Starting a new business can be one of the most challenging, stressful undertakings in life. Going it alone—without a knowledgeable small business and start-up attorney and CPA—can only make it more difficult.
My firm helps founders conceive, plan, grow, and exit their ventures. 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.
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.
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:
- entity selection
- business formation
- operating agreements
- term sheets
- securities filings
- employment agreements
- compensation planning
- license agreements
- consulting agreements
- crisis management
- contract negotiations
- joint ventures
- non-compete and non-solicitation agreements
- regulatory analysis and planning
- business tax planning (international, federal, state, and local)
- stock purchase agreements, options, and issuance plans
- start-up funding (e.g., angel, seed, and Series A rounds), and the
- protection of trade names and ideas
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.
If you don’t have an attorney and you’re thinking of starting—or already have started—a new venture, The Law Office of Chad D. Cummings, headquartered in PNC Bank Tower in Naples, Florida, is here to help.
If you retain my firm, I will meet with you individually to understand your specific needs and those of your venture.
I will also assist you to identify risks and plan for a successful, profitable business, whatever the industry.
Use the buttons below to email me at chad@cummings.law, or click here to set up a free meeting.
Time is of the essence; therefore, if you need assistance with your business venture, it is important that you retain the services of a competent Florida attorney as soon as possible.
Should you choose to contact me, we will begin with a free, no obligation thirty minute meeting—via phone or face-to-face—to discuss your situation. Then, should you choose to retain my services, I will prepare and deliver to you for your approval a formal representation agreement.
Unless and until I receive the signed representation agreement returned by you, my firm will not have accepted any responsibility for your legal needs and will perform no work on your behalf. Please contact me today to get started.
Meet Chad
/Southwest Florida Attorney and CPA

I am an attorney and Certified Public Accountant serving Southwest Florida.
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 I hold active CPA licensure in Florida and Texas and undergraduate and graduate degrees in accounting and taxation from Southern Methodist University in Dallas.
My practice emphasizes, but is not limited to, the law as it intersects small businesses and their owners. I also assist clients with insurance claims, estate planning, and other legal matters on an ad hoc basis. I live and work in Naples, Florida.
If I can be of assistance, please email me at chad@cummings.law or click here to set up a free meeting.