A convertible note is a short-term debt instrument that converts into equity at the company's next priced round rather than being repaid in cash. It typically carries four key terms: an interest rate, a maturity date, a conversion discount, and often a valuation cap, combining the speed of a loan with the upside structure of equity. It was the dominant pre-seed and seed instrument from roughly 2005 until 2013, when Y Combinator introduced the SAFE and the market gradually shifted.
The four key terms, with typical 2025 ranges:
| Term | Typical range | What it does |
|---|---|---|
| Interest rate | 4-8% per year | Accrues until conversion; rarely paid in cash |
| Maturity | 18-36 months | Note must convert, be repaid, or be extended by this date |
| Conv... |
Cashless exercise is the option-exercise method where the holder simultaneously exercises options and sells enough resulting shares to cover the strike price and tax withholding. It lets the holder convert vested options into net shares (or net cash) without putting up cash for the exercise, typically requiring a public market or a contemporaneous private secondary, making it standard at public companies but rare at private startups absent a tender offer. It is the practical solution to the cash-binding problem of traditional exercise at companies where the strike-price outlay would otherwise be substantial.
The two main cashless exercise variants:
An exit multiple is the valuation multiple at which a company is acquired or goes public, most commonly revenue, EBITDA, or ARR multiples. Common variants include revenue multiple, EBITDA multiple, ARR multiple for SaaS, or user-count multiple for consumer products. It is used to compare exits across deals, inform founder valuation expectations, and serve as a primary lens through which strategic acquirers and PE firms evaluate targets. It is the shortcut metric most M&A conversations actually run on, despite the existence of more sophisticated valuation methodologies.
The major multiples by business model: SaaS / subscription: typically valued on ARR multiple (annual recurring revenue), with public-market multiples ranging fr...
An initial public offering (IPO) is the process of selling shares of a private company to the public for the first time. Listed on NYSE, Nasdaq, or international equivalents, an IPO is traditionally the marquee exit path for venture-backed companies, with investment-bank underwriters pricing the offering, allocating shares to institutional buyers, and the company raising primary capital in the process. It is also one of the rarest exit outcomes statistically, despite getting the bulk of the press coverage.
The standard process runs roughly: file a confidential S-1 with the SEC, respond to SEC comments through 2 to 4 rounds, conduct a [Roadshow] where executives pitch institutional investors over 1 to 2 weeks, price the offering the nigh...
QSBS (Qualified Small Business Stock) is an IRS provision under Section 1202 that excludes up to $10M-$15M (or 10x basis) in capital gains from federal tax. The One Big Beautiful Bill Act (signed July 4, 2025) created a two-regime structure: stock issued on or before July 4, 2025 follows the pre-OBBBA rules ($10M or 10x cost basis cap, $50M gross-assets ceiling, 5-year hold for the full exclusion); stock issued after July 4, 2025 follows the OBBBA rules ($15M cap inflation-adjusted after 2026, $75M gross-assets ceiling, tiered holding with 50% exclusion at 3 years, 75% at 4 years, 100% at 5 years, maximum exclusion up to $750 million). The exclusion is available to founders, early employees, and early investors. It is one of the most v...
The people side of building a company. This cluster covers founder roles and dynamics, the executive lineup, the hiring sequence, sales and customer success roles, compensation and equity, performance management, layoffs and severance, and the culture and operations that determine whether the team holds together. 63 entries.
If your business succeeds or fails on hiring (most do), this is the cluster you live in.
The structural mechanics of who owns what. This cluster covers cap tables, stock classes (common, preferred, restricted), options (ISO, NSO, exercise mechanics), vesting and acceleration, anti-dilution provisions, preferred stock terms (preferences, ratchets, protective provisions), SAFEs and warrants, equity tax planning (83b, QSBS, AMT), and the administrative infrastructure (cap-table software, equity admin) that keeps it all clean. 80 entries.
This is the most consequential cluster for founder economics. The decisions here echo across every future round and exit.
Everything about raising capital, from the first SAFE to the IPO. This cluster covers every named stage (pre-seed through Series E+), the investor types (VC, CVC, angels, family offices, crossover funds, strategic vs financial), the fund mechanics that drive investor behavior (LPs, GPs, fund life, carried interest), the crowdfunding regulations and platforms, the round structures (up, down, flat, bridge, extension), and the closing mechanics that make deals real. 97 entries.
This is the most thoroughly covered cluster in the lexicon because fundraising decisions compound for years.
A prototype is a working or simulated representation of a product used to test concepts, flows, interactions, or feasibility before committing to full development. It ranges in fidelity from paper sketches to clickable mockups to fully functional code, and should be chosen at the lowest fidelity that can answer the question being asked. It is the cheapest tool in the product discovery toolbox, and the one most consistently underused by founders who jump straight to building.
The fidelity ladder runs from low to high: paper sketches (cheapest, fastest, useful for concept testing and flow validation), wireframes (digital low-fidelity layouts, Balsamiq-style or in Figma), clickable mockups (interactive Figma / Sketch prototypes that ...
A wireframe is a low-fidelity sketch of a screen showing layout, hierarchy, and core functionality, used to align on structure before investing in polish. It deliberately strips out real typography, color, imagery, and microinteractions. The deliberate ugliness is the point: a polished mockup invites feedback on visual taste; a wireframe forces feedback on the structure of the experience.
The fidelity spectrum runs roughly: paper sketches (lowest, drawn freehand on actual paper or whiteboard), low-fidelity digital wireframes (grayscale boxes-and-labels in Balsamiq, Whimsical, or Figma), high-fidelity wireframes (more refined layout but still no real visuals), mockups (full visual design but typically static), and prototypes (inter...