Earlier quoted context omitted.
Well, life doesn’t always give many chances to play a game. You can only work at so many failed startups, or have so many failed long-term romantic relationships before you’ve used your best years! Someone else already made the point about the risk of walking away empty handed, but I’m just pointing out that some domains allow for many retries and some don’t.
> Well, life doesn’t always give many chances to play a game. Disagree. Sure - you don't get many games involving millions of dollars, but you do get many for smaller amounts. I could put all my extra money into paying off a low interest mortgage (guaranteed return), or I could put it in an index fund (higher average return, with no guarantees, and a potential for a loss). And working at startups: Not sure the expect…
On startups, I think there are people who have been in situations where they have an expected value greater than something like a FAANG $300k/year over 3 years scenario (e.g. they own a large stake in a close-to-IPO company). And they should maybe still walk away, if the 50% chance of a tiny IPO payout would destroy their self esteem and make them feel even further behind their high-salary peers. (Also keep in mind that not everyone lands jobs at FAANG companies, so it shouldn't be super hard to find people who lucked into a startup where their EV is higher than their market salary over a few years). In other words: even if a startup somehow has higher EV, you may want to ignore the EV.