United States / Case studies

Case study · Enterprise software

The cap table that nearly cost a priced round

An enterprise software company reached its first priced round with undocumented SAFEs, verbal option promises and share records that disagreed with each other. Rebuilding ownership from first principles cleared the diligence hurdle — and the method is exactly what a US lead investor’s counsel will ask of you.

The engagement

What was broken

An enterprise software company had accumulated a tangled cap table over several informal funding events — undocumented SAFEs, verbal ESOP promises, and share records that did not agree with each other. As a priced round approached, the incoming lead investor required a single, reconciled source of truth before proceeding.

What we did

CapEasy reconstructed the ownership history from first principles: every issuance and conversion reconciled, the option pool formalised on paper, and the statutory registers corrected to match what had actually been issued. Discrepancies were resolved with the affected stakeholders directly, not papered over.

Where it landed

The company presented the investor with an accurate, reconciled cap table, clearing a key diligence hurdle. Ownership was documented consistently across the statutory records for the first time, and the round proceeded on a base both sides could verify.

The United States playbook

What a US priced round actually asks of your records

When a lead investor’s counsel opens diligence on a Delaware corporation, the requests are concrete: the stock ledger, every SAFE and convertible note with its signed instrument, board consents authorising each issuance, and the option grants with the approvals behind them. Delaware law expects the corporation to maintain a stock ledger as the record of who holds what — an investor’s counsel treats gaps between that ledger and the signed instruments as risk to be priced or fixed before closing.

The failure pattern in this engagement is the common one everywhere: fundraising documents live in founders’ inboxes, promises to early employees live in chat threads, and the ledger — if one exists — was last updated two instruments ago. None of that is fatal. All of it takes longer to fix during a diligence window than before one.

SAFEs sit on your books until the day they convert

A SAFE is money received without shares issued — which means it lives on the balance sheet from the day it is signed, and your bookkeeping has to carry it correctly until conversion. A priced round is precisely the conversion event, so diligence reads the SAFE schedule and the books together: the amounts raised, the caps and discounts, and whether the ledger agrees with the instruments.

The practical discipline is a SAFE schedule maintained like a reconciliation: one line per instrument, amount, date, cap, discount, and the signed document filed next to it. Kept monthly, it is a five-minute check. Reconstructed during a diligence window, it is days of inbox archaeology while counsel waits.

The rebuild method that survives scrutiny

The engagement’s method transfers directly: reconstruct ownership from first principles rather than patching the current ledger. Start from incorporation, walk every issuance, conversion and transfer in date order against its signed instrument, and resolve each discrepancy with the affected holder on paper. The output is not just a spreadsheet that looks right — it is a chain of documents in which every row of the cap table can point to the instrument that created it.

CapEasy’s part in that work is the reconstruction and the reconciliation: the document chase, the schedule, the ledger tied to the instruments. Legal opinions on the instruments themselves, and anything filed with a state or the IRS, run through your counsel and the partner CPA firms we work with across 15 US states.

What to take from it

  1. Diligence does not ask whether your cap table looks right — it asks whether every row traces to a signed instrument.
  2. A SAFE is a balance-sheet item from signature to conversion; carry it on a maintained schedule, not in an inbox.
  3. Verbal equity promises are the single hardest thing to fix during a round — formalise the option pool before you need it.
  4. Rebuild from incorporation forward, not from the current ledger backward; a patched ledger fails the same questions twice.

Primary sources

The same discipline, on your books.

A named accountant, the grinding automated, licensed partners where the law wants them.

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