Publication date: 20.11.2025
Hello! My name is Oleg Listunov. Currently, I work as a paralegal at a law firm in Boston specializing in Landlord & Tenant Law. Our firm serves clients across the entire state and covers the whole New England region — one of our major strengths. In addition, I assist individuals with immigration matters at the federal level across all U.S. states. I also help clients — both U.S. residents and foreign entrepreneurs — with starting corporations and opening business bank accounts. If you have any questions, I’ll be happy to help. Don’t hesitate to reach out!
How Oleg Listunov Resolved a Complex International Tax Dispute for a Tech Startup Expanding in the U.S. Market — A Practical Case Study
In 2025, an emerging technology startup headquartered in Eastern Europe reached out to me, Oleg Listunov, seeking urgent legal and tax advice regarding their expansion into the United States. The company was preparing to scale operations across multiple states but found themselves entangled in a complex web of international tax compliance issues threatening to halt their planned growth.
Their main challenge was navigating conflicting tax regulations between their home country and the U.S., including risks of double taxation, unclear income classifications, and the potential for costly penalties from IRS audits due to inadequate prior tax planning. The startup's leadership realized that without expert legal intervention, they faced substantial financial exposure and possible reputational damage.
Key client issues included:
— Exposure to double taxation on cross-border income streams;
— Lack of a compliant transfer pricing policy;
— Insufficient documentation for intercompany transactions;
— Potential IRS penalties exceeding hundreds of thousands of dollars;
— Ambiguous entity classification and tax residency status concerns;
— Incomplete understanding of U.S. tax treaty benefits and obligations.
Strategic Legal and Tax Approach by Oleg Listunov
To address these complicated issues, I undertook a methodical and multi-step strategy built on comprehensive analysis and actionable legal frameworks:
- Conducted a thorough review of the client’s international transactions, legal entity structures, and past tax filings to identify compliance gaps and exposure points.
- Examined relevant tax treaties between the client’s country and the United States to leverage available tax relief provisions and avoid double taxation.
- Developed a compliant transfer pricing framework aligned with OECD guidelines, creating transparent documentation and justifications for intercompany services and royalties.
- Advised on the optimal classification of entities under U.S. tax law, ensuring the startup’s subsidiaries and branches were appropriately registered and taxed.
- Facilitated proactive communication with IRS officials and prepared amended tax returns to rectify historical misstatements and reduce audit risks.
Integrating legal precision with practical tax expertise allowed us to construct a robust compliance system that protected the client from penalties while positioning them for smooth business expansion.
Implemented Practical Measures
- Drafted and submitted corrected corporate tax returns with full disclosures, effectively mitigating the risk of harsh IRS sanctions.
- Instated a comprehensive transfer pricing policy, including benchmarking studies and intercompany agreements, to defend pricing structures during possible audits.
- Regularized the client’s entity registrations and obtained necessary state and federal tax IDs for all operating units.
- Provided ongoing legal counsel for tax treaty applications and treaty-based tax exemption claims, ensuring lawful tax reduction opportunities.
- Trained the client’s finance team on U.S. international tax compliance best practices and documentation requirements.
Results Achieved
- Averted IRS penalties surpassing $300,000 through timely correction and disclosure.
- Eliminated double taxation risks by successfully applying tax treaty provisions.
- Established sustainable transfer pricing policies aligned with global regulatory expectations.
- Resolved entity classification ambiguities, gaining full compliance with U.S. state and federal tax authorities.
- Enabled the client to proceed with seamless expansion into three U.S. states without legal or tax hindrances.
Frequently Asked Questions
Question
What are the main risks of neglecting international tax compliance when expanding into the U.S.?
Answer
Ignoring international tax regulations can lead to significant liabilities including double taxation, substantial fines, reputational damage, and disruption of business operations due to audits or legal actions.
Question
How important is transfer pricing for startups operating across borders?
Answer
Transfer pricing compliance is critical even for startups as it governs how intercompany transactions are priced and scrutinized by tax authorities, affecting tax liabilities and audit risks.
Question
Can amendments to prior tax filings reduce existing tax penalties?
Answer
Yes, timely voluntary amendments prepared by experienced tax lawyers can significantly decrease penalties and improve relations with tax authorities.
Thanks to a meticulous, tailored approach integrating legal and tax expertise, I assisted this technology startup in overcoming complex international tax barriers and establishing a clear path to successful U.S. expansion.
This case showcases the vital role that specialized tax law guidance plays for businesses navigating multi-jurisdictional challenges and highlights practical solutions to reduce tax risks while promoting sustainable growth.
