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investor-update

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Use this skill when a founder, CEO, or CRO is writing to investors, board members, advisors, or prospective investors between meetings: a monthly or quarterly investor update, a pre-board narrative, a bad-news note, a fundraise progress update, or a diligence answer. Produces an update that leads with one headline, reports a consistent metrics frame, names wins, risks, and specific asks, and passes an honesty check before it ships. Use it for "investor update", "monthly update to investors", "board update", "advisor email", "update for prospective investors", "how do I tell investors about a miss", "answer this diligence question", or "nobody replies to my updates".

skills/jason-mesiarik/investor-update/SKILL.md

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Oct 20, 2026
License
MIT

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Applies to any written communication with people who fund, govern, or advise the company. Produces a short, structured update that investors read, answer, and act on.

**The doctrine:** investors fund the founder they have watched keep their word, or tell them quickly and precisely when they could not. Every update is a deposit in that record. When the big ask comes, the evidence is already in their inbox. Every update either increases or decreases the evidence behind the founder's word.

## The sequence

1. **Set audience and register.** Existing investors, the full board, advisors, prospective investors, a diligence question, or a broad recap. The audience sets the length and the tone. Read `references/structure-and-asks.md`.
2. **Open with the say-do ledger.** Restate last period's commitments exactly as written, and mark each one with a true status: done, partial, missed, changed, blocked, or dropped. No rewriting history. Read `references/say-do-ledger.md`.
3. **Numbers before words.** Pull the same metrics frame every time, in the same order: outcomes, leading indicators, survival (cash, burn, runway). Show actual, plan, prior period, and variance. When a favorable number has an unfavorable counterpart, put them side by side. Read `references/metrics-frame.md`.
4. **Write the headline.** One sentence that carries the whole update, and that an investor can repeat accurately when a partner asks what is happening at the company. One thesis per update.
5. **Build the body.** Wins, risks, asks, and a short forward look. Wins are facts, ordered by importance. Every risk comes with what is being done about it.
6. **Make the asks answerable.** One to three specific asks: a named kind of introduction, a decision, a piece of judgment. Include a forwardable blurb for every introduction. Report what happened with last update's asks.
7. **Run the honesty pass.** Check every status word, every number, and every relationship against what is actually true. Read `references/honesty-and-bad-news.md`.
8. **Send on rhythm, to a growing list.** Same day each period, same format, same metrics. Build the audience before you need it: existing investors, prospective investors, advisors. Track who replies and which metric they ask about.
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