Debi & Tom DePaola

Debi and Tom DePaola built more than homes. They built relationships, trust, family memories, and a lasting place in Cape Coral’s construction story.

A Life Rooted in Family and Community

In 1979, Debi and Tom DePaola moved from Tiverton, Rhode Island, to Cape Coral, Florida. Together, they raised three sons and became deeply connected to the community they called home.

Their lives in Cape Coral extended beyond construction. Debi and Tom were connected to local church life, school communities, youth organizations, and the relationships that make a place feel like home.

They were previously members of St. Andrew Catholic Church and became members of St. Katherine Drexel Catholic Church when the church began in 1990. They were also proud volunteers at St. Andrew Catholic School and other youth organizations.

Debra Ann DePaola
February 23, 1958 – December 4, 2021

Working Side by Side

Debi’s path in construction grew from hands-on experience, family knowledge, and a commitment to doing things right. After working in construction with Tom, she studied the industry, learned the business from the ground up, and became a Building Contractor in 1988.

Tom brought the DePaola family’s construction tradition to Cape Coral. Together, Debi and Tom continued that tradition through Tradewind Estate Homes.

A Shared Belief in Helping People

Their love of construction began with the idea of helping people design and plan projects that fit their needs, their families, and their budgets.

For Debi and Tom, construction was personal. Every home, remodel, addition, and commercial project represented someone’s plans, hopes, investment, and trust.

Thomas Jay DePaola, Sr.
August 28, 1956 – April 26, 2019

The Next Generation

Debi and Tom DePaola’s sons, Chris and Matt DePaola, grew up around Tradewind Estate Homes and the daily example their parents set.

Chris DePaola, JD

Through years of watching and working alongside their parents, Chris and Matt learned the values that shaped the DePaola family’s work: hard work, honesty, dependability, trustworthiness, patience, and doing things the right way.

Debi and Tom also instilled in their sons the importance of education, preparation, and lifelong learning.

Matt earned his MBA from the University of Florida Hough Graduate School of Business and his Bachelor of Science in Finance from Florida Gulf Coast University.

Chris earned his Juris Doctor from the University of Florida Levin College of Law and his Bachelor of Arts in Political Science and Economics from the University of Florida. He is also a member of the Florida Bar.

Those lessons continued into their own professional lives.

Today, Chris and Matt are cofounders of Tortuga Capital, a value-oriented investment firm built around patience, discipline, and long-term thinking.

Matt also leads the Fundamental Investing Institute, an educational platform focused on teaching practical, fundamentals-first investing, intrinsic value, cash-flow-based analysis, and long-term thinking. Chris also contributes to the development, content strategy, marketing, and operations of the Fundamental Investing Institute, along with Matt’s wife, Jen.

While their work is in investing and financial education rather than homebuilding, the foundation is familiar: build carefully, think long term, earn trust, and do the work with integrity.

Visit Tortuga Capital

Visit Fundamental Investing Institute

Remembering Their Legacy

This page honors Debi and Tom DePaola as family members, community members, builders, and trusted friends to many people across Cape Coral and Southwest Florida.

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