"Microsoft, Apple, Yahoo, Google, Facebook, etc." - it's interesting to see Arrington so narrowly define successful entrepreneur stories.
Dietrich Mateschitz, the founder of RedBull, was in his mid-40s when he started the company and it wasn’t until he was in his mid-50s that it really took off.
In my experience the 40s seems to be a sweet spot – resources, contacts, and experience all come together at that point . . .
One useful strategy for avoiding this affect is to move around a lot and to deliberately remain a little undereducated about the things you don't work on. That way, if you ever feel like you've grown too cynical about the field you're working in, you can switch to something else and approach it as a complete newcomer.
Software is used in so many places that it's easy to regain your newbie status any time you feel like you need it again.
I get where he's coming from, really I do. I strive to keep that attitude as well, and I put my money where my mouth is by actively living that life, not just writing about it or thinking about it from a distance. I'm the guy getting the fist bump, not the guy trying to remember how to give one.
Having said that, and agreeing with the general sentiment he is making, you can only take this thing so far. At some point, being alive for a year should give you some kind of insight you didn't have at the beginning of the year. If not, you're turnip.
As I get more and more inside of the startup community, as I finally begin to start feeling like I am figuring this thing out, I'm beginning to separate the external "business of startups" guys from the guys actually having a startup. The external guys all have googly eyes, romantic writing, praise of youth, and run in herds. The internal, real-world guys don't have time for all that bullshit and simply go get the job done. That means taking the baggage you have -- both good and bad -- and working with it.
I sure hope I am different now than before, and I sure hope I continue to be different as time moves on. Yes, youth and naiveté are a critical requirement for creating that change-the-world startup, but they are not a sufficient requirement for it. The reason startups work so well for 20-somethings is that you can throw a thousand of them at a problem and then pick out the 2 that fix it, not that somehow youth and attitude carry the day. It's a numbers game. It's the same reason that we pick 20-somethings to run up the beach on D-Day. Somebody has to take the beach, and more likely than not it's going to be somebody who never really understood what the hell they were getting into.
I think there's another age-effect for new technology, that young people will learn that, rather than enhance their skills in an existing technology.
A test: if this is true, then fields with faster-moving technology (eg. silicon, software, internet, gene-sequencing) will have a higher proportion of young entrepreneur than in other fields (eg. earth-moving equipment, iron processing, civil engineering, fast-food). Of course, the faster fields will also have more entrepreneurs in absolute terms, because they'll have a greater number of disruptive opportunities, but here I'm just considering the proportion.
Statistically, there's also greater tolerance for risk in the young because no spouse, no kids, no mortgage.
Neither factor is intrinsic, and needn't apply to a particular entrepreneur.
For every youngin' out to change the world, there are probably two oldsters who can remember why the last, similar, effort failed. But it's quite possible that while one of oldsters will stand in youngin's way, the other one will give him a boost and some good advice. Sure, Brin and Page started Google out of grad school but Terry Winograd added some good advice.
Yeah but Craigslist, Amazon, Wikipedia, ... were not started by 20 year-olds. Ok, last one is not a company...
Some interesting related links:
http://en.wikipedia.org/wiki/Late_bloomer
And in mathematics:
http://mathoverflow.net/questions/3591/mathematicians-who-we...