New York Partner Elizabeth Guidi is featured on Alaris Acquistion's podcast, "The Buyer's Boardroom." Watch How to Minimize Your Taxes on Big Transactions here. 

Your transaction outcome isn't just about the headline price - it's about what you actually keep after taxes. Most sellers focus on valuation multiples but miss how deal structure can dramatically impact their after-tax proceeds. Asset purchases with rollover equity often beat straight stock sales from a tax perspective. The "structure first" mindset can save significant dollars compared to focusing solely on purchase price negotiations.

Purchase Price Allocation

• How assets are valued affects your tax treatment
• Goodwill allocation and step-up in basis implications
• What actually moves the needle on your tax bill

Payment Timing Strategy

• Earnouts vs cash today - the tax timing trade-offs
• Working capital adjustments most sellers don't see coming
• Escrow and indemnity tax implications

Entity Structure Traps

• S-corp, LLC, and C-corp nuances that catch sellers off-guard
• Why your business structure affects deal taxation
• Planning moves that should happen before you start negotiations

Hidden Tax Landmines

• State and local tax surprises that can derail your planning
• Geographic considerations most advisors overlook
• Compliance requirements across different jurisdictions

The Pre-LOI Tax Checklist

Simple framework to get tax planning on track before negotiations begin. Getting tax and legal advisors involved early lets you design the optimal structure instead of retrofitting tax planning to a completed deal.

Elizabeth's Key Insight

Every deal is unique. Cookie-cutter approaches to M&A taxation leave money on the table. The biggest wins come from structuring transactions intelligently from the start, not trying to minimize taxes after the deal terms are set.