That's true, but it's incredibly difficult to predict all the factors that would need to happen for a given employee at a new company to end up with a significa

That's true, but it's incredibly difficult to predict all the factors that would need to happen for a given employee at a new company to end up with a significant windfall. Even if you believe in the product with all your heart, you probably don't have the transparency to make a proper valuation, and there are a whole bunch of factors completely out of your control (performance of other employees, terms of later rounds, timing of exit, competitive landscape, macroeconomic conditions, ad infinitum). It's a big gamble. That delta between your market rate and your cash comp at FancyStartup.com is the money you're taking into the casino in your pocket. Be okay with coming back out with zero of it. Take the chance on a startup because you love the product & team, because it's the right role for you in your career development, and because you can afford to allocate some of your lifetime earning potential to taking a chance on it. Okay, so you're still going to do it. Be smart about it. You're an investor: observe the company from an holistic standpoint. Ask the tough questions to give yourself as much transparency as you can get. Reevaluate your decision periodically to make sure it still makes sense. Advocate for your own interests. And be prepared to cut your losses, if need be.