Chapter 3

What Is This Actually Worth?

409A valuations, the common stock discount, running bear/base/bull scenarios, and comparing offers apples-to-apples.

What you’ll learn

  • 409A valuations and the common vs. preferred stock discount
  • Running bear, base, and bull case scenarios
  • How to calculate your potential payout at exit
  • Comparing equity across different-stage companies
  • Why valuation multiples matter more than headline numbers
  • Tools and spreadsheets for modeling your offer

The most common mistake people make with startup equity is treating it like a lottery ticket — either ignoring it entirely or assuming it'll make them rich. The smarter move is to model it. Not with false precision, but with scenario ranges that tell you whether the risk is worth taking.

Value is always relative to price paid, time invested, and alternative options foregone. A 0.5% stake sounds the same in every offer letter. But it means something very different at a $10M seed-stage company versus a $500M Series D.

In this chapter, you’ll work through the exact framework for what is this actually worth?. We cover each of the key topics with worked examples, real numbers, and actionable steps you can take immediately.

  • 409A valuations and the common vs. preferred stock discount
  • Running bear, base, and bull case scenarios
  • How to calculate your potential payout at exit
  • Comparing equity across different-stage companies
  • Why valuation multiples matter more than headline numbers
  • Tools and spreadsheets for modeling your offer
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This chapter is part of the full guide

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