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File a subchapter "S" election for your existing business.
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In under five minutes.

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Starting at under $1,500.
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As the expression goes, if you think hiring a professional is expensive, wait until you hire an amateur. Do not make the costly mistake of hiring an offshore, fly-by-night, and possibly illegal online "service" to handle your subchapter S election. Where will they be when something goes wrong? . . . Hire an experienced tax attorney and CPA, knowing you are working with a credentialed professional with a brick-and-mortar office.
— Prof. Chad D. Cummings, CPA, Esq. (emphasis added)

At The Law Office of Chad D. Cummings, we have the unique combination of legal and accounting expertise, and we are ready to help you navigate the complex process of electing S corporation treatment under the Internal Revenue Code. Our team, led by a professional who is both a Certified Public Accountant (CPA) and an experienced business attorney, is prepared to handle the intricate financial and legal concerns involved in such a move.

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Meet Chad

/Licensed Attorney and CPA

Make that S Corp Election Now

I am an attorney and Certified Public Accountant serving Florida and Texas.

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, and I hold active CPA licensure in both of those jurisdictions.

I also hold undergraduate (B.B.A.) and graduate (M.S.) degrees in accounting and taxation, respectively, from one of the premier universities in Texas. I earned my Juris Doctor (J.D.) and Master of Laws (LL.M.) degrees from Florida law schools. I also hold a variety of other accounting, tax, and finance credentials which I apply in my law practice for the benefit of my clients.

My practice emphasizes, but is not limited to, the law as it intersects businesses and their owners. Clients appreciate the confluence of my business acumen from my career before law, my technical accounting and financial knowledge, and the legal insights and expertise I wield as an attorney. I live and work in Naples, Florida and represent clients throughout the great states of Florida and Texas.

If I can be of assistance, please email me at chad@cummings.law, or click here to set up a free meeting.

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 thorough, 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

Receive a Copy Our Free Ebook: Electing S Corporation Treatment: A Comprehensive Guide

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What's Included for under $1,500:

  • ✔️ 15 minute phone consultation with Chad D. Cummings, attorney and CPA (additional time available in fifteen minute increments at additional charge, if needed)
  • ✔️ Pre-conversion eligibility review and determination
  • ✔️ Preparation and filing of IRS Form 2553 with current effective date
  • ✔️ Single-owner operating agreement drafting and execution (multi-owner available at additional charge because of added complexity)
  • ✔️ Preparation and execution of shareholder/member consent
  • ✔️ All documents prepared, reviewed, and filed by a REAL attorney and CPA (not an assistant or paralegal)

What's Not Included (Available at Additional Charge):

  • ➖ Preparation and filing of IRS Form 8832 (if required; + $199)
  • ➖ Ongoing tax filings, tax audit assistance, and bookkeeping (preferred referrals available at competitive rates)
  • ➖ Professional and local licenses (if required)
  • ➖ Employee benefit (e.g., health, retirement) plan design and implementation (available on request)
  • ➖ Executive compensation design and implementation (available by consultation)
  • ➖ Retroactive Form 2553 application (if available; + $995)
  • ➖ IRS change of address (if required; + $225)
  • ➖ State payroll tax account creation (+ $245)

Why Choose The Law Office of Chad D. Cummings?

  • ✔️ Enjoy peace of mind knowing that your documents are prepared, reviewed, and filed by a licensed attorney and CPA with Fortune 500 experience and a brick-and-mortar office, not by a fly-by-night non-attorney (and possibly illegal) online service
  • ✔️ Direct access to a real attorney by email (also available over the phone or face-to-face by appointment), not an assistant or go-between
  • ✔️ Complimentary, no obligation 15 minute phone consultation available before you buy
  • ✔️ Competitive, flat-fee pricing available
  • ✔️ 100% electronic, online filing and communication (no snail mail)
  • ✔️ Electronic signatures by Docusign when needed
  • ✔️ Digital, flexible payment options (including cryptocurrency)
  • ✔️ Weekly email status updates included at no additional charge

Get started. Flat-fee pricing.
Starting at less than $1,500.

Enter Your Business Name:

Takes less than five minutes.
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Elevate Your Business with S Corporation Taxation:

The Critical Role of a Business Attorney and CPA

Make an S Corp Election Now

Are you a small or medium-sized business owner in the United States looking to optimize your tax strategy? The decision to file an S Corporation election could be a game-changer for your business. In this comprehensive guide, we will explore the benefits, risks, opportunities, and drawbacks associated with this crucial decision, and why having an attorney-CPA like myself by your side can make all the difference.

The Benefits of S Corporation Election

1. Tax Efficiency: Whether you have an existing LLC or a corporation, one of the most significant advantages of filing an S Corporation election is the potential for substantial tax savings. Unlike traditional C Corporations, S Corporations don't face double taxation. Instead, income, deductions, and credits flow through to individual shareholders. This can lead to a significant reduction in your overall tax liability.

2. Limited Liability Protection: S Corporations provide the same limited liability protection as traditional corporations. This means that your personal assets are usually shielded from business-related debts and liabilities, offering you peace of mind as a business owner.

3. Ownership Flexibility: Electing S Corporation status allows you to enjoy ease of ownership transferability. This flexibility can make your business more attractive to potential investors and buyers, facilitating growth and exit strategies.

4. Tax-Advantaged Benefits: S Corporations offer tax-advantaged fringe benefits, including health insurance and retirement plans for both shareholders and employees. These benefits can provide a competitive edge in attracting and retaining top talent.

Why Having an Attorney-CPA Matters:

Navigating the complexities of S Corporation election requires more than just filling out paperwork. It involves legal and financial considerations that demand expertise. As both an attorney and a CPA, our firm's principal offers a unique combination of skills to ensure your business maximizes the benefits of this election while remaining compliant with regulations.

The Critical Role of Modifying Your Operating Agreement: Ensuring the Success of Your S Corporation Election

When a business makes the strategic decision to elect S Corporation taxation, it is not merely a matter of filling out a few forms and checking boxes. Instead, it involves a fundamental shift in the way the business is taxed, and this shift necessitates a comprehensive adjustment to the company's operating agreement. Failing to modify the operating agreement to account for the S Corporation election can have significant consequences, potentially leading to the failure of the election itself. In this nuanced landscape, the expertise of an attorney is not just valuable; it's indispensable.

Understanding the S Corporation Operating Agreement Modification

The operating agreement (also referred to by terms such as a "partner's agreement," "the bylaws," "the owners' agreement," and others) of a business outlines how the company is structured, managed, and how profits and losses are distributed among members, partners, or shareholders. When a company elects S Corporation status, it essentially changes its tax treatment from that of a standard LLC (Limited Liability Company) or C Corporation to a pass-through entity for federal income tax purposes. This means that the company's income, deductions, and credits will "pass through" to individual shareholders, who report them on their personal tax returns. This, of course, requires the consistent, close, and ongoing involvement of a trusted bookkeeper and tax professional. It is not simply "one and done."

To align with this new tax structure, the operating agreement must be meticulously modified. This process involves redefining how income and losses are allocated among members, the specifics of profit distribution, and the treatment of tax items. It also requires establishing mechanisms for handling potential issues that may arise, such as the departure of a member or the sale of ownership interests or shares.

The Complex Nature of Operating Agreement Modification

The complexity of modifying the operating agreement cannot be overstated. It demands a profound understanding of both legal and financial intricacies, as well as a keen awareness of how these changes can affect the business dynamics. The modified operating agreement must not only adhere to the Internal Revenue Service (IRS) regulations and applicable state law, but it must also protect the interests of the shareholders or members and ensure the company's continued smooth operation.

Why an Attorney is Essential

Given the intricate nature of this task, relying on the expertise of an attorney is not an option; it's a necessity. Attorneys focusing on business and tax law possess the insight and knowledge required to draft a modified operating agreement that both complies with IRS regulations and safeguards your business interests. They can anticipate potential challenges and proactively address them in the agreement, providing a comprehensive solution tailored to your specific business needs.

In summary, modifying the operating agreement is a pivotal step in ensuring the success of your S Corporation election. It is not optional. Neglecting this critical task can jeopardize the election and expose your business to unforeseen tax consequences. The complexity of this process underscores the importance of hiring an attorney who can navigate the legal and financial nuances, crafting an operating agreement that not only facilitates and effectuates the election but also positions your business for continued success in its new tax structure. When it comes to S Corporation elections, legal expertise isn't an expense; it's an investment in the future prosperity of your business.

The Risks of S Corporation Election

1. Ownership Limitations: S Corporations have restrictions on the number and types of shareholders. While this structure can be advantageous, it may limit your ability to raise capital and expand your shareholder base, especially if you have international (non-U.S.) owners or investors.

2. Complex Compliance: Maintaining S Corporation status demands ongoing adherence to specific rules and regulations. The intricacies of compliance can be overwhelming, but with the right guidance, you can navigate them effectively.

3. Built-In Gains Tax: If your business was previously a C Corporation before electing S Corporation status, you might be subject to the Built-In Gains tax. This tax applies to certain appreciated assets and requires careful planning to mitigate its impact.

The Risks and Opportunities with Interstate Taxation:

Interstate taxation can become a complex issue when you elect S Corporation status. Your business may have to deal with tax laws from multiple states, which can be a daunting task. However, with effective guidance and counsel, you can navigate the complexities of interstate (and intrastate) taxation and ensure that your business remains compliant.

The Opportunities with S Corporation Election

1. Income Distribution: S Corporation status allows you to distribute income and losses among shareholders in a tax-efficient manner. This flexibility can help you reduce your overall tax liability and manage your business finances more effectively.

2. Business Expansion: By electing S Corporation status, you can reinvest profits into your business, fueling growth while benefiting from pass-through taxation. This financial flexibility can be a game-changer for your business expansion plans.

3. Reduce Self-Employment Tax Burden: A desire to legally reduce or mitigate the often-oppressive burden of self-employment tax is a frequently a substantial motivation of entrepreneurs and business owners. When an "S" election is made and with the ongoing support and guidance of a qualified bookkeeper and tax professional, this benefit can be realized and maximized.

Receive a Copy Our Free Ebook: Electing S Corporation Treatment: A Comprehensive Guide


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Why Choose an Attorney-CPA?

S Corporation election isn't just about saving on taxes; it's about making strategic decisions that can shape the future of your business. As an attorney-CPA, our firm's principal bring a holistic approach to the table. He can help you not only navigate the legal and financial aspects but also align them with your long-term business goals.

The Drawbacks of S Corporation Election

1. Loss of S Status: One of the risks associated with S Corporation election is the potential loss of S Corporation status if you fail to meet IRS requirements. This can result in reverting to less favorable tax treatment, higher taxes, and potential penalties and fines for non-compliance.

2. IRS Scrutiny: Owing to the potential tax savings, S Corporations may face increased IRS scrutiny and heightened audit risk. It's crucial to have proper documentation and compliance procedures in place to navigate potential audits successfully.

3. Complex Decision-Making: Electing S Corporation status isn't a one-size-fits-all decision. The complexities involved in making this choice can be overwhelming. Ongoing support from a competent tax professional and bookkeeper is not simply "nice to have," but rather, it is mandatory.

Making an Informed Choice:

Choosing to file an S Corporation election is a strategic decision that should align with your business goals and financial objectives. It is a decision that requires a deep understanding of both legal and financial implications.

How an Attorney-CPA Can Make the Difference:

As an attorney-CPA, our firm's principal offers a unique blend of legal and financial expertise. He can guide you through the decision-making process, ensuring that you fully understand the implications of S Corporation election for your business. His goal is to help you make an informed choice that maximizes your financial efficiency and positions your business for steady success.

IRS S Corp Election Form


Filing an S Corporation election is a powerful step that can unlock a world of financial benefits for your business. With the right guidance, you can minimize risks, seize opportunities, and make the most of this strategic decision. Modifying the operating agreement is a crucial, indispensable part of that process.

Don't leave the fate of your business to chance. Choose a professional who is not only a licensed attorney but who is also a Certified Public Accountant (CPA) who understands the intricate legal and financial landscape of S Corporation elections. Work with The Law Office of Chad D. Cummings to ensure your business thrives under this tax structure, reducing your tax liability and creating opportunities for growth.

Get started. Flat-fee pricing.
Starting at less than $1,500.

Enter Your Business Name:

Takes less than five minutes.
Just click "next."