&gt; I&#x27;m going to post anonymously, but even so, I&#x27;m afraid I have to disagree with how you&#x27;re looking at this.<p>Appreciate your disagreement, but why anon? :-)<p>&gt; According to the article he made about $750k over four years at Box ($95k&#x2F;yr salary + $350k in options total), but would have made nearly 60% more, or $1.2M, working for a more firmly established post-IPO tech company during the same time (say $160k&#x2F;yr base salary + $40k&#x2F;yr bonuses + $100k&#x2F;yr in restricted stock).<p>This was in 2009, when salaries at established companies were not that high. I came from eBay, where neither of the three components were anywhere near what they are today. Also realize that he was in IT, where salaries have never been that good.<p>&gt; Still wouldn&#x27;t have been able to buy a Bay Area house (not sure why you suggest it could),<p>I didn&#x27;t say &#x27;buy&#x27;. Just down payment.<p>&gt; but he would have had all of the other payouts you listed, with basically no downside risk at all.<p>I prefer to define &quot;downside&quot; with not just money, but with the whole experience. Defining upside&#x2F;downside with money builds mercenaries; not missionaries. And in a startup, whatever level one gets in, one should be the latter. If you can&#x27;t be one, then IBM is a better place to be and to stay at.<p>If you are primarily focused on monetary payout, you won&#x27;t be able to do the best work of your life, which is an opportunity a fast-growing organization provides, which nobody else can. And when a 1000 people do the best work of their life, everyone invariably gets rewarded.<p>At that point, 350K or 500K doesn&#x27;t matter. What matters, is that you&#x27;ve spent 4 years of your life with incredible people doing incredible work. That will always open far more doors than it&#x27;ll close.<p>&gt; Seems like pre-IPO companies like Box are increasingly a bad deal for the employees. I&#x27;m genuinely sorry you guys ended up getting the short end of that stick.<p>That&#x27;s the point. We didn&#x27;t get the short end :-) Even Sutton says, that overall he is fine. Because he too, understands that it&#x27;s about the whole experience and the future credibility. He is just ranting about one piece - viz. mismatched monetary expectations and doesn&#x27;t want us to generalize.