How startups should die

I liked this article thank you. My theory on dying startups is that if its not working its better to go out with a bang (eg a crazy pivot or a high risk high reward gamble) rather than a bleed out.

FedEx was a good example of this, if I recall correctly the CEO took all the cash they had and went to Vegas with it. Usually wouldn't turn out well, but that time it did. If you need money, and have exhausted all your options you have to take a course of action that gives you a chance, no matter how slim, over the slow bleeding death which would be a long painful and hopeless experience.

Not compromising ethics like you mention is so important in life. Ethical decisions are harder in difficult circumstances (teetering over the cliff of failure) but those moments in life are when your ethics count for the most and mean the most, and as you mention they can also pay off in the long run (but this shouldn't really be a consideration from a purist ethical standpoint). The captain shouldn't go down with that ship.

Basically boils down to an 'honor code'. When you are going down imagine yourself as a great person and that history will remember every action you did. If you keep your respect and dignity people will respect you and you live to fight another day. If not no matter how successful you may or may not be, someone will someday say: "yeah its a great company but he fu*ked so so so over". You don't want to be that person. You want to be: "yeah he put 3 companies under but he always manages to pay his debt".

Just curious, but how much would a list of 1-million targeted emails go for? High five figures? Low six figures?

I'm trying to put myself in perspective of his struggle -- was he potentially buying another year of runway? Another month?

Yep, this is the lesson of not burning bridges that you worked so hard to create, even if it makes your life harder in the short run, it will work out in the long run.

Recently a guy applied to the current place I am working, and unfortunately I had to explain to my superiors about his history of poor interpersonal skills at another job that we worked together at. This guy wont be getting a job now.

Work hard to make sure that when you leave, it will pay dividends in the future.

Part of the question here is also, "What did you promise (implicitly or explicitly) when you got those email addresses?" That's really where it becomes an ethics issue. Our data gets sold every day.

Another question is, "Did everyone get paid?" He did the right thing and saw to it that everyone got made whole. If the business goes into bankruptcy and some creditors are not being made whole, it's much harder to not sell the email list if you can do so legally.

It's during tough times that you see what people's ethics really are. Great job by the OP addressing some of these.