Fred Wilson has been bravely attempting to discuss whether age is a determining factor for successful entrepreneurship — and has been taking it on the chin as a result. As I told Fred in an email, I don’t think he’s come across as being argumentative or dogmatic on the issue at all, it’s just that’s it’s a third rail of entrepreneurship. In the land of equal opportunity, everyone wants to think that they have an equal shot.

Here’s how I responded to Fred’s final post on the issue, where he attempted to pull his hand from the rail:

The reality is that age is a double-edged sword. Younger people don’t carry the baggage that often hinders innovation, but they also don’t have the experience that can prevent naive mistakes (like not seeing your dialog box options through other people’s eyes).

Saying that age is a determining factor in entrepreneurial success is like saying that tireless devotion to your idea and attention to detail are determining factors — there are many factors that are important, but strengths in some can make up for deficits in others.

What’s more important than age is probably the ability to constantly challenge your own assumptions and to see your product/service through the eyes of all of the customers you want to serve.

Perhaps it’s a bit like fiction writing — a great writer can see the world through different characters eyes and is not limited by their own identity.

I do think Fred is raising a very imporant question (and shouldn’t be mauled for asking), but perhaps he doesn’t have quite the right angle. I followed up with this by email:

Perhaps a better angle is that age matters — A LOT — in the use of media and web services. The most successful entrepreneurs will be those who can understand those differences and and tailor their products accordingly — Mark Zuckerberg has been brilliant at serving his peers, and that has been more than enough success, but it’s not clear yet that he understands as well his parent’s generation. Each entrepreneur has an advantage understanding their own age group — the successful ones will be those whose perspective transcends their own experience — that’s what I would focus on as an investor.

That, I think, is the real issue — age only matters for creators of media and web services in so much that age matters so much among users — there’s a generation gap like never before.

In my post about how Facebook still feels tailored to people under 22, Neil Cauldwell, who is in the 20-something age group, responded:

Facebook really is worth all the attention it now has, but it’s the early twenty-somethings that currently reap all the benefits from the service.

I could use Facebook all day without becoming bored. It enables me to communicate more easily with my friends, so much so that I honestly couldn’t imagine a social life without Facebook now. If you want to experience this, you have to build up a network of people that you’d communicate with regularly in the offline world even if Facebook wasn’t there. Otherwise you won’t use Facebook enough to realise how it makes your life easier to manage, i.e. birthdays, events, keeping in touch etc.

You said you prefer to use blogs to keep in touch with friends – but would you use a blog post/comment to ask someone if they were still interested in going for a drink later on that day? That’s how I use Facebook.

I can understand Neil’s perspective as a user, but as a web service provider, suggesting that a huge potential user base simply “doesn’t get it” is not a great way to grow your user base. Facebook is trying to be a one-size-fits-all platform with its core, proprietary functionality (Facebook Platform notwithstanding) — and one size just doesn’t fit all.

It’s not that old generations can’t change their habits — they all picked up web browsing and email when those proved to be killer apps — it’s tempting to aim for creating a killer app that will make everyone change, but that happens oh so rarely. Better to try to look across the often age-driven diversity of online behaviors and create applications that serve people the way they already behave online.