One of my sons is a fairly new employee at Microsoft. He started in August 2022 and has been participating in their ESOP, where he gets a 10% discount on the current price. The company buys shares for him quarterly, and it's just an automatic deal obviously that's oblivious to price and value.

Many people in these plans, from what I understand, use this discount to buy and then immediately sell the shares to capture the discount (less ST cap gain taxes). I told my son he should just amass as many shares as possible, thinking that MSFT could be a good LT investment and over the very LT he would come out better.

But with the huge recent runup in the price of MSFT is that still the case? He's about to hit the point where he could sell at the LT cap gain rate, so that's what's triggering my question I guess.

His stock portfolio is basically 50% Berkshire and 50% MSFT at this point, and his basis in MSFT is about 250.