I agree, you should join a startup for the experience of it rather than the risky upside. If you're leaving another company with an equity component, though, it

I agree, you should join a startup for the experience of it rather than the risky upside. If you're leaving another company with an equity component, though, it's a good idea to try and quantify your options. Ideally you are lucky enough to find a company that will both definitely give you the work environment you want, and probably make you wealthy. For a small startup, I recommend asking the CEO tough questions about the viability of the business and planned exit strategy. If they get upset about it, walk away. If they don't get upset, that's good. At that point, ask them to get you in contact with an early investor to ask them questions. If they aren't willing to do that, then walk away. Once you do have an offer, do an analysis. Unless you think they are giving you an abundance, then do a round of negotiation. Negotiating can only help you. Keep it fair and reasonable, though. If it's your first job and you have no experience, for example, don't expect them to budge much if at all.