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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.

QuestionDelaware C-corpLLC
What VCs expectthe standard; NVCA and YC documents assume itmany funds can't or won't invest (pass-through income creates tax problems for their tax-exempt and foreign LPs)
Preferred stock, option plansstandard, well-understoodpossible via units and profits interests, but bespoke and costly
Taxationentity pays corporate tax; shareholders taxed on dividends and salepass-through: losses and profits flow to members' returns
QSBS (§1202)eligible if the tests are metnot eligible; converting to a C-corp later starts QSBS from the conversion date
Early lossestrapped in the company as NOLsusable by members (the main LLC advantage)
When to pickyou intend to raise venture capital or grant options to many employeesbootstrapped, 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

TermConventionWhy
Founder sharesbought for cash at a tiny price (par, e.g. $0.00001–$0.0001 per share) right after incorporationprice ≈ fair value when the company is worth nothing, so no tax at grant
Authorized sharesoften ~10M authorized, most issued to foundersleaves room for a pool; watch the Delaware franchise tax (below)
Vesting4 years with a 1-year cliff: 25% at 12 months, then monthlya co-founder who leaves in month 5 takes nothing; investors expect it and will impose it if you don't
Mechanismshares issued up front, company has a repurchase right at cost on unvested shares that lapses as they vesttechnically "restricted stock", which is why 83(b) matters
Credit for time servedsome founders start with 6–12 months already vestedreasonable if real work pre-dates incorporation
Single-trigger accelerationvesting speeds up on a sale aloneinvestors dislike it: acquirers want the team incentivised after closing
Double-trigger accelerationvesting speeds up only on sale and termination without cause (or resignation for good reason) within a window, commonly 12 monthsthe 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.

VestSharesFMV/shareOrdinary income without 83(b)Tax at an illustrative 37% federal rate
Year 11,000,000$0.40$399,900$147,963
Year 21,000,000$1.00$999,900$369,963
Year 31,000,000$2.00$1,999,900$739,963
Year 41,000,000$3.00$2,999,900$1,109,963
Total4,000,000$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.

MetricFormulaNotes
CAC (customer acquisition cost)sales & marketing spend in period ÷ new customers in perioduse fully loaded S&M (salaries, tools, ads); "blended" includes organic customers and flatters; "paid" CAC counts only paid channels
ARPArevenue ÷ accounts (monthly)per account, not per user, for B2B
Gross margin(revenue − COGS) ÷ revenueCOGS = hosting, third-party APIs/model inference, payment fees, support, onboarding
Contribution margin(revenue − all variable costs) ÷ revenuealso subtracts variable costs below gross profit (e.g. per-order fulfillment, sales commissions)
Churn cccustomers lost ÷ customers at start (per month)average lifetime ≈ 1/c1/c months
LTV (simple)LTV=ARPA×GMc\text{LTV} = \dfrac{\text{ARPA} \times \text{GM}}{c}margin, not revenue: revenue LTV overstates by 1/GM1/\text{GM}
LTV (discounted)LTV=ARPA×GMc+d\text{LTV} = \dfrac{\text{ARPA} \times \text{GM}}{c + d}dd = monthly discount rate; payments start next month
LTV:CACLTV ÷ CACheuristic target ≥ 3
CAC paybackCACARPA×GM\dfrac{\text{CAC}}{\text{ARPA} \times \text{GM}} monthsheuristic 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.

MeasureCalculationResult
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 − r36r^{36}) ÷ 0.04, with r=0.97/1.01r = 0.97/1.01$7,665 (LTV:CAC 1.3)
CAC payback$6,000 ÷ $40015 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):

ModelTypical gross marginWatch
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

MetricDefinition / formula
MRRmonthly recurring revenue from subscriptions (normalize annual contracts to /12; exclude one-off fees)
ARRMRR × 12 (or annual contract value of the recurring base)
New MRRfrom customers who weren't paying last period
Expansion MRRupgrades, seats, usage growth from existing customers
Contraction MRRdowngrades from customers who stay
Churned MRRfrom customers who cancel
Net new MRRnew + expansion − contraction − churned
Logo churncustomers lost ÷ customers at start
Revenue churn(contraction + churned MRR) ÷ starting MRR
GRR (gross revenue retention)start−contraction−churnstart\dfrac{\text{start} - \text{contraction} - \text{churn}}{\text{start}}, capped at 100%
NRR (net revenue retention)start+expansion−contraction−churnstart\dfrac{\text{start} + \text{expansion} - \text{contraction} - \text{churn}}{\text{start}}, can exceed 100%
Rule of 40revenue growth % + profit margin % ≥ 40
Burn multiplenet burnnet new ARR\dfrac{\text{net burn}}{\text{net new ARR}} (same period)
Magic number(revq−revq−1)×4S&Mq−1\dfrac{(\text{rev}_q - \text{rev}_{q-1}) \times 4}{\text{S\&M}_{q-1}} (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).

MetricOriginRough bands
Rule of 40popularised by Brad Feld, Feb 2015 (opens in a new tab), who heard it from a late-stage investormeant for SaaS companies at scale (Feld: think $50M+ revenue); meaningless at seed
Burn multipleDavid 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 numbercoined 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).

ItemValue
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 / lost80 / 10
NRR(1,200 + 240 − 60 − 120) ÷ 1,200 = 105%
GRR(1,200 − 60 − 120) ÷ 1,200 = 85%
Logo churn vs revenue churn10 ÷ 80 = 12.5% vs 180 ÷ 1,200 = 15%
Revenue growth, free-cash-flow margin60%, −35% → Rule of 40 score 25
Net burn $3.0M, net new ARR $1.5Mburn multiple 2.0
Quarterly revenue $500k → $600k, prior-quarter S&M $450kmagic 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

TermDefinition
Gross burntotal cash out per month (payroll, rent, tools, COGS)
Net burncash out − cash in per month (gross burn − collected revenue)
Runwayrunway (months)=cashnet burn\text{runway (months)} = \dfrac{\text{cash}}{\text{net burn}}
Default aliveon current expenses and the recent revenue growth rate, you reach profitability before cash runs out
Default deadyou don't; you need new money or cuts
Ramen profitablerevenue 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 growthOutcome
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 groupContentsTips
Opening cashbank balances, all accountsreconcile to the bank every week
Receiptscollections by customer (dated by expected payment, not invoice), grants, financingenterprise customers pay 30–60+ days after invoice; model that
Payrollnet pay, payroll taxes, benefits on actual pay datesthe biggest and least flexible line
Operating paymentsrent, cloud, SaaS tools, contractors, insuranceannual prepayments create lumpy weeks
Othertaxes (incl. Delaware franchise tax by 1 March), capex, loan payments
Closing cashopening + receipts − paymentsflag 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.

LayerContents
1. Driversleads or sign-ups, conversion rates, ARPA and price changes, churn, expansion, sales capacity (quota per rep, ramp months), collection terms
2. Revenuecustomer count and MRR roll-forward by month (new, expansion, contraction, churn); bookings vs revenue vs cash collected for annual prepaid contracts
3. Headcounthiring 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 COGShosting and inference as % of revenue or per user; tools per head; rent; marketing tied to CAC and new-customer targets
5. Cashnet 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

ScenarioTypical assumption changesUse
Baseyour honest planthe budget
Downsidegrowth half of plan, raise slips 6 months, a big customer churnswhat you cut, and when (write the trigger down: "if cash < 9 months by Q2, freeze hiring")
Upsidegrowth 1.5× planwhen to hire ahead; whether to raise early
No raiseno new money everthe default-alive test; how to get there by cutting

Pricing

Pricing is covered in more depth on launch and iterate; the finance view:

ApproachHowFit
Value-baseda fraction (often quoted as 10–20%) of the value the customer gets: hours saved, revenue gained, risk avoidedbest for B2B; requires knowing the customer's economics
Cost-plusunit cost × (1 + markup)hardware, services; sets a floor, not a price; software's marginal cost is near zero so it underprices
Competitiveanchor to alternatives, including spreadsheets and doing nothingcrowded 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

SourceRough sizeWhat you giveBest forWatch
Bootstrappingsavingsyour time, personal riskproving demand cheaplypersonal runway; don't mix funds
Customer revenueanydelivery obligationseverything: non-dilutive and validatingcustom work that becomes a consultancy
Grants (SBIR/STTR)Phase I tens to a few hundred $k; Phase II largerreporting, IP and data-rights terms; US ownership rulesdeep-tech, defense, health, climate R&Dslow cycles; programs lapsed Oct 2025–Apr 2026 (see below)
Friends & family$10k–$250kequity (usually a SAFE)the very first monthsonly take money people can afford to lose; most should be accredited
Angels$10k–$250k per checkSAFE or equitypre-seed/seed; help and introsmany small checks = a messy cap table
Acceleratorse.g. YC $500kequity, timenetwork, credibility, demo dayread the deal; see below
Pre-seed / seed VC~$0.5M–$5M (varies by market and year)~10–25%building to product-market fitsets expectations of venture-scale growth
Venture debtoften sized as a fraction of the last equity roundinterest, fees, warrants, covenantsextending runway after an equity roundcovenants and repayment when you're weakest
Revenue-based financinga multiple of monthly recurring revenuea % of revenue until a fixed cap is repaidpredictable-revenue businesseseffective cost can be high; needs revenue already
Crowdfunding (Reg CF)up to $5M per 12 monthsequity/SAFEs to many small investors via a registered portalconsumer brands with a communitydisclosure 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)).

TermMeaning
Post-money valuation capthe 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
Discountconverts at a discount to the priced round's price (e.g. 20% off = 80% "discount rate")
MFNif you later issue SAFEs on better terms, the holder may amend its SAFE to match (one amendment, no cherry-picking)
Pro rata side letterright 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 conversiongreater 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.

Company Capitalization=pre-SAFE fully diluted shares1−∑iamounticapi\text{Company Capitalization} = \frac{\text{pre-SAFE fully diluted shares}}{1 - \sum_i \dfrac{\text{amount}_i}{\text{cap}_i}}

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.

SAFEAmountPost-money capOwnership bought
A (early angel)$500,000$5,000,00010%
B (seed fund)$1,000,000$10,000,00010%

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.

StepCalculationResult
1. SAFE ownership500k/5M + 1M/10M20%
2. Company Capitalization9,000,000 ÷ (1 − 0.20)11,250,000
3. Safe PricesA: $5M ÷ 11.25M; B: $10M ÷ 11.25M$0.4444; $0.8889
4. Conversion sharesA: $500k ÷ $0.4444; B: $1M ÷ $0.88891,125,000 each
5. Pool increase XXsolve 600,000+X=0.10×1.25×(11,250,000+X)600{,}000 + X = 0.10 \times 1.25 \times (11{,}250{,}000 + X)921,429
6. Seed price$12M ÷ (11,250,000 + 921,429)$0.9859
7. Seed shares$3M ÷ $0.98593,042,904
8. Checkboth 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

FeaturePost-money SAFEConvertible note
Legal formcontract for future equitydebt that converts
Interestnoneaccrues (YC quotes 2–8% as typical); converts into more shares
Maturitynoneyes (commonly 12–24 months); at maturity holders can demand repayment or renegotiate
Cap / discountcap, discount, MFNcap and/or discount, same idea
Priority on insolvencybehind all debtahead of equity (it is debt)
Cost and speedone standard document, lowest costmore negotiation
When still useddefault at pre-seed/seedbridges 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).

TermFormula
Post-money valuationpre-money + new money
Investor ownershipnew money ÷ post-money
Price per sharepre-money ÷ pre-money fully diluted shares (incl. converted SAFEs and any pool increase)
New sharesnew 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 treatmentPrice/shareInvestorPoolFoundersEffective pre-money to founders
No pool$1.20020%0%80.0%$12.0M
15% pool created after the round (dilutes everyone)$1.20017%15%68.0%$12.0M
15% pool in the pre-money (standard ask)$0.97520%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 d1,d2,…d_1, d_2, \dots (including pool increases),

ownershipafter=ownershipbefore×∏k(1−dk)\text{ownership}_{\text{after}} = \text{ownership}_{\text{before}} \times \prod_k (1 - d_k)

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

TermFounder-friendly / standardAggressiveWhy it matters
Liquidation preference1× non-participatingparticipating, or >1×decides who gets paid in modest exits
Anti-dilutionbroad-based weighted averagefull ratchetcost to founders of a down round
Pro rata rightsmajor investors can buy their share of future roundssuper pro ratacrowds out new investors later
Boardseed: often 2 founders + 1 investor, or founders only; Series A: 2 common + 1 investor, or 2–1–1 with an independentinvestor majority earlycontrol of hiring/firing the CEO and of a sale
Protective provisionspreferred vote on new senior securities, charter changes, sale, dividendsvetoes on budgets and operationsblocking rights
Drag-alongholders must vote for a sale approved by board + majority of preferred (+ often common)low thresholds, no floor on pricelets a majority force a sale
ROFR / co-salecompany (then investors) can buy shares founders sell; investors can sell alongsidelimits founder secondary sales
Information rightsannual audited/unaudited statements, quarterly financials, budget for major investorsmonthly everything to allreporting burden
Dividendsnon-cumulative, only if declaredcumulative (compounding preference)rare but expensive
Redemptionnoneinvestor can force a buyback after N yearsa 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 valueNon-participating: preferredNon-participating: everyone elseParticipating: preferredParticipating: everyone elsePro 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):

CP2=CP1×A+BA+CCP_2 = CP_1 \times \frac{A + B}{A + C}

CP1CP_1 old conversion price; AA shares outstanding before the new issue (broad-based: fully diluted, including options and pool); BB shares the new money would buy at CP1CP_1; CC shares actually issued. Full ratchet: CP2CP_2 = 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). B=2.5MB = 2.5\text{M}, C=5MC = 5\text{M}: CP2=1.00×52.5/55=0.9545CP_2 = 1.00 \times 52.5/55 = 0.9545 ($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)
Whoemployees onlyemployees, advisers, contractors, directors
Tax at exerciseno regular income tax; spread is an AMT adjustmentspread is ordinary income (wages for employees, withholding)
Tax on salelong-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 yearsstrike ≥ FMV to avoid §409A
After leavingmust exercise within 3 months to keep ISO statusper 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.

DecisionOptionsOpinion
Exercise window after leaving90 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 exerciselet 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 optionsRSUs 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 2025Stock acquired after 4 Jul 2025
Holding period / exclusion100% after more than 5 years; nothing before50% at 3 years, 75% at 4 years, 100% at 5+ years
Per-issuer cap on excluded gaingreater of $10M or 10× basisgreater 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.

MethodRuleExample: 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 capitalassumed 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 atEvidence
Teamwhy you, technical depth, founder–market fit
Marketcredible bottom-up size, why now
Tractionrevenue/usage growth rate, retention cohorts, NRR, customer quotes
Efficiencyburn multiple, CAC payback, gross margin
The roundamount, use of funds, milestones it buys, runway
Cleanlinesscap 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 allowedallowed
Investorsunlimited accredited + up to 35 non-accredited but sophisticated in any 90 days (who then must get extensive disclosure; in practice, avoid)accredited only
Verificationinvestor's representation is typicalissuer 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)
FilingForm D within 15 days after the first sale, plus state notice filingssame

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.

PhaseDo
Prepareclean 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 processbatch first meetings into 2–4 weeks so interest overlaps; ask each investor about process and check size; keep a pipeline sheet
CloseSAFEs 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

ItemMinimumWhy
Bank accounta business account in the company's name from day one; never pay company costs from personal cards without documented reimbursementlimited liability and clean books
Bookscash 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 closereconcile bank, categorize, produce P&L, balance sheet, cash flow (financial statements)runway numbers you can trust
Board consentswritten consents for stock issuances, option grants, SAFEs, 409A adoption, officer appointmentsunapproved issuances are void or need ratification
Cap tablein a dedicated cap-table tool or a rigorously maintained spreadsheet matched to signed documentsevery financing starts with cap-table diligence
Stock recordssigned stock purchase agreements, 83(b) proof, option grant noticeslost 83(b) proof is painful in diligence
Payrollreal payroll (withholding, payroll taxes) for founders once paid; contractors vs employees classified correctlypenalties; R&D payroll offset needs it
Taxes and filingsfederal corporate return every year (even with no revenue), Delaware annual report by 1 March, state registrations where you have employeespenalties accumulate silently
InsuranceD&O once you have outside board members; others as contracts require

Common mistakes

MistakeConsequenceFix
No 83(b) (or filed on day 31)ordinary income tax on every vest at rising values; no capital-gains or QSBS clockcalendar day 1 of every stock purchase; file online and keep confirmation
No founder vestinga co-founder leaves after 4 months with 30% of the company; investors won't fund the dead equity4-year vest, 1-year cliff, repurchase right, from day one
Missing IP assignmentthe company may not own its codeassignment 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 seeda running cap table with every SAFE converted
Ignoring the pool shuffleheadline $12M pre is really $9.75Mnegotiate pool size against a hiring plan
Misunderstanding liquidation preferencesa "good" $30M exit pays common almost nothing after $25M of stacked preferencemodel the waterfall at several exit values before signing
Optimizing valuation over termshigh 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" raisingforced bridge on bad terms, or deathstart raising with 9+ months of runway; default-alive plan B
Paying Delaware's authorized-shares invoicetens of thousands wastedrecalculate with the assumed par method
Granting options without a current 409A§409A penalties for employees409A before first grants; refresh after each round
Mixing personal and company moneypierced veil risk, messy diligenceseparate accounts, documented reimbursements
Accepting money from non-accredited friends casuallysecurities-law problems, rescission rightsaccredited 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 A

13-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 documents

SAFE 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 matched

References