Having been through 3 exits at diff stages from millions to unicorns, the biggest issue with this is actual hours worked to comp.

If you work 40hrs/wk for 100K at Big Co vs 80hrs/wk for 100K at Little Startup you need to now make 50K in equity *per year* just to match. https://twitter.com/yanda/status/1299050301429694465

If the company goes out of business (which is more statistically probable) then you basically lost $50,000 in a year. In 2 years you've lost $100,000. Yikes.

Having done the actual calcs I would have made more ultimately by working at Microsoft for 10 years than 3 exits.

Microsoft or Google pays way more, like double, so immediately you're derisking loss. Secondly, they still give you equity but there's is real equity you can sell. You can't just sell all your shares at a startup. If you're real lucky they will let you sell maybe 30% of them.

I prefer startups for the culture and challenge. I like wearing lots of hats and smaller teams and having a large impact. However, don't let anyone trick you into thinking you'll be rich with equity in a startup.

Might as well buy lottery tickets