Cap Table
Cap table writing: option pools, dilution, SAFEs vs priced, and keeping founders on the right side of the waterfall.
13 articles
Should I Take On Investors? A Decision Framework for Profitable Small Businesses
Most fundraising advice assumes you should raise. Seven questions to determine whether equity funding is right for your profitable business. Covers what you give up, alternatives…
Down Rounds, Washout Rounds, and Navigating Startup Financial Distress
Model distress scenarios before they happen. Options include down rounds, washout rounds, debt restructuring, and acquihires. Cap table implications matter more than valuation…
Alternative Financing: Revenue-Based Financing, Grants, and When Not to Raise Venture Capital
Revenue-based financing means no dilution, no board seats, no covenants. Payments flex with revenue. VC is one option on a financing menu, not the default. When alternatives make…
The PE Rollover: How the Second Bite Can Double Your Exit Returns
PE acquisitions involve retaining 20-40% equity for the second exit. Lower cash at close but potentially higher total returns over 3-5 years.
Strategic vs Financial Buyers: How to Choose and What Each One Means for Your Exit
Strategic acquirers offer 90-100% cash at close. PE firms offer 60-80% with rollover equity. The second bite can double total returns.
Multi-Round Dilution Tracker: How Founder Ownership Erodes from Seed to Series B
Cumulative dilution across Seed, Series A, and Series B with real numbers. Option pool refreshes, anti-dilution, and what founders actually own at exit.
Founder Dilution: How Much Equity You Lose Each Funding Round
Dilution math per round (15-25% at seed), option pool mechanics, founder ownership trajectory from 100% to 35%, and how to negotiate better terms.
Post-Acquisition Finance: What Happens to Your Cap Table, Escrowed Funds, and Earnouts
Most acquisitions include escrow and earnouts. These create cash flow timing issues and tax complexity for shareholders.
Equity Packages That Actually Work: 409A Valuations, Strike Prices, and Vesting
409A valuations determine tax treatment. Strike price is the option exercise price. Vesting is typically 4 years with 1-year cliff.
The Option Pool Game: How to Plan for Dilution Before It Is Too Late
An option pool is shares reserved for employees. Typically 10-15 percent depending on hiring plans.
Pro Rata Rights, Board Seats, and Anti-Dilution: What You Are Actually Negotiating
Pro rata rights let investors maintain ownership. Board seats give voting power. Anti-dilution protects investors in down rounds.
The Cap Table: What Every Founder Must Understand Before Taking a Single Dollar
The cap table is the ledger of who owns what percentage of your company. Every round you raise changes it. Most founders do not understand how dilution works until they have…
Venture Debt: The Startup Financing Tool Nobody Explains Properly
Venture debt is a loan product designed for venture-backed startups. It is not equity and does not dilute founders, but it comes with covenants, warrants, and a maturity date…