The Diamond Podcast: The Oasis Group's John O'Connell

Artificial intelligence is creating new opportunities for financial advisors to improve efficiency, strengthen client relationships, and build more scalable businesses. But with AI capabilities evolving almost daily, determining where to start – and which solutions will deliver meaningful results – has become increasingly complicated.

John O’Connell, Founder and CEO of The Oasis Group, works with RIAs, broker dealers, trust companies, and family offices to evaluate, implement, and integrate technology. His firm’s AI WealthTech Map has grown from 17 to 135 companies in approximately 18 months, offering a revealing look at the expanding universe of AI solutions available to advisors.

In this conversation with Louis Diamond, John explains how firms can identify valuable AI use cases, evaluate vendors, establish appropriate safeguards, and prepare for a future in which clients are becoming increasingly sophisticated users of AI themselves.

His central message: Start with the business problem, become an educated buyer, and remember that human judgment remains essential.

The Storyline

The challenge isn’t finding AI. It’s knowing what to do with it.

A new AI tool launches, an existing wealth management platform announces additional capabilities, or a colleague shares an impressive demonstration. For advisors eager to improve efficiency and stay competitive, the temptation to adopt the latest technology is understandable.

But John O’Connell believes that approach often puts the technology ahead of the business need.

As Founder and CEO of The Oasis Group, John helps wealth management firms make smarter technology decisions, from selecting and implementing platforms to integrating data and developing effective workflows. His experience offers a perspective on both the opportunities AI creates and the practical challenges firms encounter when putting it to work.

And those challenges are becoming more complicated.

The Oasis Group’s AI WealthTech Map now includes 135 individual companies, representing approximately 550 variations of capabilities and licensing options. That doesn’t include established wealth management technology providers that are incorporating AI into their existing platforms.

For advisors, the sheer number of choices makes it increasingly important to understand what they’re buying, what their existing technology can accomplish, and whether a new solution will actually solve a problem.

John’s advice is to start small, but think strategically.

He shares a surprisingly simple first use case: Ask AI to interview the employee who knows how to perform an undocumented business process. The result can be a documented workflow that reduces operational risk while helping employees learn how to use AI effectively.

From there, firms can begin identifying opportunities with greater potential impact, including client acquisition, internal knowledge management, operational efficiency, and business scalability.

But successful implementation requires more than identifying promising applications.

John explains why advisors should establish detailed requirements before attending vendor demonstrations, understand the limitations of APIs and Model Context Protocols (MCPs), and create AI policies that address data protection, employee training, and accountability.

The conversation also examines an important distinction between employee and independent advisors.

While large firms have substantial technology resources, independent advisors may have greater flexibility to adopt emerging tools and develop AI capabilities more quickly. John believes that advantage is particularly relevant as clients increasingly use AI to analyze financial plans, evaluate investment costs, and question recommendations.

Ultimately, he sees AI as an opportunity to strengthen – not replace – the value of human financial advice.

By automating certain tasks and making information more accessible, advisors can spend more time developing relationships, exercising judgment, and helping clients navigate the complex personal decisions that technology alone cannot address.

Topics Covered

AI adoption in wealth management: Why implementing AI successfully requires more than purchasing software or activating existing features.
Identifying the right AI use cases: How to prioritize business problems, operational bottlenecks, and opportunities for meaningful improvement.
Practical applications and ROI: From documenting workflows and improving meeting management to strengthening referrals and internal knowledge sharing.
Evaluating AI vendors: Why detailed business requirements should drive technology selection, rather than impressive demonstrations.
Wirehouse versus independent AI capabilities: How technology control, implementation speed, and open architecture influence advisors’ ability to adopt AI.
The expanding AI WealthTech landscape: What The Oasis Group’s map reveals about the growing number of solutions available to financial advisors.
Technology integration and data access: Understanding APIs, MCPs, and direct data feeds—and why connectivity alone doesn’t guarantee functionality.
AI governance and cybersecurity: Establishing acceptable use policies, protecting client information, and maintaining human accountability.
Training the next generation of advisors: How AI is changing traditional responsibilities and creating new opportunities for professional development.
The future of human financial advice: Why AI may enable advisors to serve more clients while making personal relationships and judgment even more valuable.