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

---

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

---

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."

---

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):
2. New option pool shares = Target % × Post-Money Fully Diluted

3. Example: 15% post-close pool on 12M post-money FD shares = 1.8M options reserved

4. Calculate price per share:

5. Pre-Money FD shares (including new pool) = existing shares + new pool shares

6. PPS = Pre-Money Valuation / Pre-Money FD shares

7. Convert SAFEs:

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

9. SAFE shares = Investment / Conversion Price

10. Issue new investor shares:

11. New shares = Investment / PPS

12. 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

---

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?"

---

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.

---

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 — 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

---

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."