our Services

M&A Tax Advisory Services

We help startup founders, mid-market businesses, investment funds, and high-net-worth individuals navigate tax challenges with confidence—pairing sophisticated expertise with responsiveness and real-world ROI.

Specialized Tax Support for Complex M&A Deals

The tax implications of a transaction can make or break its value. Structuring a deal without fully understanding its tax consequences can lead to missed opportunities, unexpected costs, and long-term complications—especially when navigating multiple entities, jurisdictions, or ownership groups, or when dealing with a target’s tax exposures.

At Sapowith Tax Advisory, we bring deep technical experience across corporate, partnership, and cross-border transactions. From due diligence to structuring to post-deal integration, we help buyers, sellers, and investors uncover risk and deliver lasting results.

Your Trusted Partner

Having worked on numerous transactions, with deal sizes averaging between $20 million and $250 million, I am adept at vetting and optimizing deals to achieve a real cash tax advantage.

At Sapowith Tax Advisory, I bring that experience to every engagement, helping our clients anticipate risks, unlock value, and move forward with confidence.

Holistic Transaction Structuring and Review for Businesses and Their Owners

We provide sophisticated technical expertise throughout each stage of a transaction, thoroughly considering both the business and its stakeholders while also addressing aspects such as international and state & local taxes. Whether you are a buyer, seller, or investor, our services aim to safeguard your interests by minimizing risk, enhancing value, and ensuring that your deal rests on a solid tax foundation.

Transaction Planning

We help clients maximize tax benefits from transactions by optimizing structures to reduce or defer tax liabilities, all while aligning with their business objectives.

  • Asset & Stock Transactions: We guide clients through the tax implications and subtleties of asset vs. stock deals, helping choose the most efficient transaction structure based on entity type, basis step-up vs. carryover considerations, and state and international impacts.
  • Installment Sales & Other Deferral Structures: We structure installment sales and other deferral mechanisms to spread tax liabilities and improve post-deal cash flow.
  • Reorganizations & Spin-Offs: We design and refine tax-deferred reorganizations and divisive transactions, ensuring significant tax savings while complying with legal and judicial requirements.
  • Debt Workouts and Restructuring: We help with the planning for tax implications of modifying debt such as cancellation of debt income (CODI), deemed taxable asset transactions, and exclusions from CODI recognition such as tax attribute reduction.
  • Partnership Formations, Mergers, and Divisions: We leverage our extensive knowledge of partnership concepts and pitfalls to design partnership formations, mergers, and divisions that optimize tax benefits while maintaining desired economic arrangements.

Our guidance assists clients in structuring deals that withstand scrutiny, minimize unnecessary tax leakage, and provide greater post-tax value—whether you're buying, selling, or reorganizing.

Tax Attribute & Technical Analyses

We conduct in-depth technical analyses to identify available tax attributes, evaluate their limitations and tax implications, and ensure accurate reporting.

  • Qualified Small Business Stock Planning: We assess eligibility and planning opportunities for Qualified Small Business Stock, including the Section 1202 gain exclusion and the Section 1045 gain rollover, enabling clients to potentially reduce their transaction tax liabilities significantly.
  • Financial Instrument Tax Assistance: We assist in structuring and providing guidance on all types of financial instruments, from complex debt instruments to various hybrid alternatives such as SAFEs and convertible debt, covering areas including debt versus equity analyses and Original Issue Discount calculations.
  • Section 280G ("Golden Parachute" Rules) Exposure Analysis: We perform Section 280G calculations and exposure reviews to help clients prepare for and possibly reduce both excise tax risks and restrictions on compensation deductibility in change-of-control scenarios.

Together, we’ll help you make informed decisions, avoid reporting missteps, and preserve valuable tax benefits often overlooked in fast-paced transactions.

Due Diligence & Transaction Review

We support clients in evaluating transactions through the full lifecycle of a deal, identifying tax exposures, validating key assumptions, and ensuring that the client's tax considerations and concerns are accurately addressed in the transaction documents.

  • Tax Due Diligence: We conduct both buy-side and sell-side tax due diligence, evaluating and quantifying a comprehensive range of tax exposures, including federal and state income taxes, sales and use tax, other state and local indirect taxes, international taxes, employment taxes, and credits and incentives - helping clients avoid surprises and strengthen their negotiation positions.
  • Transaction Document Reviews: We examine transaction agreements, disclosure schedules, and related documents for tax-sensitive language, including representations and warranties, indemnities, structuring terms, and tax elections.

Our involvement instills confidence at the negotiating table by identifying and quantifying exposures, managing those risks, and ensuring that deals are executed with tax precision while aligning with the client's intentions.

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