Whether you are starting a small business or running an established company, it is vital to understand business laws and regulations. But that is easier said than done. My goal is to provide business-related legal services so that you can spend more time dealing with the actual business and less time with legal intricacies of operating your business. My services include:

Business formation

You have a new and innovative product or service and you are interested in forming a new business. You may have concerns about liability, taxes, investors and other considerations. As your small business lawyers, we will assist you in deciding whether your startup business should organize as a limited liability company (LLC), partnership, S corporation or C corporation. We will form the most appropriate business organization for your new business and register the business in all jurisdictions in which it will conduct business.

Mergers and acquisitions

If your business is fortunate to thrive and become a merger or acquisition target, we can represent you as the seller; or if you are on the other side and looking to acquire a business, we can assist with the due diligence in purchasing a business. We will review various approaches in purchasing a business through merger or acquisition. We will discuss with you various structures in purchasing the stock or purchasing the assets of an acquisition target. In either case, your business will need thoughtful and comprehensive representation in all aspects of a merger or acquisition.

Government contracting

Government contractors face numerous issues when contracting with the government. And with a hands-on approach and substantial experience, we will help you navigate those legal issues. We prepare teaming agreements, subcontracts and joint venture agreements and can handle a variety of other government contract matters. As government contract lawyers for your small business, we can assist you in applying for programs for HUBZones, service-disabled veteran-owned small businesses or women-owned businesses. If your company is facing debarment or suspension because of allegations of corruption or bribery, we can assist in your defense before the U.S. government or the World Bank.

Business transactions

Once you have an ongoing business, however organized, you will have a host of various commercial transactions. We prepare agreements with lenders, lessors, partners, customers, employees, and consultants. We provide business legal services for your company, preparing confidentiality agreements, nondisclosure agreements, licensing agreements, distribution, employment agreements, independent contractor agreements, lease agreements, and many others. We will help you understand what each part of these agreements require and make sure that these agreements provide protection to you and your business.

Corporate law

Once your startup business has been created, your company will have ongoing requirements to maintain its separate status. We will assist in guiding you on how to prepare corporate minutes or resolutions of the company to maintain the corporate form and other steps to protect the limited liability of your company. You will also have to make sure that your bylaws or operating agreement continues to reflect the needs of the business organization. We are available to assist you in addressing these issues. And once your company is ready to raise additional capital from investors, we can work with you to determine whether you are subject to securities laws or fall within one of the exemptions.

Business disputes

Few businesses are immune to business disputes. If your small business was well-advised, you have an agreement that will provide guideposts on how to resolve your business dispute. If you are unable to settle your dispute, you may have a dispute resolution mechanism such as mediation or arbitration in the agreement. An alternative dispute resolution mechanism such as arbitration or mediation generally can provide a relatively quick resolution of your business dispute. If not, then you may have to consider litigation. We handle business disputes, including pre-litigation matters, mediation, arbitration and litigation.

Anti-corruption compliance

Every company should have procedures and policies to minimize its exposure to allegations of corruption or bribery. An integrity compliance program (ICP) is essential for businesses doing work internationally for the United States government or work financed through one of the development banks. We can assist in reviewing or preparing an ICP to assure that is consistent with the anti-bribery and anti-corruption guidelines from the World Bank. If your company is facing debarment or suspension because of allegations of corruption or bribery, we can assist in your defense before the U.S. government or the World Bank.

Non-profit law

We work with organizations to obtain their tax exempt status under Section 501(c)(3) of the Internal Revenue Code. There have been recent changes to obtaining 501(c)(3) status and we have worked with organizations in submitting successful applications on the simplified track by filing a 1023-EZ and the more rigorous 1023 application for larger organizations. Nonprofits also face similar legal challenges to assure that they comply with business requirements and additional requirements to assure that they do not jeopardize their tax exempt status. As a law firm for nonprofits, we work with nonprofit organizations to guide them through these issues.

FAQ Small Business Attorney in DC

What is considered a small business?

Almost all our clients fall within the definition of small business/startup as determined by the Office of Advocacy of the U.S. Small Business Administration. Under this definition, a small business has fewer than 500 employees. Small businesses encompass about 99.9% of all business organizations in the United States.

Which industries do you serve as a small business attorney?

Most of our clients are service providers such as consulting companies, law firms, accounting and bookkeeping services, cybersecurity consultants, video production companies, and lobbyists, just to name a few. We also represent foreign and domestic manufacturers and software developers.

As a small business lawyer in DC, we represent some retail operations, such as bookstores and restaurants. We also represent numerous nonprofits with varying missions. Our government contractors clients hold various IDIQs (Indefinite Delivery, Indefinite quantity Contracts) and GSA schedules.

In which areas of the law does a small business or startup need legal assistance?

Most times, small businesses/startups need the services of outside general counsel. As outside general counsel for small businesses, we can handle most matters as a small business attorney that small businesses generally encounter. Usually, anything with the word agreement or contract is within our practice areas. This includes operating and shareholder agreements, which are used for small businesses and startups that are formalizing their relationships with their owners. Once a business is formed, then we prepare and review a host of other agreements, such as service agreements (which may be referred to as client agreements or consulting agreements), independent contractor agreements (which may be referred to as subcontracting agreements), employment agreements, teaming agreements, purchase and sale agreements, merger agreements, option agreements, license agreements, lease agreements, and the list goes on.

What factors should a small business and startup look for in retaining the services of a lawyer for small businesses?

With our extensive experience of working as a small business attorney in DC for decades now, background and experience should come right at the top of the list when looking for a small business lawyer. We think that accessibility and communication are essential for a successful relationship between an attorney and a client. Hourly rate is important but not as important as quality of service.

What kind of experience do you have in advising small businesses as an attorney?

Keith Rosten has not only legal experience but also business and practical experience that allows him to relate to the trials and tribulations of a small business owner. Keith has BigLaw experience before working for small and medium-sized businesses, first at his own law firm focused on small businesses and then with Berliner Corcoran & Rowe LLP.

Keith has substantial business experience. He received an MBA from the Tuck School at Dartmouth College. During his business studies, he worked on several group projects with small businesses, including a furniture manufacturer, a manufacturer of leak location precision equipment, real estate developer. After business school, Keith operated a successful real estate business in California and overcame numerous issues, such as asbestos abatement and underground storage tank remediation.

Keith worked as a legal adviser to a government contractor and was a legal adviser to a major initiative in Russia. Keith ran another small business, selling and marketing solar energy equipment. The business had an e-tailer component, hosted the largest solar energy forum online, and sold solar energy equipment to the government. Keith negotiated two GSA schedules for the business and obtained HUBZone certification for the business. Keith was also president of the Dartmouth Entrepreneurial Network – Washington, a networking organization for small businesses in the greater Washington, DC community.

Keith has also volunteered for Compass Pro Bono, working with local business professionals to conduct long-term consulting engagements for local nonprofits in fundraising, governance, and strategy.

With this breadth of legal and business experience, Keith is attuned to some of the challenges facing small businesses, which allows him to provide effective advice and guidance.

As a small business lawyer, do you take in-person meetings only?

Yes. We are located in downtown Washington DC and host many of our clients. For those clients who cannot come into our offices, we usually meet over Zoom or by telephone.

How do you charge for your services as a small business attorney?

We charge our clients based on hourly fees. We usually provide a budget of how much certain matters cost so that startups and small businesses know in advance the ballpark cost of the matter.

What if a client does not like our services?

Clients can terminate our services anytime if they don’t find it satisfactory.

Should my small business lawyer or startup lawyer be in the same state as me?

No, not always necessary and may depend on multiple factors. For example, though we are an expert small business lawyer in DC, we have also provided consultation to other cities’ clients.

Political Challenges for Nonprofits

From Public Interest to Political Target

The legal environment for nonprofits has undergone significant changes under the Trump administration. These changes are not overt bans or direct defunding but rather subtle tactics—referred to as “lawfare”—that weaponize compliance regulations, redefine national security parameters, and blur the line between advocacy and extremism.

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This article explores the evolving challenges nonprofits face, from traditional regulatory frameworks to the emerging threats of today. It also provides practical strategies for enhancing organizational resilience.

Related article: Nonprofits and the Public Interest

Historical restrictions and the legal foundations of risk

The tension between nonprofit advocacy and government control has existed since the inception of the modern charitable system. Section 501(c)(3) of the Internal Revenue Code grants tax-exempt status to organizations “operated exclusively for charitable, religious, or educational purposes,” but it imposes strict limitations on lobbying and political campaigning.

Lobbying by 501(c)(3) organizations must remain “insubstantial,” a vague term that has led to inconsistent enforcement and a chilling effect on advocacy. The IRS’s discretion in defining “insubstantial” has further complicated compliance.

Political campaigning is “absolutely prohibited” for 501(c)(3) organizations, which are barred from endorsing candidates or engaging in direct political activities.

Following the September 11, 2001, attacks, the Patriot Act’s “material support” provisions expanded legal risks for nonprofits. Humanitarian groups operating in conflict zones were sometimes accused of indirectly supporting terrorism, with even minor associations—such as shared vendors or financial transactions—leading to investigations or asset seizures. These practices normalized conflating dissent, international aid, and humanitarian engagement with subversive activity.

Current flashpoints

National Security Memorandum (NSPM-7)

In October 2025, the administration issued the National Security Presidential Memorandum on Countering Domestic Terrorism and Organized Political Violence (NSPM-7). While presented as a framework for interagency coordination, its broad language allows for sweeping interpretations. References to organizations whose advocacy could allegedly be “exploited by extremists” open the door to heightened scrutiny of civil-rights, environmental, and humanitarian groups whose work challenges government policies.

NSPM-7 permits agencies like the Department of Justice, the Treasury’s Financial Crimes Enforcement Network (FinCEN), and the IRS Criminal Investigations division (IRS-CI) to share data on tax-exempt entities. This coordination risks eroding the boundary between legitimate oversight and intrusive monitoring, especially if investigations are politically motivated.

The “Nonprofit Killer Bill” (H.R. 9495)

H.R. 9495, dubbed the “Nonprofit Killer Bill,” proposes conditioning tax-exempt status on a certification that an organization “does not materially contribute to political unrest.” Its vague language mirrors NSPM-7, framing public dissent as potential disorder. Legal scholars fear that even if the bill is not enacted, its proposal signals bipartisan willingness to politicize nonprofit oversight.

Politicization of the IRS-CI Unit

The Wall Street Journal reports that there are plans to restructure the IRS Criminal Investigations division to target “left-leaning” nonprofits and donors. Internal documents allegedly list philanthropists like George Soros as potential targets, equating progressive philanthropy with “terror finance.” Such changes could transform tax enforcement into a tool for political retribution, allowing Treasury and Justice to refer nonprofits for prosecution with minimal evidence.

Labeling advocacy as terrorism

Advocacy on issues like Palestine, climate change, and racial justice is increasingly portrayed as extremism, creating reputational damage akin to official actions. Donors withdraw, partner organizations hesitate, and a chilling effect sets in. Nonprofits now face the burden of proving their innocence, with congressional inquiries demanding donor lists and internal records to exhaust resources and discourage participation.

Effect on the public interest mission

Chilling effect

Even preliminary inquiries silence advocacy. Community groups remove DEI materials from websites, scrub references to “equity” or “racial justice,” and avoid political labeling. Lawyers report clients declining to sign coalition letters or participate in demonstrations for fear of IRS retaliation.

Funding disruptions

Financial institutions under federal oversight are increasingly conservative about transferring funds to advocacy organizations, especially those operating internationally. Foundations face “derisking” measures reminiscent of post-Patriot Act banking compliance, effectively deputizing grant makers as enforcement agents.

Mission drift and self-censorship

Faced with uncertainty, many nonprofits retreat to “safe” programming. Environmental groups shift from policy advocacy to tree-planting; human-rights organizations focus on education rather than litigation. This narrowing of civic imagination mirrors tactics used by restrictive regimes elsewhere.

Erosion of public trust

Unsubstantiated allegations corrode credibility. Once a charity’s name is linked with “terrorism” or “domestic extremism,” the reputational cost lingers. In a polarized media environment, accusation itself becomes conviction.

The burden of legal uncertainty

Ambiguous terms like “political unrest” or “advocacy exploited by extremists” leave enforcement to administrative discretion. This ambiguity prompts organizations to over-comply and discourages challenges to authority.

Lessons from the field

Several cases illustrate these patterns:

University-based nonprofits hosting protests over Gaza or environmental divestment face threats to their tax-exempt status.

Humanitarian groups report frozen transfers and heightened vetting demands.

Coalitions promoting voter registration and police accountability are subpoenaed for donor lists under congressional “oversight” inquiries.

Strategies and other paths forward

Governance and compliance

Conduct periodic audits of lobbying, political, and foreign-funding activities.

Maintain board oversight committees for legal risk management.

Document program rationales to demonstrate alignment with charitable purposes.

Transparency and documentation

Transparency is the best defense against mischaracterization. Publicly accessible impact reports, audited financials, and clear policy rationales build trust. However, transparency must be strategic to protect the privacy and security of staff and beneficiaries.

Legal preparedness and partnerships

Develop connections with experienced legal advisors, especially a nonprofit lawyer, and collaborate with nonprofit networks to share expertise and resources. Pooling legal support lowers costs, promotes consistency, and strengthens collective readiness.

Strategic communications

Develop a crisis-response plan that emphasizes values and facts, not defensiveness. Engage sympathetic media outlets and community leaders early. Train staff to handle inquiries without speculation.

Collective action

Fragmentation is vulnerability. Sector-wide alliances amplify advocacy for due-process protections and raise public awareness of the stakes. As one legal analyst observed, the best defense against isolation is collective strength—building solidarity across legal, financial, and storytelling fronts.

Conclusion: reclaiming the public interest

Nonprofits have always walked a delicate line—independent yet regulated, outspoken yet accountable. The present moment is marked by a systematic effort to redraw that line in favor of political control, with agencies once tasked with enabling charitable trust now policing ideology.

Today’s organizations must document their integrity, build alliances, and demand fairness. Legal compliance is necessary, but the path forward requires vigilance and courage—qualities that have long defined the nonprofit tradition. In reaffirming their role as guardians of the public interest, nonprofits affirm something larger: that a free and democratic society depends on the freedom to serve it.