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Hidden Pitfalls of U.S. Taxation

Launching a startup in the United States is a strategic move for many Ukrainian entrepreneurs. The U.S. offers access to one of the largest consumer markets in the world, abundant investment opportunities, and a strong reputation as a global tech hub. However, behind this appeal lies a complex and often underestimated system of tax regulation.

In a recent webinar featuring an international tax advisor (author of the US Startup Tax Guide) and a legal expert assisting Ukrainian startups with U.S. incorporation, participants discussed common mistakes made by foreign entrepreneurs and the risks of operating under U.S. jurisdiction for tech businesses. Below are key insights and practical recommendations.

The Illusion of Simplicity: Why “Easy Entry” Doesn’t Mean Easy Survival

It’s true that starting a company in the U.S. can take just a few days and be done online. But this low barrier to entry creates a deceptive sense of ease, overshadowing the real legal and tax consequences. Among the most frequent mistakes are:

  • Choosing a C Corporation without understanding the implications of double taxation;
  • Ignoring IRS filing requirements — even for transactions as small as $1;
  • Misjudging state nexus, i.e., having taxable presence in a state without a physical office.

Administrative penalties for late filings can reach up to $25,000 — regardless of the company’s size or revenue. This is the paradox: the system is open, but it is unforgiving toward negligence.

Why a C Corporation Isn’t Always the Best Choice

Many entrepreneurs default to creating a C Corporation — a legal entity taxed both at the corporate level and again when dividends are distributed to shareholders. Double taxation may only make sense under certain conditions:

  • The company plans an IPO or seeks major venture capital;
  • Significant profits are expected to be retained within the company for a long time;
  • A standard structure is needed to meet U.S. investor expectations.

For smaller international startups, alternatives like LLCs, partnerships, or hybrid structures using IRS Form 8832 to elect tax classification can be more suitable.

Tax Planning: Why It’s Necessary Before Your First Deal

Many founders follow the principle: “Let’s make money first, then deal with taxes.” While this might work in less-regulated countries, it’s a risky strategy in the U.S.

The U.S. tax system requires:

  • Early planning for ownership structures, profitability, and income flows;

  • Understanding mandatory filing obligations, including:


    • Form 5472 — required for single-member LLCs with foreign ownership;
    • Form 1120 — for corporations;
    • Form 1065 and Schedule K-1 — for partnerships;
    • Form 8805 — when earning income from U.S. sources;
    • Form 8832 — to elect or change tax classification;
    • W-8BEN / W-9 — to determine the tax status of counterparties.

Failing to file even one form can lead to penalties, audits, or disqualification in the eyes of investors.

Effectively Connected Income (ECI): The Hidden Tax Trap

Even if your company is not incorporated in the U.S., economic presence alone can trigger U.S. tax obligations. Effectively Connected Income (ECI) arises if:

  • You have employees or an office in the U.S.;
  • You operate through agents located in the U.S.;
  • You host servers, warehouses, or infrastructure in the U.S.;
  • You sign contracts with U.S. clients while physically present (even temporarily).

The IRS pays close attention to IT businesses operating under SaaS, consulting, or know-how transfer models. In these sectors, it’s easy to unintentionally cross the line between “exporting services” and “establishing economic presence.”

Transparent Structures and International Conflicts

Many startups opt for an LLC as a simple business form. But in the U.S., an LLC is a “pass-through” entity — it doesn’t pay taxes itself, but its income is taxed on the owners' personal returns. In other countries (such as Ukraine), LLCs may not be recognized as pass-through entities, creating hybrid mismatches and regulatory conflicts.

This may result in:

  • The need for dual tax accounting;
  • Risk of the structure being rejected by foreign tax authorities;
  • Reporting confusion and inability to benefit from tax treaties.

IT Company Scenarios: 5 Models, 5 Approaches

In the software industry, five common monetization models each carry different U.S. tax implications:

  1. Online platforms (SaaS, streaming): recurring payments, high ECI risk.
  2. IP licensing: dependent on exclusive rights, may involve royalties and withholding taxes.
  3. License renewals: recurring revenue, often classified as services.
  4. Know-how sales: complex classification, potential disputes with the IRS.
  5. Consulting and outsourcing: high likelihood of creating a permanent establishment (PE) and ECI.

Each model requires its own structure — from both a tax and IP strategy perspective, considering IRS requirements and investor expectations.

Startup To-Do List: What You Should Do Today

  • Don’t delay tax planning: Even a brief consultation with a tax expert at the start can save tens of thousands of dollars.

  • Assess your U.S. presence: If you engage clients, have agents, or use infrastructure in the U.S., you may already have tax obligations.

  • Involve international tax professionals: Preferably those with experience in the tech industry.

  • Formalize internal agreements: Create founders’ agreements, partner contracts, and policies for related-party transactions.

  • Stay up to date: Even if using tools like ChatGPT or public sources, remember that data without context is only half the truth.

Conclusion

The U.S. tax system isn’t your enemy — but it won’t forgive sloppiness. For Ukrainian startups entering the American market, it’s not enough to have a strong product and a bold idea. A solid legal foundation is essential. The “let’s make money first” approach only works until the first IRS notice arrives. From there, it’s not just about money anymore — it’s about reputation, investor confidence, and your right to stay in the game. That’s why tax planning isn’t optional — it’s vital.

How to Pay Taxes in the USA Correctly? AVITAR & iFindTaxPro

How to Pay Taxes in the USA Correctly? AVITAR & iFindTaxPro (Part II)

How to Pay Taxes in the USA Correctly? AVITAR & iFindTaxPro (Part III)

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‍Contact us: business@avitar.legal

Authors:

Violetta Loseva

,

6.18.2025 15:20
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