[baccredited]

I was around employee 100. Had options that were worth about 1.5 million at the peak, then the internet bubble popped and by the time I was fully vested and able to sell it was maybe 1/10th that--$150K or so.

In hindsight, I could have shorted the stock at the peak to lock in the price of the unvested shares.

The whole experience makes me think most engineers should value options at basically zero. Save an aggressive part of your regular salary so you can retire by 50 years old. If you get a windfall great, if you don't you are working on a strategy to become wealthy with a near 100% success rate.

[technofiend]

Not an IPO but I was hired by a company that was supposed to extend me an offer including stock options, unfortunately there was miscommunication about shares vs options, netting me 1/100th of what I expected. I was so angry I seriously considered taking a short position against the original amount of stock I was promised, but in the end it just didn't feel right to bet against my employer. A year later and their stock had dropped from $43 to 50 cents which would have netted a huge windfall. The money would have been nice but I don't regret standing on principle.

[baccredited]

I agree with you.

My short would not have been a bet against my employer, more about being satisfied with turning paper gains into locked in, real money gains.

[marketgod]

In many cases you aren't allowed to short employer stock, it's sometimes in the employment contract you sign. In other cases, shorting your employer can get you investigated for insider trading. Also, your employer might fire you. Probably want to talk to an attorney before doing that in the future.

[tmp192489]

The current tech boom is nothing like the dot-com bubble...

[jdsully]

Uber and Lyft giving out dollar rides for $0.90 with almost no competitive moat. Pretty similar situation I think.