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The Conversion: Same Shares, Different Price.

Buying the same preferred stock for less can change more than ownership.

Post Money Problems4 min read
A cream folded promissory note transforms through an architectural arch into two uneven columns of blue share certificates
Post Money Problems, Editorial illustration, 2026. Illustration.
October 2026 dossier / Published October 1, 2026The complete collection ↗

Our fictional investor wants the same shares the next investor receives. It would prefer to pay less for each one. The phrase same shares has made the request sound modest.

The shaded passages are from our fictional note, not verbatim Cooley clauses. Comments explain the trade, suggest a counterproposal, and translate our imaginary investor’s incentives. Structural references: Cooley’s CC0 Series Seed form; the tougher selected economics and fictional commentary are ours. An ask is not an agreed change or a guarantee you will get it.

Part II issued 540,000 note shares at $1 while cash investors paid $2. If both receive preferred shares with a $2-per-share liquidation preference, the note's $540,000 converting balance acquires $1.08 million of stated preference.

That result depends on the assumed charter. A discounted note does not invariably receive it, and a preference is not a guaranteed payment.

The arithmetic

Worked example / Fictional terms
540,000 note shares. Assumed cash-round preference: $2 per share.
TreatmentSharesPreference/shareStated preference
Same preferred series540,000$2.00$1,080,000
Adjusted shadow series540,000$1.00$540,000

Swipe or scroll the table for all columns →

Illustrative arithmetic, not a forecast or transaction-specific advice. Definitions and exclusions appear in the specimen and accompanying text.

Multiply 540,000 note shares by the assumed $2 preference. The answer is $1.08 million. New cash investors' one million shares carry $2 million of preference on $2 million invested.

Actual payouts still depend on proceeds, senior claims, other preferences, participation, conversion elections, and the charter. The table compares the preference bases before applying any waterfall.

At Post Money Capital, equal treatment has been an extremely rewarding principle.

The shadow series counterproposal

Clause 4 / From the fictional note

Same stock, larger first claim

No separate shadow series or adjustment of per-share liquidation preference is promised.

Read the full clause and its qualifications ↗

What it means
The discounted shares receive the future cash investors' stock rights. If that stock has a $2 preference per share, our 540,000 shares bought through $540,000 of conversion dollars carry $1.08 million of stated preference. That amount is not a guaranteed exit payment.
Why it helps you
Joining one series can simplify documentation and avoid another class with separate consent machinery. The early investor has also genuinely taken risk that the new cash investors did not take.
Where it bites
The ownership discount can accidentally become a larger preferred claim ahead of common as well. The actual charter, available proceeds, seniority, and participation rules determine how painful that becomes.
Ask for this
Ask for properly defined shadow preferred with price-linked rights tied to the note's conversion price. In this example, $1 per share gives $540,000 of preference without removing the 540,000 shares. Review anti-dilution price and dividend calculations too; fixing only one line can leave another mismatch.
A counterproposal to discuss with counsel

Permit a shadow series that votes with the cash-investor series but bases preference, price-based anti-dilution, and relevant dividend amounts on the actual conversion price. Reconcile it to the charter.

Commercial request, not execution-ready legal language. It is not an agreed change to the specimen.

Source boundary. Cooley §2.1 includes an optional shadow-series provision. Its valuation-cap article also discusses adjusted preferred and other solutions. Our same-series example intentionally omits that protection. [1][3]

Cooley's public note includes an optional shadow-series provision that ties specified price-linked rights to the conversion price.1 Our specimen intentionally leaves it out. Its valuation-cap guidance also discusses the mismatch and possible alternatives.3

An appropriately drafted shadow series can preserve the 540,000 shares while setting this example's preference at $1 per share, or $540,000 total. The ask corrects the preference base; it need not revoke the agreed ownership discount.

Check the other linked terms too. An anti-dilution calculation or dividend still pegged to the cash investors' original issue price may preserve a mismatch after you fix liquidation preference. Counsel needs the note and charter together.

More votes can mean a different coalition

If preferred votes with common on an as-converted basis, more shares can also mean more votes. Class votes, protective provisions, and major-investor thresholds can create other consequences.

Our note grants no current board seat or operating veto. On conversion, the holder signs the applicable financing documents and obtains the stock's rights. Ask what continuing rights those documents grant and whether thresholds measure dollars invested or discounted shares.

A shadow series can introduce class mechanics of its own. Do not solve the economic mismatch by casually inventing another blocking class.

Conversion needs a closing map

The schedule should name each instrument, principal, accrued interest, conversion price, shares, stock class, preference base, and continuing rights. Reconcile it to the charter and final capitalization.

Our specimen converts all interest and settles fractional shares in cash. Those details are not universal. The note's information covenant lasts while the note is outstanding; reporting after conversion needs a continuing basis in the new documents.

If the schedule cannot explain where every share came from, the closing dinner is early.

What the founder asks for

Request the draft charter, a complete conversion schedule, and exit examples with the actual preferences. Propose the shadow treatment before signing away the option to use it.

The investor's early risk can justify a better entry price. That does not settle whether the bargain also includes a larger claim ahead of common. If you accept both in exchange for something else, identify the exchange.

We offered the same shares. Nobody said they would arrive with the same arithmetic.

The receipts

Sources and qualifications for the factual claims in this piece.

  1. Cooley LLP — Series Seed convertible promissory note. Public-domain CC0 form in Cooley's repository, reviewed October 1, 2026. Its alternatives inform the mechanics examined here. Our fictional note is an original educational example with deliberately selected terms, not a Cooley-endorsed form.
  2. Cooley Go — Convertible Debt. A short primer on debt that may convert to equity. Transaction-specific advice and documentation still require counsel.
  3. Cooley Go — Understanding the Valuation Cap. Context for capitalization definitions and the liquidation-preference issue. Our numbers use the explicit convention printed in the fictional note.
  4. Y Combinator — Safe Financing Documents. Primary reference for the distinct SAFE instrument. Do not import a SAFE's mechanics into this interest-bearing, maturity-bearing note.
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