I used to be good at tennis.  Really good.  When I was 11.  I treasured my Jack Kramer Autograph (until I got a Futabaya), never really wanted a T-2000 even though I loved Connors, and thought Ille Nastase was fabulous.  I grew up in the golden age of Connors, Borg, and McEnroe (and Guillermo Vilas, and Vitas Gerulaitis, and Eddie Dibbs, and the ever present Ion Tiriac.)  I could beat most 12 year old boys and almost all the 13 year old girls except for Heather Harrison who regularly kicked my ass.  I thought Prince oversized racquets were for old ladies.

I watched Federer bury Roddick last night 7–6, 7–6, 6–2.  My mouth was hanging open for much of the second half of the match.  Roddick hung in there for a while (there we no breaks in the first two sets although Federer manhandled Roddick in both tiebreakers.)  However, once Federer broke Roddick in the third set it was quickly over.

Federer makes the phrase “poetry in motion” come to life.  Charlie Rose has a long (about an hour) interview with Courier, Federer, McEnroe, Collins, Laver, and Nadal discussing the man who will likely become known as the best player ever in the game of tennis.  If you are a tennis fan, fire it up in your browser and listen while you catch up on your email this morning.

A few weeks ago I met with Brett Familoe and Zach Hubbell of the Pursue the Passion project.  A gang of four – Brett, James, Noah, and Zach are recent college grads that are road tripping around the US meeting with “passionate professionals” and interviewing them.  They just put up a short part of the interview with me up on the web where I state that “passion is critical but not sufficient” and then explain what I mean.  I guess I should have said “necessary but not sufficient” but I was feeling a little passionate when I made the statement.

One of my favorite New Yorker cartoons is “On the Internet, Nobody Knows You’re a Dog.”  Nick Bradbury – the creator of FeedDemon (one of the NewsGator products) is having an online argument with Calvin on his blog.  Nick lobs in the first bomb with My Dog is an Asshole.  Calvin responds with My Master is an Asshole (a Response From Calvin).  Priceless.

As I was writing my previous post about The Constipation of Scale I got an email from a co-investor talking about a CEO / CTO conflict.  It had an interesting phrase in it that I realized applies to many CEO / CTO relationships – “CEO needs to lighten up and CTO needs to tighten up.” 

While this isn’t always the order (sometimes the CEO needs to tighten up!), the source of conflict like this is pretty predictable.  I’ve seen this over and over and over again – as an investor you see the natural (and healthy) tension between CEO and CTO.  If the CEO and CTO don’t know how to play together (or are both experiencing their roles together for the first time) this healthy tension often continues to evolve until armageddon looms.  One day you wake up and realize you’ve got an issue.

Ironically, it’s an easy one to address.  Our friendly neighborhood CTO needs to tighten up and our CEO needs to lighten up.  Now – I said it’s easy to address – not “to solve” as this behavior change often feels like a chinese finger trap – they harder you work at it, the more ensnared you get.

As I reflect on this, these situations spiral out of control more frequently when the CEO and CTO are not co-founders (e.g. one or the other is hired in after the company is founded.)  As CTO’s are natural technical founders, this dynamic often appears when a CEO is hired – even very early (e.g. < 10 people in the company), especially if the CTO / founder never actively acknowledges the dynamics between a CEO and CTO (e.g. the CEO is the ultimate boss.)

The success cases are ones where the CEO and the CTO work hard on their relationship from the start, recognize that they are different people, have different styles, have different roles, and actively engage in figuring out an effective working relationship.

Like most things that are out of balance, you can get in balance quickly by shifting your behavior a little.  This doesn’t just apply to CEO / CTO relationships – it applies to negotiations, political views, marriages, and even relationships with your dog.  If you are naturally “tight”, try lightening up.  If you are naturally “light”, try tightening up.  In either case, it’s a lot easier than dealing with a meltdown.

Every successful startup goes through it.  I got a note from a friend yesterday in response to an email I sent him about one of his startups where I said “feature X should be a no-brainer to implement.”  He responded “One of my concerns is that much of the focus at YYZ for the past three months has been on reliability and scalability and that has caused them to get behind on features.”

Every single successful (and many of the unsuccessful) web-based companies I’ve been involved with have had this experience.  You come out of the gate strong with a cool new web service, get some users, add features, hit a seam and get popular, and then spend almost all of your time and energy trying to build out your infrastructure so you can scale.  There’s nothing new about this phenomenon – I can cite plenty of examples dating back to the mid-1990’s.

Your now very popular system falls over regularly.  Feature constipation sets in and for a while new feature development ceases.  All of your engineering discussions are about “scale.”  If you’ve raised VC money, your board meetings are increasingly annoying as your VCs keep asking silly questions like “when are we actually going to have have neat feature X, Y, and Z.”  If it goes on for too many months, VC frustration sets in, your CTO and VP Engineering (or VP Ops – or whatever title you gave him) gets increasingly stressed out, and you (assuming you are the CEO) start to feel your head spinning around in circles.

It’s a curse and a blessing (at least you’ve got a popular child.)  I’ve met very few CEO’s and CTO’s that know how to build scale behind the scenes in parallel with the growth of their business, especially since the slope of one of the curves (user adoption) is an unknown until it happens. 

Occasional constipation is a reality of life.

There are three long weekends each year that I love – Memorial Day, Labor Day, and Thanksgiving.  My entire world disconnects for each of them and they are great transitions for me.

Amy and I spent the weekend up in Keystone with our friends Dave and Maureen.  I had a couple of great runs, lots of naps, read a couple of books (Poop Culture: How America Is Shaped by Its Grossest National Product and The Logic of Failure: Recognizing and Avoiding Error in Complex Situations), watched a bunch of US Open tennis, and ate well.  Oh – and I watched The U.S. vs. John Lennon – a magnificent and disturbing movie that helped solidify John Lennon’s image in my mind as a heroic figure.

I love my Qx vacations (where I disconnect from the grid entirely for a week) but I also feel incredibly refreshed after these long weekends.  Sounds like some of my friends do also.