“Be a yardstick of quality. Some people aren’t used to an environment where excellence is expected.“

Steve Jobs

“Let us perceive clearly our shortcomings.“

Gautama Buddha

“I was taught that the way of progress was neither swift nor easy.“

Marie Curie

“Tough times don’t last, but tough people do!“


“With some people, if they don’t know, you can’t tell them!“

Louis Armstrong


/The Law Office of Chad D. Cummings

The Law Office of Chad D. Cummings PLLC is a full-service law practice serving business owners, real estate developers, and their families throughout Florida and Texas. I am an attorney and Certified Public Accountant helping people conceive, plan, grow, and exit their ventures and develop effective estate plans to support their endeavors.

My law practice focuses on business law, commercial law, real estate development and management, corporate law, partnership and LLC law, business transactions, commercial real estate, business tax planning, non-profit, estate planning for entrepreneurs and high-net worth individuals, and other areas of law affecting trade and commerce.

My practice also delivers financial analysis and planning, forensic accounting, and tax expertise in the context of our legal engagements, particularly though not exclusively in buy- and sell-side due diligence.

I also help innovators and creators in the disruptive technology space (e.g., blockchain, generative AI and LLM, FinTech, Web3, DeFi, crypto, esports, 4D printing, disintermediation) to protect their bold ideas and maximize their return.

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An Introduction

/Meet Chad

I am an attorney and Certified Public Accountant serving Florida and Texas with dual licensure in both states. I hold a number of other finance and accounting credentials which I apply in my law practice for the benefit of my clients.

Previously, I served in operations and finance with the world’s largest accounting firm (PricewaterhouseCoopers), airline (American Airlines), and bank (JPMorgan Chase & Co.). I have also created and advised a variety of start-up ventures.

I am a member of The Florida Bar and the State Bar of Texas. I hold two law degrees: the Juris Doctor (J.D.) and the Master of Laws (LL.M.). I also hold active CPA licensure and undergraduate and graduate degrees in accounting and taxation, respectively, for a total of four degrees.

I live and work in Naples, Florida, and I serve clients throughout both states.



Client Testimonials

”I hired Mr. Cummings to litigate for me. I hired a company to perform a job and it became a nightmare. . . . He very quickly acted and got the job done quickly for me. He made it happen in a few weeks and I had been waiting over a year. He looked out of me and what was best for me as his client. To me that is what you want when looking for a lawyer to represent you. I will be referring clients and friends to him.“

Client in Naples, Florida

“The much maligned legal profession got a definite lift when Chad decided to take up law. He brings a sharp mind, commonsense thinking and focus on details that allow any client to breathe a sigh of relief. His response time is fast, accurate and explanations are clear and concise. You won’t be left wondering “what did he say” after a conversation about the legal ramifications and available options. We are excited to share that Chad represents our firm. You will be too.“

Client in Dallas, Texas

“Chad is extremely detailed, very through, and professional. Highly recommended and will help you get the results. He was able to get us a very favorable settlement . . . he made a very detailed case which made the difference.“

Client in Naples, Florida

“Chad helped me relocate my small business from Texas to Florida and I could not have asked for a better person to do it than Chad. His service was PERFECTION from start to finish. He is clear and transparent with the fee and always punctual, detailed, and prompt with his answers for any question I had along the way. He is such a trustworthy person. I highly recommend Chad for any business-related case and for future business, I will absolutely come back to him without thinking twice.“

Client in Miami, Florida

“Chad is a kind and caring attorney who works tirelessly to help his clients. He is competent and thorough. He makes sure everything is up to date with current laws and he explains everything in a way so you can understand. I highly recommend him for your legal work.“

Client in Naples, Florida

“Chad advised me on a few business formation issues earlier this year, and I could not be more appreciative of his services. His real world experience in the business world coupled with his grasp of the law make for an invaluable advisor. I highly recommend his services.“

Client in Tampa, Florida

Practice Overview

As an attorney and CPA, I deliver full-stack legal services on an ongoing and ad hoc basis to my clients—including general representation and transactional advisory—at every stage of the lifecycle at a fraction of the cost of retaining a traditional, high-overhead firm. Upon request, I also assist clients with their estate planning needs to develop a 360° view of their legal, financial, and tax objectives.

My specific practice areas include general commercial law, commercial real estate, corporate law, partnership law, buy-sell agreements, redomestications, subchapter “S” elections, crowdfunding structuring, contract negotiation and review, employment law, intellectual property law, federal and state tax law, executive compensation planning, and estate planning services for entrepreneurs and high-net worth (HNW) individuals and their families.

I also help existing clients on myriad other subjects on an as-needed basis.

My Philosophy and Style

I have built a technology-first, nimble solo practice by building automations and tools to minimize the amount of time spent on administrative and other non-value added tasks, allowing me (and my clients) to focus energies on the issues at hand. These are “first principles” which define my approach to the practice of law.

For example, my firm uses 100% self-service, electronic scheduling to keep overhead costs (and clients’ fees) in check. I operate a paperless law practice.

Whenever possible, I leverage software (backed up by my human expertise) to minimize bottlenecks and frustrations traditionally associated with the practice of law. Most of my prospective clients appreciate and prefer these efficiencies.

For example, the most common criticism clients have of their attorneys generally is ineffective and infrequent communication; therefore, I send written status updates almost every week to clients with open matters at no additional charge, providing a roadmap and “next steps” suitable for dissemination to internal and external stakeholders, as needed.

I work exclusively with clients who:

  1. are comfortable using technology;
  2. are decisive; and
  3. view their attorney not as a servant and operating expense to be minimized but as a trusted advisor and capital investment to be optimized.

For those that are uncomfortable leveraging technology in this way or who prefer a more traditional, manual approach, I am happy to provide referrals.

Starting Your Business

/If you’re just getting started, start here.

I often receive inquiries from new and would-be entrepreneurs, small business owners, and start-up founders about the most common legal questions and issues they face in conceiving and managing their ventures. To that end, I have compiled a small library addressing the most commonly asked questions, which I have made available at no cost. Click the button below to get started.