Cap Table Basics

Cap Table Basics

When to Use

Use this skill when:

• A user asks to build, audit, or interpret a capitalization table at any stage from incorporation through Series B
• A user wants to calculate ownership percentages before or after a financing round, including SAFE conversions, convertible note conversions, or priced equity rounds
• A user needs to model dilution scenarios: option pool increases, new investor tranches, follow-on pro-rata participation, or secondary sales
• A user asks how employee stock options affect ownership, what the difference is between issued shares and fully diluted shares, or how an option pool shuffle works
• A user wants to understand share classes (common vs. preferred), understand what "fully diluted" means, or trace how their ownership has changed across multiple financing events
• A user is preparing for a funding conversation and wants to understand what their ownership will look like after the round closes
• A user received a term sheet and wants to understand the economic implications before engaging counsel
• A user is onboarding employees and needs to explain what an equity grant means in context of total ownership

Do NOT use this skill when:

• The user needs legal advice on shareholder agreements, stock purchase agreements, 409A valuations, or securities law compliance -- direct them to a startup attorney and a licensed accountant
• The user wants public company stock analysis, trading decisions, or portfolio management (use an investment analysis skill)
• The user needs a full three-statement financial model or DCF valuation (use financial-model-structure)
• The user is asking about the intrinsic valuation methodology for the company itself -- cap tables show ownership structure, not enterprise value
• The user needs modeling of complex liquidation preference waterfalls, participating preferred economics, or anti-dilution ratchets in detail -- these require legal review and dedicated cap table software like Carta, Pulley, or Capshare
• The user is asking about public company equity compensation (RSUs, ESPPs, incentive stock options at a public company) -- these have different tax and regulatory frameworks

Process

Step 1: Gather the Full Equity Structure

Before building anything, collect complete information. Incomplete inputs produce misleading cap tables.

• Company stage: Pre-incorporation, incorporated (pre-seed), seed, Series A, or later. Stage determines which instruments are likely outstanding and which complexities to expect.
• Authorized share count: The total shares the corporation's charter permits it to issue. A standard Delaware C-Corp startup typically authorizes 10,000,000 shares at incorporation. This is the ceiling, not the current count.
• Founders and their allocations: Full names (or anonymized labels), share counts, share class (almost always Common Stock for founders), grant date, vesting schedule, and cliff status. Note whether any founder shares are subject to repurchase (reverse vesting).
• Existing investors: For each investor, collect the investment amount, instrument type (priced preferred, SAFE, convertible note), key terms (valuation cap, discount rate, interest rate, maturity date), and the round in which they invested.
• Option pool: Total authorized pool size, options granted (broken down by grantee if available), options exercised, and options cancelled and returned to the pool. Whether the pool is pre-money or post-money in any pending round.
• Convertible instruments outstanding: For each SAFE or convertible note, the principal amount, any accrued interest (for notes), valuation cap, discount rate, MFN clause, and whether it is a pre-money or post-money SAFE (Y Combinator's post-money SAFE became standard after 2018 -- this distinction is critical).
• Any secondary transactions: Shares that have been transferred between parties, repurchased by the company, or acquired in secondary sales affect outstanding counts.

Step 2: Establish the Authorized and Outstanding Share Structure

Distinguish three critical counts that users frequently confuse:

• Authorized shares: Set in the certificate of incorporation. Changing this requires a stockholder vote and legal filings. It is the upper bound on issuance.
• Issued and outstanding shares: Shares that have actually been issued to someone. This is the denominator for basic (non-diluted) ownership percentages.
• Fully diluted shares: Issued and outstanding shares PLUS all options granted (vested and unvested) PLUS the ungranted option pool PLUS shares issuable upon conversion of all convertible instruments (SAFEs, notes, warrants). This is the standard denominator for startup cap table analysis and what investors mean when they say "ownership percentage."
• Authorized but unissued (non-pool): Authorized shares minus issued shares minus option pool. This is headroom for future rounds without a stockholder vote to increase authorization. At incorporation with 10M authorized and 9M issued plus a 1M pool, headroom is zero -- a Series A would require a charter amendment.
• Show all four numbers at the top of every cap table. Users often only know one of them.

Step 3: Build the Pre-Money Cap Table

Construct the current state before any new transaction:

• List every holder in rows: founders first (typically), then investors by round seniority, then advisors, then the option pool (split into granted and ungranted).
• For each row: holder name, share class, share count, percentage of issued-and-outstanding, and percentage of fully diluted. Show both columns -- investors care about fully diluted; founders sometimes focus on issued-and-outstanding and are surprised when investors use the other number.
• For option grants, note vesting status: "2,400 shares granted, 600 vested (25%), 1,800 unvested on 4-year/1-year cliff schedule." For cap table totals, include all granted options regardless of vesting status.
• Validate: All shares sum to the total authorized or explain any gap. Fully diluted percentage must sum to exactly 100.00%.
• Flag any red flags: option pool below 10% (likely needs top-up before next round), authorized headroom near zero, convertible instruments that will substantially change the table upon conversion.

Step 4: Convert All Outstanding Convertible Instruments

This is the most mechanically complex step and the most common source of error:

For a pre-money SAFE (the original Y Combinator SAFE, pre-2018):

• The SAFE converts immediately before the priced round closes
• Shares issued = SAFE investment amount / conversion price
• Conversion price = the LOWER of: (a) valuation cap / pre-money fully diluted shares, or (b) price per share in the new round × (1 - discount rate)
• The shares issued by SAFE conversion become part of the pre-money fully diluted count, which raises the denominator and slightly reduces the new investor's price per share
• Example: $500K SAFE with $4M cap, 20% discount, on a company doing a $6M pre-money round with 10M pre-money FD shares. Cap price = $4M / 10M = $0.40. New round price = $6M / 10M = $0.60; discounted = $0.60 × 0.80 = $0.48. Cap price ($0.40) is lower, so the SAFE converts at $0.40. Shares = $500K / $0.40 = 1,250,000.

For a post-money SAFE (Y Combinator standard post-2018):

• The SAFE holder's ownership percentage is locked at the time of investment: SAFE amount / valuation cap
• The post-money SAFE does NOT dilute from the new investor's perspective -- it dilutes only the pre-SAFE shareholders
• Shares issued at conversion = ownership percentage × fully diluted shares after all SAFEs convert (circular calculation; typically solved iteratively or with the YC SAFE cap table model)
• The post-money SAFE is economically cleaner for SAFE holders but can surprise founders when multiple SAFEs stack up

For convertible notes:

• Accrue interest: maturity principal × (1 + annual interest rate) ^ (years outstanding), or simple interest: principal × annual rate × (days / 365)
• Total conversion amount = principal + accrued interest
• Conversion shares = total conversion amount / conversion price
• Conversion price uses the same cap/discount comparison as pre-money SAFEs
• Show the accrued interest calculation explicitly: a $200K note at 6% simple interest outstanding for 18 months accrues $18,000 ($200K × 6% × 1.5 years), converting $218,000 total

Sequencing matters: Convert all instruments before computing the new investor's price per share if they are pre-money instruments. Post-money instruments do not affect the new investor's price per share.

Step 5: Model the New Funding Round

If the user is contemplating or modeling a round, execute these calculations precisely:

• Establish the pre-money capitalization: This is the fully diluted share count AFTER all converting instruments have been converted, and AFTER the option pool has been set to its required post-round level (if the pool is being created or topped up pre-money, which is standard).
• Option pool shuffle (critical): If the term sheet requires a 15% post-round unallocated option pool and the current pool is only 8% post-round, the pool must be expanded pre-money. This means the pool expansion dilutes only the existing shareholders, not the new investor. Walk through this explicitly:
  • Target: 15% of post-round fully diluted shares must be unallocated pool
  • This is a circular calculation: solve for X (new pool shares) where X / (current FD shares + X + new investor shares) = 15%
  • Alternatively, approximate: if post-round will be ~12.5M shares at 15% pool, pool must be 1,875,000 shares; if current pool is 800,000 unallocated, need to add ~1,075,000 shares pre-money
• Price per share: Pre-money valuation / pre-money fully diluted shares (after pool expansion, after SAFE/note conversion)
• New shares issued: Investment amount / price per share
• Post-money valuation: Pre-money valuation + investment amount
• Investor ownership (%): Investment amount / post-money valuation (this is the shortcut; the long way is new shares / post-round total FD shares -- both give the same answer if the math is consistent)
• Validate: New investor's shares / post-round FD shares = investment / post-money valuation. If these differ, there is an error.

Step 6: Calculate Dilution for All Existing Holders

Dilution is one of the most emotionally significant outputs of the cap table:

• Absolute dilution: Pre-round ownership % minus post-round ownership %. Example: 45.0% to 36.0% = 9.0 percentage points of absolute dilution.
• Relative dilution: Absolute dilution / pre-round ownership %. Example: 9.0pp / 45.0% = 20.0% relative dilution. This is how much of their stake they "lost."
• Show both. Founders often fixate on one or the other; presenting both gives full context.
• Dilution sources: Identify what caused the dilution. In a standard round it comes from (a) new investor shares, (b) option pool expansion, and (c) SAFE/note conversions. Break out how much each source contributed if there are multiple.
• Pro-rata rights: If an existing investor has pro-rata rights and participates in the new round, they maintain their ownership percentage. Show their participation separately. Pro-rata is usually contractual from the prior round's investment documents; note that exercising it requires the investor to write another check.
• Anti-dilution: If preferred stockholders have broad-based weighted average anti-dilution protection and the new round prices below the previous round (a down round), their conversion ratio adjusts. Flag this scenario clearly and recommend legal counsel -- the math requires the full preferred stock terms.

Step 7: Build the Fully Diluted Cap Table and Dilution Waterfall

The final deliverable should show the complete picture and history:

• Final post-round cap table: All holders, all share classes, shares, percentage of issued-and-outstanding, and percentage of fully diluted. Separate preferred from common from options from the unallocated pool.
• Dilution waterfall: A table that shows ownership percentage at each capitalization event from founding through the current round. This is the single most useful educational output for founders. It shows how each event (option pool creation, seed round, Series A) has affected each founder's stake over time.
• Share class summary: Show a secondary table summarizing by share class -- total common, total preferred (by series), total options (granted/ungranted), total warrants, total fully diluted. This is the view that legal counsel and auditors use.
• Economic vs. voting vs. liquidation: Note that the basic cap table shows economic ownership on an as-converted basis. Voting rights may differ (super-voting common is common for founder shares at certain stages). Liquidation preference means preferred holders may receive more than their pro-rata share in a sale below a certain value. Flag these complexities and note they require separate modeling beyond the basic cap table.

Output Format

## Cap Table: [Company Name]
### As of: [Date] | Stage: [Pre-Seed / Seed / Series A / etc.]

---

### Share Authorization Summary
| Category | Shares |
|---|---|
| Authorized shares (charter) | [X] |
| Issued and outstanding | [X] |
| Option pool (granted) | [X] |
| Option pool (ungranted / available) | [X] |
| Reserved for convertible instruments | [X] |
| **Total fully diluted** | **[X]** |
| Authorized but unissued (non-pool headroom) | [X] |

---

### Current Cap Table (Fully Diluted)

| Holder | Share Class | Shares | % Issued & O/S | % Fully Diluted | Notes |
|---|---|---|---|---|---|
| Founder A | Common | [X] | [X]% | [X]% | 4-yr vest / 1-yr cliff; [X] shares vested |
| Founder B | Common | [X] | [X]% | [X]% | 4-yr vest / 1-yr cliff; [X] shares vested |
| Angel Investor (Seed) | Series Seed Preferred | [X] | [X]% | [X]% | $[X] @ $[X]/sh |
| SAFE Holder 1 | SAFE (pending conversion) | [X] est. | -- | [X]% | $[X] cap; converts at [next event] |
| Option Pool -- Granted | Common (options) | [X] | [X]% | [X]% | [X] vested / [X] unvested |
| Option Pool -- Available | Common (options) | [X] | -- | [X]% | Ungranted |
| **Total** | | **[X]** | **100.00%** | **100.00%** | |

---

### SAFE / Convertible Note Conversion Detail (if applicable)

| Instrument | Holder | Principal | Accrued Interest | Total Converting | Valuation Cap | Discount | Cap Price | Discounted Price | Conversion Price Used | Shares Issued |
|---|---|---|---|---|---|---|---|---|---|---|
| SAFE (pre-money) | [Name] | $[X] | N/A | $[X] | $[X]M | [X]% | $[X] | $[X] | $[X] (cap) | [X] |
| Conv. Note | [Name] | $[X] | $[X] | $[X] | $[X]M | [X]% | $[X] | $[X] | $[X] (discount) | [X] |

---

### Funding Round Model: [Round Name] ([Year])

#### Round Terms
| Term | Value | Notes |
|---|---|---|
| Pre-money valuation | $[X] | As negotiated |
| Option pool pre-money adjustment | +[X] shares | Pool expanded to [X]% post-round unallocated |
| Pre-money FD shares (post-pool, post-conversion) | [X] | Denominator for price per share |
| Price per share | $[X] | Pre-money valuation / pre-money FD shares |
| Investment amount | $[X] | |
| Post-money valuation | $[X] | Pre-money + investment |
| New shares issued | [X] | Investment / price per share |
| Investor ownership (% FD post-round) | [X]% | Investment / post-money valuation |

#### Post-Round Cap Table

| Holder | Shares | Pre-Round % (FD) | Post-Round % (FD) | Abs. Dilution | Rel. Dilution |
|---|---|---|---|---|---|
| Founder A | [X] | [X]% | [X]% | [X]pp | [X]% |
| Founder B | [X] | [X]% | [X]% | [X]pp | [X]% |
| [Prior Investor] | [X] | [X]% | [X]% | [X]pp | [X]% |
| SAFE Holder (converted) | [X] | [X]% | [X]% | [X]pp | [X]% |
| [New Investor] | [X] | 0.00% | [X]% | N/A | N/A |
| Option Pool | [X] | [X]% | [X]% | [X]pp | [X]% |
| **Total (FD)** | **[X]** | **100.00%** | **100.00%** | | |

---

### Dilution Waterfall

| Event | Founder A | Founder B | [Investor 1] | [Investor 2] | Option Pool | Notes |
|---|---|---|---|---|---|---|
| Incorporation | [X]% | [X]% | -- | -- | -- | [X]M shares authorized |
| + Option Pool | [X]% | [X]% | -- | -- | [X]% | [X] shares reserved |
| + SAFE / Seed Note | [X]% | [X]% | [X]% | -- | [X]% | $[X] converting instruments |
| + [Round Name] | [X]% | [X]% | [X]% | [X]% | [X]% | $[X] @ $[X]M pre |

---

### Key Observations
- [Flag any ownership concern: e.g., "Option pool will be below 10% post-round; Series A investors typically require 10-15% unallocated."]
- [Flag any dilution concern: e.g., "Founders will each hold below 20% post-Series A if a 20% Series A is raised on top of existing structure."]
- [Flag any instrument complexity: e.g., "Two pre-money SAFEs convert before the round; confirm with counsel whether conversion is at cap or discount."]

Rules

1. Never conflate issued-and-outstanding with fully diluted. These produce meaningfully different ownership percentages. Always specify which denominator you are using. Default to fully diluted unless the user specifies otherwise, and note the difference.

2. Always identify SAFE vintage (pre-2018 pre-money vs. post-2018 post-money) before calculating conversion. These are fundamentally different instruments. The post-money SAFE fixes the investor's ownership at the cap, which has very different dilution mechanics -- especially when multiple post-money SAFEs stack. Using the wrong model produces materially wrong numbers.

3. Never place the option pool expansion after the new investor's price calculation. The standard term sheet requires the option pool to be created or expanded pre-money. Founders who miss this pay for the pool expansion, not the investor. Making the pool post-money (which would distribute the dilution across all post-round holders) is highly unusual and must be explicitly negotiated.

4. Round share counts to whole numbers only; percentages to two decimal places. Fractional shares create legal and administrative problems. Round share counts down and accept a rounding residual in the authorized-but-unissued column. Never round percentages to fewer than two decimal places -- a 0.5% difference represents real money in a liquidation.

5. Always validate that post-round ownership percentages sum to exactly 100.00%. If they do not, there is a calculation error -- typically a double-counted instrument, an incorrect conversion share count, or a rounding error compounded across many rows. Identify and fix the error before presenting.

6. Flag the option pool sufficiency for the next stage, not just the current one. If the post-round pool is 8% and the next round will require 15%, the company will need to expand the pool again. Proactively note this. Series A investors standardly require a 10-15% unallocated pool in the post-round cap table. Series B investors often require 10%.

7. Show all conversion math step by step, not just results. Users often need to verify or explain these numbers to co-founders, attorneys, and future investors. A black-box result builds no understanding. Show: principal + interest, cap price calculation, discounted price calculation, which is lower, resulting share count.

8. Do not assume a valuation -- always surface the assumption. If the user has not provided a pre-money valuation and asks to model a round, present scenarios at two or three valuation levels (e.g., $4M, $6M, $8M pre-money) rather than choosing one. The choice of pre-money valuation is one of the most consequential decisions in the financing and it belongs to the user.

9. Distinguish economic ownership from voting control. A founder with 35% of fully diluted shares on a standard one-vote-per-share structure has minority voting rights. If founders have 10:1 super-voting common (common at Series A+ for founder-controlled companies), their economic stake and voting control diverge. Note this distinction without modeling it in detail -- super-voting structures require legal review.

10. Always note what the cap table does NOT capture. Liquidation preferences, participation rights, anti-dilution provisions, drag-along rights, and right of first refusal all affect the economic outcome in a liquidity event but are not reflected in a basic ownership percentage table. After delivering the cap table, include a brief note that these terms exist and direct the user to their investment documents and counsel for a full picture.

Edge Cases

Multiple SAFEs with Different Caps and Vintages (Pre- and Post-Money Mixed)

This is the most common and most confusing scenario at seed stage. Convert each SAFE individually:

• Sort SAFEs into pre-money (pre-2018 YC model or equivalent) and post-money (post-2018 YC model)
• Convert all pre-money SAFEs first. Their shares add to the pre-money FD share count, which affects the price per share for the new round.
• Post-money SAFEs have ownership percentages fixed at signing (SAFE amount / cap). They do not affect the price per share calculation for the new investor. Their share count is determined by the final post-round fully diluted share count (circular -- solve iteratively or use the YC post-money SAFE model spreadsheet).
• If a SAFE has both a cap and a discount, apply both and use whichever gives more shares to the SAFE holder (i.e., the lower conversion price). Show both calculations.
• If a SAFE has an MFN (Most Favored Nation) clause and a lower-capped SAFE was issued after it, the MFN SAFE may be entitled to adopt the lower cap. Flag this -- it requires legal review before finalizing the conversion.
• Example: Three SAFEs -- $300K at $4M cap pre-money, $500K at $5M cap pre-money with 20% discount, $200K post-money at $3M cap. Convert the first two as pre-money (add to pre-money FD shares). Convert the third post-money (fixed ownership = $200K / $3M = 6.67% of post-round FD).

Option Pool Shuffle -- Precise Mechanics

The "option pool shuffle" is one of the most founder-unfavorable and least-understood aspects of term sheets:

• A term sheet states a pre-money valuation AND a required post-round option pool size (e.g., "15% of post-financing fully diluted capitalization").
• If the current unallocated pool is smaller than required, the company must increase the pool before the round closes.
• Because this happens pre-money, the expanded pool dilutes only the existing holders (founders, previous investors), not the new investor.
• The practical effect: a $6M pre-money valuation on a 10M FD share base implies $0.60/share. But if the pool must be expanded from 1M to 1.5M shares pre-money, the effective pre-money FD base becomes 10.5M, so the investor's price per share is $6M / 10.5M = $0.571 -- founders gave up $0.029/share of value.
• The founder counter-tactic (legitimate and common): negotiate the pre-money valuation up to compensate for the pool expansion, or negotiate that only the incremental shares needed to fill grants in the next 12-18 months must be added pre-money.
• Show the before/after effect of the pool shuffle explicitly so founders understand what they are agreeing to.

Founder Departure Before Full Vesting

A departing founder creates a sensitive but calculable scenario:

• Unvested shares are typically subject to repurchase by the company at the original purchase price (often $0.0001 per share), effectively returning them to the authorized-but-unissued pool. Confirm this against the stock purchase agreement -- terms vary.
• Show the post-departure cap table with the unvested shares removed from the departing founder's row and added to "repurchased/cancelled" (then available for reissuance or cancellation).
• Recalculate all ownership percentages. The remaining founders are anti-diluted (their percentages go up) because the total FD share count decreases.
• Tax implications: the departing founder may have tax obligations on any shares already vested, particularly if an 83(b) election was filed. Flag this strongly and direct them to a tax professional.
• If the company is in a live funding conversation, the departure will require disclosure to the new investor and may require updating the corporate data room. Note this.

Down Round -- Modeling Anti-Dilution

A down round (new price per share below prior round's price) triggers anti-dilution provisions for prior preferred holders:

• Broad-based weighted average anti-dilution (most common): The conversion ratio of prior preferred stock adjusts using a formula that considers the total shares outstanding. The adjustment is less severe than full ratchet.
• Full ratchet anti-dilution (rare, very punitive for common): Prior preferred automatically adjusts to the new round's price, as if it had always been priced at the lower level. Can dramatically increase the shares available to preferred holders.
• For basic cap table work, flag that a down round is occurring, show the headline dilution numbers, and note that anti-dilution adjustments must be calculated from the exact preferred stock terms in the certificate of incorporation. Do not attempt to model the anti-dilution math without those terms.
• Down rounds also affect employee morale (options may be underwater) and require board and stockholder approval. Flag all of this.

Equal Co-Founder Split and Future Investor Pushback

A 50/50 founder split is mathematically straightforward but creates a strategic concern:

• Many Series A investors view 50/50 splits as a risk factor: unclear decision-making authority, potential for deadlock. Note this without recommending a specific split.
• Common patterns and their rationale: 60/40 (one founder is CEO or brought the original concept), 70/30 (significant experience or capital disparity), 50/50 with a tiebreaker mechanism (board structure or casting vote to CEO).
• If the user wants to change the split post-incorporation, the mechanism is either a stock repurchase and reissuance (has tax implications, requires legal work) or a negotiated transfer between founders (also has tax implications). Flag that changing a cap table retroactively is a legal transaction, not just a spreadsheet update.
• Model whatever split the user specifies, but note the tradeoffs.

Series A With Preferred Stock Complexity

By Series A, the cap table gains meaningful complexity:

• Series A Preferred Stock typically has: 1x non-participating liquidation preference (most common), broad-based weighted average anti-dilution, optional conversion to common at any time (1:1 initially, adjustable for anti-dilution), automatic conversion to common at IPO or by majority preferred vote.
• On the cap table, show Series A Preferred as a separate line item, noting the liquidation preference per share and total preference stack ($X million must be returned to Series A investors before common holders receive anything in a sale).
• A fully diluted as-converted cap table shows Series A Preferred as if converted to common -- this is the standard format. A liquidation analysis is a separate waterfall model.
• Series A will typically have a Board seat; note governance changes alongside ownership changes. These are not captured in the cap table but are equally important outcomes of the round.

Very Early Stage -- Incorporation Cap Table

The cleanest scenario, but common mistakes still occur:

• Standard Delaware C-Corp setup: 10,000,000 authorized shares, all Common Stock initially. No preferred stock until the first priced round (adding preferred requires a charter amendment).
• Founders typically purchase their shares at par value ($0.0001/share) immediately at incorporation, triggering an 83(b) election within 30 days of grant to lock in low ordinary income tax treatment. Flag the 83(b) deadline urgently if the user is recently incorporated.
• Do not authorize more shares than needed for founders + option pool + anticipated first round headroom. Unnecessary authorized shares add complexity without benefit.
• Typical clean setup: 8,000,000 founder shares (split however negotiated), 1,000,000 to 1,500,000 option pool (10-15%), leaving 500,000 to 1,000,000 authorized but unissued for advisors, early hires, and bridge instruments before the first priced round.
• Recommend 4-year vesting with 1-year cliff as the nearly universal standard for founders. Deviation (e.g., no cliff, 3-year total vest) is a yellow flag for later investors and should be a deliberate choice.

Example

Input: "We're two co-founders, split 60/40. We incorporated with 10 million authorized shares and set up a 10% option pool (1 million shares). We then raised $250K on a YC pre-money SAFE with a $4M valuation cap and no discount. Now we're raising a $2M seed round at an $8M pre-money valuation. The investors require a 15% unallocated option pool post-round. Walk me through the whole cap table."

Step 1: Pre-SAFE Cap Table at Incorporation

Authorized: 10,000,000 shares

Notes: Founders hold 9M shares total (90%). Option pool is 10% of 10M FD shares. Authorized headroom is zero -- any new issuance requires either using the option pool or a charter amendment.

Step 2: SAFE Conversion Calculation

The $250K SAFE is a pre-money SAFE with a $4M valuation cap and no discount.

Cap price: $4,000,000 / 10,000,000 = $0.40 per share

New round price (pre-pool expansion): $8,000,000 / 10,000,000 = $0.80 per share

Discounted price: N/A (no discount)

Conversion price used: $0.40 (cap price is lower -- SAFE holder gets more shares at the cap)

SAFE shares issued: $250,000 / $0.40 = 625,000 shares

These 625,000 shares are issued before the round closes and become part of the pre-money capitalization. The company must amend its charter to authorize additional shares to issue these (the 10M authorized cap was fully utilized). Note this legal step in practice -- assume for modeling purposes that authorization is increased to 12,000,000 or more before the round.

Step 3: Option Pool Expansion (Pre-Money)

The investors require 15% of post-round fully diluted shares to be unallocated option pool.

Post-SAFE, pre-pool-expansion FD shares: 10,000,000 + 625,000 = 10,625,000

The post-round FD share count will be: 10,625,000 + pool_expansion + new_investor_shares

Target: unallocated pool / post-round FD shares = 15%

Current unallocated pool: 1,000,000 shares (no options have been granted yet in this example)

Let P = total unallocated pool post-expansion, and let N = new investor shares.

Post-round FD = 10,625,000 + (P - 1,000,000) + N, and P = 15% of post-round FD.

Also: N = $2,000,000 / price per share, and price per share = $8,000,000 / (10,625,000 + (P - 1,000,000)).

This circular system is solved iteratively. A good approximation:

Approximate post-round FD (ignoring circularity as first pass):

• New investor will own 20% of post-round (= $2M / ($8M + $2M) = 20%)
• So pre-round FD / post-round FD = 80%, meaning post-round FD ≈ pre-round FD / 0.80
• Pre-round FD (post-pool) / 0.80 = post-round FD; pre-round FD (post-pool) = 10,625,000 + expansion
• Pool must be 15% of post-round FD: we solve for the expansion that makes this work

Iterative solution:

After one iteration (detailed calculation omitted for brevity; the closed-form solution):

• Required post-round unallocated pool = approximately 1,897,059 shares (15% of ~12,647,059 total post-round FD)
• Pool expansion needed = 1,897,059 - 1,000,000 = 897,059 shares (round to 897,000 shares for whole numbers)
• Actual unallocated pool post-expansion = 1,897,000 shares

Pre-money FD after pool expansion: 10,625,000 + 897,000 = 11,522,000 shares

Step 4: New Investor Pricing

Note on pool %: The iterative approximation yields ~13.2% rather than exactly 15% due to rounding. In practice, exact pool sizes are negotiated and set in the option plan, and the final number is often close but not precisely on the target. Increase the pool by a further ~250,000 shares (via a second iteration) to hit closer to 15%. For this example we will proceed with the first iteration result.

Step 5: Post-Round Cap Table

*Rounding residual of 0.01% due to whole-number share rounding. Acceptable.

Dilution Waterfall

Key Observations

1. Founder dilution is significant: Founder A goes from 54% at incorporation to 37.49% post-seed -- a 30.6% relative dilution. Founder B goes from 36% to 25%. This is typical for a seed round with a converting SAFE and pool expansion, but founders should model Series A before committing to this structure to understand their likely ownership at A (often 15-25% each depending on round size).

2. Option pool over-expansion may be unnecessary: The investors asked for 15% unallocated post-round. The first-iteration result is ~13.2%. Adding another ~250K shares would bring it closer to 15% but would further dilute founders by roughly 1.7 percentage points combined. Negotiate with investors on whether 13-14% unallocated is acceptable given the company's near-term hiring plan.

3. SAFE conversion at cap: The SAFE converted at $0.40 vs. a new round price of $0.69 -- the SAFE holder received a 42% discount to the new investor's price, as intended. This is a meaningful reward for early risk.

4. Charter amendment required: The company was authorized for 10M shares at incorporation; it now has approximately 14.4M FD shares outstanding. The certificate of incorporation must be amended (typically to 20-25M authorized) before or at the close of this round. Flag for the company's attorney.

5. Series A planning: Post-seed, the unallocated option pool is ~13%. Series A investors will likely require 10-15% unallocated post-Series A. If the pool needs to be expanded again pre-Series A money (standard), founders should anticipate additional dilution of 3-7 percentage points depending on the required pool size and their current granted vs. ungranted split.