A new generation of investors has arrived, and they are changing the rules. Millennials and Gen Z now represent the fastest-growing segment of retail investors. They expect immediate answers, personalized insights, and digital experiences that match the polish of their favorite consumer apps.
What they are finding instead are legacy brokerage platforms that feel slow, static, and out of touch. The result: a widening gap between what these investors want and what financial institutions currently provide.
Many have turned to general AI tools to fill that gap, often with mixed results. While these tools can explain basic concepts, they also produce inaccurate or outdated information that leads to confusion and, in some cases, poor investment decisions. The intention is curiosity; the outcome is risk.
A Generation That Expects More
Younger investors are not asking for speculation or shortcuts. They are asking for context—information that helps them understand what is happening in the market and how it relates to their holdings. They want engagement that feels personal, not generic.
As Roy Michaeli, co-founder and CEO of WNSTN AI, explains, "This generation is proactive. They want to learn as they go, but they need trusted systems that guide them in the right direction. The experience should build confidence."
Building the Right Kind of AI for Finance
WNSTN AI was created to help financial institutions deliver that experience. Its technology is built for the structure and scrutiny of capital markets, combining interactive design with rigorous compliance oversight.
Instead of relying on broad, open-domain models, WNSTN uses financial-grade, verified data drawn from filings, earnings reports, and regulated sources. This ensures that every response is grounded in current, factual information that can be audited and explained.
Equally important are the guardrails that define how the system interacts with investors. WNSTN's platform includes agentic oversight that supervises all activity across the product. When a user asks a question that crosses into advice or speculation—such as "What should I buy?"—the agent redirects the conversation toward education. Each exchange is documented, creating a clear audit trail for regulators and internal compliance teams.
Turning Curiosity into Confidence
A common barrier for newer investors is not knowing where to start or what to ask. WNSTN addresses this by using intelligent prompts that encourage users to explore relevant topics; for example, how interest-rate decisions might affect certain sectors, or how their portfolio performance compares to the broader market.
Once a user engages, the platform delivers concise explanations of what moved the market and what events lie ahead. By turning complex data into accessible insight, it helps investors connect information to impact—a key ingredient in long-term engagement.
A Better Deal for Brokers
The same system also gives brokers and financial publishers a clearer view of what their users care about. Through WNSTN Connect, institutions can track trending questions, emerging themes, and patterns in investor behavior. This transforms raw interaction data into business intelligence that can guide product development and client outreach, all while maintaining privacy and regulatory standards.
"Clicks and time on site are surface metrics. They don't explain why someone engages," says Jamie Rakover, WNSTN's co-founder. "We focus on intent: understanding curiosity, motivation, and behavior. That's how firms build lasting loyalty in the digital age."
Bridging a Generational Divide
Millennials and Gen Z are not rejecting financial institutions. They are rejecting friction. They want tools that respond to them, speak their language, and help them make sense of the market.
WNSTN's approach shows that this can be done responsibly. By combining real-time insight, educational design, and strict compliance oversight, the company helps brokers engage a new generation of investors without compromising on accuracy or governance.
"The goal isn't to replace human advisors," Michaeli says. "It's to make every digital interaction smarter, safer, and more meaningful."
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