cap-table-validator

Business

Validates cap table accuracy, identifies issues, models option pool impact

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Source SKILL.md: https://github.com/a5c-ai/babysitter/blob/HEAD/library/specializations/domains/business/venture-capital/skills/cap-table-validator/SKILL.md

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Cap Table Validator

Overview

The Cap Table Validator skill provides systematic validation of capitalization tables during due diligence. It verifies ownership accuracy, identifies potential issues, and models the impact of option pools and future financing on ownership structure.

Capabilities

Cap Table Verification

Verify share counts against stock ledger
Reconcile against Articles/Charter documents
Check convertible instrument calculations
Validate vesting schedules and exercise prices

Issue Identification

Identify missing or incorrect 83(b) elections
Flag accelerated vesting provisions
Detect anti-dilution trigger scenarios
Identify founder equity concentration issues

Option Pool Modeling

Model option pool expansion impact
Calculate fully diluted ownership
Analyze option overhang and burn rate
Project pool runway based on hiring plans

Convertible Modeling

Model SAFE and note conversions
Calculate pre-money vs. post-money impacts
Analyze discount and cap mechanics
Model multiple conversion scenarios

Usage

Validate Cap Table

Input: Cap table, supporting documents
Process: Verify calculations, reconcile documents
Output: Validation report, discrepancies found

Identify Issues

Input: Cap table, charter documents
Process: Check for common issues, flag concerns
Output: Issue list, severity assessment

Model Option Pool

Input: Current pool, hiring plan, grant guidelines
Process: Project pool usage, calculate dilution
Output: Pool projection, ownership impact

Model Convertibles

Input: Convertible instruments, conversion scenarios
Process: Calculate conversion outcomes
Output: Conversion analysis, ownership projections

Validation Checklist

Category	Key Checks
Shares Outstanding	Match charter, stock ledger, cap table
Options	Verify grants, vesting, exercise prices
Convertibles	Terms accuracy, conversion mechanics
Documents	Board approvals, stock certificates
Tax	83(b) elections, ISO limits, AMT

Integration Points

Legal Due Diligence: Core cap table review
Cap Table Modeler (Agent): Support agent analysis
Dilution Analyzer: Feed validated data for analysis
Waterfall Calculator: Provide ownership for waterfall

Common Issues

Outstanding convertibles not reflected
Vesting calculation errors
Exercise price discrepancies
Missing or late 83(b) elections
ISO/NSO classification errors
Incorrect anti-dilution provisions
Conflicting document versions

Best Practices

Request source documents, not just spreadsheets
Verify against Carta, Pulley, or stock admin system
Model all outstanding convertibles
Check for pending but unexecuted grants
Review recent charter amendments