Would you consider leaving your competitive, well benefited job for a startup that could potentially make you quite wealthy if it does well? How do you know when the risk is worth it?

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Depends on financial situation, kids and family plus what kind of cushion you have.

Then there’s the no risk, no reward argument, but I think it would depends if it’s only me that affected or others as well.

Yep. Absolutely. But of course, there's no way to tell so you have to consider if you're stable enough in the event it doesn't go as planned. We can't wait to hear what you do!

Corporate jobs are regarded for providing decent work/life balance, but startups are notorious for being all work, no play. It all boils down to whether the extra money is worth the missed time.

I would take that offer to my boss and leverage the competition to getting a more competitive pay and benefits. If you still think the startup would still top what they counter with, then go for it.

Startups aren't all sunshine and rainbows though. Quite a few of them are terribly unorganized. There are few processes in place, communication routes are ad hoc, as are command chains, and so on. That may be excruciatingly annoying.

Consider the benefits. Start-ups do not receive the same insurance discounts as major corporations. Examine their insurance coverage and how much your rates will be. Also, most start-ups do not provide 401K matching, assuming they provide a 401K at all. The money adds up.

This is too much of a blanket statement - it really depends at what stage a startup is at. Many late stage startups have similar benefits to corporations.

Stock options seem nice, but the chances of that company ever going public or being in a position to benefit from them are fewer than 5%, and even that is optimistic. So don't hold your breath. They may not be the next Google or Amazon, no matter how passionate they are or what they believe.

What stage of funding is the startup at? A series a startup is in a completely different stage than a startup with series D or more funding. You may actually find similar benefits and competitive salary at later stage startups. However even at later stage startups they’re still startups and can be chaotic.

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