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Comment by cabaalis | Hacker News Reader

Hanging onto stock from a company I co-founded a few years ago has caused me tons of stress because that company constantly files for tax extensions forcing me to do so as well.

I have other financial processes which rely upon timely processing of my completed tax filing, and every year it causes me trouble. So if something is thought to be worthless and about to fold, "just hang onto it" could cause a non-zero amount of headaches.

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Guessing you're a member of an LLC or shareholder of an S-Corp with pass-through taxation. Can't agree more what a pain it is to wait on your old partners to do their taxes every year before you can do your own.

If you're just holding shares/options in a corporation that isn't going through ownership changes, that problem doesn't exist.

That said, there are still valid reasons to cut ties with past partners/employers.

I feel for the original commenter. My cofounders and I traded the hassle of personal tax involvement for double taxation with my C-corp, and it was truly one of the best business decisions we have ever made.

What's required to let go of the stock? Is a simple signed document sufficient or is it necessary for money to change hands, like in the article?

Sympathy from me.

It is not strange that tax laws favour the well healed lawyered up.

This isn't an us vs them situation. There is nothing wrong with filing a extension. If you don't like it, give the stock back

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