Agree. In my case I'm not as diversified as I would like. I have a excessive position in my previous employer whose CEO and other execs I know and respect. Problem is my tax cost is very low and selling any of this stock would cost me big tax dollars. I know I should do it at some point and will-probably over time. In the meantime they are doing exceptionally well and I expect them to resume dividend increases within a year. The pension plan is very well funded too.
Wanna hear some devil's advocating?
A couple years ago I had another poster on this board call me out for my lack of diversification in a similar situation. In this case the CEO is Warren Buffett and the other execs are Berkshire Hathaway employees. We'd held those shares since 2001 and they'd more than doubled in price. And yeah, we took a humongous cap gain when I finally got off my dead assets.
I'm really glad this friend hit me upside the head with a 2x4, because we reluctantly rebalanced in Feb 2008 and the share price still hasn't recovered to that lofty [-]plateau[/-] peak. We were talking most of the kid's college fund and nearly a fifth of our ER portfolio. The former is now all in CDs (she starts college in 109 days) and the latter is now slightly more diversified.
I didn't appreciate it at the time, but just eight months later we were able to wipe out all of that nasty cap gain-- through humongous cap losses on tax-loss swap sales of the rest of our portfolio. We even have cap losses to carry forward for 5-10 years. Hopefully you don't have the same "opportunity".
So I don't know if your CEO is in the same respect class as Warren Buffett, and you probably know your CEO/execs better than I know Buffett & team, but I doubt that will offer you much comfort if their share price drops by over 50% from its peak. It tested my comfort level.
If we're as good at investing as we say we are, then we shouldn't base selling decisions upon taxes. In fact, paying cap-gains taxes should be the fervent desire of every stock transaction. Hopefully long-term cap gains taxes, but short-term cap gains are better than some of the alternatives.
Dividends & pension plans... yeah, I bet that dividend rate looks twice as good when the share price is whacked in half. We have another poster who followed Bank of America's downward spiral (and ever-rising dividend rate) right down until the dividend was cut to a penny. And 401(k)s are a lot easier to fund after the layoffs.
Black swans. I'm just sayin'.