I have only skimmed the memo, so I may be missing something, but calling this an "ultimatum" and saying things like "adopt holacracy or leave" seems awfully overdramatic. If a CEO says "Hey, we're rearranging the org chart now," and you can't can't bear the thought of working under the new org chart, then unless you're in a position to talk him out of it, your only real option is to quit. Nobody has to mention the option explicitly; it's understood. That's not an "ultimatum," it's what being an employee means.
This guy is explicitly bringing it up because he's offering extra benefits to anyone who chooses to quit. He's being more accommodating than the average CEO, not less.
I am sorry that I cannot leave a comment of greater value, but this makes me wonder if Zappos needs to reduce the number of employees they have, and if this is a good way to essentially perform a stealth layoff by getting rid of those least willing to be true believers.
I have no reason based in fact to believe that this would be the case; this is just speculation based on my previous impression of Tony Hsieh with respect to his controversial impact on downtown Austin. He seems to be rather invested in being a visionary (if not messianic) figure.
It does flat out say anyone who doesn't like it will be given an offer. I assume that refers to the offer you get when you first join where they pay you to quit. So the letter does flat out say, join the holocracy, no more management, if you don't like it, we have a retirement offer for you.
Sure, but explicitly saying "if you don't like it, have a retirement offer" seems a lot more pleasant than the implicit "if you don't like it, don't let the door hit you in the ass on the way out" that comes with basically any major corporate communication. Those are always your two choices when changes come down from on high. All this guy's doing is making option #2 explicit.
This guy is explicitly bringing it up because he's offering extra benefits to anyone who chooses to quit. He's being more accommodating than the average CEO, not less.