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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) and in the distributed autonomous organization (DAO), entrepreneurship through acquisition (ETA), and search fund spaces to protect their bold ideas and maximize their return.
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 in Naples, Florida
Client in Dallas, Texas
Client in Naples, Florida
Client in Miami, Florida
Client in Naples, Florida
Client in Tampa, Florida
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.
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:
For those that are uncomfortable leveraging technology in this way or who prefer a more traditional, manual approach, I am happy to provide referrals.
I often receive inquiries from new and would-be entrepreneurs, small business owners, and start-up founders (including those going the entrepreneurship through acquisition/search fund route) 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.
Bar Admissions
/Federal, State, and Local
United States Tax Court, Washington, D.C.
United States Court of Appeals, Eleventh Circuit, Atlanta, Georgia
United States Bankruptcy Court, Middle District of Florida, Orlando, Florida
United States District Court, Middle District of Florida, Orlando, Florida
Florida Supreme Court, Tallahassee, Florida
Supreme Court of Texas, Austin, Texas
Collier County Bar, Naples, Florida
Miami-Dade Bar, Miami, Florida
Credentials
/Licensure & Education
Attorney and Counselor at Law
The Florida Bar
State Bar of Texas
Certified Public Accountant
Florida Division of Certified Public Accounting
Texas State Board of Public Accountancy
Forensic Certified Public Accountant
Society of Forensic Certified Public Accountants USA
Certified Management Accountant
Institute of Management Accountants
Certified Internal Auditor
Institute of Internal Auditors
Certified Fraud Examiner
Association of Certified Fraud Examiners
Certified Information Systems Auditor
Information Systems Audit and Control Association
Certification in Risk Management Assurance
Institute of Internal Auditors
LL.M., Real Property Development
University of Miami School of Law
Coral Gables, Florida
Juris Doctor, cum laude
Ave Maria School of Law
Naples, Florida
M.S., Taxation
Southern Methodist University, Cox School of Business
Dallas, Texas
B.B.A., Accounting, with departmental honors
Southern Methodist University, Cox School of Business
Dallas, Texas
Firm Services
My practice emphasizes, but is not limited to, the law as it intersects small- and medium-sized businesses (including early stage start-ups) and their stakeholders.
I personally deliver concierge Chief Legal Officer services (also characterized as general counsel services) to my clients without the many drawbacks of bringing attorneys on payroll, in-house.
When clients hire me, I apply not only my legal knowledge, but also my skills and expertise I accrued in operations and finance at the world’s largest accounting firm, airline, and bank, bolstered by my insights from forming and growing my own ventures.
Prospective clients particularly appreciate this confluence of experience and find it a tremendous value as compared with the costs of onboarding one or more “consultants,” attorneys, accountants, and tax advisors.
Clients enjoy direct access to me (without a middle man, assistant, or go-between) by phone, email, and face-to-face.
Among other things, I assist clients with:
Because I am an attorney and also a CPA, I bring to the table a dual-view, delivering deep subject matter knowledge of financial reporting, accounting, and analysis.
The reality is that many competent, experienced attorneys are uncomfortable with financial statements and analysis and many competent, experienced CPAs are simply not licensed nor equipped to practice law.
My practice also provides strategic advisory and counsel for real estate and business ventures at every stage, from ideation through final sale.
If you prefer, email me instead.
Commercial real estate and business law are my firm’s primary areas of focus. Additional areas of focus include estate planning, tax, insurance, and consumer law.
As a graduate of the University of Miami School of Law Robert Traurig-Greenberg Traurig LL.M. in Real Property Development program, I possess advanced training in real estate law above-and-beyond the standard law school curriculum.
Examples of subject matter I address in my practice include:
This list is illustrative, not exhaustive. Contact me or schedule time to speak using the button below to learn more.
Whether for retail, industrial, hospitality, medical, or any other commercial application, commercial lease preparation and negotiation is an art form and carries with it significant complexity. I have advanced, targeted knowledge of commercial leasing and can address it from a panoply of perspectives: owner, property manager, tenant, and assignee/sublessee.
For example, special consideration must be given to renewal options; CAM reconciliation and audit rights; transfer and assignment; the use of personal guarantees and letters of credit; and rights of first offer (“ROFO”)/rights of first refusal (“ROFR”).
Concrete examples of general business legal matters that I address within my practice include:
This list is illustrative, not exhaustive. Contact me or schedule time to speak using the button below to learn more.
Purchasing or selling a company is often one of the most important and formative moments in an entrepreneur’s life. No transaction of this sort is ever routine. From preliminary, informal discussions through final closing and disbursement, I assist clients to protect their interests at every stage of the process.
More than simply negotiating the highest and best sales price, I support clients in developing a comprehensive framework to strike not only the best price but also the most sensible and sustainable outcome in line with their unique lifestyle and business goals.
As an attorney and CPA, I am pleased to offer full-stack M&A transaction advisory services to small- and medium-sized businesses and their principals on a cost- and time- efficient basis, including IRC section 368 transactions, reverse mergers, SPACs, direct equity investments, and IPOs.
Timing is everything in these deals. There are two common mistakes entrepreneurs commit when approached by a prospective purchaser or partner: (1) fixating on the purchase price at the expense of the other substantive deal terms; and (2) waiting until the 11th hour to retain experienced legal counsel and tax advisors to protect themselves. Email me today to get started.
For new businesses, I will assist clients with ideation, formation, and structuring of their businesses to minimize compliance risk, allowing start-ups and their principals to focus on value creation, not paperwork. I prepare not only articles of formation, but also operating agreements and corporate governance documents to position businesses for long-term success.
Beyond filing articles of incorporation, I assist clients in developing corporate bylaws, policies, and governance to minimize operational, legal, and financial risk. As a business attorney and CPA, my knowledge of internal controls, risk management, and forensic accounting are particularly beneficial to clients.
I assist business owners in evaluating overall tax strategy generally and the desirability and timing of making an election under subchapter “S” of the Internal Revenue Code specifically.
As part of this process, I counsel clients in determining whether their business venture qualifies for treatment under this provision of the Code; assist clients with preparing and filing the requisite paperwork; and refer clients to qualified tax preparers and bookkeepers to maintain compliance on a go-forward basis.
Whether assisting business owners in raising equity by adding new stakeholders or partners through a “buy-in” agreement or redeeming existing stakeholders or partners through a so-called “buy-out” or severance agreement, equity transactions are nuanced but need not be adversarial. I assist clients to structure these transactions to minimize risk and optimize the outcome.
Commencing January 2024, the Corporate Transparency Act requires virtually every small- and medium-sized business in this country to report information on so-called beneficial ownership, including the equity owners of a business, as well as anyone who exerts significant influence or control over decision-making.
Contrary to the name of the Act, the law does not apply only to corporations, but also to LLCs, partnerships, and trusts.
This sweeping federal law carries with it significant fines and penalties (including the possibility of jail time in exceptional cases) for non-compliance. I assist clients in preparing and filing Beneficial Ownership Information (BOI) reports with the relevant federal regulatory body.
I counsel and advise clients who are relocating their business to Texas or relocating their business to Florida from other states—a process known as “redomestication” or “redomiciling.”
Contrary to popular belief, the redomestication process is not merely a paperwork exercise; it requires significant planning and thorough execution, demanding close coordination with the Secretaries of State, and in some cases, states’ taxation authorities, to accomplish a redomestication.
In most cases, I am able to offer redomestication services on a flat fee basis.
At the outset, and especially for technology-oriented small businesses and new ventures, a company’s only assets might be brand and intellectual property. For this reason, it is imperative that founders register trademarks to protect themselves and their investors early in the game.
I assist clients in preparing and filing trademarks with the United States Patent and Trademark Office (USPTO).
As an attorney and Certified Public Accountant, I routinely assist entrepreneurs and other successful individuals craft bespoke estate plans tailored to their unique circumstances and goals.
I do not operate a “will mill.” Each estate plan is personalized to meet the objectives of each client which are developed through a series of conversations over time, and my pricing and availability reflect this reality.
Effective estate planning is not a “check-the-box” exercise. It is an iterative process that requires ongoing commitment and interest from client and attorney alike. To that end, I am please to offer estate planning services to prospective clients who benefit from this individualized approach.
Although my practice is laser-centered on the above areas of focus, I recognize that there exists a business-personal continuum, especially for founders and business owners where their venture is their primary focus in life.
With that in mind, I assist clients with matters above and beyond what I have outlined above, including in other domains of law, on an ad hoc basis. Please contact me to learn more.
Legal fees are usually at the forefront of prospective clients’ minds. Legal fees vary tremendously dependent upon the scope, timing, and complexity of the proposed work.
Prior to undertaking any work together, I provide prospective clients with transparent, clear pricing for their consideration, thereby allowing them to make an informed decision. I do not “hide the ball.” I discuss legal fees in the first consultation, providing a general, high-level estimate.
I am not a “consultant,” nor do I charge “consulting fees.” I am a licensed attorney operating a full-service law practice and a CPA with Fortune 100 experience, and the legal fees I charge are proportionate to the level of complexity and expertise required by clients’ matters.
My rates are competitive with other firms and attorneys and vary by subject-matter and engagement. However, for clients whose only consideration is price, I am happy to provide referrals to low- and no-cost legal resources.
Should we agree to work together, legal fees and costs will be clearly delineated in a formal engagement letter. A reasonable deposit or retainer is usually required at the beginning of an engagement. Clients are usually invoiced monthly on the first business day, and payment is expected upon receipt unless other terms have been agreed in advance.
Depending on the nature of the engagement, one or more traditional or alternative payment options may be suitable.
Most engagements will be on an hourly basis because of the inherently unpredictable nature of legal work. In certain matters where the scope of work is fairly routine and predictable, I may offer to perform work on a “flat-fee” basis. Finally, in limited circumstances, a contingency (“percentage”) fee may be appropriate.
There is no “one-size-fits-all” approach. I am happy to work with clients to keep legal fees in check by employing, as appropriate, scope limitations, fee caps, and other creative arrangements within the limits of state bar rules. I also offer non-traditional payment options, detailed below.
My firm accepts a variety of cryptocurrencies, as well as Goldbacks and precious metals (e.g., gold, silver), as alternatives to remitting funds in US Dollars.
Please ask about this option during your initial consultation. I will be happy to prepare invoices and accept payment using these alternatives for any services my firm offers pursuant to terms we discuss and finalize in a written representation agreement.
When permitted by state law and professional ethics, I will accept equity in lieu of cash from some start-ups. This proposition is inherently complex and may be prohibited in some cases.
These arrangements are only suitable where there is mutual interest and viability in forming a long-term working relationship. Given the many nuances of these arrangements, I advise clients to seek external representation when discussing and negotiating them—but it CAN be done.
Selected Publications
/Recent Writings
Six Common Pitfalls Small Business Owners Must Avoid When Selling Their Business
Entrepreneur Magazine
How the Feds Could Regulate Crypto (and Why All Is Not Lost for Investors)
Entrepreneur Magazine
Transhumanism: Morality and Law at the Frontier of the Human Condition
Ave Maria Law Review; also available on Amazon
Non-Fungible Tokens: A New Way to Securitize Digital (and Real-World) Assets
Entrepreneur Magazine
Finally, the Feds Are Cutting Startups Some Slack: Why the New Tax Law Is a Game-Changer
Entrepreneur Magazine
Cryptotax is Here to Stay: Understanding Tax Implications for Bitcoin Miners and Traders
Tech Bullion
Year End Tax Planning for Crypto Traders
LinkedIn (self-published)
More About Chad
/Attorney and CPA
I am an attorney, CPA, and advisor serving small- and medium-sized ventures and their entrepreneurial owners. I help people start, grow, manage, and exit their creations. In addition to my law practice, I also teach Business Law to undergraduates at Florida Gulf Coast University.
I have served in operations and finance with the world’s largest accounting firm, airline, and bank. I chose to pivot from my career in finance to pursue law as my next profession. I am now admitted to The Florida Bar and the State Bar of Texas.
I completed my Juris Doctor on full-tuition merit scholarship. While in law school, I served on the Law Review Editorial Board where my monograph— Transhumanism: Morality and Law at the Frontier of the Human Condition—was selected for publication in the school’s law journal. I passed the July 2022 administration of the Florida Bar Examination and the February 2023 administration of the Texas Bar Examination.
Following the completion of my J.D., with honors, in Naples, Florida, I joined and graduated from the advanced post-graduate Real Property Development LL.M. program at the University of Miami School of Law in Coral Gables, Florida. I hold active CPA licensure in Florida and Texas and undergraduate and graduate degrees in accounting and taxation from the Edwin L. Cox School of Business at Southern Methodist University in Dallas, Texas.
Previously, I supported capital investment decision-making and financial reporting for the commercial real estate and legal divisions at American Airlines at their headquarters in Fort Worth, Texas.
Prior to that, I co-founded Food on the Fly, a data mining and logistics start-up leveraging mobile connectivity and transactional analytics to deliver premium meals in-terminal to transiting, time-constrained air passengers. My work on this venture is ongoing.
Before making the jump to the entrepreneurial realm, I started my career in the private equity and financial services tax compliance and consulting practice (“SALT-FS”) at PricewaterhouseCoopers in their Dallas office where I engineered technical solutions to more effectively serve VC/PE clients including Texas Pacific Group, Goldman Sachs, First Reserve, HGGC, and others.
I also hold the Forensic Certified Public Accountant, Certified Management Accountant, Certified Internal Auditor, Certified Information Systems Auditor, Certified in Risk Management Assurance, and Certified Fraud Examiner credentials. I maintain professional memberships with the Institute of Management Accountants, Institute of Internal Auditors, Association of Certified Fraud Examiners, Society of Forensic Certified Public Accountants, Information Systems Audit and Control Association, state CPA societies, the State Bar of Texas, and The Florida Bar, among others.
In my spare time, I research and explore the taxation and valuation of virtual assets and novel applications thereof. I also serve as a mentor and coach for university-age small business creators. I live and work in sunny South Florida and serve clients throughout Florida and Texas.
Important Notices and Disclaimers
/Please read the following very carefully.
This website and the material provided here is for informational purposes only, and does not constitute tax, accounting, or legal advice. No person should rely on, or act, or refrain from acting on the basis of any matter or information contained in this website without seeking appropriate legal or other professional advice.
The attorney-client relationship is only created by the execution and delivery of a formal engagement letter and payment of any required deposit or retainer. Any initial conversations we may have by phone, email, or otherwise do not give rise to an attorney-client relationship, nor does the mere act of contacting our firm nor scheduling a consultation.
Unless and until a formal engagement letter is executed and delivered and deposit or retainer is paid and accepted, our firm accepts no responsibility for your matter and will perform no work on your behalf. In the event of any conflict between this website and an engagement letter, the terms and provisions of the engagement letter shall control.
Please be aware that there are statutes of limitations and strict deadlines by which to file certain documents; therefore, time is of the essence. If you do not retain my firm to handle your matter, you should immediately seek the services of another attorney without delay.
The transmission of information from this website is not intended to create, and its receipt does not establish, an accountant-client, attorney-client, or any other fiduciary relationship. Nor do any interactions or communications we may share via social media, email, or other media create such a relationship in the absence of an executed representation agreement. Except for existing clients, any unsolicited materials transmitted to me using the contact information above should not be considered privileged or confidential, and I accept no responsibility for the security or privacy of information you transmit to me via social media, email, or some other mechanism except as required by law.
This website does not constitute an offer to sell, a solicitation of an offer to buy, or a recommendation of any security. You are solely responsible for determining whether any investment, investment strategy, security, or related transaction is appropriate for you based on your personal investment objectives, financial circumstances, and risk tolerance. All investments involve risk, including the risk of loss of principal.
Reproduction, distribution, republication, and retransmission of material contained within this website or in any of my articles or publications hosted on other websites or fora is prohibited without my prior permission.
