Cummings & Cummings Law is a technology-forward, multi-state law practice representing business owners, executives, real estate developers, and their families. Our firm pioneered the Law as a Service (LaaS) model, replacing the traditional, archaic approach to the practice of law with a low-friction model that leverages technology (backed up by human expertise) to eliminate bottlenecks and non-value-added work.
Our clients range from Series A two-person technology startups to Fortune 100 organizations. Our attorneys cumulatively wield decades of experience working with and for firms including American Airlines, PricewaterhouseCoopers, JPMorgan Chase & Co., Dell Technologies, Walmart, Halliburton, and others.
We remain a small firm by choice and are selective with the clients and matters we accept, just as clients should be discerning in retaining a law firm.
We counsel clients on how to structure, grow, and transition ventures while aligning legal decisions with tax, wealth preservation goals, and lifestyle goals.
Our practice includes business and commercial law, corporate governance, LLC and partnership matters, business transactions and dispute resolution, commercial real estate, executive compensation, ERISA, business tax planning, nonprofit matters, and estate planning for entrepreneurs and high-net-worth individuals. We also counsel clients on commercial real estate development and management.
Our attorneys integrate risk management, financial analysis, forensic accounting, and tax perspective into our engagements, particularly in mergers and acquisitions, joint ventures, private lending, fundraising, and diligence-driven transactions.
Additionally, we represent clients building or investing in technology and emerging verticals, including blockchain and digital assets, fintech, quantum computing, and AI.
We are not the cheapest law firm, nor is that our objective. We work exclusively with clients who view incisive legal counsel not as an operating expense to be minimized but as a capital investment to be optimized.
Founding Attorney and Chief Executive Officer
Chad is an attorney and Certified Public Accountant serving Florida and Texas with dual licensure in both states. He holds a number of other finance, accounting, tax, and risk management credentials which he applies in his law practice for the benefit of his clients.
Previously, he served in operations and finance with the world’s largest accounting firm (PricewaterhouseCoopers), airline (American Airlines), and bank (JPMorgan Chase & Co.). He has also created and advised a variety of start-up ventures.
He is a member of The Florida Bar and the State Bar of Texas and holds two law degrees: the Juris Doctor (J.D.) and the Master of Laws (LL.M.). He also holds active CPA licensure and undergraduate and graduate degrees in accounting and taxation, respectively, for a total of four degrees and ten professional licenses and certifications.
He lives and works in Bonita Springs, Florida and serves clients throughout Florida and Texas.
Attorney and Executive Vice President
Lisa A. Cummings’ legal career spans five decades and several sectors and enterprises, including, for example, in-house counsel and other roles—domestic and international—with Halliburton, Dell Technologies, Walmart, Mercer, Kerr-McGee (now Occidental Petroleum), Cadbury Schweppes (now Keurig Dr. Pepper), Plains Capital Bank, Chesapeake Energy (now Expand Energy), Hertz, Michaels Stores, Cityblock Health, and others.
She holds an undergraduate (B.S.) degree in accountancy from the University of Oklahoma and a Juris Doctor (J.D.) from the University of Oklahoma School of Law. She is admitted to the Oklahoma Bar Association and counsels clients on matters involving ERISA, the Internal Revenue Code, executive compensation, employee benefits, and complex multi-state employment law matters.
She lives and works in Bonita Springs, Florida and Dallas, Texas and serves clients nationwide and globally on matters of federal law.
Chief Administrative Officer
For more than 30 years, Jeanne has dedicated her career to implementing and managing comprehensive employee health and welfare and retirement programs and supporting Fortune 100 enterprises. Her passion lies in ensuring benefit strategies that not only safeguard the well-being of employees but also drive organizational success. With a steadfast work ethic, a keen eye for detail, and a leadership mindset, she takes pride in delivering solutions that balance cost-effectiveness with industry-leading best practices.
Jeanne’s decades of experience span myriad sectors, enterprises, and roles, including Benefits Connection, Dell Technologies, Rockport Healthcare Services, Cadbury Schweppes (now Keurig Dr. Pepper), Hertz, Michaels Stores, and others.
She applies her multinational experience, cross-functional expertise, and project management acumen in her role as Chief Administrative Officer at Cummings & Cummings Law to deliver outstanding service to internal and external stakeholders alike and to assist in developing and realizing the firm’s strategic vision.
She lives and works in Southern California and supports firm operations globally.
We 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, we have compiled a small library addressing the most commonly asked questions, which we have made available at no cost. Click the button below to get started.
Practice Verticals
/ Our Areas of Focus
Our practice emphasizes, but is not limited to, the law as it intersects businesses (ranging from early stage start-ups to Fortune 100 enterprises) and their stakeholders.
When clients hire our firm, we apply not only our legal knowledge, but also our skills and expertise accrued in operations, finance, and legal departments at some of the largest ventures in the world, bolstered by our insights from forming and growing our 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.
Cummings & Cummings Law serves entrepreneurs, businesses, and high-net-worth individuals at the complex intersection of law, finance, taxation, and corporate strategy. From early-stage startups to Fortune 100 companies, the firm offers legal counsel grounded in real-world business experience and deep technical subject matter expertise.
The firm advises clients on a wide range of corporate and operational legal matters, including:
New and evolving businesses rely on the firm to ensure sound legal and financial structuring:
The firm counsels employers, founders, and executives on executive compensation and benefit plan design, including under ERISA:
The firm offers advanced legal counsel for commercial and mixed-use real estate developments, including:
The firm prepares and negotiates commercial leases for retail, industrial, hospitality, and medical facilities, addressing:
Cummings & Cummings Law provides personalized estate planning for entrepreneurs and high-net-worth individuals, including:
Cummings & Cummings Law facilitates seamless redomestication to effectuate the change in domicile of corporations and limited liability companies into Texas and Florida, including:
To protect intellectual property assets, the firm provides trademark registration services, including:
While our firm does not offer traditional public accounting services such as audits or bookkeeping, Cummings & Cummings Law is a leader in advanced forensic accounting and analysis, particularly in the contexts of due diligence, fraud prevention, detection, and correction, internal control implementation, and tax, including:
Important Notices and Disclaimers
Please read the following with care. Use of this website or communication with the firm or any of its members constitutes acceptance of the following terms, conditions, notices, and disclaimers and of the privacy policy linked in the footer of this page.
General Informational Purpose. This website and all material provided on or through it are for informational purposes only and do not constitute legal, tax, or accounting advice. No person should rely on, act on, or refrain from acting on the basis of any matter or information contained on this website without first obtaining appropriate legal or other professional advice.
No Professional Relationship Without an Engagement. No attorney-client, accountant-client, or other fiduciary relationship (an “Engagement“) is created by the use of this website, by any communication with the firm and its members (whether by telephone, email, text message, videoconference, social media, or any other medium), or by the scheduling or completion of a consultation. An Engagement arises only upon the execution and delivery of a formal, written letter of engagement (a “Letter of Engagement“) and the payment and acceptance of any required deposit or retainer. To the fullest extent permitted by law, neither the firm nor its members shall have any duties or obligations to any person in the absence of an Engagement, and where an Engagement exists, the duties and obligations of the firm and its members shall be limited to those set forth in the applicable Letter of Engagement. In the event of any conflict between this website and a Letter of Engagement, the terms and provisions of the Letter of Engagement shall control.
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Statutes of Limitations and Filing Deadlines. The firm and its members disclaim all responsibility for statutes of limitations, filing deadlines, and other time-sensitive obligations in the absence of an Engagement. Persons who do not retain the firm should seek the services of another attorney without delay. Time is of the essence.
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Verbal Communications. Oral statements, telephone conversations, and preliminary discussions with the firm and its members are informational in nature and shall not be relied upon as legal, tax, or accounting advice. Only written statements directed to a client in a current Engagement shall constitute legal, tax, or accounting advice, as the case may be determined by a Letter of Engagement.
Communications with Non-Clients. Any communication with persons who are not clients of the firm does not constitute legal, tax, or accounting advice, does not create any fiduciary or professional duty, and shall not be treated as confidential or privileged, except to the extent required by law.
Past Results. Past results do not guarantee future outcomes. Descriptions of prior matters, case results, or client outcomes are provided for informational purposes only and are not predictive or indicative of future results.
Jurisdictional Limitations. The firm and its members are licensed to practice only in the jurisdictions described in the footer of this page. The firm and its members shall not represent or offer to represent any party outside of those jurisdictions, and persons outside those jurisdictions should not contact the firm.
Third-Party Content and External Links. The firm and its members disclaim all responsibility for any third-party content, resources, or websites accessed through links on this website or referenced in communications from the firm and its members. References to third-party entities, services, or websites are provided for informational purposes only and do not constitute an endorsement, recommendation, or affiliation.
No Obligation to Update. The firm and its members do not undertake any obligation to update, correct, or revise any material contained on this website or in any publication or medium, and no inference should be drawn that any information on this website is complete or current. Further, the firm and its members undertake no duty or obligation to update, correct, or revise any material or advice supplied to a client or perform any further work after the conclusion of an Engagement unless and until a subsequent Engagement is created.
Tax Disclaimer. Any discussion of tax matters contained on this website or in any communication from the firm and its members is not intended or written to be used, and shall not be used, by any taxpayer for the purpose of avoiding penalties that may be imposed by the Internal Revenue Service or any other taxing authority.
No Securities Recommendation. This website does not constitute an offer to sell, a solicitation of an offer to buy, or a recommendation of any security. Each person is solely responsible for determining whether any investment, investment strategy, security, or related transaction is appropriate based on that person’s own investment objectives, financial circumstances, and risk tolerance. All investments involve risk, including the risk of loss of principal.
Limitation of Liability. The firm and its members disclaim all liability for any loss, damage, or injury of any kind arising out of or resulting from any person’s use of this website, reliance upon any information contained on this website, or inability to access this website, to the fullest extent permitted by law.
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Attorney Advertising. This website may be considered attorney advertising under the rules of certain jurisdictions. The hiring of a lawyer is an important decision that should not be based solely upon advertisements.
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Modification. The firm and its members reserve the right to modify, amend, or replace these notices and disclaimers at any time without prior notice. Continued use of this website following any such modification constitutes acceptance of the modified terms. The firm and its members are under no obligation to notify any person of changes to these notices and disclaimers.
Severability. If any provision of these notices and disclaimers is found by a court of competent jurisdiction to be invalid, illegal, or unenforceable, such finding shall not affect the validity, legality, or enforceability of any other provision, and the invalid, illegal, or unenforceable provision shall be modified to the minimum extent necessary to make it valid, legal, and enforceable.
