Bryan bought Gawker after it went bankrupt. He also had a +$200m exit. So he's doing something right. Coincidentally, the company (j2 Global) that bought your former employer worked with the current Gizmodo CEO. That company is now worth ~$4.5b.
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It's not a win if the company was fragile enough to be sold in such a way that made your options meaningless. Wouldn't that options have been $0 if it just went bankrupt?
I wish your options would have made you rich. But both Gawker and Mashable made poor business decisions. And I hope new ownership can fix them and make the companies super profitable.