The equity side is pretty rough. Founders are very sensitive about disclosing important information about company performance. They are sensitive about disclosing the cap table. Some will share info with investors that they don't share with employees. And they are sometimes trying to pitch optimistically and leaving out items that don't fit the narrative. So you end up with a very vague sense of where the company actually is when you are interviewing. A much better stance is "awesome opportunity, and these are our problems, come help us fix them". Standardization on more disclosure would push hiring toward a higher local maximum.
Something like Geoff's https://blog.ycombinator.com/transparency-in-startup-investi... for hiring companies. For workatastartup.com, you could say "if we make an offer, we'll show you this critical info". It's probably a bit much to expect companies to disclose this in public job postings.
Sam's thoughts on equity at https://blog.samaltman.com/employee-equity are spot on. Especially the 10 year exercise period.
Scenario one. You leave a company after 5 years. You think they will be successful but best case is 5 years before liquidity and 10 years is very possible. It will take most of your savings to buy the stock and pay taxes. You helped with the $20 million to $800 million valuation growth. Now you have no savings, and the money is still at risk because $800 million dollar startups die all the time. You get to bet all your savings that a die rolls 1-2 for 10 times your savings. Roll 3-6 and you lose it all. The expected value is great, but it's a pretty hard bet to take.
Scenario two. Your coworkers realize this and hang on at the company long after they want to move on. Now 20% of your team is just showing up and the company culture is dying. Everyone worries about retention, we should worry about over retention too. It's better for the golden handcuffs be "if I stay, I'll vest these options" rather than "I must stay to preserve the options I vested 4 years ago".
These and 10 other bad scenarios like them are definitely on the con side.
And so easily fixed!