Due Diligence VCventure capitalfounder assessmentinvestment thesis

VC Cyber Diligence Workbook

Stage-aware VC diligence for Pre-Seed through Series B+ — founder assessment, investment thesis scoring, pipeline tracking, cap table analysis, and IC memo output. 16 tabs built around the question: what would have to go right for 10x?

VC diligence has fundamentally different mechanics from M&A. M&A asks "what risks am I buying?" VC asks "what would have to go right for 10x?" That mindset shift drives the entire tool.

Investment Thesis comes first — Before any deal evaluation, you define the fund's screening criteria across 40+ fields (Fund Basics, Stage Focus, Sector, Geography, Founders, Market/Product, Traction, Values, Operational). Every deal gets scored against thesis fit. Fill once, screen forever.

Founder Assessment is the flagship tab — 30+ dimensions across 6 areas (Background, Team Dynamics, Execution, Vision, Character, Coachability) with 1-5 scoring, color-scale gradient, and a Flag column (None/Monitor/Concern/Dealbreaker). Auto-calculated Overall Founder Score with 5-tier interpretation from HIGH CONVICTION to PASS. At Pre-Seed/Seed, this is the investment.

Deal Pipeline — 30-row tracker with 14-status funnel (New Inbound → Initial Screen → … → Closed). 8 pre-seeded example deals spanning Pre-Seed through Series B with conditional formatting on Thesis Fit Score.

Stage-aware throughout — Every tab has stage-relevance markers (Pre-Seed / Seed / Series A / Series B+) so you know what to weight heavy and what to skip entirely.

Financials & Cap Table — 12 KPIs with benchmarks, Current Cap Table (12 rows), and a SAFE/Convertible Note Stack Analysis (8 rows) targeting the SAFE pile-up pattern that kills Series A deals when founders discover their actual dilution.

Term Sheet tab — 30+ standard terms organized by Economics / Control / Anti-Dilution / Founder Terms / Transfer & Exit. Market Standard column pre-populated with Your Position and Flex columns for negotiation tracking.

IC Memo output — 2-page template with 10 sections (One-liner, Why Now, Why Them, Why Win, Traction, Deal Structure, Risks, Asks). Short-memo discipline enforced by design.

Also includes: Market Assessment (TAM/SAM/SOM with "Why Now" filter), Product & Technology (AI/ML-specific diligence with EU AI Act exposure), Legal & IP (pre-incorporation IP trap and prior-employer noncompete check), GTM & Traction (customer reference call framework), Red Flags Register (25 rows, 5 seeded examples), Post-Investment Monitor (monthly/quarterly/annual cadence for the 7-10 year relationship), and a 41-term Glossary covering fund mechanics, financial instruments, term sheet items, and unit economics.

The User Guide's 22 sections cover the VC vs M&A diligence comparison, the stage-aware weighting matrix, the backchannel rule for founder assessment, the TAM trap, AI-specific 2026 diligence questions, the SAFE pile-up pattern, the five term sheet terms that matter most, and the three reference check questions that reveal the most.