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

keep it real
leave it better than you found it

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

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Joe M. Sergi

CFO

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Anthony Casaccio

COO and Special Counsel

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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

Sue Caporale

Executive Coordinator

Kailey Cooper

Executive Coordinator

Lauren Kearney

Executive Coordinator

Strong Foundations

Family Office Ventures

Clear Height Properties

Proven industrial real estate expertise

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EnRoads Paving

Improvements with an owner's perspective

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RidgePoint Facility Services

Commercial property maintenance

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Conversion Energy Systems

Turning plastic waste into electricity

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Dimora Capital

Multifamily Midwest acquisitions

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Lavoro Services Corp

Skilled on-demand union labor

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LSC Demolition

100% union demolition crews

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Dominic A. Sergi

CEO

Dominic Sergi is the co-founder of Westshore Capital Group, his family’s investment company. Under his leadership, the broader Westshore team deploys capital across a wide range of assets and businesses through direct investments, lending, and strategic partnerships. He is also Co-Founder and Partner of Dimora Capital, a real estate investment firm focused on acquiring and operating multifamily assets, and Co-Founder and CEO of Clear Height Properties, a vertically integrated industrial real estate investment and management company that has bought and sold more than $1 billion in assets to date.

Previously, Dominic co-founded Cresco Labs, which he helped take public in 2018, and played a key role in building it into a leading national cannabis operator. He retired from its board in 2021, the year the company reported nearly $1 billion in annual revenue.

Dominic also serves as Treasurer of the Nicholas D. Sergi (NDS) Foundation, established by his family in memory of Nicholas Sergi. Through its annual fundraising events, the foundation has raised more than $1 million to support causes spanning youth and agricultural education, family and community services, healthcare, faith, and military support.

Joe M. Sergi

CFO
Joe Sergi is the co-founder of Westshore Capital Group, his family’s investment company, which he established alongside his brother, Dominic. An entrepreneur and private investor, Joe focuses on building and growing operating companies through strategic investments, strong leadership, and operational excellence. He plays an active role across Westshore’s portfolio, working closely with management teams to strengthen operations, develop leadership, and drive long-term enterprise value.
 
With extensive experience in construction, commercial real estate, and business operations, Joe has been instrumental in the development and growth of several companies, including Clear Height Properties, EnRoads Paving, RidgePoint Facility Services, LSC Demolition, and Lavoro Services Corp. Previously, he held leadership positions at Rex Electric & Technologies, including Senior Vice President of Sales and head of its Technology Division, and worked in commercial real estate with Newmark Knight Frank.
 
Joe is also a co-founder of the Nicholas D. Sergi (NDS) Foundation, established by his family in memory of his brother, Nicholas. His philanthropic involvement has included the USO of Illinois, City of Hope, and the Leukemia & Lymphoma Society, which recognized him as its 2009 Man of the Year.

Anthony V. Casaccio

COO and Special Counsel
Anthony V. Casaccio is Chief Operating Officer and Special Counsel at Westshore Capital Group, a Chicago-area family office focused on building and preserving wealth across generations. He also leads AVC Law Group, LLC, advising clients on commercial real estate and corporate transactions. Across his legal career, he has been responsible for acquisitions and dispositions totaling more than $1 billion.
 
At Westshore, Anthony oversees day-to-day operations and supports the family’s investments and businesses through strategic planning, transaction structuring and execution, corporate governance and risk management. He works closely with the family’s principals, business leaders, and outside advisers to align investment decisions and operations with long-term objectives.
 
Anthony began his career at Inland Development, gaining firsthand experience in complex real estate development and transactions. He entered legal practice at Amari & Locallo, focusing on real estate property tax law, before joining Schain, Banks, Kenny & Schwartz, where he was quickly named a partner. His practice encompassed land use and entitlements, acquisitions and dispositions, commercial leasing for landlords and tenants, and financing transactions for borrowers and lenders.
 
He later served as Associate General Counsel at Cresco Labs, responsible for all legal matters involving its national real estate portfolio. He handled leasing and sale-leaseback transactions totaling well over $300 million, navigating complex transactions across multiple jurisdictions within the highly regulated cannabis industry.
 
Today, Anthony brings that combination of development experience, legal judgment, and operating perspective to his leadership at Westshore and his practice at AVC Law Group. His approach is practical and business-focused: understand the objective, manage the risks, and get the deal done.