I spent ~3 years at Twitter (2010-2013) as an engineer and manager. Made a competitive salary while there. Left with almost $2m in equity (ISOs + RSUs).
I sold the bulk of my position quickly due to serious concerns about tying the bulk of my net worth to a single company's future.
After strike price, AMT, and income tax I ended up with roughly $1m in cash. Probably could have been closer to $1.2m if I knew what I was doing tax-wise.
Not a reproducible pattern to be sure, but it was a nice outcome.
Stories like this one make me feel foolish. I recall not applying to Twitter in 2008 partly because I thought that they were already too successful and famous for the equity to be worth much. Clearly, I was mistaken. (It is a small comfort that I probably would not have received an offer anyway, due to my skills and experience level not being a great match for the open positions that they had at that time.)
Hindsight is 20/20. I thought I had missed the boat in 2007 when Facebook was valued at $500 million. "Clearly they couldn't go much higher than that!" I thought.
I have a friend who got an offer from a startup in 2011 w/ 0.15% equity. He didn't take the offer. The company was WhatsApp and his equity would have been worth $27 million.
I sold the bulk of my position quickly due to serious concerns about tying the bulk of my net worth to a single company's future.
After strike price, AMT, and income tax I ended up with roughly $1m in cash. Probably could have been closer to $1.2m if I knew what I was doing tax-wise.
Not a reproducible pattern to be sure, but it was a nice outcome.