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Cap Table Manager

by @samledger67-dotcom

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

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πŸ“– About This Skill


name: cap-table-manager version: 1.0.0 description: > Equity cap table management for startups and growth-stage companies. Models SAFEs, convertible notes, priced equity rounds, token allocations, dilution scenarios, and 409A valuation prep. Outputs investor-ready cap tables, waterfall analyses, and scenario models. tags: - finance - equity - startup - cap-table - saas - legal author: PrecisionLedger / Sam Ledger

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 β€” 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

  • Core Concepts

    Share Classes

  • Common Stock β€” founders and employees; lowest liquidation preference
  • Preferred Stock β€” investors; liquidation preference + conversion rights
  • Options/Warrants β€” unissued; part of fully diluted but not issued shares
  • SAFEs β€” Simple Agreement for Future Equity; convert at next priced round
  • Convertible Notes β€” 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 βˆ’ New Investment | | Price Per Share | Pre-Money Valuation / Pre-Money Fully Diluted Shares | | Dilution % | 1 βˆ’ (Old Shares / New Fully Diluted Shares) | | Liquidation Preference | Investment Amount Γ— Preference Multiple |


    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   | β€”      | β€”   | $250K @ $5M cap, 20% discount
    Angel 2     | SAFE   | β€”      | β€”   | $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."


    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 % Γ— 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 Γ— (1 βˆ’ 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 β€” 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 Γ— 0.80 = $0.6737 Conversion at: $0.625 (lower) SAFE shares: $250K / $0.625 = 400,000 shares

    SAFE #2 conversion (MFN β†’ 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


    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 Γ— 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?"


    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 β€” 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 Γ— $1.21 = $2,903,226

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

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


    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

  • 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

  • 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",
    


    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 |


    Quick Reference β€” 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 Γ— (1 - Discount Rate)
    Cap PPS                  = Valuation Cap / Pre-SAFE FD Shares
    Option pool shares       = Target % Γ— Post-money FD Shares  [if post-money basis]
    Dilution %               = New Shares / (Old FD + New Shares)
    Ownership %              = Stakeholder Shares / Total FD Shares
    


    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)

  • 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."

    ⚑ When to Use

    TriggerAction
    - 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)