Stock Market: you have access to the cap table, debt, overhang, etc.

Startup Equity: Unknown denominator. Unknown multipliers.

Stock Market: you can sell almost any time (unless you're trading penny stocks, etc.)

Startup Equity: you wait for a liquidity event, or hope your company is large enough to have an active secondary market.

Stock Market: you can buy/sell at any time

Startup Equity: you have the privilege of exercising an option into IL-liquid holding that you pay for now (sometimes forced to if you leave the company) but have little idea of the future value of.

To be fair, i'm working at a startup, I left a public company to do so. I'm here because I have huge impact on my product, I'm learning more, have more impact at the company level, low BS, low regulatory strangle, dynamic team, etc. I think it is rare to have positive expected value on startup equity unless 1. You are the founder or 2. It is a pre-IPO company. Your odds are probably better buying out-of-money NASDAQ Compsite options.

This go-around, there is a lot of private capital, so companies stay private for a decade or longer and lock employees out of liquidity events (meanwhile, founders can negotiate to take some cash off the table during a financing round.) The incentives are skewed. In the 90s bubble, companies with a $50M valuations could go IPO -- you could hopefully sell after your lockout. (Oh, and houses cost a tenth of what they do now.)

This go-around, there is HN, Quora, Blind, and so it is harder for people to get suckered into starry visions.

That said, it is still worth considering working at startups for the high-learning, low-BS environments you can find as compared to big companies.

How is that not obvious already?