I think what articles like this accurately capture is that stock options are a crapshoot. What they don't accurately capture is that if your only goal is to max

I think what articles like this accurately capture is that stock options are a crapshoot. What they don't accurately capture is that if your only goal is to maximize expected earnings over the next 4 years, then startups are unlikely to be the best strategy. I think an analogous mistake would be interviewing someone at Google who says they hoped to advance their career and learn a lot about common software frameworks and programming languages, and instead they only got promoted once or twice and mostly learned things that are unavailable and unheard of outside of Google. That doesn't mean Google is a bad place to work, but it does mean that it wasn't the right place for the person given their initial goals. Some of the things startups are good for: 1) Higher potential earnings. EV might be higher or lower depending on the startup. At Google, you get a $175k salary and a $300k stock grant over 4 years. The stock might double or triple but won't 10x or 30x. If you joined a company like Pinterest or Uber 3-4 years ago, you might've gotten $100k salary and a S300k stock grant over 4 years, but that stock has gone up 10x or 30x and is now worth $3m or $10m (at least on paper). 2) Better shot of quickly shooting up the career ladder, having a lot of responsibility, and so on. 3) Great opportunity to learn things outside of your current comfort zone. Startups are not good for: maximizing steady salary + predictable equity, blending into the crowd and having more free time outside of work, going really deep on one area instead of working on a lot of different areas, and so on. Finally, I think using Box in the article is potentially misleading. By the end of 2011, according to https://equityzen.com/blog/box-path-to-ipo/ https://equityzen.com/blog/box-path-to-ipo/, Box was already valued at $600m. The current valuation is only 3x that, despite the company having 20x more employees. There are other startups with a similar trajectory, like Etsy. However, there are also companies like LendingClub or Lyft or Uber, where joining 4 years ago would've provided a 10x or even 50x for an employee. 10x or 50x on a $200k or $300k initial grant is huge.