quietone1

I see many, many homeless people everyday. Last week I was in a hurry and sat down on the subway next to a homeless man. Within seconds I almost passed out from the overpowering stench of his clothes and body. For some reason, perhaps pity, I didn't want him to see me get up and move to the other end of the car. So I sat there for an agonizing 10 minutes until my stop, and gasped for fresh air when I emerged from the underground. I thought about it - what if I was him, and all I wanted was to not smell like that. How would I do it? I'd need a shower with soap, and new clothes - no way we could clean those old ones. With no friends or support, I had no idea how I'd do it short of begging enough for a bar of soap and then jumping into a chlorinated fountain in a park. And then what? Maybe I smell better for a day or two and then it starts all over again. I'll try to be less judgmental about the homeless, after realizing that.

attractive: empathy valuable: empathy learnable: empathy

note: empathy <> sympathy

you may question whether empathy is valuable by your income-centric definition, but the ability to understand the other side's perspective, to put yourself in their shoes, has served me very well in business negotiations.

Not stuck, I choose to be an employee. There's also a sense of loyalty since the leadership treated me well even when it wasn't clear we were going to make it, and I still enjoy the work I do. In some ways I picked the right company even if we would have never IPO'd.

You missed my point. By pre-exercising my ISOs and filing an 83(b) with the IRS showing that the exercise price and the market price were in fact the same when I exercised, the gain was zero, even for the purposes of AMT. Not everyone will be so lucky to be in that situation where the prices match, but I was.

I was an mid-seniority employee and netted in the low eight figures when I sold my equity stake after our IPO.

A couple important points I didn't see others mention: 1. When I got an offer, I asked if I could take a lower salary to get more equity. They said yes.

2. I pre-exercised all my options. So as far as the IRS was concerned, there was no tax liability when I exercised the shares. This meant by the time I sold, it was a long term gain instead of a short term gain on a same-day exercise+sell. Highest federal + CA income tax rate is 53%, so I would have kept less than half if I didn't get to pre-exercise.

3. I was able to sell when the Bush-era tax cuts were in place. So LTCG federal + CA rate was 25% for me. If I sold those shares today, it would be 37%.

So it worked out for me, but I'm still an engineer and 99% of my coworkers aren't rich - which means I don't talk about it, I don't flaunt it so no Lambo in the parking lot, and I still try to nod in sympathy when they tell me about how expensive private school or summer camp is for their kids. In other words, my life hasn't changed much aside from my bank accounts.