Options are a lottery ticket
A company I used to be associated with sent out an email yesterday that essentially explained that everybody’s shares were now worth a great deal less, and that preferred shares were now common stock. I’m not mad about it: in fact, I think the restructuring was a good thing, and the cap table is now optimized for employees of the current phase of the company, which is how it should be. (The company, which will remain nameless, used to be troubled but is now doing really well under a new CEO. I like both the old and new CEOs very much, and there seems to be alignment between them on what needs to happen, which helps.)
I did not exercise my options at that company, so I have lost exactly nothing. In fact, I’ve never exercised options at any company I’ve been a part of.
This is maybe a bit of a self-own: that implies I’ve never been a part of a company that I felt strongly enough about that I wanted to own part of it. That’s actually not true. I own a significant chunk of Latakoo, the company that powers video delivery for news networks around the world — but I bought those shares as a direct investment at a low price while I was a very early employee, rather than as options. I also own shares in a few other companies that I’ve either advised or been a part of. (I’m also always interested in advisory roles in other companies in exchange for equity.)
