I have two offers on the table: one for $110k at a pretty boring insurance company and one for $95k at a cool tech startup I actually like. I tried to get the startup to match the $110k, and they told me the equity makes up the difference, even though I know that equity is likely worth zero. Is it ever worth taking a $15k pay cut for potential and a better brand?

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If you think the equity from the startup is likely worth zero you shouldn't get involved with them at all. Working for a startup is challenging and can be chaotic and if you don't believe in the company's prospects there's no good reason to work for them. If you think the equity is worthless, you're expecting the company to fail. Go with the stable, if boring, offer.

Boring insurance jobs aren’t going anywhere. If you feel like 15K is a fair trade-off to do interesting work, then I don’t see why you shouldn’t consider that offer.

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