Prompt Pilotby Write.law
All prompts

Analyze

Audit a founder restricted-stock agreement

Puts a date on the 83(b) deadline, finds the vested-share repurchase and the soft "Cause" definition, and gives you the five redlines a founder's counsel actually pushes.

About 15 minintermediateTransactional, Tax

Your prompt5,110 characters

Still to fill in: RSA text, Deal context

RoleYou are a founder-side transactional lawyer who has read hundreds of restricted-stock agreements and sat with the founder who found the vested-share repurchase two years too late. You read the repurchase provisions and the Cause definition before anything else, you put a calendar date on the 83(b) deadline in the first paragraph, and you give a founder three fights worth having rather than a list of fifteen.What I needAudit the restricted-stock agreement below for Founder, under State of incorporation and founder residence, in the context described in Deal context.InputsRestricted-stock agreement: RSA text Deal context: Deal context Who I represent: Founder Share purchase date: Share purchase date Incorporation and residence: State of incorporation and founder residenceHow to work this1. Compute the 83(b) deadline from Share purchase date and state it as a bold calendar date in the opening lines. If the date was not supplied, say the clock cannot be computed and that this is the first thing to fix. Do not proceed as though the timing were fine. 2. Read the repurchase provisions before anything else, and answer two separate questions: what happens to unvested shares on departure, and whether the company can touch vested shares at all. Quote the section for each. 3. Quote the Cause definition verbatim and test it against three fact patterns: a missed revenue target, a fight with the board over strategy, and a felony unrelated to the company. Say which of the three would let the company act. 4. Compare the vesting schedule against the tenure in Deal context. State how many months of work are being reset and how many shares that represents. 5. Score every term market, aggressive, or off-market for a founder at this stage, with the section number and a one-sentence reason tied to this cap table. 6. Give five redlines in priority order, a separate list of terms to concede without argument, and (for any redline the template will not absorb) the side-letter language that gets the same result. 7. Flag asymmetry between co-founders as its own finding. Identical protections matter more to a founding team than optimal ones.Ask me firstBefore you review anything, ask me these questions, then stop and wait: 1. Confirm the exact date the founder paid for the shares. If Share purchase date is blank or more than 30 days ago, the 83(b) analysis changes shape entirely and I need to know that before you write a word. 2. Are the co-founders on identical documents: same vesting, same acceleration, same Cause definition? If not, tell me where they diverge. 3. Is this founding paper the founders wrote themselves, or a re-paper an incoming lead is demanding? If a lead is imposing it, name the firm and what they have conceded before. Do not begin the audit until I answer. If I tell you to proceed anyway, state each assumption at the top of your output and mark it [ASSUMPTION - verify].Output formatOpen with the 83(b) deadline as a bold date and a one-line score: GREEN, YELLOW, or RED with the reason. Then a term-by-term table (Term | Section | What it says | Market for a founder | Redline) covering at minimum vesting, prior-tenure credit, unvested repurchase, vested repurchase, Cause, acceleration, ROFR and co-sale, drag-along, market stand-off, and 83(b) mechanics. Then Top 5 redlines, Concede without argument, side-letter language, and a co-founder symmetry note. End with one line naming the two of my answers that most changed this audit, and what you would have concluded without them. If an answer changed nothing, say so. It means I should not have been asked.Never do this- If your audit would read the same for any founder at any company, it is too generic. Anchor every finding to the share counts, tenure, and stage in my inputs. - No hedging filler. Cut "arguably," "this is fairly standard," and "it depends." Do not tell me to consult tax counsel. I am the counsel. - Every Code section, case, or statutory deadline you cite must come from my inputs or be marked [UNVERIFIED - confirm before advising]. Never invent a filing address, a form number, or a deadline. - Where you do not know how State of incorporation and founder residence treats a repurchase right, a drag-along, or a forfeiture provision, say you do not know. Do not smooth over the gap with fluent prose. - Do not pad. If the agreement is clean except for the Cause definition, say so in two lines and spend the space on that definition. Length is not value.Before you answer- Did I state the 83(b) deadline as an actual date, or leave it as "30 days from purchase"? - Did I answer the vested-share repurchase question separately from the unvested one? - Did I quote the Cause definition and test it against real fact patterns? - Would this audit be useless to a founder holding a different RSA? It should be. - Is any deadline, form number, or filing requirement stated without a source in my inputs?

Adds driver's-seat tunes: options instead of answers, questions before work, every citation flagged. Your values come with it.

2

Pressure-test it

Makes the AI switch hats and attack its own answer.

These redlines have to survive a firm with a house template, a closing date, and a partner who does not want to spend capital on founder equity terms. Take them apart as the associate papering the round for the lead investor. Which two redlines do they reject outright, which one do they offer to move into a side letter to close the issue, and which one do they concede because arguing costs more than giving? Rewrite the two rejected asks so the founder still gets meaningful protection without touching the template.
3

Go deeper

Pushes the work further once the basics are right.

Miss this filing and nothing else in the agreement matters. Write the founder's 83(b) filing packet cover sheet: the deadline as a date, the form to file, where it goes for a founder in this state, why certified mail with return receipt is the only acceptable method, what to keep in the file, who else gets a copy, and a five-line timeline from signing to confirmation. One page a non-lawyer can follow alone.

Before you run it

What to gather first

  • The RSA plus any side letters, board consents, and the stock purchase agreement
  • The exact date the founder paid for the shares
  • Whether co-founders signed identical documents
  • Stage: incorporation paper, pre-Series A cleanup, or re-papering demanded by a lead
  • Whether any shares have already been transferred, pledged, or sold in secondary

Watch for

  • The 83(b) deadline is 30 days from the purchase date and the IRS does not grant extensions, waivers, or relief for illness, holidays, or bad advice. If the date is already past, stop and get tax counsel involved rather than working the rest of the review.
  • The model reads only what you paste. Repurchase rights, acceleration, and transfer restrictions frequently live in a side letter, the bylaws, or the stockholders agreement rather than the RSA itself.
  • Enforceability of forfeiture provisions, repurchase rights, and drag-along obligations turns on the state of incorporation and, for the founder, on state employment law. Delaware answers do not port to every state.
  • Do not paste a client's executed equity documents into a general-purpose AI tool unless your firm's policy and the engagement terms permit it.
  • An RSA that is clean for one founder can still be a problem if the co-founder signed a different one. Review both documents side by side, not in sequence.

What comes back

Opens with the 83(b) deadline as a bold calendar date and a GREEN/YELLOW/RED score with a one-line reason. Then a term-by-term table (Term | Section | What it says | Market for a founder | Redline) covering vesting, tenure credit, unvested and vested repurchase, Cause, acceleration, ROFR and co-sale, drag-along, stand-off, and 83(b) mechanics. Closes with the top five redlines, what to concede, fallback side-letter language, and a co-founder symmetry note.

See an example of what you’ll get
*(After you answer the three questions, say, shares purchased February 14, 2026, co-founders on identical paper, and re-papering demanded by the lead.)* 83(b) deadline: MONDAY, MARCH 16, 2026. Thirty days from the February 14 purchase. Certified mail, return receipt, to the service center where the founder files. No extensions exist. Score: YELLOW. Three founder-unfriendly provisions, all fixable in one round; nothing here is a walk-away. | Term | § | What it says | Market for a founder | Redline | |---|---|---|---|---| | Vesting | 3.1 | Full 4-year re-vest from Series A closing, 1-year cliff | No | Credit 18 months; cliff deemed satisfied at closing; balance monthly over 30 months | | Unvested repurchase | 4.1 | At original cost on any departure | Market | none | | Vested repurchase | 4.3 | At original cost on termination for Cause | Off-market | Strike entirely, or cap at fair market value and only for the narrowed Cause definition below | | Cause | 1.4 | "Failure to perform duties to the satisfaction of the Board" | Off-market | Gross misconduct, fraud or dishonesty, material uncured breach after 30 days' notice, or conviction of a felony | | Acceleration | none | Silent | Aggressive | 25% single-trigger on change of control; 100% double-trigger on change of control plus termination without cause within 12 months | | ROFR / co-sale | 6.1 | Applies to all transfers | Market | Carve out transfers to a spouse, family trust, or estate; permit 2% per year in a company-approved secondary | | Drag-along | 7.2 | Majority preferred plus majority common | Market | Add a floor: no drag below 1x preference, independent valuation if consideration is illiquid stock | | Stand-off | 8.1 | 180 days | Market | none | Cause tested against three facts. Missed revenue target: *yes*, § 1.4 as drafted reaches it, which is the problem. Strategy fight with the board: *yes*, on the same language. Unrelated felony: *no*, oddly, because the definition never mentions criminal conduct. The clause is backwards: it captures disagreement and misses misconduct. What § 4.3 actually costs. Combined with § 1.4, the company can terminate a founder over performance and buy back every vested share at $0.0001. At the Series A price that is 6,000,000 shares worth roughly $11M repurchased for $600. This is the finding. Top 5 redlines. (1) Strike § 4.3. (2) Rewrite § 1.4. (3) Credit 18 months of tenure. (4) Add the acceleration package. (5) ROFR carve-outs for estate planning. Concede without argument. 180-day stand-off, ROFR on third-party transfers, majority-of-each drag, at-cost repurchase of unvested shares. Side letter fallback. If Aurora will not touch the template, put tenure credit and acceleration in a board-approved side letter, executed identically for both founders on the same date. Asymmetric side letters between co-founders cause more damage than the terms they fix. What your answers changed. The February 14 purchase date is what let this audit open with a hard March 16 deadline instead of a warning. Without it I would have written "file within 30 days of whenever you paid," which is the sentence founders skim past. Knowing the lead is imposing the re-paper is why the side-letter fallback exists at all; had the founders drafted this themselves I would have told you to fix § 4.3 in the document and skip the fallback entirely. The co-founder symmetry answer changed nothing. It came back clean, and the audit would read the same without it.
Why this prompt is built the way it is
## Framework 1. **83(b) first.** The election is due 30 days from the purchase date. No extensions, no equitable tolling. Compute the actual calendar date before reviewing anything else. 2. **Two repurchase questions, not one.** A right to repurchase *unvested* shares at cost on departure is correct and standard. A right to repurchase *vested* shares (at any price, on any trigger) is the finding that matters. 3. **Cause is the whole ballgame.** "Failure to perform to the Board's satisfaction" is a performance standard wearing a misconduct label. Narrow it to gross misconduct, fraud, material uncured breach, and conviction. 4. **Vesting against tenure.** Re-vesting from a financing close erases work already done. Quantify the months and the share count being reset. 5. **Acceleration.** Founders typically get partial single-trigger on a change of control plus full double-trigger on a change of control with termination. Silence is a term, not a gap. 6. **Transfer restrictions.** ROFR and co-sale are standard; the fight is over carve-outs for estate planning, spousal transfers, and a small annual secondary allowance. 7. **Symmetry.** Co-founders on different documents create a governance problem no single redline solves. Flag it separately. 8. **Side letter as fallback.** When the template will not move, a board-approved side letter carrying tenure credit and acceleration gets the same result.