process and concept of 'Hip Hop Times Finance', the educational impact of the book, content strategy and client growth, AI integration in content creation, and content creation habits and routine. The discussion also highlights the use of AI in content creation and the challenges of integrating AI into the content strategy.

Takeaways

• Content strategy and AI
• Connecting music and finance
• Authenticity and creativity in content
• AI integration in content creation

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.