Not me but my friends: My first job was at Sendmail. A few friends exercised all their options when they left, writing checks to the company for 6 months of s

Not me but my friends: My first job was at Sendmail. A few friends exercised all their options when they left, writing checks to the company for 6 months of salary. A decade later they company sold for a fraction of what they took from VCs, and no one made any money (and only the VCs got anything back). Ten years before they could finally write off their loss!