The Most Expensive Equity Doesn't go to Investors

Why do founders fight over giving an investor 15% but hand out huge chunks to co-founders, employees, and advisors with far less certainty of return? The episode argues that investor dilution is often the cleanest trade because cash and terms are clear, while “everyone else pays in maybes and promises.” It warns that early-stage equity feels worthless but represents 100% of a company’s future value, so giving away 50% to a near-stranger can become a permanent cap table problem that also costs speed, optionality, and sanity. Practical fixes include vesting, cliffs, tying equity to real value creation, defining what happens if someone stops contributing, and putting breakup terms in writing early. The discussion also critiques employee equity as time-based rather than performance-based, and advisor equity as often unaccountable, where tiny percentages can hide very expensive outcomes.

What to listen for:

00:00 Investor vs Founder Equity

01:26 Equity Is Priceless

03:43 Co-Founder Split Hangover

06:04 Why People Underperform

11:15 Fairness Turns To Resentment

12:44 Will's Unsubscribe Story

15:53 Vesting And Breakup Terms

18:17 Early Employees Option Pool

20:26 Equity As Compensation Trade

21:59 Paying Twice With Equity