Thriving Across Generations

Building Wealth and Creating Legacies

At Westshore Capital Group we believe you have to do good before you can do great. It’s why our Core Purpose is “Building Wealth and Creating Legacies.” Not just for ourselves, but everyone we come in contact with. From the investments that we make to the donations that we give, we do this through the lens of our Core Values. It’s what makes us who we are.

Guiding Every Decision

Westshore Capital Group Core Values

Grounded in Philanthropy

Giving Forward for Generations to Come

By 2027, we aim to be giving $1,000,000 each year.

Giving Makes You Smile

In addition to providing ongoing support for the mission of The Nicholas D. Sergi Foundation, we take our brother Nick’s motto, Giving Makes You Smile to heart.

To that end, we aim to make significant contributions to established and emerging nonprofits that support underserved communities throughout the Chicago area.

Trusted Partnerships, Enduring Value

Relentless Focus on Relationships

At Westshore, we believe private equity, real estate, and other collaborative investment ventures should be more than transactions — it’s about enduring relationships built on trust, transparency, and a shared vision for success. We view every investment as a partnership, working closely with our stakeholders to create value and deliver long-term growth. Our collaborative approach ensures that our partners, residents, and communities experience the full benefit of our expertise and dedication. With a steadfast commitment to personalized service, we engage deeply at every stage of the investment lifecycle, from acquisition and management to growth and reinvestment. These relationships are the foundation of our success and the reason we continue to thrive in an evolving market.

Family Services

Our Family Services encompass a range of essential functions designed to ensure the long-term continuity of the Family’s wealth, while also supporting the seamless day-to-day operations of the Family Office.

These services include estate planning, tax preparation, Family Office governance, succession planning, insurance management, financial planning and reporting, and information management.

To deliver these services effectively and efficiently, we draw on a combination of in-house capabilities and carefully selected third-party experts. This integrated approach allows us to provide thoughtful, customized solutions aligned with the Family’s values and long-term goals.

Investment Management

Our Investment Management services are designed to preserve and grow the Family’s wealth across generations, guided by a disciplined, long-term approach.

We oversee all aspects of portfolio construction and management, including asset allocation, investment selection, risk management, and performance monitoring. Our strategy blends in-house expertise with insights from a trusted network of external partners, ensuring that every investment decision is made with rigor and care.

With a focus on diversification and capital preservation, we tailor our approach to meet the Family’s unique goals and evolving needs, providing clear reporting and proactive guidance every step of the way.

Passionate Leadership

Meet the Westshore Capital Group Team

Dominic A. Sergi

CEO

Joe M. Sergi

CFO

Anthony Casaccio

COO and Special Counsel

Kailey Cooper

Executive Coordinator

Lauren Kearney

Executive Coordinator

Sue Caporale

Executive Coordinator

Strong Foundations

Family Office Ventures

Clear Height Properties

Proven industrial real estate expertise

EnRoads Paving

Improvements with an owner's perspective

Conversion Energy Systems

Turning plastic waste into electricity