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I don't know how much of a bag holding exercise it is instead of a "treat yoself" moment. Half a million shares at $50/share is $25 mil, minus 50% taxes is $12.5 mil.
That isn't that much money in the bay area. Don't get me wrong. It's a lot. But that's just a $4 million house with another $1 million in furnishings, and I'm guessing a nice car or two. Take the other $6 mil and invest in a diverse portfolio. They've basically sold their stock so they can square away their personal lives.
Won't somebody think of the poor shareholders.
When I treat myself, it's to a takeaway meal that's like $20. Reddit has "never made a profit"™. Siphoning $16mil out of it on day one is obscene.
In what way do you think they've siphoned $16mm out of Reddit?
Awarded themselves shitloads of stock, then sold a quarter of their shares each as soon as humanly possible. That money is not being invested in the company, it's going straight in these individual's pockets.