No. of Recommendations: 8
The problem is that you have too much of your financial life invested in one company. Your paycheck and your investments.
His stock portfolio is basically 50% Berkshire and 50% MSFT
BRK is okay, it is essentially a very diversified mutual fund. But 50% in any single company like MSFT and you are subject to the risk of not being diversified.
When I was at Motorola one of my co-workers put 100% of his 401K into Motorola stock, and was planning to retire (early) in the next year. This was in the late 1990's. Then 2000 happened and Moto crashed from 200 down to 50. Needless to say, he had to cancel his early retirement plan.
He was still working there when I left in 2006.
A 10% discount is a gain of 11%. Take the money and put it in S&P 500. To get LTCG, just wait a year to sell it.
