"Act like an owner." You heard it in your first week, maybe in the offer, dressed up as equity. Then you read the paperwork: four-year vest, one-year cliff, a 90-day window to buy your own shares after you leave, or forfeit them. Most people can't scrape together that check, so they walk away from stock they were told made them an owner. That's not a loophole. It's the standard deal.
Say you make it anyway. You vest, you exercise, the company sells. The money doesn't split by who owns what. It splits by who holds a liquidation preference, and the people who wired in the capital wrote themselves to the front of that line. On a great exit there's still real money for common stock. On the far more common exit, the preference stack eats the number and the people who were told to act like owners get a rounding error.
I call this ownership theater: the rituals a company performs to get owner-behavior out of people it carefully arranged not to make owners. Equity engineered, through cliffs an
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