A variable prepaid forward gets you cash and downside protection on a concentrated stock without a sale. Bought from a bank, it is a black box. Built yourself, every price is visible.
If you hold a large, low-basis stock position, a private bank has almost certainly pitched you a variable prepaid forward. It is a genuinely useful structure: you get a big slug of cash today, downside protection, and no taxable sale, with the gain deferred for years. The mechanics of how it works are in our full explainer on the synthetic variable prepaid forward. This is about a narrower question: should you buy the bank's version, or build your own?
The answer, most of the time, is build. Here is why.
A bank's VPF is one contract that bundles everything: the downside protection, the upside cap, and the upfront cash advance, all priced together by the bank's desk. It is convenient. It is also opaque. You are handed a single number, and inside it sits an embedded spread you cannot see, a counterparty who is on the other side of every leg, and terms set by them rather than you.
The same economics can be assembled from two transparent, publicly priced pieces. First, a collar: buy a put to set your floor and sell a call to set your cap, at strikes you choose, at prices quoted in the open options market. Second, borrowing against the now-protected position through a box spread, which raises cash at a rate close to Treasuries rather than a rate set by a lending desk. Protected, liquid, and deferred, the same three outcomes, built from parts you can see.
Same three outcomes: protected, liquid, deferred. The difference is whether you can see what you are paying for.
When you assemble the structure yourself, you see every price, you set your own protection band instead of accepting the bank's, and you borrow at a market rate instead of a marked-up one. Just as important, the pieces are independent. If the stock moves, or your plan changes, you can roll the collar or repay the box on its own timeline rather than being locked into a single rigid contract.
The synthetic version is not free of complexity, and it is honest to say so. It has more moving parts, and it takes an advisor who can run options and financing as one coordinated position rather than two disconnected trades. The box spread is borrowed money that has to be rolled and repaid, and a drawdown works against it. And the same rule governs both versions: a collar set too tight can trip the constructive-sale rule under Section 1259 and accelerate the very gain you were deferring, so the band has to be built with room to breathe.
We build the structure leg by leg around your basis, your price, and how much cash you actually need, and we price it against the bank's packaged quote so you can see the difference in plain numbers. Constructive-sale limits are respected at every step, and the whole thing is coordinated with your CPA. The point is not to be clever. It is to give you the same protection and liquidity without paying for a black box. The broader menu for a position like this is in our guide to concentrated stock positions.
For informational and educational purposes only. Options, collars, box spreads, and prepaid forward structures involve significant complexity, costs, and risk, including the risk that tax deferral fails if the structure is built incorrectly, and are not suitable for everyone. Rules such as the constructive-sale rule are summarized and simplified here and are subject to change. This is not personalized tax, legal, or investment advice. Consult qualified professionals about your situation.
Been pitched a variable prepaid forward on a concentrated position? Send us the bank's terms and we will price a synthetic version against them, leg by leg, so you can see what the black box is really costing.
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