I think your overall point is fair -- you own less, but of a more valuable asset now, so you should come out ahead. However, in my experience the ones that say

I think your overall point is fair -- you own less, but of a more valuable asset now, so you should come out ahead. However, in my experience the ones that say dilution doesn't matter are often the ones that are likely to be "made whole" at dilution events or have anti-dilution protections. If you're not experiencing dilution the same way that rank-and-file employees are, I think it's a bit disingenuous to tell them that it doesn't matter. As for its overall importance, most companies simply aren't going to be homeruns. I was at one company that passed on an acquisition offer of $X and opted to take an additional round of funding. A year later, the company sold for the same $X that it passed on. For sure, it was hoping to go much bigger than it ultimately did. But in addition to having to wait for all liquidation preferences to be settled, the employees all got to experience additional dilution for no additional gain. It's great to shoot for the stars and everyone joining a startup hope that's the outcome. But I don't think it's out of place to also think about the median case. An early stage employee takes a lot of risk with few protections.