Investor Update Generator

Validate a draft monthly investor update against a rubric of what makes them work — and provide a starting template if you don't have one yet.

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Keywords

investor update, monthly update, founder update, investor communication, fundraise, lead investor, board, KPIs, asks

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Clarify First

Before generating the update, confirm these inputs. If any is unknown or vague, ASK — do not assume:

• Stage & cadence — early-stage monthly vs later-stage quarterly changes which sections the rubric expects
• This period's metrics — the same defined set every month; re-defining metrics signals dishonest reporting
• Specific asks — what you need from investors (intros, hires, advice); the highest-leverage section
• Bad news / risks — strong updates lead with these, so they must be surfaced, not buried

Stop rule: ask only the 2-3 that most change the output. If the user says "just draft it," proceed and list your assumptions at the top of the artifact.

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Quick Start

1. Draft your update as update.md
2. Run: python scripts/investor_update_validator.py update.md
3. Address any missing sections; aim for the rubric score > 80

OR start from scratch with assets/investor_update_template.md.

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Core Workflows

Workflow 1: Monthly Update Production

1. First of month: pull metrics dashboard, last update, current asks
2. Draft against assets/investor_update_template.md
3. Validate: python scripts/investor_update_validator.py update.md
4. Send within 5 business days of month-end

Time Estimate: 1-2 hours/month.

Workflow 2: Update Cadence Establishment

1. Read references/what_makes_good_updates.md
2. Decide cadence: monthly is standard for early-stage; quarterly for later-stage
3. Pick distribution: investors only, or extended (advisors, helpful operators)
4. Commit publicly — once you start, don't skip months

Time Estimate: 1 week to set up; recurring monthly thereafter.

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Tools

investor_update_validator.py

Scans an update markdown file for the structural sections of a strong update and scores it.

python scripts/investor_update_validator.py update.md
python scripts/investor_update_validator.py update.md --json

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Reference Guides

• references/what_makes_good_updates.md — What separates good investor updates from bad

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Templates

• assets/investor_update_template.md — Monthly update template

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Best Practices

• Send the bad news first. Investors notice when they only hear the good.
• Asks specific. "Help with sales" is too vague; "Intros to VPs of Engineering at SaaS companies 100-1000 employees in NA" is actionable.
• Cadence > perfection. A consistent OK update beats a perfect annual one.
• Same metrics every month. Defining and re-defining metrics signals dishonest reporting.
• One page (or one screen). Past two screens, attention drops.