Startup finance
The money side of going from idea to MVP to a first priced round, for a technical first-time founder with a US Delaware C-corp: founder stock and the 83(b) election, unit economics and SaaS metrics, burn and runway, SAFEs, priced rounds, cap tables, term sheets, employee equity, startup tax breaks and the admin you can't skip. Accounting rules are in accounting, the statements in financial statements, and DCF and VC-method theory in valuation. The product pipeline is the idea-to-MVP playbook; YC's fundraising advice is summarized on Y Combinator.
Entity, founder stock and vesting
Default for a venture-backed startup: a Delaware C-corporation. An LLC is fine for a lifestyle or services business, but it is the wrong vehicle if you plan to raise from VCs.
| Question | Delaware C-corp | LLC |
|---|---|---|
| What VCs expect | the standard; NVCA and YC documents assume it | many funds can't or won't invest (pass-through income creates tax problems for their tax-exempt and foreign LPs) |
| Preferred stock, option plans | standard, well-understood | possible via units and profits interests, but bespoke and costly |
| Taxation | entity pays corporate tax; shareholders taxed on dividends and sale | pass-through: losses and profits flow to members' returns |
| QSBS (§1202) | eligible if the tests are met | not eligible; converting to a C-corp later starts QSBS from the conversion date |
| Early losses | trapped in the company as NOLs | usable by members (the main LLC advantage) |
| When to pick | you intend to raise venture capital or grant options to many employees | bootstrapped, profitable-from-day-one, or real-estate/services |
Incorporate with a startup lawyer or a standard incorporation service that produces: certificate of incorporation, bylaws, board consents, founder stock purchase agreements with vesting, IP assignment (every founder assigns code and inventions to the company), and an equity incentive plan.
Founder stock and vesting
| Term | Convention | Why |
|---|---|---|
| Founder shares | bought for cash at a tiny price (par, e.g. $0.00001–$0.0001 per share) right after incorporation | price ≈ fair value when the company is worth nothing, so no tax at grant |
| Authorized shares | often ~10M authorized, most issued to founders | leaves room for a pool; watch the Delaware franchise tax (below) |
| Vesting | 4 years with a 1-year cliff: 25% at 12 months, then monthly | a co-founder who leaves in month 5 takes nothing; investors expect it and will impose it if you don't |
| Mechanism | shares issued up front, company has a repurchase right at cost on unvested shares that lapses as they vest | technically "restricted stock", which is why 83(b) matters |
| Credit for time served | some founders start with 6–12 months already vested | reasonable if real work pre-dates incorporation |
| Single-trigger acceleration | vesting speeds up on a sale alone | investors dislike it: acquirers want the team incentivised after closing |
| Double-trigger acceleration | vesting speeds up only on sale and termination without cause (or resignation for good reason) within a window, commonly 12 months | the common founder/executive compromise; often 100% for founders, less for employees |
The 83(b) election
Under IRC §83 (opens in a new tab), property subject to a "substantial risk of forfeiture" (unvested stock) is taxed as ordinary income when it vests, on (value at vesting − price paid). Section 83(b) lets you elect to be taxed at transfer instead, on (value at transfer − price paid), which for founder stock is about zero. After that, all growth is capital gain, the capital-gains holding period starts, and so does the QSBS clock.
- Deadline: 30 days after the stock is transferred (the purchase/grant date, not the vesting date). No extensions, no late elections. Miss it and the usual workarounds (e.g. canceling and reissuing stock at today's value) are costly and imperfect.
- Filing online: since July 2025 the IRS accepts Form 15620 (opens in a new tab) online through an IRS account (ID.me sign-in); you get a timestamped confirmation to keep. Only Form 15620 can be filed online, and law-firm alerts (e.g. Sidley, August 2025 (opens in a new tab)) reported quirks such as a 999,999-share cap per submission and two-decimal prices, which can bite on founder stock at $0.0001; check the current form, or mail it.
- Paper: mail to the IRS address for your return, by certified mail with return receipt; keep the proof. File one way only. Give a copy to the company. Since 2016 you no longer attach a copy to your tax return.
- The election is irrevocable. If you later forfeit unvested shares, you don't get the tax back (a tiny amount for founder stock, which is the point).
- It also applies to early-exercised options (see employee equity).
Worked example: 83(b) vs no 83(b)
A founder buys 4,000,000 shares at $0.0001 ($400), 4-year vesting with a 1-year cliff. Simplify vesting to four annual tranches of 1,000,000 shares, and suppose common stock's fair value at each vest is $0.40, $1.00, $2.00 and $3.00 as the company raises.
| Vest | Shares | FMV/share | Ordinary income without 83(b) | Tax at an illustrative 37% federal rate |
|---|---|---|---|---|
| Year 1 | 1,000,000 | $0.40 | $399,900 | $147,963 |
| Year 2 | 1,000,000 | $1.00 | $999,900 | $369,963 |
| Year 3 | 1,000,000 | $2.00 | $1,999,900 | $739,963 |
| Year 4 | 1,000,000 | $3.00 | $2,999,900 | $1,109,963 |
| Total | 4,000,000 | $6,399,600 | $2,367,852 |
That tax is due in cash on illiquid stock you can't sell. With a timely 83(b): income at purchase = $400 − $400 = $0, no tax now, and gain is taxed only on sale, as long-term capital gain (and possibly excluded under QSBS). State tax and payroll withholding questions come on top; personal tax basics are on retirement and taxes.
Unit economics
Unit economics ask whether one customer is worth more than it costs to get and serve. Pre-product-market fit the numbers are noisy; track them anyway so you notice when they stabilize.
| Metric | Formula | Notes |
|---|---|---|
| CAC (customer acquisition cost) | sales & marketing spend in period ÷ new customers in period | use fully loaded S&M (salaries, tools, ads); "blended" includes organic customers and flatters; "paid" CAC counts only paid channels |
| ARPA | revenue ÷ accounts (monthly) | per account, not per user, for B2B |
| Gross margin | (revenue − COGS) ÷ revenue | COGS = hosting, third-party APIs/model inference, payment fees, support, onboarding |
| Contribution margin | (revenue − all variable costs) ÷ revenue | also subtracts variable costs below gross profit (e.g. per-order fulfillment, sales commissions) |
| Churn | customers lost ÷ customers at start (per month) | average lifetime ≈ months |
| LTV (simple) | margin, not revenue: revenue LTV overstates by | |
| LTV (discounted) | = monthly discount rate; payments start next month | |
| LTV:CAC | LTV ÷ CAC | heuristic target ≥ 3 |
| CAC payback | months | heuristic target ≤ 12 months; 5–7 is strong |
The ≥ 3 and ≤ 12-month thresholds come from David Skok's SaaS Metrics 2.0 (opens in a new tab) (For Entrepreneurs): he suggests LTV:CAC above 3 (the best businesses reach 7–8) and recovering CAC within about 12 months (5–7 is better). They are rules of thumb from venture-backed SaaS, not laws; a business with 90-day payback and LTV:CAC of 2 can be excellent, and one with LTV:CAC of 5 can die if payback is 30 months and cash runs out first.
Why simple LTV overstates. It assumes churn is constant forever (early cohorts churn fast, so a 3% monthly number measured in month 2 is usually wrong in month 20), ignores the time value of money, often uses revenue instead of margin, and extrapolates lifetimes far longer than the company has existed. Cap the horizon (3–5 years) and use cohort data once you have it.
Worked example. ARPA $500/month, gross margin 80%, monthly churn 3%, CAC $6,000, discount rate 1%/month.
| Measure | Calculation | Result |
|---|---|---|
| Monthly gross profit per account | $500 × 0.80 | $400 |
| Revenue "LTV" (wrong) | $500 ÷ 0.03 | $16,667 (LTV:CAC 2.8) |
| Simple LTV | $400 ÷ 0.03 | $13,333 (LTV:CAC 2.2) |
| Discounted LTV | $400 ÷ (0.03 + 0.01) | $10,000 (LTV:CAC 1.7) |
| Discounted, 36-month cap | $400 × (1 − ) ÷ 0.04, with | $7,665 (LTV:CAC 1.3) |
| CAC payback | $6,000 ÷ $400 | 15 months |
Verdict: below every heuristic. Levers, in rough order of power: churn (fix the product), price (see pricing), CAC (channel mix), gross margin (infrastructure costs).
Gross margin norms (commonly quoted rough ranges, vary widely):
| Model | Typical gross margin | Watch |
|---|---|---|
| Software / SaaS | ~70–85% | AI products with heavy inference costs can sit well below this |
| Marketplace (on net revenue / take rate) | ~60–80% | report GMV and net revenue separately; payment and trust-and-safety costs sit in COGS |
| E-commerce / D2C | ~30–50% | shipping and returns can erase it |
| Hardware | ~20–50% | inventory ties up cash before revenue |
| Tech-enabled services | ~20–50% | people costs scale with revenue |
SaaS metrics
| Metric | Definition / formula |
|---|---|
| MRR | monthly recurring revenue from subscriptions (normalize annual contracts to /12; exclude one-off fees) |
| ARR | MRR × 12 (or annual contract value of the recurring base) |
| New MRR | from customers who weren't paying last period |
| Expansion MRR | upgrades, seats, usage growth from existing customers |
| Contraction MRR | downgrades from customers who stay |
| Churned MRR | from customers who cancel |
| Net new MRR | new + expansion − contraction − churned |
| Logo churn | customers lost ÷ customers at start |
| Revenue churn | (contraction + churned MRR) ÷ starting MRR |
| GRR (gross revenue retention) | , capped at 100% |
| NRR (net revenue retention) | , can exceed 100% |
| Rule of 40 | revenue growth % + profit margin % ≥ 40 |
| Burn multiple | (same period) |
| Magic number | (one common variant) |
Measure NRR and GRR on a cohort: take the customers paying 12 months ago and compare their revenue now; new customers are excluded. Logo and revenue churn diverge: losing many small accounts gives high logo churn but modest revenue churn, and vice versa. Report both. Skok notes that 2% monthly revenue churn already loses about 22% of revenue a year (paraphrased, SaaS Metrics 2.0).
| Metric | Origin | Rough bands |
|---|---|---|
| Rule of 40 | popularised by Brad Feld, Feb 2015 (opens in a new tab), who heard it from a late-stage investor | meant for SaaS companies at scale (Feld: think $50M+ revenue); meaningless at seed |
| Burn multiple | David Sacks, The Burn Multiple (opens in a new tab) (Craft Ventures, 23 April 2020) | as widely reproduced from his table: <1 amazing, 1–1.5 great, 1.5–2 good, 2–3 suspect, >3 bad; he expects ~3 at seed falling with stage |
| Magic number | coined by Rory O'Driscoll of Scale Venture Partners in the 2000s while looking at Omniture (Scale, 2020 (opens in a new tab)) | Scale uses ~0.7 as a healthy baseline; widely repeated folklore: below ~0.75 fix go-to-market before spending more, above it spend more |
Worked example (one year, a 60%-growth startup).
| Item | Value |
|---|---|
| ARR from customers active 12 months ago | $1,200,000 |
| Their expansion / contraction / churned ARR over the year | +$240,000 / −$60,000 / −$120,000 |
| Customers at start / lost | 80 / 10 |
| NRR | (1,200 + 240 − 60 − 120) ÷ 1,200 = 105% |
| GRR | (1,200 − 60 − 120) ÷ 1,200 = 85% |
| Logo churn vs revenue churn | 10 ÷ 80 = 12.5% vs 180 ÷ 1,200 = 15% |
| Revenue growth, free-cash-flow margin | 60%, −35% → Rule of 40 score 25 |
| Net burn $3.0M, net new ARR $1.5M | burn multiple 2.0 |
| Quarterly revenue $500k → $600k, prior-quarter S&M $450k | magic number = 100k × 4 ÷ 450k = 0.89 |
Monthly roll-forward for the same kind of company: start MRR $100,000 + new $15,000 + expansion $6,000 − contraction $2,000 − churn $4,000 = end MRR $115,000 (net new MRR $15,000).
Burn, runway and default alive
| Term | Definition |
|---|---|
| Gross burn | total cash out per month (payroll, rent, tools, COGS) |
| Net burn | cash out − cash in per month (gross burn − collected revenue) |
| Runway | |
| Default alive | on current expenses and the recent revenue growth rate, you reach profitability before cash runs out |
| Default dead | you don't; you need new money or cuts |
| Ramen profitable | revenue covers the founders' (frugal) living costs; buys time and negotiating power |
Paul Graham's Default Alive or Default Dead? (opens in a new tab) (2015) and Ramen Profitable (opens in a new tab) (2009) are summarized on Y Combinator. His warning: founders assume investors will appear; investor interest is a function of growth and is fickle, so plan as if they won't.
Use net burn from the bank statement (cash basis) for runway, and use a trailing 3-month average, not the best month. Runway shrinks faster than the formula says when burn is rising, which it usually is after a raise.
Worked example. Cash $1.8M, gross burn $180k/month (flat), revenue $30k/month. Net burn $150k → runway 12 months on today's numbers. Default alive or dead depends on growth (month-by-month simulation, expenses flat):
| Monthly revenue growth | Outcome |
|---|---|
| 5% | default dead: cash runs out in month 13 |
| 8% | default dead: cash runs out in month 15 |
| 10% | default dead, just: cash runs out in month 16 |
| 12% | default alive: revenue passes $180k in month 16 ($184k) with ~$200k left |
The gap between 10% and 12% monthly growth is the difference between needing investors and not. That is why PG says to ask the question early: in month 3 a modest cut in burn can flip the answer; in month 10 it usually can't.
Forecasting and scenario planning
Two models, two jobs: a 13-week cash forecast (weekly, operational: can we make payroll?) and a 24-month operating model (monthly, strategic: how much to raise and what it buys). Keep both in a spreadsheet you understand line by line; a model you can't explain in a board meeting is a liability.
13-week cash forecast
Direct method: actual cash receipts and payments by week, not accrual revenue and expenses. Update weekly; compare last week's forecast with actuals (variance) to learn where you're wrong. Layout in templates.
| Row group | Contents | Tips |
|---|---|---|
| Opening cash | bank balances, all accounts | reconcile to the bank every week |
| Receipts | collections by customer (dated by expected payment, not invoice), grants, financing | enterprise customers pay 30–60+ days after invoice; model that |
| Payroll | net pay, payroll taxes, benefits on actual pay dates | the biggest and least flexible line |
| Operating payments | rent, cloud, SaaS tools, contractors, insurance | annual prepayments create lumpy weeks |
| Other | taxes (incl. Delaware franchise tax by 1 March), capex, loan payments | |
| Closing cash | opening + receipts − payments | flag any week below your minimum cash buffer |
24-month operating model
Build it driver-first: a few assumptions flow through to cash. Change a driver, see the cash date move.
| Layer | Contents |
|---|---|
| 1. Drivers | leads or sign-ups, conversion rates, ARPA and price changes, churn, expansion, sales capacity (quota per rep, ramp months), collection terms |
| 2. Revenue | customer count and MRR roll-forward by month (new, expansion, contraction, churn); bookings vs revenue vs cash collected for annual prepaid contracts |
| 3. Headcount | hiring plan by role and start month at fully loaded cost (salary + payroll taxes + benefits + equipment, commonly 1.2–1.4× salary); usually most of a software startup's spend |
| 4. Opex and COGS | hosting and inference as % of revenue or per user; tools per head; rent; marketing tied to CAC and new-customer targets |
| 5. Cash | net burn, cumulative cash, runway, month cash hits the minimum buffer; financing on its own line so you see the plan with and without the raise |
Scenarios
| Scenario | Typical assumption changes | Use |
|---|---|---|
| Base | your honest plan | the budget |
| Downside | growth half of plan, raise slips 6 months, a big customer churns | what you cut, and when (write the trigger down: "if cash < 9 months by Q2, freeze hiring") |
| Upside | growth 1.5× plan | when to hire ahead; whether to raise early |
| No raise | no new money ever | the default-alive test; how to get there by cutting |
Pricing
Pricing is covered in more depth on launch and iterate; the finance view:
| Approach | How | Fit |
|---|---|---|
| Value-based | a fraction (often quoted as 10–20%) of the value the customer gets: hours saved, revenue gained, risk avoided | best for B2B; requires knowing the customer's economics |
| Cost-plus | unit cost × (1 + markup) | hardware, services; sets a floor, not a price; software's marginal cost is near zero so it underprices |
| Competitive | anchor to alternatives, including spreadsheets and doing nothing | crowded markets; risks a race to the bottom |
- Charge from the start. Payment is the strongest validation signal and funds the company.
- Price is the most powerful unit-economics lever: a price rise flows straight to gross margin, LTV and payback.
- Annual prepaid plans (often with a discount) pull cash forward and cut churn; they also create deferred revenue on accrual books.
Funding options
| Source | Rough size | What you give | Best for | Watch |
|---|---|---|---|---|
| Bootstrapping | savings | your time, personal risk | proving demand cheaply | personal runway; don't mix funds |
| Customer revenue | any | delivery obligations | everything: non-dilutive and validating | custom work that becomes a consultancy |
| Grants (SBIR/STTR) | Phase I tens to a few hundred $k; Phase II larger | reporting, IP and data-rights terms; US ownership rules | deep-tech, defense, health, climate R&D | slow cycles; programs lapsed Oct 2025–Apr 2026 (see below) |
| Friends & family | $10k–$250k | equity (usually a SAFE) | the very first months | only take money people can afford to lose; most should be accredited |
| Angels | $10k–$250k per check | SAFE or equity | pre-seed/seed; help and intros | many small checks = a messy cap table |
| Accelerators | e.g. YC $500k | equity, time | network, credibility, demo day | read the deal; see below |
| Pre-seed / seed VC | ~$0.5M–$5M (varies by market and year) | ~10–25% | building to product-market fit | sets expectations of venture-scale growth |
| Venture debt | often sized as a fraction of the last equity round | interest, fees, warrants, covenants | extending runway after an equity round | covenants and repayment when you're weakest |
| Revenue-based financing | a multiple of monthly recurring revenue | a % of revenue until a fixed cap is repaid | predictable-revenue businesses | effective cost can be high; needs revenue already |
| Crowdfunding (Reg CF) | up to $5M per 12 months | equity/SAFEs to many small investors via a registered portal | consumer brands with a community | disclosure costs; hundreds of shareholders |
YC's standard deal (ycombinator.com/deal (opens in a new tab), checked Sept 2026): $500,000 in two SAFEs: $125,000 on a post-money SAFE for 7% (an implied $1.79M post-money cap) plus $375,000 on an uncapped MFN SAFE that converts on the terms of the lowest-cap SAFE (or other most favorable terms) issued between roughly the start of the batch and the priced round. YC's own example: if the next SAFEs are at a $15M post-money cap, the $375k converts into 2.5%. YC also gets a pro rata right.
SBIR/STTR status: the programs' authority expired on 30 September 2025; the Small Business Innovation and Economic Security Act (S. 3971) was signed on 13 April 2026 and reauthorised them through 30 September 2031 (SBA (opens in a new tab)). Check sbir.gov (opens in a new tab) for current solicitations and any new per-company proposal limits.
Reg CF: SEC (opens in a new tab): up to $5 million in 12 months, only through an SEC-registered broker-dealer or funding portal, with limits on what non-accredited investors can put in.
SAFEs and convertible notes
A SAFE (simple agreement for future equity, YC, 2013) is a right to shares in a future priced round. It is not debt: no interest, no maturity. The post-money SAFE replaced the original (pre-money) SAFE as YC's standard in 2018 and is what almost everyone means by "a SAFE" today (YC documents (opens in a new tab)).
| Term | Meaning |
|---|---|
| Post-money valuation cap | the maximum valuation at which the SAFE converts, including all SAFE money but excluding the priced round's new money and its new pool top-up |
| Discount | converts at a discount to the priced round's price (e.g. 20% off = 80% "discount rate") |
| MFN | if you later issue SAFEs on better terms, the holder may amend its SAFE to match (one amendment, no cherry-picking) |
| Pro rata side letter | right to buy its pro rata share of the priced round in which the SAFE converts: conversion shares ÷ Company Capitalization |
| Forms YC posts (US) | cap only; discount only; uncapped MFN (the user guide also describes a cap-and-discount variant) |
| On a sale before conversion | greater of money back or the as-converted amount; ranks like non-participating preferred: behind debt, level with other SAFEs and preferred, ahead of common |
How conversion works (post-money SAFE)
Per the SAFE text, on the priced round the SAFE converts at the Safe Price = cap ÷ Company Capitalization, where Company Capitalization counts (as-converted) all outstanding shares, issued and promised options, the existing unissued pool, and all converting securities, but not the new money or the round's pool increase (except to cover promised options). The holder gets the greater number of shares under the Safe Price or the round's price.
The practical upshot: each capped post-money SAFE owns exactly amount ÷ cap of the company as it stands just before the priced round. Selling $500k at a $5M cap sells 10%, whatever else you raise on SAFEs.
Worked example. Founders hold 8,000,000 shares; the pool has 1,000,000 shares (400,000 granted, 600,000 unissued). Fully diluted: 9,000,000.
| SAFE | Amount | Post-money cap | Ownership bought |
|---|---|---|---|
| A (early angel) | $500,000 | $5,000,000 | 10% |
| B (seed fund) | $1,000,000 | $10,000,000 | 10% |
A seed round follows: $3M new money at $12M pre-money ($15M post), with the unissued pool topped up in the pre-money so it is 10% of the post-money fully diluted count.
| Step | Calculation | Result |
|---|---|---|
| 1. SAFE ownership | 500k/5M + 1M/10M | 20% |
| 2. Company Capitalization | 9,000,000 ÷ (1 − 0.20) | 11,250,000 |
| 3. Safe Prices | A: $5M ÷ 11.25M; B: $10M ÷ 11.25M | $0.4444; $0.8889 |
| 4. Conversion shares | A: $500k ÷ $0.4444; B: $1M ÷ $0.8889 | 1,125,000 each |
| 5. Pool increase | solve | 921,429 |
| 6. Seed price | $12M ÷ (11,250,000 + 921,429) | $0.9859 |
| 7. Seed shares | $3M ÷ $0.9859 | 3,042,904 |
| 8. Check | both Safe Prices are below $0.9859, so the caps apply (not the round price) | ✓ |
Founders go from 88.9% (pre-SAFE, fully diluted) to 71.1% after the SAFEs convert and 52.6% after the seed (full table in cap tables). Had they raised only SAFE A, A would still own 10% and founders 80.0% before the seed; SAFE B's 10% came entirely out of the founders' and option holders' share.
The pre-money SAFE (original 2013 form) set its cap on a pre-money basis and included the priced round's pool increase in the conversion denominator, so the ownership sold depended on every other SAFE and on a future pool negotiation. SAFE holders diluted each other and founders couldn't compute what they had sold. Avoid it for new rounds.
SAFE vs convertible note
| Feature | Post-money SAFE | Convertible note |
|---|---|---|
| Legal form | contract for future equity | debt that converts |
| Interest | none | accrues (YC quotes 2–8% as typical); converts into more shares |
| Maturity | none | yes (commonly 12–24 months); at maturity holders can demand repayment or renegotiate |
| Cap / discount | cap, discount, MFN | cap and/or discount, same idea |
| Priority on insolvency | behind all debt | ahead of equity (it is debt) |
| Cost and speed | one standard document, lowest cost | more negotiation |
| When still used | default at pre-seed/seed | bridges from existing investors; some non-US markets; investors who want creditor status |
Priced rounds and the option pool shuffle
A priced round sells a new series of preferred stock at a set price per share, with the full document set (NVCA model documents (opens in a new tab): certificate of incorporation, stock purchase agreement, investors' rights, voting, ROFR and co-sale agreements).
| Term | Formula |
|---|---|
| Post-money valuation | pre-money + new money |
| Investor ownership | new money ÷ post-money |
| Price per share | pre-money ÷ pre-money fully diluted shares (incl. converted SAFEs and any pool increase) |
| New shares | new money ÷ price per share |
The option pool shuffle. Investors usually require the pool to be enlarged so that the unissued pool is some % of the post-money fully diluted count, and they require it in the pre-money. That makes the founders (and other existing holders) pay for the whole pool, and it quietly lowers the effective valuation.
Worked example. Founders own 10,000,000 shares. Term sheet: $3M at $12M pre ($15M post), 15% post-money unissued pool included in the pre-money.
| Pool treatment | Price/share | Investor | Pool | Founders | Effective pre-money to founders |
|---|---|---|---|---|---|
| No pool | $1.200 | 20% | 0% | 80.0% | $12.0M |
| 15% pool created after the round (dilutes everyone) | $1.200 | 17% | 15% | 68.0% | $12.0M |
| 15% pool in the pre-money (standard ask) | $0.975 | 20% | 15% | 65.0% | $9.75M |
Effective pre-money = headline pre-money − value of the new pool = $12M − 15% × $15M = $9.75M. The counter: build a hiring plan showing the options you'll actually grant before the next round, and size the pool to that, not to a round number.
Typical dilution. Carta's State of Private Markets: 2025 in Review (Q4 2025) reports median dilution at both seed and Series A of roughly 19–20%, slightly lower than two years earlier; medians vary by sector and year. Brian Ralston's 2016 YC guide (paraphrased): 10% in a seed round is great, most give up to 20%, and try not to exceed 25%.
Cap tables and dilution
Fully diluted shares = issued common + preferred (as converted) + granted options/RSUs + unissued pool + shares issuable on SAFEs and notes. Investors price and quote ownership on a fully diluted basis; your percentage "on the cap table" as outstanding shares is higher and misleading.
Dilution per round multiplies: after rounds selling (including pool increases),
Worked cap table continuing the SAFE example: after the seed, 1,000,000 options are granted from the pool; then a Series A of $10M at $40M pre-money ($50M post), again topping the unissued pool up to 10% post-money in the pre-money. Series A price = $40M ÷ (15,214,333 + 1,577,558) = $2.3821; new shares 4,197,976.
Holder Founding Pre-SAFE +SAFEs* Post-seed Post-A
Founders 8,000,000 100.0% 8,000,000 88.9% 8,000,000 71.1% 8,000,000 52.6% 8,000,000 38.1%
Options granted – 400,000 4.4% 400,000 3.6% 400,000 2.6% 1,400,000 6.7%
Pool unissued – 600,000 6.7% 600,000 5.3% 1,521,429 10.0% 2,098,987 10.0%
SAFE A ($500k @ $5M) – – 1,125,000 10.0% 1,125,000 7.4% 1,125,000 5.4%
SAFE B ($1M @ $10M) – – 1,125,000 10.0% 1,125,000 7.4% 1,125,000 5.4%
Seed ($3M @ $12M pre) – – – 3,042,904 20.0% 3,042,904 14.5%
Series A ($10M @ $40M) – – – – 4,197,976 20.0%
Total fully diluted 8,000,000 100% 9,000,000 100% 11,250,000 100% 15,214,333 100% 20,989,867 100%
* SAFEs shown as if converted at the Company Capitalization, before the seed money.
Percentages rounded; each column sums to its total.
Seed pool increase 921,429; Series A pool increase 1,577,558.Read it like an investor: founders own 38% of a company valued at $50M post (about $19M on paper, as common behind $14.5M of preference). The two pool top-ups together (about 2.5M shares) cost the founders more than both SAFEs combined (2.25M).
Term sheet essentials
| Term | Founder-friendly / standard | Aggressive | Why it matters |
|---|---|---|---|
| Liquidation preference | 1× non-participating | participating, or >1× | decides who gets paid in modest exits |
| Anti-dilution | broad-based weighted average | full ratchet | cost to founders of a down round |
| Pro rata rights | major investors can buy their share of future rounds | super pro rata | crowds out new investors later |
| Board | seed: often 2 founders + 1 investor, or founders only; Series A: 2 common + 1 investor, or 2–1–1 with an independent | investor majority early | control of hiring/firing the CEO and of a sale |
| Protective provisions | preferred vote on new senior securities, charter changes, sale, dividends | vetoes on budgets and operations | blocking rights |
| Drag-along | holders must vote for a sale approved by board + majority of preferred (+ often common) | low thresholds, no floor on price | lets a majority force a sale |
| ROFR / co-sale | company (then investors) can buy shares founders sell; investors can sell alongside | limits founder secondary sales | |
| Information rights | annual audited/unaudited statements, quarterly financials, budget for major investors | monthly everything to all | reporting burden |
| Dividends | non-cumulative, only if declared | cumulative (compounding preference) | rare but expensive |
| Redemption | none | investor can force a buyback after N years | a disguised debt claim |
Liquidation preference waterfall
One preferred series: $10M invested for 20% (post-money $50M). Everyone else (founders, employees, other holders) owns 80% on an as-converted basis.
- 1× non-participating: investor gets the greater of $10M or 20% of proceeds (it converts to common when 20% of the exit exceeds $10M, i.e. exits above $50M).
- Participating (uncapped): investor gets $10M and 20% of what's left ("double dip").
| Exit value | Non-participating: preferred | Non-participating: everyone else | Participating: preferred | Participating: everyone else | Pro rata (80%) for comparison |
|---|---|---|---|---|---|
| $5M | $5.0M | $0 | $5.0M | $0 | $4.0M |
| $20M | $10.0M | $10.0M | $12.0M | $8.0M | $16.0M |
| $50M | $10.0M | $40.0M | $18.0M | $32.0M | $40.0M |
| $100M | $20.0M (converts) | $80.0M | $28.0M | $72.0M | $80.0M |
| $300M | $60.0M (converts) | $240.0M | $68.0M | $232.0M | $240.0M |
At a $20M exit, the "80%" owners get half the money, not 80%. Real companies stack preferences (seed + A + B, usually pari passu or senior by series), so total preference outstanding is the number to know: exits below it pay common little or nothing. Model this before accepting a high valuation with heavy terms.
Anti-dilution
Triggered when a later round is priced below this series' price (a down round). It lowers the conversion price so the series converts into more common.
Broad-based weighted average (NVCA standard):
old conversion price; shares outstanding before the new issue (broad-based: fully diluted, including options and pool); shares the new money would buy at ; shares actually issued. Full ratchet: = the new round's price, whatever the size of the round.
Example. Series A: 10M shares at $1.00; 50M fully diluted. Down round: 5M shares at $0.50 ($2.5M). , : ($0.9545 a share). Series A now converts into 10.48M common (+476k). Under full ratchet it converts into 20M (+10M), all of it out of common.
Employee equity
| ISO (incentive stock option) | NSO (non-qualified stock option) | |
|---|---|---|
| Who | employees only | employees, advisers, contractors, directors |
| Tax at exercise | no regular income tax; spread is an AMT adjustment | spread is ordinary income (wages for employees, withholding) |
| Tax on sale | long-term capital gain if held 2 years from grant and 1 year from exercise; otherwise a disqualifying disposition (ordinary income) | capital gain on growth after exercise |
| Limits | $100k of stock (at grant value) first exercisable per year; excess is NSO; strike ≥ FMV (110% and 5-year term for 10% holders); term ≤ 10 years | strike ≥ FMV to avoid §409A |
| After leaving | must exercise within 3 months to keep ISO status | per plan |
Statute: IRC §422 (opens in a new tab). AMT and personal tax are on retirement and taxes.
409A valuations. Options must be granted with a strike price at least equal to fair market value of common on the grant date, or they become deferred compensation under §409A (immediate income plus a 20% additional tax for the holder). The regulations (opens in a new tab) give a presumption of reasonableness (safe harbor) to an independent appraisal used within 12 months (refresh sooner after a financing or material event), and to a written good-faith valuation by a qualified person for an illiquid start-up under 10 years old with no sale expected within 90 days or IPO within 180 days. Common is valued below the preferred price because it has no liquidation preference, no protective provisions and is less liquid; a 409A after a seed commonly lands well under the preferred price.
| Decision | Options | Opinion |
|---|---|---|
| Exercise window after leaving | 90 days (ISO rule) vs extended (e.g. 5–10 years, converts to NSO after 3 months) | extended windows are fairer to early employees who can't afford to exercise; cost is a slower-recycling pool |
| Early exercise | let employees exercise unvested options (company repurchase right) and file 83(b) | at seed-stage 409A prices it can cost little and start capital-gains and QSBS clocks; risk: paying for shares that end up worthless |
| RSUs vs options | RSUs taxed on vest (and need a liquidity trigger in private companies) | options are the norm before late stage |
Pool sizing (heuristics, not rules): commonly 10–20% of post-money fully diluted at seed/Series A. Better: list the hires until the next round with a grant % each (early engineers and executives get the most), sum, add a buffer.
Taxes
QSBS (§1202)
IRC §1202 (opens in a new tab) excludes gain on qualified small business stock: stock acquired at original issue from a domestic C-corp (for cash, property or services) whose aggregate gross assets never exceeded the threshold before and immediately after issuance, with at least 80% of assets used in an active qualified business. Excluded fields include, among others, health, law, engineering, architecture, accounting, financial services, banking, insurance, farming, extraction, hospitality, consulting, brokerage, and any business whose principal asset is employees' reputation or skill. The One Big Beautiful Bill Act (signed 4 July 2025) changed it for stock issued after that date:
| Stock acquired 28 Sep 2010 – 4 Jul 2025 | Stock acquired after 4 Jul 2025 | |
|---|---|---|
| Holding period / exclusion | 100% after more than 5 years; nothing before | 50% at 3 years, 75% at 4 years, 100% at 5+ years |
| Per-issuer cap on excluded gain | greater of $10M or 10× basis | greater of $15M (inflation-indexed after 2026) or 10× basis |
| Gross-asset test | $50M | $75M (inflation-indexed after 2026) |
Partial exclusions leave the non-excluded part taxed at the special 28% rate for §1202 gain; state conformity varies. Why it matters to founders: a timely 83(b), a C-corp from day one, and keeping records of the gross-asset test at each issuance can make millions of gain tax-free. Get a QSBS memo from your accountant before any sale.
R&D credit and the payroll-tax offset
The federal research credit (§41) can be used by startups with no income tax against payroll taxes. A qualified small business (gross receipts under $5M in the year and none before the 5-year period ending that year) can elect up to $500,000 a year (up from $250,000; Inflation Reduction Act, tax years beginning after 31 Dec 2022), first against the employer share of Social Security tax and then Medicare, for up to 5 years (IRS (opens in a new tab)). Elect on Form 6765 with a timely-filed original return (not an amended one), then claim on Form 8974 with the quarterly Form 941. Engineers' wages building novel software commonly qualify; keep contemporaneous records.
§174 research expenses
From 2022 the TCJA forced domestic research and experimental (R&E) costs, including software development, to be capitalized and amortized over 5 years (15 for foreign), which gave loss-making startups taxable income. OBBBA added §174A: domestic R&E is deductible immediately again for tax years beginning after 31 Dec 2024; foreign R&E stays at 15-year amortization. Transition (Rev. Proc. 2025-28 (opens in a new tab)): taxpayers can deduct remaining unamortised 2022–2024 domestic amounts over 1 or 2 years, and small businesses (average gross receipts ≤ $31M under the §448(c) test) could elect to apply §174A retroactively to tax years beginning after 2021; the main deadline for that retroactive election was 6 July 2026, now passed. Ask your accountant what was filed.
Delaware franchise tax trap
Delaware's default invoice uses the authorized shares method, which punishes the typical 10M-authorized-share startup. You may instead pay under the assumed par value capital method, which needs total gross assets and issued shares (Delaware Division of Corporations (opens in a new tab)). Annual report and tax due 1 March; $50 report fee; late filing costs a $200 penalty plus 1.5% interest a month.
| Method | Rule | Example: 10,000,000 authorized, 8,000,000 issued, par $0.00001, gross assets $500,000 |
|---|---|---|
| Authorized shares | $175 up to 5,000 shares; $250 for 5,001–10,000; +$85 per extra 10,000 (max $200,000) | $250 + 999 × $85 = $85,165 |
| Assumed par value capital | assumed par = gross assets ÷ issued shares (or stated par if higher); × authorized shares; $400 per $1M or part (min $400) | $500,000 ÷ 8M = $0.0625; × 10M = $625,000 → $400 |
Don't pay the scary invoice; recalculate on the Delaware site and file the annual report with issued shares and gross assets.
Fundraising process and securities law
How much to raise: enough for 18–24 months of runway to the milestones the next round's investors will want to see, plus a buffer (Ralston's 2016 YC guide said 12–18 months; 18–24 is the figure most commonly quoted now). Work backwards: milestones → plan → cumulative burn.
Example: burn ramps linearly from $120k to $250k a month over 24 months: 24-month spend $4.44M (18 months: $3.02M). Raise ~$4.5M for 24 months, or ~$3M plus revenue for 18. At 20% dilution, $3M implies a $15M post-money.
| Investors look at | Evidence |
|---|---|
| Team | why you, technical depth, founder–market fit |
| Market | credible bottom-up size, why now |
| Traction | revenue/usage growth rate, retention cohorts, NRR, customer quotes |
| Efficiency | burn multiple, CAC payback, gross margin |
| The round | amount, use of funds, milestones it buys, runway |
| Cleanliness | cap table, IP assignments, 83(b)s, no disputes |
Securities law basics. Every SAFE or share sale is a securities offering that must be registered or exempt; startups use Regulation D Rule 506.
| 506(b) (opens in a new tab) | 506(c) (opens in a new tab) | |
|---|---|---|
| General solicitation (public posts, demo-day publicity naming the raise) | not allowed | allowed |
| Investors | unlimited accredited + up to 35 non-accredited but sophisticated in any 90 days (who then must get extensive disclosure; in practice, avoid) | accredited only |
| Verification | investor's representation is typical | issuer must take reasonable steps to verify (tax returns, letters from advisers; since a March 2025 SEC staff no-action letter, a high minimum investment of $200k for individuals / $1M for entities plus written representations can suffice) |
| Filing | Form D within 15 days after the first sale, plus state notice filings | same |
Accredited investor (individual, SEC (opens in a new tab)): income over $200,000 ($300,000 with spouse or partner) in each of the last two years with the same expected; or net worth over $1 million excluding the primary residence; or holding a Series 7, 65 or 82 license; directors and executive officers of the issuer also count for its own offering.
| Phase | Do |
|---|---|
| Prepare | clean cap table and round model; data room (incorporation docs, 83(b)s, IP assignments, financials, metrics); deck; target list ranked by fit |
| Run a tight process | batch first meetings into 2–4 weeks so interest overlaps; ask each investor about process and check size; keep a pipeline sheet |
| Close | SAFEs close investor by investor; priced rounds close together with a lead setting terms; countersign, collect wires, update the cap table, file Form D, send executed documents |
Admin and bookkeeping minimums
| Item | Minimum | Why |
|---|---|---|
| Bank account | a business account in the company's name from day one; never pay company costs from personal cards without documented reimbursement | limited liability and clean books |
| Books | cash basis at first; accrual once you sell annual contracts or raise a priced round (deferred revenue, see accounting) | investors and diligence expect GAAP-style monthly statements |
| Monthly close | reconcile bank, categorize, produce P&L, balance sheet, cash flow (financial statements) | runway numbers you can trust |
| Board consents | written consents for stock issuances, option grants, SAFEs, 409A adoption, officer appointments | unapproved issuances are void or need ratification |
| Cap table | in a dedicated cap-table tool or a rigorously maintained spreadsheet matched to signed documents | every financing starts with cap-table diligence |
| Stock records | signed stock purchase agreements, 83(b) proof, option grant notices | lost 83(b) proof is painful in diligence |
| Payroll | real payroll (withholding, payroll taxes) for founders once paid; contractors vs employees classified correctly | penalties; R&D payroll offset needs it |
| Taxes and filings | federal corporate return every year (even with no revenue), Delaware annual report by 1 March, state registrations where you have employees | penalties accumulate silently |
| Insurance | D&O once you have outside board members; others as contracts require |
Common mistakes
| Mistake | Consequence | Fix |
|---|---|---|
| No 83(b) (or filed on day 31) | ordinary income tax on every vest at rising values; no capital-gains or QSBS clock | calendar day 1 of every stock purchase; file online and keep confirmation |
| No founder vesting | a co-founder leaves after 4 months with 30% of the company; investors won't fund the dead equity | 4-year vest, 1-year cliff, repurchase right, from day one |
| Missing IP assignment | the company may not own its code | assignment signed by every founder, employee and contractor |
| Stacking SAFEs without modeling | "only $250k each" at various caps adds up to 25–30% sold before the seed | a running cap table with every SAFE converted |
| Ignoring the pool shuffle | headline $12M pre is really $9.75M | negotiate pool size against a hiring plan |
| Misunderstanding liquidation preferences | a "good" $30M exit pays common almost nothing after $25M of stacked preference | model the waterfall at several exit values before signing |
| Optimizing valuation over terms | high price with participating or 2× preference, or a valuation you can't grow into (down round, anti-dilution) | clean terms at a fair price |
| Running out of cash while "almost" raising | forced bridge on bad terms, or death | start raising with 9+ months of runway; default-alive plan B |
| Paying Delaware's authorized-shares invoice | tens of thousands wasted | recalculate with the assumed par method |
| Granting options without a current 409A | §409A penalties for employees | 409A before first grants; refresh after each round |
| Mixing personal and company money | pierced veil risk, messy diligence | separate accounts, documented reimbursements |
| Accepting money from non-accredited friends casually | securities-law problems, rescission rights | accredited investors only unless your lawyer structures it |
Templates
Runway calculator
RUNWAY CALCULATOR Month: ________
Cash in bank (all accounts) A ____________
Committed but unreceived financing B ____________
Monthly gross burn (3-mo avg) C ____________
Monthly cash collected (3-mo avg) D ____________
Net burn E = C − D
Runway, months F = A / E
Runway incl. committed money G = (A + B) / E
Minimum cash buffer (e.g. 3 × C) H ____________
Months until buffer reached I = (A − H) / E
Start fundraising no later than month I − 6
Default alive? revenue growth g = ____ %/month
months to breakeven n = ln(C / D) / ln(1 + g)
cash needed ≈ sum of net burn over n months → vs A13-week cash forecast
13-WEEK CASH FORECAST Wk1 Wk2 Wk3 ... Wk13 Total
Opening cash ___ ___ ___ ___
+ Customer collections ___ ___ ___ ___
+ Grants, refunds, financing ___ ___ ___ ___
= Total receipts ___ ___ ___ ___
− Payroll, taxes, benefits ___ ___ ___ ___
− Contractors ___ ___ ___ ___
− Cloud / APIs / inference ___ ___ ___ ___
− Software, rent, marketing ___ ___ ___ ___
− Taxes, insurance, legal ___ ___ ___ ___
= Total payments ___ ___ ___ ___
Closing cash ___ ___ ___ ___
Below minimum buffer? (flag) ___ ___ ___ ___
Last week: forecast vs actual ___ reason ____________Cap table
CAP TABLE (fully diluted) As of: __________
Holder Class Shares Price Invested FD %
Founder 1 Common _______ _____ ________ ____
Founder 2 Common _______ _____ ________ ____
Options Granted _______ 409A – ____
Pool Unissued _______ – – ____
SAFE holders (as-conv.) _______ _____ ________ ____
Seed Pref Seed _______ _____ ________ ____
Series A Pref A _______ _____ ________ ____
TOTAL _______ ________ 100%
Liquidation preference outstanding: $__________
Check: sum of FD % = 100%; shares match signed documentsSAFE conversion worksheet
SAFE CONVERSION (post-money SAFEs, cap applies)
1. Pre-SAFE fully diluted shares (incl. pool) F = ________
2. For each SAFE i: own_i = amount_i / cap_i
SAFE 1: ______ / ______ = ____ %
SAFE 2: ______ / ______ = ____ %
Sum S = ____ %
3. Company Capitalization CC = F / (1 − S) = ________
4. Safe Price_i = cap_i / CC ; shares_i = own_i × CC
5. Priced round: pre-money V, new money M, pool target p
pool increase X solves:
unissued + X = p × (1 + M/V) × (CC + X)
price P = V / (CC + X) ; new shares N = M / P
6. Check each SAFE: if P < Safe Price_i,
it converts at P instead (more shares)
7. Post-round FD = CC + X + N ; recompute all %Fundraising checklist
FUNDRAISING CHECKLIST
[ ] Delaware C-corp in good standing; franchise tax paid
[ ] Founder stock agreements with vesting; 83(b) proofs
[ ] IP assignments from all founders, staff, contractors
[ ] Cap table reconciled to signed documents
[ ] Board consents for every issuance and grant
[ ] Current 409A (if options granted)
[ ] Monthly financials (accrual if annual contracts)
[ ] Metrics: MRR/ARR, growth, NRR/GRR, churn, burn multiple
[ ] 24-month model: base, downside, no-raise scenarios
[ ] Round size = milestones + 18–24 months runway + buffer
[ ] Pro forma cap table: all SAFEs converted, pool shuffle
[ ] Waterfall at 3–5 exit values for the proposed terms
[ ] Investor list, pipeline sheet, data room
[ ] Securities: 506(b) vs 506(c) decided; accredited only
[ ] After close: Form D within 15 days; state notices;
update cap table; send executed docs; bank wires matchedReferences
- Y Combinator: SAFE financing documents (opens in a new tab): post-money SAFE forms (cap, discount, MFN), pro rata side letter and the SAFE User Guide with conversion examples
- Y Combinator: The YC deal (opens in a new tab): $125k for 7% plus $375k uncapped MFN SAFE
- Y Combinator: SAFE vs convertible note (opens in a new tab): YC's comparison, incl. typical note interest
- Brian Ralston, A Guide to Seed Fundraising (YC, 2016) (opens in a new tab): round sizing and dilution guidance
- Paul Graham, Default Alive or Default Dead? (2015) (opens in a new tab) and Ramen Profitable (2009) (opens in a new tab)
- NVCA model legal documents (opens in a new tab): standard priced-round documents, incl. weighted-average anti-dilution language
- IRC §83 (opens in a new tab), §422 (opens in a new tab) and §1202 (opens in a new tab) (Cornell LII): restricted property and 83(b), ISOs, QSBS as amended in 2025
- Treas. Reg. §1.409A-1 (opens in a new tab): 409A valuation safe harbors
- IRS Form 15620 (opens in a new tab): the 83(b) election form; Morrison Foerster (July 2025) (opens in a new tab) on online filing
- IRS: Qualified small business payroll tax credit for increasing research activities (opens in a new tab)
- IRS Rev. Proc. 2025-28 (opens in a new tab): §174A elections for domestic research expenditures
- Delaware Division of Corporations: franchise tax calculation (opens in a new tab) and annual report and tax (opens in a new tab)
- SEC: Rule 506(b) (opens in a new tab), Rule 506(c) (opens in a new tab), Regulation Crowdfunding (opens in a new tab), accredited investors (opens in a new tab)
- SBA: SBIR/STTR reauthorisation (13 April 2026) (opens in a new tab)
- David Skok, SaaS Metrics 2.0 (opens in a new tab): LTV:CAC, CAC payback and churn guidelines
- David Sacks, The Burn Multiple (Craft Ventures, 2020) (opens in a new tab)
- Brad Feld, The Rule of 40% for a Healthy SaaS Company (2015) (opens in a new tab)
- Scale Venture Partners, SaaS Metrics: A History of the Magic Number (2020) (opens in a new tab)
- Carta, State of Private Markets: 2025 in Review (opens in a new tab): median seed and Series A dilution
- Brad Feld and Jason Mendelson, Venture Deals, 4th ed. (Wiley, 2019): term sheets explained clause by clause