I recently had a conversation with a friend of mine who is the COO of a startup, we were talking the ins and outs of where they were, how the company was doing , and the fact that they are looking to raise an additional round of funding. His company is a Web 2.0 company (isn’t every startup in the Internet space labeled that now?) although it is in a space that I am unfamiliar with, but it is intriguing nonetheless. As we were discussing their fund raising activities, he made a comment that struck me as very interesting. He said that as they are going in to various meetings with investors pitching themselves as a Web 2.0 company and in walks the CEO and he is a “gray hair”, it seems as if it immediately turns off investors. So it made me think, do investors have a certain expectation / profile of what a Web 2.0 company should look like in terms of C level executives?

Fred Wilson has written several blog posts around this topic, what the average age of an entrepreneur is, and many people responded and even wrote their own posts offering their opinions, but the general consensus is that an entrepreneur these days tends to be on the younger side. So why is it that investors are so keen to invest in the younger entrepreneurs versus the older ones (at least that is what it seems like, I could be completely off here)? If you take a look at the recent crop of YCombinator companies, and even the TechStars companies of last summer, you will find that the majority of the founders of those companies fall more on the younger side than older side.

I can understand to a certain degree why investors are attracted to the younger entrepreneurs. For one, they are full of passion and drive and understand the web space fairly well, afterall most of them have grown up in an age where the internet has always been a part of their daily lives. In addition to that, younger entrepreneurs are not saddled with the same responsibilities that some of the older counterparts are (family, mortgages, etc) and therefore can get their startup going for far less capital. Also, they seem to be willing to work around the clock to get their company launched (that is not to say that older entrepreneurs are not, but again they may have certain obligations that may prevent that). With all that, the one thing that the older entrepreneurs have on their side that the younger ones may not have is experience. Industry experience, or perhaps even previous startup experience, experience nonetheless that should account for something.

So there does not seem to be a one size fits all when it comes to the genetic makeup of a Web 2.0 company. Those investors that are willing to take a look at all walks of entrepreneurs seem to me to be better positioned to invest in the best of the best, regardless of the genetic makeup.