How do you actually value equity in a company that hasn't gone public yet? I’ve been headhunted for a dream role at a startup, but the pay cut is making me sweat. The stock options are technically worth a fortune on paper, but if they never IPO, they’re basically worth nothing. It’s so tempting to trade a guaranteed salary for a chance at a windfall, but I’m terrified of being the guy who took the gamble and lost.

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Sometimes the risk is worth it. If I was young and hungry still, I might go for the opportunity. Now that I am older though, I really value stability so that isn't a risk that I would want to take.

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It’s definitely a risk but if it does go IPO, the definitely worth it. I would risk it if I truly believe in that company and its values.

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