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Comment by cuca_de_chumbo | Hacker News Reader

Also, I'd be leaving a job I really don't like at a Silicon Valley spinoff. $150K salary, 0.75% equity, shiny CEO with regular Fox-Business-News appearances, rising company notoriety, selling into a hot market. The company will never raise more "venture" funding, the parent will structure future injections as debt (at a reasonable interest rate, likely, but probably less onerous than VC).

This current company has a highly dysfunctional development culture, no automated testing, poor choice of deployment vehicle, a VP high on the DK spectrum. I can't bear it.

The place has a very high likelihood of acquisition in the next 2 years. It's a question of how long product dev can go on before the product implodes vs how quickly the shiny CEO can attract a good buyer for the polished turd. I lose a bit of my soul every day.

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Are you there for the money or for the love? If money, stay and suck it up. If work represents a large portion of your happiness, bail.

2 years is not really a long time to live in suck-it-up mode, although your perspective will depend on which side of 30 you're on.

On the way-later side of 30!

The current company is legacy-land as far as development tools goes (though they're reliable and in the right hands do very well). The prospective startup would involve new tools I need to "keep up-to-date".

I did a short (paid) project for them involving some popular scripting significantly-hipper-than-Perl language and delivered it in serviceable, idiomatic form that I know they were very happy with, using all the right libraries. I picked it up the tool/language quickly enough. I feel I need that experience and exposure to maintain my longevity in the SW market. Sticking with the current company is 2 more years I become more of a dinosaur.

Honest (but uncomfortable) question. You wrote:

I feel I need that experience and exposure to maintain my longevity in the SW market. Sticking with the current company is 2 more years I become more of a dinosaur.

Is the new company aware that you feel like this, both about their tools and about your career?? If so, I wonder if they're compensating you as a more junior developer, simply because it sounds like you think that you need them!

Are you able to get the payout for that equity if you leave that job? That is, are you vested and can you exercise the options without significant pain?

Exercise != payout

Exercising options generally gives you shares in the company, not a payout. A payout would require selling the shares. Normally you can exercise vested options at any time very easily. Selling those shares you received from the exercise for cash is not as easy.

I understand all that. But typically you must exercise incentive stock options within three months of leaving a job, or lose them.

If the OP can exercise his options right now for an amount of money he considers not terribly significant, then he could quit his job now, and if the old company monetized in the next couple of years (which he stipulates is reasonably likely), then he can still get the payout for it.

If on the other hand his options are not vested, or he can't afford to exercise them speculatively, then if he changes jobs now, he throws away significant equity that he thinks has a good chance of monetizing.

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