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Equity cap table management for startups and growth-stage companies. Models SAFEs, convertible notes, priced equity rounds, token allocations, dilution scena...

Security Scan

The skill is an instruction-only cap‑table modeling assistant whose declared requirements and runtime instructions are coherent with its stated purpose and request no unexpected privileges or credentials.

Purpose & Capability

The name/description (cap table modeling, SAFEs, options, dilution, waterfalls) matches the SKILL.md content: calculation steps, templates, and example prompts. No unrelated binaries, credentials, or config paths are requested.

Instruction Scope

The SKILL.md provides formulas, step‑by‑step workflows, prompts, and example calculations. It does not instruct the agent to read system files, environment variables, or transmit data to external endpoints. It mentions exporting to CSV/Sheets/Excel in terminology only and does not include instructions to call external APIs or upload data.

Install Mechanism

No install spec and no code files are present (instruction‑only), so nothing will be written to disk or downloaded as part of the skill itself. This is the lowest‑risk install profile.

Credentials

The skill declares no required environment variables, credentials, or config paths. The modeling use case does not justify additional secrets. (If a user or platform connects this agent to Google Drive/Sheets, those connectors are outside the skill and should be reviewed separately.)

Persistence & Privilege

always is false and the skill is user‑invocable with normal autonomous invocation enabled — standard for skills. The skill does not request persistent system presence or modify other skills/configuration.

Assessment

This is an instruction‑only cap table modeling skill and appears coherent and low risk: it requests no credentials and installs nothing. Before using, avoid pasting full sensitive documents (e.g., private personal data or private keys) into the agent; if you want the agent to publish results to Google Sheets/Drive/other connectors, confirm that any connector credentials are supplied deliberately and that you trust the destination. Remember outputs are modeling/educational and not a substitute for legal or tax advice — consult counsel/CPA for binding actions.

Cap Table Manager

Manage equity ownership from Day 1 through exit. Model rounds, dilution, SAFEs, options pools, and token side-tables. Output investor-ready cap tables and scenario analyses.

When to Use

• Modeling pre-seed / seed / Series A+ rounds and dilution impact
• Tracking SAFE conversions (MFN, pro-rata, discount, valuation cap)
• Building a convertible note conversion schedule
• Calculating fully diluted share counts and ownership percentages
• Scenario planning: best / base / bear case valuations and payout waterfalls
• Preparing 409A valuation support materials
• Modeling option pool expansion (pre-money vs post-money shuffle)
• Token allocation tables alongside equity (hybrid company structures)
• Generating investor-ready cap table exports (CSV, Google Sheets, Excel)

When NOT to Use

• Public company equity management (use Carta, Shareworks, or a transfer agent)
• Complex secondary transactions requiring legal execution (refer to securities counsel)
• Tax advice on stock option grants, ISOs vs NSOs (refer to CPA with PTIN)
• Cap table maintenance in a state with specific securities filing requirements — flag for attorney review
• Replacing a cap table tool of record (Carta, Pulley, LTSE) for an active company with >25 stakeholders
• Anything requiring custodianship, ledger finality, or board-authorized record keeping

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Core Concepts

Share Classes

• Common Stock — founders and employees; lowest liquidation preference
• Preferred Stock — investors; liquidation preference + conversion rights
• Options/Warrants — unissued; part of fully diluted but not issued shares
• SAFEs — Simple Agreement for Future Equity; convert at next priced round
• Convertible Notes — debt converting to equity at a discount or cap

Key Metrics

Metric	Formula
Ownership %	Shares Held / Total Fully Diluted Shares
Pre-Money Valuation	Post-Money − New Investment
Price Per Share	Pre-Money Valuation / Pre-Money Fully Diluted Shares
Dilution %	1 − (Old Shares / New Fully Diluted Shares)
Liquidation Preference	Investment Amount × Preference Multiple

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Workflows

1. Build a Baseline Cap Table

Collect and structure current ownership:

Stakeholder | Class | Shares | % Ownership | Notes
------------|-------|--------|-------------|------
Founder A   | Common | 4,000,000 | 40% | Vesting 4yr/1yr cliff
Founder B   | Common | 3,000,000 | 30% | Vesting 4yr/1yr cliff
Option Pool | Options | 1,000,000 | 10% | 2024 Plan, unissued
Angel 1     | SAFE   | —      | —   | $250K @ $5M cap, 20% discount
Angel 2     | SAFE   | —      | —   | $100K MFN SAFE
TOTAL (pre-conversion) | | 8,000,000 | 80% issued |

Calculation prompt:

"Build me a cap table. Founders: Alice 4M shares, Bob 3M shares. Option pool: 1M shares. Pre-money fully diluted: 8M shares. We have a $250K SAFE at $5M cap and 20% discount, and a $100K MFN SAFE. We're raising a $2M seed at $8M pre-money. Show post-close ownership for all parties."

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2. Model a Priced Round

Inputs needed:

• Pre-money valuation
• Investment amount
• New option pool size (if expanding pre-money)
• Existing cap table (issued + options + SAFEs outstanding)

Step-by-step:

1. Calculate post-money option pool (if pre-money shuffle):

   • New option pool shares = Target % × Post-Money Fully Diluted
   • Example: 15% post-close pool on 12M post-money FD shares = 1.8M options reserved

2. Calculate price per share:

   • Pre-Money FD shares (including new pool) = existing shares + new pool shares
   • PPS = Pre-Money Valuation / Pre-Money FD shares

3. Convert SAFEs:

   • Conversion price = lower of: (PPS × (1 − discount)) OR (Cap / Pre-SAFE FD shares)
   • SAFE shares = Investment / Conversion Price

4. Issue new investor shares:

   • New shares = Investment / PPS

5. Rebuild fully diluted table post-close

Example — Seed Round:

Pre-money valuation:     $8,000,000
New investment:          $2,000,000
Post-money valuation:    $10,000,000

Pre-money FD shares (incl. pool shuffle): 9,500,000
Price per share: $8M / 9.5M = $0.8421

SAFE #1 conversion ($250K @ $5M cap, 20% disc):
  Cap price:      $5M / 8M pre-SAFE shares = $0.625
  Discount price: $0.8421 × 0.80 = $0.6737
  Conversion at:  $0.625 (lower)
  SAFE shares:    $250K / $0.625 = 400,000 shares

SAFE #2 conversion (MFN → matches best terms = $0.625):
  SAFE shares:    $100K / $0.625 = 160,000 shares

New investor shares: $2M / $0.8421 = 2,375,012 shares

Post-close fully diluted: 9,500,000 + 400,000 + 160,000 + 2,375,012 = 12,435,012

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3. Option Pool Modeling

Pre-money pool shuffle (standard VC ask):

New pool is carved out pre-close, diluting founders not investors.

Target post-close option pool: 15%
Post-money FD shares (target): X
New pool = 0.15 × X

Solve: X = existing_shares + new_pool + investor_shares
       X = existing_shares + 0.15X + (investment / PPS)
       PPS = pre_money / (existing_shares + 0.15X)

Use iteration or algebra to solve. Common shortcut: model in a spreadsheet with goal-seek on ownership %.

Prompt template:

"I have 8M fully diluted shares pre-round. VC wants 20% post-money ownership for $3M. They also want a 15% option pool post-close, pre-money shuffle. What's the pre-money valuation implied, PPS, and final ownership table?"

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4. Waterfall Analysis (Exit Scenarios)

Model liquidation preference payout order at various exit values.

Standard waterfall order:

1. Debt repayment (if any)
2. Preferred liquidation preferences (1x non-participating is most common)
3. Common stock (pro-rata with preferred if participating, or preferred converts)
4. Option/warrant holders (exercise if in-the-money)

Example — 1x non-participating preferred:

Exit value: $15,000,000
Preferred investment: $2,000,000 (Series Seed, 1x non-participating)
Common shares: 10M | Preferred shares: 2.4M | FD: 12.4M

Option A (preferred takes preference):
  Preferred gets: $2,000,000 (1x)
  Remaining for common: $13,000,000
  Common per share: $13M / 10M = $1.30

Option B (preferred converts to common):
  All shares pro-rata: $15M / 12.4M = $1.21/share
  Preferred gets: 2.4M × $1.21 = $2,903,226

Preferred chooses: Option A ($2M) vs Option B ($2.9M) → converts to common

Build exit scenarios at: $5M, $10M, $20M, $50M, $100M — show each stakeholder's payout.

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5. 409A Valuation Prep

Gather inputs for a 409A (required before each option grant):

Required inputs:

• Current cap table (fully diluted, all classes)
• Most recent priced round (date, PPS, investors)
• Any SAFEs or convertible notes outstanding
• Company financials: revenue, ARR, burn rate, cash runway
• Comparable company multiples (revenue multiple, EBITDA multiple)
• Any material events since last 409A (new contracts, pivots, key hires)

Common 409A methods:

Method	Best For	Common Weight
Market Approach (OPM)	VC-backed, priced rounds	60–80%
Income Approach (DCF)	Revenue-generating	10–30%
Asset Approach	Pre-revenue / distress	0–20%

Output to provide to 409A firm:

• Fully diluted cap table (CSV)
• Most recent investor presentation / pitch deck
• 3 years of financials (actuals + projections)
• List of comparable public companies or recent M&A transactions

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6. Token Allocation Table (Hybrid Structures)

For companies with both equity and token components:

Token Allocation (Total Supply: 1,000,000,000)
-----------------------------------------------
Team & Founders:   20% = 200M tokens | 4yr vest, 1yr cliff
Investors:         15% = 150M tokens | 2yr vest, 6mo cliff
Ecosystem/DAO:     30% = 300M tokens | 5yr linear release
Public Sale:       10% = 100M tokens | Unlocked at TGE
Treasury:          15% = 150M tokens | DAO governed
Advisors:           5% =  50M tokens | 2yr vest, 6mo cliff
Liquidity/Market:   5% =  50M tokens | Unlocked at TGE

Equity ↔ Token relationship:
- Token grants to equity holders: [document separately]
- Anti-dilution protection: [specify if tokens trigger]
- Side letter required for investor token rights

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7. CSV/Sheets Export Format

Standard investor-ready cap table columns:

Stakeholder,Type,Share Class,Shares Issued,Options,Warrants,SAFE (Unconverted),Fully Diluted Shares,Ownership %,Investment,Note
Alice Chen,Founder,Common,4000000,,,,,32.2%,,4yr vest 1yr cliff
Bob Smith,Founder,Common,3000000,,,,,24.2%,,4yr vest 1yr cliff
Option Pool,Employees,Options,,1500000,,,1500000,12.1%,,2024 Equity Plan
Sequoia Capital,Investor,Series Seed Pref,2375012,,,,,19.1%,"$2,000,000",1x non-part
SAFE Holder 1,Investor,Common (converted),400000,,,,,3.2%,"$250,000",Converted @ $0.625
SAFE Holder 2,Investor,Common (converted),160000,,,,,1.3%,"$100,000",MFN converted
TOTALS,,,9935012,1500000,,,12435012,100%,"$2,350,000",

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Common Errors & Watch-Outs

Issue	Symptom	Fix
Double-counting SAFEs	FD shares too high	Only count SAFEs post-conversion
Pre/post money confusion	Wrong PPS	Confirm: pre-money = before investment, post-money = after
Option pool shuffle missed	Founders less diluted than expected	Confirm pool created pre-close
Participating preferred math	Payout too high	Check if preferred also gets pro-rata after preference
Wrong discount application	SAFE converts at wrong price	Discount on PPS, cap on pre-SAFE FD shares

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Quick Reference — Useful Formulas

Post-money valuation     = Pre-money + New Investment
Price Per Share (PPS)    = Pre-money / Pre-money FD Shares
SAFE conversion shares   = SAFE Amount / min(Cap PPS, Discount PPS)
Discount PPS             = PPS × (1 - Discount Rate)
Cap PPS                  = Valuation Cap / Pre-SAFE FD Shares
Option pool shares       = Target % × Post-money FD Shares  [if post-money basis]
Dilution %               = New Shares / (Old FD + New Shares)
Ownership %              = Stakeholder Shares / Total FD Shares

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Escalation Triggers

Flag to attorney or CPA when:

• Preferred stock has complex liquidation preferences (2x, participating, caps)
• Anti-dilution provisions (broad-based vs narrow-based weighted average, full ratchet)
• Drag-along, tag-along, or ROFR rights affect modeling assumptions
• 83(b) election windows, ISO limits ($100K/yr rule), or QSBS eligibility
• Token rights embedded in equity instruments (side letters, token warrants)
• Company has international founders or investors (foreign private issuer rules)

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Example Prompts

Round modeling:

"We're raising a $5M Series A at a $20M pre-money. Current cap: 8M founder shares, 1.5M option pool, $500K SAFE at $8M cap 20% discount. VC wants 15% post-money option pool, pre-money shuffle. Show me the full post-close cap table."

Dilution check:

"How much will founders dilute if we raise $3M at $12M pre-money with a 20% post-close option pool?"

Exit waterfall:

"Model our exit waterfall at $10M, $25M, $50M. We have: 2x participating preferred ($2M invested), then common. Show who gets what at each exit."

SAFE conversion:

"We have three SAFEs: $200K at $4M cap, $100K at $6M cap 15% discount, $150K MFN. We're pricing a round at $10M pre-money with 9M pre-money FD shares. Calculate conversion prices and resulting shares for each SAFE."

409A prep:

"Prepare the inputs list for our 409A valuation. Last priced round: $2M seed at $8M pre-money, closed January 2025. Current ARR: $180K. Cash: 18 months runway. Provide the document checklist and financial data template."