Ever wonder while growing up that your parents just never got "it". And ever tell yourself that when you grow old, you are not going to be like them? That you will be open-minded and try understand the younger generation?
Well, good luck.
I am 31, and am probably going through the worst identity crisis - I neither belong to the young, cool and hip school & college-going generation, neither am I a responsible, "mature" and boring adult, yet. I do not understand why my 20 year old brother loves Abercrombie, and I really do not understand what my 12-year old niece does on myspace and giggles all day about while chatting with her friends.
And now it dawns on me that the speed at which the world is moving, the generation gap is only going to get larger over time.
Which means that entrepreneurs have to try harder. Most businesses start off, because an entrepreneur was frustrated with a problem he/she was having and decided to fix it with their own business. Over time, the problem did get solved, but the entrepreneur slowly graduates to a different "phase of life", however the user generation does not. And there-in starts the generation gap - between the business and the users. Newer problems surface for the users and its time for another business to startup and fix it.
The key to stay successful is to try and pretend to be your user's generation as much as you can. And if you simply suck at it - just hire someone who can understand the user better & trust that person.
The world changes, the problems change, and your solution ought to adapt the faster than your competitors.