Sort of a devil's advocate question, but does the value of the options deal depend a lot on a person's ability to choose and join good startups? One example I'

Sort of a devil's advocate question, but does the value of the options deal depend a lot on a person's ability to choose and join good startups? One example I'm thinking of is Josh Elman who seemingly got into the VC game just on having worked at three companies that went on to IPO (LinkedIn, Twitter, FB) and so that was a track record that could stand in place of an investment record. It doesn't seem that impressive to me to have known that those three companies were going to do well, even pre-IPO. But is that repeatable? Basically, if you are getting into top tier startups then a lot of your lottery tickets hit at least a little bit. Sure, nothing beats a FAANG salary for average financial gain. But even little hits do a lot to even out the lower paying years. I've been getting equity since 2005 and my experience is that there are a lot of winners around me. Is that just luck (to some extent, I'm sure). But could a person gauge a bit whether they are in the in-crowd of companies that seem likely to do well? Options for the first 50-100 employees do make a meaningful difference in someone's life, so you can join a company pretty late and have a pretty good sense of their traction. I had or have equity in Odeo which would have led to Twitter stock if I'd stayed longer, Calm, Medium, Beyond Meat. I turned away Pinterest's corp dev when they were hunting to acquire a mobile team (not sure how serious, but I think we would have been a good team for them). So, that's a lot of winners that either actually hit, seem like they might hit, or that I was very close to. I had equity in Wesabe which I think would have been Intuit's acquisition target if Mint (an abnormally excellently executed startup) hadn't gotten their first. That would have been $500k to me. Also had equity in Branch, acquired by FB and Neighborland. Those are the "losers." I keep a loose accounting of how my friends did too, which is also a big part of why it feels like I've been working inside of an in-crowd. I started and then shut down a two person company. That other person went to Yammer (employee 70-ish) and made a big chunk of money. Wesable's CEO ended up VPE at Etsy and Stripe pre-IPO. That Stripe equity has got to be massive. A lot of the Wesabe team has done a stint at Stripe. The VP of Product at Odeo was the VP of something as Fitbit IPOd. The Branch founders got the FB acquisition and also had some Beyond stock. The people who've left my current company have all landed in good places including Squad which just got acquired by Twitter. A lot of my former team is at Medium (which I'm close enough to to feel pretty confident is a winner). Our employee #1 went on to be employee #57 at Pinterest. Again, I'm not comparing this to FAANG. But I never wanted to work for those companies. Instead, I wanted to work for startups because that's what interested me. But I also want to be able to retire and own my home and so for me, Options, are a big part of the mix that made that possible.