- name:
- investor-update
- description:
- 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".
Investor update
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
- 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. - 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. - 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. - 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.
- 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.
- 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.
- 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. - 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.
What good looks like
- The expert's tell: the update opens with last period's commitments and their true status. Twelve months later, the ledger is the founder's strongest fundraising evidence.
- The repeatable sentence: the headline is something an investor can say to a partner and be accurate. Not "interesting things with AI" but "doubled enterprise ARR with burn flat, and three of five target customers are in contracting."
- The common mistake: an update that reads like a press release. "Thrilled to share" and "transformative quarter" carry no information, and sophisticated readers discount everything that follows.
- The second mistake: framing that makes investors find the other half of the truth themselves. Investors tolerate bad numbers. They do not tolerate discovering that management knew which numbers would change their reading and chose not to show them.
- The third mistake: generic asks. "Any intros welcome" produces nothing. "An introduction to a CRO at a $10M to $30M ARR company who has rebuilt a forecast process" produces meetings.
- How to know it worked: investors reply, asks get fulfilled, and bad news never reaches them from someone else first. Over a year, the update record becomes the strongest slide in the next fundraise.
- Field cases:
references/worked-examples.md. Templates for each update type:references/templates.md. Score withreferences/update-rubric.md. Ship at 90 or above.
Rules
- MUST open with the say-do ledger, commitments restated exactly, each marked done, partial, missed, changed, blocked, or dropped.
- MUST lead with a one-sentence headline; NEVER build to the point.
- MUST report the same metrics, in the same order, every period, with actual, plan, prior, and variance, and runway always included.
- MUST place a favorable number beside the unfavorable number that changes its meaning.
- MUST mark anything unmeasured as unmeasured; NEVER estimate silently.
- MUST pair every risk with the action being taken.
- MUST make every ask specific and answerable, and report on last period's asks.
- NEVER describe a relationship, deal, or hire as further along than it is. "Sent, no reply" is a status. "In motion" is not.
- MUST deliver material bad news before the investor can hear it elsewhere.
- NEVER disclose customer names, bank balances, or confidential terms beyond the audience entitled to them.
