As I live my Digital Life theme, I realize that sometimes I need to take a step back to take a step forward.  This happened today when I was in the shower.

When I switched to an iPhone, I lost the ability to synchronize Outlook/Exchange Tasks.  I’m a heavy Task user and a zero inbox person, so I spent a few weeks trying to find a good workaround.  I didn’t find it yet.  So – I started typing my tasks into a page in the Notes application on the iPhone and emailing the page to me at the end of each day.  I then cut and pasted the individual entries into my task list.  Stupid, but it was the best option up to that point that still integrated with my Outlook workflow (yes – I tried Evernote and a bunch of other similar things.)

For the past two weeks, I’ve been carrying around a little moleskin notebook that my friends at WordPress game me and scribbling down notes in the notebook.  I’ve had fun with this approach and realized that having the freedom to just scribble down my thoughts as "items" liberated me some from the more task oriented view I have taken for the past N years.

In the shower this morning, I realized that this was exactly what I was doing in Notes on my iPhone with a few minor tweaks to the formatting.  I was resisting Notes because I really thought I wanted Tasks and this was blocking my ability to see that the Notes approach actually worked better.  Of course – if I could automagically have selected Notes go into my Task list, that would be even better, but I’ll live without it.

By working on paper for a few weeks, I made a minor behavior modification to my own workflow that I think will be more effective for me.  Interesting.

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.

If Google is really serious, they’ll do what Apple did – license Microsoft ActiveSync and immediately create transparent integration with Exchange (hey – don’t forget to write the 74 lines of code that will sync tasks.)  I’m a month into using my iPhone and it’s here to stay – it is so superior to Windows Mobile 6 on a Dash that I can’t even begin to describe my pleasure with it as an integrated mobile device.  I’ve gotten used to the keyboard and can now type on it about as fast as I could on my Dash and my old Sidekick.  I continue to hear this as the major complaint from semi-converts, but I just don’t see it.  You definitely have to change a few things about how you type on a small keyboard, but I had to do that with the Sidekick (thumb clicks anyone?) and the Dash (keep your fingernails really short.)  Yeah, there are still plenty of things that could be improved, but with each incremental release I see them get fixed.

As I ponder Foundry Group’s digital life theme, including the hour long conversation I had with a new Microsoft friend at dinner last night, I realize that I believe forced migration of an individual’s legacy data simply won’t work.  I have so much legacy data associated with all my different devices, on so many different platforms, in so many different places, across so many different people / relationships that the new devices and software I use, whether by Apple, Google, Microsoft, StartupCo, or FooCo, are going to have to "respect" all that stuff.  When I dig into Android a little, I see the potential for that, but I also see resistance to that concept.  iPhone 1.0 had this problem; iPhone 2.0 is doing a much better job of not having this problem.

I’m spending the day at Microsoft’s Annual Venture Capital Summit and expect to hear a lot about Cloud Computing and Mesh.  I have my Microsoft Venture Capital Advisory board meeting tomorrow where the topic is all around where Windows Mobile is going.  Against the background of Google, Android, the iPhone, and all the various "cloud computing initiatives", it’ll be interesting to see if Microsoft has really reconciled – at least conceptually – issues that led to the MSN / Vietnam problem that still hinder it today.  Simultaneously, it’s interesting to watch and see if Google is wandering into their own Vietnam(s), or if they will deftly sidestep them.

I love working with / on this stuff and – after watching Fred Wilson’s video on the last 15 years in the New York Internet scene (and how prosaic things look like from 1995) – I’m so amused when I think about what things will be like in 2023.

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. 

One of the 2007 TechStars companis, IntenseDebate, announced during the presentation that they had just been acquired by Automattic, the makers of WordPress.  There was a ton of positive buzz yesterday in the blogosphere about this – huge congrats to the IntenseDebate gang as well as everyone involved in Automattic.  Vator.tv captured Toni Schneider (the CEO of Automattic) up on stage with Tom Keller (the CEO of Intense Debate) talking about the deal.

This is the second acquisition of a TechStars 2007 company following AOL’s acquisition of SocialThing last month.  As part of this one, I’ve agreed to become a "raving WordPress fanboy" so look for me to finally migrate my various blogs over to WordPress.  I’m also very much enjoying writing in my new WordPress moleskin notebook and putting little WordPress stickers on things wherever I go, including up and down University Avenue today on my morning run.

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.

We were off the grid – mostly.  I had a few work related things that reared their head during the week – none required a lot of time but each harshed my mellow a little bit.  I was typically agitated for the first few days, which is a sign that I really needed a total disconnect to recharge my batteries.  After four days of sleeping more than 12 hours a night, I started to calm down.  The daily runs, swims, tennis, massages, books, and adult activities helped.

During our Q-vacations, I turn off my computer and cell phone.  My assistant Kelly reads my email and calls me if there is something I have to pay attention to.  However, we do watch TV – mostly movies – as we lay in bed before we fall asleep.

This week, the best movie on TV was CNBC Europe as our bed time correlated to the last hour of the market in the US.  I never watch CNN / CNBC / MSNBC / Bloomberg / local news so it’s a rare treat to watch a chunk of it.  Last week was a doozy.  If we hadn’t turned the TV on at all and just checked the Dow Jones index on Friday when we left for Europe and Sunday a week later when we reconnected, we would have noticed a measly 30 point drop in the Dow.  Instead, we got to watch talking head after talking head analyze, speculate, prognosticate, fluctuate, pontificate – basically everything except masturbate – while chart after chart appeared with radically spikey looking graphs that changed every few seconds.

In the midst of this noise, we watched a few movies (I finally saw Ironman – yes – the first half was much better than the second half) and I reread Nassim Nicholas Taleb’ brilliant book The Black Swan: The Impact of the Highly Improbable.  I reached a very simple conclusion – everything that I was watching being discussed on CNBC was probably incorrect and, more importantly, likely irrelevant.  The actual events that occurred would take me less than five minutes to read the following week when I skim BusinessWeek in the bathroom.  The commentary was just noise.

But I knew this already so this wasn’t my key insight.  Over the weekend, we ended up watching Davis Cup Tennis (Andy Murray is going to give Nadal and Federer some trouble) while avoiding the endless Ryder Cup coverage.  I tried to understand cricket (still no luck), watched some rugby (or is that Australian football?), and watched the soccer highlights (why suffer through a game when you can watch the highlights.)

And now for the insight.  During the week, we have CNBC.  Over the weekend, we have ESPN.  They are exactly the same – just with different uniforms and commentators.  As Taleb would suggest, the only way to keep your eyes wide open about what is going on is to turn off the TV and stop reading the newspapers.

I just yawned, so it must be time to end this "welcome back" post, close my eyes, and dream of fields of golden retriever puppies.  I wonder if that’s what Hank Paulson is doing.

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.

As I climbed the rest of the way to 14,270, I checked my watch on a periodic basis.  My rough guess is that the elevation accuracy was +/- 30 feet at any particular moment.  Pretty cool.

I’ve been intrigued with mapping and geolocation for a long time – one of our investments is Quova, the market leading geolocation data provider.  I run into lat and long all the time in geotagged data but I rarely run into altitude (aka elevation).

Anyone that flies an airplane knows how critically important altitude is.  As airplanes start to have Internet access, the jetpack that NASA promised me as a kid arrives, and IP-based flying robots start to appear, altitude will emerge as an important part of geolocation.  Today, geolocation is still mostly just x and y data.  Our friend the z axis is starting to make an appearance.

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.

I’ve worked hard in my life to understand what a "sunk cost" was an how best to deal with one.  While I’m not perfect, I’m pretty good at assessing the situation and removing the notion of the sunk cost from my going forward analysis.

When you have difficulty understanding how to deal with a sunk cost and you get tangled up in a complicated mistake, a real mess occurs.  You keep trying to fix the complicated mistake and justify the ongoing future investment of time, energy, and money based on what is essentially a sunk cost that you are unlikely to recover.  Rather than valuing your sunk cost at zero and simply evaluating the future potential of the opportunity, you compound the complicated mistake even further.

My solution to these situations is to simplify. Completely write off the sunk cost.  Ignore (or void) as many of the historical decisions that created the complicated mistake.  Figure out what your real current reality is and what you want your future state to be.  Then create a plan that connects your current reality to your desired future state.

Start by simplifying things.

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.