Benjamin Greenlee

Benjamin Greenlee is the founder of Highbridge Financial Services, an independent advisory firm focused on helping successful individuals and families make more informed, efficient decisions around wealth, taxes, and long-term financial structure.

Ben’s path to financial planning began in service. A graduate of Dickinson College and its Army ROTC program, he commissioned as an Infantry Officer in the United States Army. He went on to complete Ranger School before serving with the 10th Mountain Division, including a deployment to Afghanistan during Operation Enduring Freedom.

After nearly five years of active duty service, Ben transitioned into financial services. Early in his career, he began to recognize a pattern—many individuals were doing the right things financially: saving consistently, investing prudently, and working toward long-term goals. Yet despite this discipline, critical gaps remained.

Over time, he observed that these gaps were rarely the result of poor effort. Instead, they often stemmed from structural blind spots—particularly in areas such as tax planning, risk exposure, and the long-term consequences of distribution decisions.

At the same time, Ben came to understand that the traditional large-firm model, while built with strong intentions, can introduce constraints that limit how comprehensively advice is delivered. Internal structures, product limitations, and growth objectives may subtly influence planning decisions over time—often without the client ever realizing it.

Highbridge Financial Services was built to remove those constraints.

Ben focuses exclusively on helping clients evaluate decisions through a broader lens—one that considers not only investment strategy, but also taxation, income sequencing, liability exposure, and intergenerational impact.

A central theme in his work is the recognition that the greatest risks to long-term wealth are often not market-driven. In many cases, they are structural—particularly when it comes to taxation. Without careful planning, the way assets are distributed over time can materially impact outcomes for both clients and future generations.

Many of the individuals Ben works with have accumulated wealth through discipline and thoughtful decision-making. They are often well-prepared on the surface. However, they have not always fully accounted for second- and third-order effects—how taxes, legal exposure, and incomplete planning structures can influence outcomes long after they are gone.

His role is to help bring clarity to those variables.

Ben works best with individuals and families who value thoughtful decision-making, are open to collaboration, and understand the importance of surrounding themselves with the right advisors. His approach is grounded in long-term relationships, with a focus on building strategies that extend beyond a single lifetime.

In addition to his advisory work, Ben is a multi-unit business owner, giving him firsthand perspective into the operational and financial realities faced by business owners and high-income professionals. He also continues his service as a senior officer in the United States Army Reserve, maintaining a leadership role grounded in discipline, accountability, and service.

As a husband and father, Ben approaches planning with a deep awareness of responsibility—not just to the client in front of him, but to the people and generations impacted by the decisions made today.

This is general information and not individualized financial advice.