schmitt,
As I have posted here before, I was with AFC and also saw what happened at Calix early on.
AFC had a unique option feature - the exercising of unvested options. The idea was to allow employees to exercise when the price was miniscule and hold to post-IPO results. This basically eliminated the AMT concerns for folks if done right. The problem was is that some people used that in 1998 post-IPO. If you go look at a stock chart from then, you will see AFC's trouble post-GTE/China (stock wise anyway). The loss of the CEO was compounded on this and this led to a 90% drop in value over the first 9 months of the year (there was a small recovery in the Q4). There were 2 problems with this. First, people could not sell those unvested shares and had HUGE AMT issues. Second, the stock hit low enough that people had margin calls in their brokerage accounts (imagine financing your home with a margin loan - it did happen).
Calix provided people with loans to allow them to exercise early and start the LTCG clock. This was early on and some folks took advantage of it. Of course, the IPO took a really long time AND there was a big layoff in the early days. People had the bank call the loan at the termination of employment. Which was a problem since people had been paying it off using payroll deduction. Another tough spot.
So, yes I have always same day exercised ISOs (in other words treated them as NonQuals). I am a conservative investor by nature and have seen what can be horribly wrong when you don't cover yourself. I have 5 humorous rules for investing (and I will put my sountrack next after each rule).
1 - Buy Low - There are a good number of momentum investors out there. Me I invested in Real Estate after the bubble collapsed. Buy at the bottom or low. The popular (like Social Networking) means high valuations for not obvious reasons.
2 - Sell High - The other half of 1. Which leads me to...
3 - Take a Profit - You have to have a sale price on any investment. That includes companies by the way. I can not tell you how many times post-optical bubble I heard..."But Cisco offered me $500M a year ago!" And I would think, "And you should have said YES!"
4 - Pay the Taxes - These two posts are all about that. If you are paying taxes then you are making money, but risk based on tax avoidance has to be weighed like any other risk.
5 - Never, EVER, invest in Tech - This is my statement about risk. Do you think Infinera's employees truly understand the future of their company? If you think they do, I can offer 1,000 versions of them not understanding it. If they don't how can you? If you can not predict how exactly they will win, why (for the love of God) are you paying a huge premium for that priviledge of riding their risk. Now as the high risk/reward part of your portfolio...okay. But seriously, consider how much you have at high risk!
The problem with investing is that emotion gets tied up in it. I recall AFC's CFO doing an Investing 101 class for employees during the Optical Bubble. He put up all kinds of numbers that showed how overpriced the market was and that we were all fools for holding onto our tech stocks. He was right and sold nothing himself. Which meant even HE could not buy his own logical arguments. Too much emotion not enough cold hard logic.
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