Every dealmaker knows the obvious deal killers: bad timing, poor communication, misaligned expectations.
But there’s one factor that quietly destroys more transactions than most people realize — taxes.
In the latest episode of This Is M&A, host Steven Monterroso sits down with Christine “Chrissy” Green, Member and Tax Attorney at Steptoe & Johnson PLLC, to pull back the curtain on the tax pitfalls that derail deals from the inside out.
And her message couldn’t be clearer:
If you’re not planning for taxes early, you’re planning to lose leverage.
The Hidden Tax Traps Lurking in Every Deal
While most deal teams are focused on valuation, diligence, and negotiation, Chrissy warns that tax structure is shaping the outcome long before anyone realizes it.
The biggest mistake she sees?
Bringing in tax experts too late.
By the time a tax attorney is looped in, key terms are already baked into the LOI or modeled into the valuation. Options narrow. Leverage evaporates. Buyers and sellers are boxed in by decisions that—had they been made differently—could have unlocked massive tax advantages or avoided painful liabilities.
Asset vs. Equity: The Fork in the Road That Changes Everything
One of the earliest and most overlooked decisions in any deal is the asset-versus-equity structure.
Chrissy breaks down why this choice is far more than a legal nuance — it’s a tax hinge that shifts risk, basis, future planning options, and real dollars.
- Buyers may prefer asset deals for step-ups in basis and liability protection.
- Sellers typically push for equity to minimize tax hit and simplify the transaction.
But picking the wrong direction—or picking it too late—can turn a deal from tax-efficient to tax-explosive.
The “Big Beautiful Bill” and New QSBS Developments
Chrissy also sheds light on two major tax areas dealmakers often misunderstand:
1. The “Big Beautiful Bill”
Washington is moving on tax legislation with potentially massive implications for how deals are structured and taxed. Chrissy breaks down what’s in play, what’s posturing, and what’s real enough to plan for.
2. Changing Rules Around QSBS
Qualified Small Business Stock has long been a tax planning gem — but recent and proposed changes are reshaping what founders, investors, and acquirers can count on.
Chrissy explains why QSBS can no longer be an afterthought and why early planning is now more important than ever.
Early Tax Planning = Deal Leverage
Chrissy’s advice to dealmakers is simple:
Bring tax strategy to the table early — before valuations are set, before structures are chosen, before expectations calcify.
That’s how you keep your options open, protect deal value, and avoid becoming another cautionary tale of a transaction undone by unforeseen tax consequences.
Listen to the Full Episode
If you want to keep your next deal alive — and keep more of its value — don’t miss this episode.
🎧 Listen now to hear Chrissy Green’s full breakdown on tax traps, leverage, and smarter deal structuring.
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