Full-stack legal services for entrepreneurs“CUMMINGS.LAW”

“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!“



/The Law Office of Chad D. Cummings

My firm helps founders conceive, plan, grow, and exit their start-ups. I also help innovators in the disruptive technology space (e.g., blockchain, Web3, DeFi, crypto, esports, disintermediation) to protect their ideas and maximize their return.

I deliver full-stack Chief Legal Officer services to my clients—including general representation, transactional advisory, and litigation—at every stage of the business lifecycle at a fraction of the cost of retaining a traditional firm.

My specific practice areas include corporate, partnership, crowdfunding, contract, employment, intellectual property, tax, executive compensation, and labor law. I also help existing clients structure real estate deals and obtain visas for their team members as needed.

I tap into my deep professional network of colleagues, peers, and mentors across all domains of professional services, including other lawyers, accountants, and advisors, to supplement my knowledge and meet the needs of my clients on a cost- and time-effective basis.


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.

Firm Library: Resources for Founders


An Introduction

/Meet Chad

I am an attorney and Certified Public Accountant serving Florida and Texas with dual licensure in both states.

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 also hold active CPA licensure and undergraduate and graduate degrees in accounting and taxation, respectively, from Southern Methodist University in Dallas.

I live and work in Naples, Florida.


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Connect on LinkedIn

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

State and Local

Florida Supreme Court, Tallahassee, Florida

Supreme Court of Texas, Austin, Texas

Collier County Bar, Naples, Florida

Miami-Dade Bar, Miami, Florida


/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

Certified Management Accountant
Institute of Management Accountants

Certified Internal Auditor
Institute of Internal Auditors

Certified Fraud Examiner
Association of Certified Fraud Examiners

LL.M., Real Property Development In Progress
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 businesses (especially 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 start-ups.

Start-up founders 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 cell (including after-hours by call and text), email, and FaceTime, recognizing that start-ups and their principals routinely need access to their counsel outside the nine-to-five.

I assist start-ups and small businesses to grow and protect their interests. 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.

My practice also provides strategic advisory and counsel for real estate and business ventures at every stage: ideation, iteration, growth, and exit.

Unlike many other firms and legal services providers, I prioritize the development of long-term working relationships with my clients in lieu of piecemeal, “one-off” transactions.

I am also available face-to-face locally and globally to serve my clients, depending upon their unique needs.

In this sense, I enmesh myself with founders and their teams and offer many of the benefits of in-house counsel without the unaffordable price tag.

Book a Free Meeting

If you prefer, email me instead.

Pricing and Availability

/Fee Arrangements

Recognizing the unique challenges faced by start-ups and their founders, especially in the early stages, I am proud to offer flat-fee, hybrid and non-traditional fee arrangements, including equity arrangements where permitted by state law and ethical rules. I am also pleased to offer alternative payment mediums (e.g., crypto) for all my services.

These terms allow start-ups to deploy their precious resources where needed most—product development and growth—rather than tying up cash in hiring attorneys and advisors.

Subscription Services

Outsourced Chief Legal Officer (CLO), month-to-month

I offer fractional, outsourced Chief Legal Officer services to high-growth start-ups and small businesses. The CLO is a relatively recent addition in the C-suite. CLOs, as compared with General Counsels (GCs), are expected to have a deeper understanding of business processes and strategy.

CLOs help companies craft a strategic, long-term plan to tackle not only operations and growth (primarily, but not exclusively, from a legal standpoint), but also policy, risk management, crisis management, and creative problem solving.

The basic “package” includes:

I will work with clients to find the right level of service and price point to ensure they are not being overcharged or underserved. Outsourced CLO services are offered on a month-to-month basis, unless otherwise agreed, and may be cancelled by the client at anytime with a prorated refund as required by the state law and bar rules.

Outsourced CLO: Get Started

À la Carte Services

Tax Free Mergers, Purchase, and Sale Agreements

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.

Business Transactions: Get Started

Start-up Formation

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.

One-time start-up formation services encompass:

Start-up Formation: Get Started

Federal Trademark Search and Filing

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.

My firm’s trademark search and registration service includes:

Trademark Search and Filing: Get Started

Additional Services

Although my practice is laser-centered on entrepreneurial and small business law, 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.

Alternative Payment Options: Crypto, Goldbacks, Precious Metals, and Equity

Crypto, Goldbacks, and Precious Metals

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.

Equity Arrangements

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.

Book a Free Consultation

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., I joined the post-graduate Real Property Development LL.M. program at the University of Miami School of Law. I hold active CPA licensure in Florida and Texas and undergraduate and graduate degrees in accounting and taxation from 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 Certified Management Accountant, Certified Internal Auditor, and Certified Fraud Examiner credentials.

In my spare time, I freelance as a journalist and researcher exploring 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.

View my CV

Important Notices and Disclaimers:

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.

Please be aware that there are statutes of limitations and strict deadlines by which to file certain documents. If you do not retain my firm to handle your matter, you should immediately seek the services of another attorney.

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.