By Steven Bernstein, President – Stonewater Financial
Artificial intelligence is changing the way we live and invest. Machine learning can crunch numbers, analyze performance, and recommend portfolios in seconds. They can even adjust allocations automatically as markets move. On the surface, it feels like technology has all the answers. But when it comes to building wealth that supports your life, the question isn’t just whether AI can manage your portfolio. The real question is: can it understand you?
AI “learns” about you by analyzing inputs, your age, income, timeline, or how much risk you say you can tolerate. The more data you provide, the more precise the recommendations. Yet AI is limited by the information it’s given. If the questions don’t capture the full picture, the results fall short. A system might recommend a growth-heavy portfolio because you’re in your 40s, but it doesn’t know you plan to buy a business in three years. It might register that you have a moderate tolerance for risk, but it doesn’t know how you felt the last time the market dropped 20%. AI can recognize patterns, but it can’t read between the lines.
A financial advisor also learns about you, but in a different way. Instead of relying on static inputs, an advisor learns through conversation. They don’t just record your answers, they ask follow-up questions. They notice hesitation in your voice when you talk about risk. They connect details from one part of your life to another, like how a conversation about your children’s education reveals insights about your legacy planning. And the better an advisor knows you, the more efficient your strategy becomes. Allocation isn’t just numbers on a screen, it’s tailored to your actual needs and goals.
This difference shows up clearly in portfolio design. AI might suggest a “rule of thumb,” like holding 30 stocks to attempt to stay diversified. But an advisor will dig deeper. Does owning $5,000 worth of a stock in a $10 million portfolio actually matter? Probably not. Are you holding too much in one position that could derail your plan if things turn? Possibly. These aren’t simply mathematical questions; they’re questions of context, and context only comes out in conversation.
That’s the real advantage of working with someone who knows you. AI is powerful, but it doesn’t have curiosity. It won’t reframe your answers or challenge your assumptions. A financial advisor will. And when the stakes are as high as your financial future, that difference matters.
This isn’t about rejecting technology. AI is a valuable tool. At Stonewater Financial, we use technology to analyze data quickly, spot patterns, and improve efficiency. But technology alone isn’t enough. What drives results for clients is the combination of insight and relationship, using every tool available while making sure your strategy reflects who you are, not just what an algorithm predicts.
At the end of the day, both AI and advisors can learn about you. The distinction is that the right advisor knows how to ask the right questions. And when your allocation is based on the right questions, it’s tailored to you, not just to a model.
Disclosures:
Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual
All investing involves risk, including loss of principal. No strategy assures success or protects against loss.




