About Jonathan D. Woods, Esq.

30 Years of Legal Experience. Reimagined for the AI Era.

A seasoned Florida attorney leveraging technology to deliver affordable, high-quality legal services with transparent flat fees.

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Bar Admissions

The Florida Bar - #0145017

Meet Jonathan D. Woods, Esq.

Jonathan D. Woods, Esq. brings over 30 years of legal experience to every client engagement at JD Woods Law PLC. A licensed member of The Florida Bar (#0145017), he has built a career spanning litigation, business transactions, real estate development, and now, AI-enhanced legal services.

After earning his JD from Chicago-Kent College of Law in 1995, where he received two American Jurisprudence Awards, Mr. Woods began his career in litigation in Chicago. He later shifted focus to business and investment transactions in Florida, serving as General Counsel for an international real estate franchise, managing bank-owned asset portfolios post-2008, and founding Orlando Direct Investment LLC to develop a 500-acre mixed-use PUD.

Today, as a retired investor turned legal innovator, Mr. Woods is redefining how legal services are delivered. Frustrated by the inefficiencies of hourly billing and inspired by the potential of AI, he established JD Woods Law PLC to offer flat-fee services that combine technological precision with seasoned legal judgment.

"After 30 years of practice, I saw the legal industry charging by the hour for work that technology could make faster, better, and cheaper. I built JD Woods Law to prove that flat-fee, AI-enhanced legal services can deliver more value, with a real attorney behind every document."

Career Highlights

1995-1997

Litigation Practice

Chicago, IL

Represented clients in complex civil litigation matters.

1997-2023

Business & Investment Transactions

Florida

Focused on business law, real estate, and investment deals.

2002

Founded Orlando Direct Investment LLC

Orlando, FL

Developed a 500-acre mixed-use Planned Unit Development.

Post-2008

Investment Manager for Bank-Owned Assets

Florida

Managed asset portfolios for Wachovia National Bank.

1998-Present

JD Woods Law (est. 1998)

Florida

Continuous operation since founding. Now delivering AI-enhanced, flat-fee legal services to clients statewide.

Education

Juris Doctor (JD), 1995

Chicago-Kent College of Law

Two American Jurisprudence Awards: Comparative Law, Professional Responsibility

BA, Criminal Justice, 1990

Michigan State University

International Law Studies, 1994

University of Innsbruck, Austria

Certifications & Credentials

International Comparative Law Certificate

Environmental & Energy Law Certificate

CIPS Investment & Financial Analysis (NAR, 2008)

Publications & Speaking

Over the course of his career, Mr. Woods has delivered more than 40 speaking engagements and published works across the legal, medical, and real estate industries. Organizations include:

  • Illinois Institute for Continuing Legal Education (IICLE)
  • Illinois State Bar Association (ISBA)
  • Illinois Trial Lawyers Association
  • National Business Institute (NBI, multiple engagements)
  • American Medical Association (AMA, multiple engagements)
  • Certified Commercial Investment Member Institute (CCIM, multiple engagements)
  • The March Group (US Virgin Islands)
  • BBC Exposition (England)
  • Grand Magazine

Community Involvement

Founding Board Member

St. Johns County Sheriff Foundation

Supporting law enforcement initiatives and community safety in St. Johns County, Florida.

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Legal services backed by 30 years of expertise and modern AI. Contact us to get started.

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