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Not investment advice. Educational reading. See Disclaimer.
L.3 · ADVANCED · 2 MIN

Deal Structure: Cash, Stock, or Both?

The choice between cash, stock, or mixed consideration is one of the most consequential decisions in deal design. It signals confidence, determines tax treatment, and allocates risk between buyer and seller.

Quiz · 5 questions ↓
§ 01
ConsiderationBuyer SignalSeller ImpactTax Treatment
All cashHigh confidence (puts own money at risk)Certainty of value; taxable eventImmediate capital gains tax
All stockMay believe own stock overvaluedTied to buyer’s future performanceTax-deferred (reorganization)
Cash + stock mixModerate confidencePartial certainty, partial upsideMixed — cash portion taxable
§ 02

When a buyer insists on paying with stock, ask: do they believe their stock is overvalued? If a CEO thinks their stock is cheap, they’d prefer to pay cash and keep the upside. Stock payment can be a signal of overvaluation.

§ 03
Look at a recent M&A announcement. Was it cash, stock, or mixed? Consider what the payment method signals about the buyer’s view of their own stock price.
§ 04
A company with a $100B market cap offers to buy a target for $10B in all stock. What risk does the target’s shareholders now bear?
§ 05

In stock deals, look at the exchange ratio and whether it’s fixed or floating. A fixed exchange ratio means the target gets a set number of shares regardless of price changes. A floating ratio adjusts to maintain a fixed dollar value.

§ 06
You're evaluating an M&A deal structured as 100% cash. The acquirer is issuing $10B of debt to fund it, pushing leverage from 2.5x to 4.5x. What's the hidden risk?
Five questions · AI feedback

Sit with the ideas.

A $20B acquisition is financed with 60% cash (from new debt at 5%) and 40% stock (buyer's P/E is 20x). The target's P/E is 12x. Is the cash portion or stock portion more accretive?

Why:
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