A little over a year ago — sometime last August or September — I started faffing about with Twitter, as early adopters here in SF started to spread the word about it.

I liked it immediately, thought it was perhaps a wee bit twee. But we liked enough here at Vodpod we built a way to let you “tweet” a video from vodpod last December, just weeks after we launched our service. And we spent a great couple of hours dissecting its appeal with some very smart lads, Matt Webb and Jack Schulze.

Twitter really exploded in the Spring of this year, championed by Scoble and getting a lot of attention at SXSW. Funny, though, my interest in and attention to the service waned about then.

So I’ve been delighted to re-engage with it the past week or so. In part, it’s been for prosaic reasons. I saw that Rafe Needelman was doing a Twittercast from Web 2.0, and I’ve been checking out the various AIR (totally loving Twitterific) and iPhone clients and playing with twittering from the road. The Twitter folks get an A+ for their API work, something we’re trying to emulate here at Vodpod.

It’s fun to be back using the service. For my money, it’s a far more interesting than the other hyped up service of the day. In the end, both are really about communication, but there is a richness and layered-ness to Twitter I just don’t find with Facebook. And interesting lesson given how much more complex Facebook is, and how simple Twitter is by comparison.

VC Fred Wilson started an interesting conversation of few weeks ago about “the mid-life entrepreneurial crisis” in which he noted how few entrepreneurs are over 40.

His initial post was followed by many others.

I’m a first-time entrepreneur in my early 40s, so I’ve found the arguments and debate interesting.

Based on my own experience the past year, I have my own personal theory about this.

I’ve come to the conclusion that a critical attribute — maybe the most important attribute — of a successful entrepreneur is the willingness to be deeply, profoundly contrarian. The fundamental creative, productive act for most entrepreneurs is placing a bet on an idea and product and market that seems compelling and logical to them, but that others perceive as, well, not sensible.

Look at the biggest success story of the web to date, Google. Their success, in hindsight, seems so obvious, but we’ve all heard what seem like countless tales of Sergey Brin and Larry Page going into meetings in the late 1990s, and being laughed at for thinking search was relevant or interesting or likely to ever make anyone any money.

I think this is why we see more successful entrepreneurs starting companies in their 20s — it’s just easier for people to hold deeply contrarian beliefs at that age. Push an idea that seems crazy or unlikely, you’ll probably look like a romantic, rebel or revolutionary to your peers — even if you fail.

Whereas it’s harder to do this in your 40s. You are less likely to look cool and revolutionary when you’re betting on a deeply contrarian idea (i.e., an idea that your friends and family and peers will all think is ridiculous or dumb or crazy), and more likely to look like that 40-year-old bachelor on the dance floor, with a paunch, strutting your white-man overbite moves to 50 Cent.

Perhaps this explains why many startup veterans become VCs in their late 30s and 40s? It allows them to back crazy ideas pushed by young entrepreneurs, while appearing stable, reasonable and rational to their friends, family and peers.

When SecondLife hype swept the land a few months ago, the recent spasm of SecondLife backlash was sadly predictable.

I’ve been wanting to jump in and offer a comment about all this, and the related Bubble Watch & “Web 2.0 DeadPool” fetishes that currently grip the Silicon Valley commentariat for a couple of weeks. And I will do that in a day or two, but first let us celebrate this lovely related development mentioned yesterday on BoingBoing.

Which is: a hardly original (but so many had to just gush, “Hilarious!”) parody of SecondLife hit the web the last day or two called GetaFirstLife. Get it? Hilarious! Totally original! So wry! That’s the exlamation point-with-irony-on, by the way.

SecondLife aka LindenLabs, to their credit, took this in stride and issued a “Proceed and Permitted” letter (instead of a Cease & Desist letter) to the creator of the parody. As the BoingBoing article (and creator) point out, a classy move — and in my book, more clever than the parody that prompted it.

Since last Fall, at the Web 2.0 conference, or maybe even last spring, the "new bubble" meme has been gathering momentum among digerati. Like night following day, it has been followed by the "bad time to do a start-up" meme, captured best by these two posts.

I more or less agree with everything Caterina Fake writes in her post, and the list David Hornik posts is frightening even though it doesn't even begin to capture all of the start-up activity out there.

So, why the headline? Because I think there is a counter-intuitive argument to be made that the tail of an expanding bubble oftent provides a great environment for disciplined entrepreneurs and start-ups, and I think the tail-end of this mini-bubble is six to twelve months away.

There are two points to make here. First, take a look at the list Hornik provides. In addition to the length of the list, what is most stunning is that, if you look deeply at many of these companies, many are trying to do the exact same thing, chasing after a very small number of opportunities, and solving just a few significant consumer problems. Most of them have not through their business models or strategies. And, in many instances, they are going after the exact same audiences — there is an amazing amount of activity concentrated around the under-24 segment right now, for example.

So ironically, despite the super-abundance of start-ups, there remains a decent amount of "white space" — i.e., entrepreneurial opportunities to solve real, significant problems for real people. Disciplined entrepreneurs will find and discover this white-space, stay focused, and learn to treat this incessant buzz of activitity as the white noise it is. And, they can be confident that 90% of these lemming-like start-ups will fail and run out of money in the next 12 to 24 months, and the list probably won't be as extensive in two years time as it is now. Remember the difference between, say, January 2000 and July 2001?

(As an aside, there is an interesting sociological post to be written about why this is so. I think it's basically because alpha geek culture, in many respects, can be monolithic and lemming-like during bubble-periods like this one. Many of the folks doing these start-ups read the same blogs, talk to the same small group of people, go to the same conferences, and get consumed with a limited set of problems. Blogging and services like Flickr give us the ability to watch and document all this from the comfort of our couches).

The second point is one I make with less confidence, with just some anecdotal recollection from the last bubble/boom for support, but which I think is true and that others could support with more detailed evidence. And that is that the height or tail end of a bubble is a great time to get financing. The valuations are better, the entrepeneur can raise more money with less dilution, and potentially have more in the bank to get through the dire times — which will come again with certainty.

While it was certainly a great time to start a company in 2001-2003 — there was such a dearth of activity, and doing just about anything was interesting — it was hard to raise money, and nearly impossible to do so with advantageous valuations.

So this coming period seems to me to offer, potentially, the best of both worlds. It's a pretty decent time to try to raise money, it seems, and there are plenty of interesting opportunities out there. This happened in the last bubble period. Google is clearly exhibit A for this during the last boom — it raised a bunch of cash at a decent valuation at the height of the bubble, focused on an idea that was deeply out of favor with the reigning digerati at the time, stayed focused, survived the bust with their cash, and we all know what happened after that. While Google was certainly the most spectacular example of this, I can, as I sit here typing, think of at least half a dozen other similar outcomes.