Dilution — The Silent Value Thief
How funding rounds shrink your slice, the option pool shuffle, and red flags to watch for.
What you’ll learn
- ✓How dilution works mathematically across funding rounds
- ✓The option pool shuffle — how investors dilute you before they invest
- ✓Anti-dilution provisions (broad-based vs. narrow-based weighted average)
- ✓Pro-rata rights and why early investors fight for them
- ✓How to model dilution across expected future rounds
- ✓Red flags: excessive option pools, participating preferred, stacked preferences
Dilution is the mechanism by which your ownership percentage shrinks over time, even when you do nothing wrong. Every time a company issues new shares — to raise money, hire employees, or bring on advisors — the existing pie is divided into more pieces. Your slice gets smaller.
This isn't inherently bad. If a company raises $50M at a $200M valuation and uses that capital to grow 5x, dilution was worth it. The math that matters isn't the percentage — it's the absolute value of your shares. But dilution has a dark side that catches people off guard.
In this chapter, you’ll work through the exact framework for dilution — the silent value thief. We cover each of the key topics with worked examples, real numbers, and actionable steps you can take immediately.
- ✓How dilution works mathematically across funding rounds
- ✓The option pool shuffle — how investors dilute you before they invest
- ✓Anti-dilution provisions (broad-based vs. narrow-based weighted average)
- ✓Pro-rata rights and why early investors fight for them
- ✓How to model dilution across expected future rounds
- ✓Red flags: excessive option pools, participating preferred, stacked preferences
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