I would've killed back in 2001 when I bought my first iPod to get a hold of some Apple shares since I knew right then that Apple was onto something.
On the other hand, Microsoft, which happened to have some extra cash laying around, once again didn't have a clue at the time:
All told, Microsoft spent a little over $151 million to acquire 18.2 million shares of Apple stock, for roughly $8.31 per share. Microsoft confirmed that it sold all of its AAPL holdings some time ago, and likely did so at a healthy profit—after all, AAPL has traded significantly higher than $8 for many years. But what if Microsoft had held on to that investment just a little longer?
I bet whoever had the power to sell those stocks at Microsoft feels like a total twit!