Investor Update Generator

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.

Keywords

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

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.

Quick Start

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

OR start from scratch with assets/investor_update_template.md.

Core Workflows

Workflow 1: Monthly Update Production

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

Time Estimate: 1-2 hours/month.

Workflow 2: Update Cadence Establishment

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

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

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

Reference Guides

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

Templates

• assets/investor_update_template.md — Monthly update template

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.