Hindsight
I really wish I had some apple stock. Should have bought it back in the 90s
Hindsight is wonderful, isn't it?
Regret isn't.
Unless you have a crystal ball or time machine and saw the future and did not act on what you knew, then there should be no regrets.
No one knew where Apple would be today.
Anything could happen. That is what life is about. What if something had happened to Steve Jobs earlier than it had? What if Ivie had left Apple? What if Apple had a fail in confidence on the iPhone? What if the iPod had failed?
What if? What if? What if?
Apple was so close to failure and shutdown back in the day, that Steve Jobs knew it COULD have happened. That's what the stock options scandal was all about.
Anyway, for peace of mind, you may wish to read this book by John Bogle:
http://www.amazon.com/Little-Book-Common-Sense-Investing/dp/0470102101
Index funds beat professional stock (managed fund) people 80% of the time.
I feel that Apple stock has been high risk up until recently. Steve Jobs was truly very key to its early success. He had the crazy passion and vision. Apple's success for the very most part is because of one person.
Would you bet your money on one person? What if back in 2001 he'd eaten a bad piece of raw fish at a sushi restaurant?
Most people should keep their money in broad-based low-cost index funds. Maybe have a little play money for stocks, but the index funds will beat most people guessing most of the time.
Peace