One of my favorite quotes of all times was Ted Leonsis’s statement in the mid-1990’s that “MSN will be Microsoft’s Vietnam.” Ted said this around the time that MSN launched (on a proprietary platform – pre-Internet) to compete directly with AOL. 15 years later this seems like such a prescient statement. I have no idea if Android will be Google’s Vietnam. We’ll have to look back 15 years from now to really know. But as I watched the T-Mobile G1 Video and read through some of the Android early criticism (and praise), I kept asking myself “why?” I have my own guesses as to the answer, and I know the public answers, but when I sit on the outside looking in, I have way more questions than answers.

Fred Wilson gave a phenomenal speech at Web 2.0 Expo NY titled New York’s Web Industry From 1995 to 2008: From Nascent to Ascendent. It’s about 25 minutes long – worth watching from beginning to end. It’s a fantastic history lesson that details the rise, fall, and re-emergence of the Web industry in New York. As part of this, Fred makes a plea to “bury the name Silicon Alley.” He hates it in the same way I’ve always hated the names “Silicon Flatirons” and “Silicon (whatever)” to describe the tech communities in other geographies than Silicon Valley. Fred appropriately suggests that we should call “New York” simply “New York” – which I completely agree with.

Bambi Francisco was at TechStars Investor/Demo Day in Silicon Valley yesterday and did a short interview with me on how TechStars works. Mom – please listen to at least the first 30 seconds as Bambi calls me a technology luminary!

Yesterday was an exciting first day back from vacation for me. I spent the morning at the Microsoft Campus doing our TechStars Demo and Investor Day for Silicon Valley. It was well attended and showcased a number of the 2007 and 2008 TechStars companies. Dan Kaplan at VentureBeat had a detailed write up on it titled At TechStars, twelve teams show that Boulder, CO can produce some fantastic tech and Jason Kincaid at TechCrunch weighed in with his views in the post titled TechStars Demo Day: Acquisitions Galore As Twelve Companies Strut Their Stuff. 

I’m sitting in my hotel room in Palo Alto after 20 hours of travel from Hampshire, England. Amy and I took our Q3 vacation in the English countryside at the Hampshire Four Seasons where we had a glorious week off of the grid. I find myself really wanting to be tired, but I am so far beyond tired that I’m wide awake well past midnight California time. Our Q3 vacation was dynamite. I would have never thought to choose the English countryside, but Amy loves horses and our Q3 vacation is near her birthday, so we go wherever she wants to go. The weather cooperated in some sort of pleasant karmic-recovery from our abysmal Alaska weather (yes, I know they are uncorrelated events, but one can fantasize), my runs along with Basingstoke Canal were awesome, and the food surpassed expectations.

As I was hiking up Quandary Peak on Saturday, I regularly looked at my Garmin 305. I had four data fields displaying – distance, total time, heart rate, and lap time. After about two miles, I asked Dave how high he thought we were. He pulled out a topo map, looked at it for about 15 seconds, and said “around 12,500 feet.” Up to this point, I was doing a simple calculation between distance and elevation based on the assumption that there was approximately a straight line between the start of the climb at 10,750 feet and the peak 3.3 miles later at 14,270 feet. While I was doing this calculation in my head at the two mile mark, I looked at my watch and realized it had a data setting for elevation. Doh. And yes, we were at about 12,500 feet.

Recently, I’ve found myself in several situations where I realized the complexity of each one had spun out of control. Rather than be able to make a rational assessment of the situation, collect a set of specific data, and make a decision I found myself in a discussion that was going around in circles. When I was a kid, my dad used to refer to these situations as “complicated mistakes.” You’d make a mistake and, in an effort to deal with it, you’d pile another mistake on top of it. Before you knew it, you had a complicated mistake which was much harder to deal with.

Santo Politi has a great post up today titled Election 2008 and Price of Crude. We were in a meeting together today and he mentioned it (but didn’t mention the content.) Santo’s cynicism is right on the money as well as his concerns. It’s definitely worth a read.

A CEO friend (who also is an excellent salesman) sent me a fun post titled Sales 101 with the comment “here’s one that will make you laugh in a sad but true kind of way.” Yup – this pretty much sums up the dark underbelly of high tech sales. If you are a VP of Sales in a high tech companies, read slowly and see what you can do to improve the situation.