Hosts: Alan Darby & Jaclyn Martinez
Guest: Elizabeth Guidi, Tax Attorney at Kilpatrick Townsend

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
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Hidden Tax Landmines

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

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.

Bottom Line - Smart tax planning isn't about finding loopholes - it's about legally structuring your transaction to keep more of what you built. Start the conversation with tax advisors before you sign the LOI, not after.