My post on talking more about failure resulted in a surprisingly large amount of email and positive feedback.  In addition to plenty of private emails and a few comments, Andrew Fine emailed that he was inspired to write about the recent failure of his company Cryptine Networks.  He’s just put up a post titled Key Lessons From Cryptine Network’s Failure.  While I don’t personally know anything about what happened, Andrew writes a balanced and thoughtful summary of what he thinks went wrong.  Praise to Andrew for being brave enough to write publicly about this in a way that is instructive.

I know I’m in a bitching about my computer mood.  I’m particularly grumpy because I’m on day two of the update / reboot cycle, which is just stupid. 

Among other things, my Microsoft Outlook config in Homer isn’t connecting to our Exchange server because we modified our email configuration about six months ago.  Ross is on vacation until tomorrow so I don’t want to bother him, so I figured I’d just use OWA, which works fine.  However, I noticed that I was running the IE 7.0 Beta 1 (which I must have installed 10 months ago – we are just now on beta 3) so I decided to try to upgrade to IE 7.0 Beta 3 since there are lots of noticeable bugs (and a weak feature set for IE 7.0 Beta 1.)

Thirty minutes later and two reboots later I gave up.  I can’t get past the Install Windows Internet Explorer “Internet Explore 7 is already installed on this computer.  Please use ‘Add or Remove Programs’ in the Control Panel to uninstall it.” error message.  Of course, IE 7 is not listed in Add or Remove Programs messing around with Add/Remove Windows Components simply deleted IE from my quick launch toolbar, but didn’t actually get rid of it.

For a brief moment, I thought I’d lost IE forever (it was gone, but I couldn’t get past the IE 7 is already installed message) so I said (and I think I said this out loud because Amy turned and looked over at me) “fuck it – I’ll just use Firefox for OWA.”  I fired it up and then remembered the reason I use IE for OWA is that when OWA sees Firefox as the user agent, it gives me the crappy last version instead of the pretty good current version.

I dug around for IE 7B1 on my machine and found it pretty quickly, so I’m back to where I started 30 minutes ago.  And I thought I was pretty good at this.

I’ve been in Homer for 24 hours and my desktop computer – which I turned on for the first time in 10 months yesterday – is still downloading software, updating itself, and rebooting.  I caught a note by Alex King about the same issue (he’s only been away from his PC for two weeks.)  I’ve got four desktops (Eldorado Springs, Homer, Office, and Treadputer) that have “identical configurations.”  It’s remarkable how much “updating” is going on to this one, and I’ll still only have current versions of the software on it – my configuration is far from the same as my other three machines (which are pretty close, but each have their own special software quirks.) 

The worst part of this is figuring out what special configs I need for certain things that I depend on all day long.  Fortunately I have my laptop with me to help figuring things out.  It seems like there should be a simple way to keep all your computers “in sync” – there used to be this briefcase thing, right?  Yeah yeah, I know, switch to a Mac and use .Mac.

Oops – Adobe is telling me “Your system must be restarted to continue this update.  Click the Reboot Now button to reboot your computer…”  Time to go.

Irving Wladawsky-Berger – IBM’s VP of Technical Strategy and Innovation (and one of the few “must-read” IBM employee blogs that I’m aware of) has a good post up summarizing Eric von Hippel’s work on Democratizing Innovation.  Eric was my doctoral advisor at MIT (I didn’t finish) and has built 30 years of really important academic research (and a worldwide research community) on the idea he stated around 1978 that “innovation comes from users, not manufacturers.”  Today we might say something like “yeah – uh huh”, but in 1978 this was a radical thought.

There was plenty of discussion about “users” and the importance of them – especially in the product development cycle – at Gnomedex last week.  Wladawsky-Berger does a nice job condensing von Hippel’s ideas down into a few paragraphs.  Eric’s latest book – Democratizing Innovation – is full of examples that build out his framework (and is available as a free PDF and licensed under a Creative Commons License.)

As a wise man once said to me when I was a young student, “wouldn’t manufacturers be irrelevant without users?”

My long time friend (since 1984 – wow) and extremely experienced entrepreneur / CEO Will Herman has another great post up today – this time it’s about firing someone.  Will’s advice – When Firing Someone, Focus on Those Who Remain – is important and well articulated.

The view from our living room window.  Enough said.

As I sit in the Anchorage airport waiting for my flight to Homer, I was missing Colorado a little.  Of course, it didn’t help that I’ve been sitting for the past hour in the middle of a romper room (I count 10 kids running around screaming at each other with parents who couldn’t appear to care less, except for the one yelling at his kid to “shut up and stop crying.”)  As someone sitting next to us on our flight the other day from Denver to Seattle said after having a third bag dropped on his head “it’s a holiday weekend and the amateurs are out in force.”

I remembered that New West Network has put up a new photo gallery so I went and took a look.  Awesome stuff, even over EVDO.  I dug around a little more and found a Flickr group titled NewWest.Net — Voice of the Rocky Mountains – I’ve joined and now will have a steady stream of Colorado / Rocky Mountain photos coming my way.  I promise that – in return – I’ll send you some nice Alaska photos over the next few weeks.

As I sit in the Seattle airport waiting to board my delayed flight to Anchorage (Dear Alaska Airlines: Since it’s a “mechanical delay”, please feel free to delay it as long as you want until you are absolutely sure the airplane works), I was pondering a conversation I had at the very end of Gnomedex with an entrepreneur that I’d met for the first time.

We had a good chat about his business (definitely interesting stuff) and then he asked me a few questions.  One of them was something like “what are the characteristics of the best CEOs that you’ve worked with”?)  This was in the context of him currently being a CEO, but feeling like he should ultimately be the CTO and was starting to think about bringing a CEO into the company.

While answering this question, I commented that the “not so great” CEO’s often “overcompensate for their strengths.”  I guess this was either a good sound bite or an incomprehensible comment because he stopped me and asked me to tell me more about what I meant.

CEO’s of entrepreneurial companies tend to come from five backgrounds: (1) random, (2) engineering, (3) sales, (4) finance, and (5) operations.  Forget about random, or the first time entrepreneur / CEO – let’s just focus on the experienced CEO that is hired into a company or is a first time CEO, but multi-time entrepreneur.  Let’s also talk only about the “not so great ones.”

In these cases, the weakest part of the leadership of the organization is often the CEO’s strength.  So – a CEO that used to be a VP of Sales often does not hire a strong VP of Sales.  Same with the ex-CFO – his CFO tends to be less experienced.  The engineering oriented CEO does better, but often ends up with several “engineering leads” rather than a super strong VP Engineering.

Now – this doesn’t always translate into a weak organization below the leadership.  For example, while the sales oriented CEO might hire a weak VP of Sales, he overcompensates for this, spends a lot of time “leading sales”, and ends up with an effective sales organization.  However, the CEO neglects other parts of their organization because he spends to much time on sales, and as a result is a less effective CEO.

I’ve experienced this a number of times.  I amusingly recall a discussion I had with a first-time CEO of one of the companies I had done a first round investment in.  He was a very experienced COO / CFO of two previously successful startups where he was a founder.  This was the first company that he’d founded as a CEO.  For the first six months, the financials were extraordinarily well analyzed, the board packages were beautifully done, and the processes within the company were rock solid.  However, we were making less progress than we would have liked on the product, the strategy, and the early customer relationships.  At some point, we had a hysterical conversation in a board meeting where I said something like “dude – the financials are irrelevant – I know you have $1.5m in the bank and are spending $150k / month ramping to $200k and I can figure out the number of months left before you slam into the wall.  Ok – that took 15 seconds.  Let’s spend the next 1 hours, 59 minutes, and 45 seconds talking about what we are going to do to make this business great.”  Fortunately he immediately got what I was trying to say.  The last two years with him at the helm of the company have been very satisfying.

If you are a CEO, step back and think about your historical background / strengths. Then – think about the person you have in the VP of Your Strength role.  Is this person an absolute superstar?  If so, get out of her way and spend most of your time on the other parts of the business that you might be less comfortable with.  If not, go get a rock star for this position so you can stop overcompensating.

In case you are really curious about what’s actually happening at Gnomedex, here’s Chris Pirillo thinking small.