Ok – enough of that announcement stuff on a Sunday morning (although I can’t resist inviting you again to the CSIA DEMOgala 2007 event.) 

I regularly get emails that ask questions like “I wanted to ask if you ever considered writing a post on your blog about your method of keeping your priorities organized, deciding where to spend your time, and your ability to accomplish so much. If only the rest of us could be as productive as you!  I thought of it as I read in your Q3 post, “this past year has required unyielding focus.”

I was pondering this in the background as I went through my daily morning routine.  It’s currently 6:51am and I’m about two hours into my “wake up, feed the dogs, make a cup of coffee, clear my email inbox, read my daily web stuff, read my RSS feeds, write a blog” cycle.  I do this almost every day (Monday through Friday + 1 weekend day) and use it as my daily “stay organized” anchor.

As I reflected on this – and the question posed above – it occurred to me that “staying organized” and “staying focused” are two entirely different things.  Rather than try to tackle them both, I’m going to only riff on staying organized this morning.

I’ve never used any particular organizational tools or methodologies.  Rather, I’ve created my own and borrowed from whatever interesting trends appear.  For example, a long time ago (twenty years?) I heard someone say “don’t ever touch a piece of paper more than once – do something with it immediately.”  This concept has evolved and is often embedded in many self-help books, but it’s at the core of how I stay organized. 

I have a long list of tactical stuff that I do such as always have an empty inbox (e.g. don’t use your inbox as a todo list), schedule everything, use a task list rather than email folders, and process all paper immediately, but I realized as I thought about this that the most important construct that I use to stay organized was non-tactical.

Specifically, I believe in rhythms.  Short term ones (daily / weekly), medium term ones (monthly, quarterly), and long term ones (annually, deca-annually.)  I use rhythms to stay both organized and focused – the short term ones are all about staying organized and the medium / long term ones are all about staying focused.

I’m a morning person, so my days usually start at 5am (unless I’m fried) and end around 10pm (when I’m basically useless to the world.)  I use the first four hours of the day to do three things: (1) sit quietly in front of my computer and do my daily information processing routine, (2) run, and (3) connect with Amy.  I try to use the last hour or two of the day to connect with Amy (e.g. no email or calls after I get home at night, unless something is previously scheduled.) 

I aggressively schedule the balance of my day so I know what to do next.  I have a “random day” every other week to meet or talk to folks I don’t really know but want to spend time with.  I make (and take) very few unscheduled phone calls throughout the day so I leave myself room to get through my schedule.  I schedule everything for a minimum of 30 minutes so I have plenty of slack time (most things take 5 to 15 minutes) to respond to email, make calls, chat with my partners when things come up, or deal with the classical “urgent high priority” things that inevitably appears independent of one’s schedule.

If I have to write something that will take more than 10 minutes, I schedule it.  I don’t fantasize that I can squeeze anything in – over the last 20 years I’ve learned that approach merely results in endless procrastination for me.  I clean up on weekends – my best weekends are ones where I don’t have much cruft from the week sitting around and I can just chill out.

I realize everyone is different.  Some folks operate (at least in their minds) effectively at the other end of the spectrum – namely “no scheduled meetings.”  I can’t deal with this – I love the comfortable rhythm of “a day.”  While each one is different, the basic structure gives me plenty of touch points that help me crank through an enormous amount of stuff.

Remember – this is about being organized – not about being focused.  I’ll deal with “staying focused” separately in some other post.

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.

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.

The WSJ has an excellent article titled The Secrets of Serial Success.  The “serial entrepreneur” is a mysterious beast and entrepreneurship sociologists have been poking and prodding at it for some time.  Most articles I read about the “motivation of serial entrepreneurs” falls short – this one nails a lot of the things I’ve observed and experienced.

My friends Tim Miller and Ryan Martens from Rally Software both have parts in the article.  Tim and Ryan had a nice success with their previous company (Avitek – acquired by BEA) and are now working hard at their next company.  They typify the “serial entrepreneur species” (of the “entrepreneur genus”.)

If you are a regular reader of this blog, you’ll know that one of my curious obsessions is bathrooms.  I don’t have an explanation for it – just chalk it up to self-awareness (that I view at it as a curious one.)

Five years ago, I had a conversation with Heidi Roizen.  She had recently been approached by Stanford (her alma mater) about participating in a capital campaign for a new building.  She offered to sponsor a bathroom; Stanford denied this request (something like “not dignified enough.”)  I said “I bet that I can get a bathroom sponsored at MIT” (where I went to school.)  After we had a good laugh, she told me I was on.

I tried.  For a year.  I made several different offers.  Ultimately I was denied.  I never really got a straight answer, but I can only imagine the conversations that were held in the MIT development office.  My inference was that there was a concern that my gift would undermine the name sponsor on whatever building the bathroom was in. 

At MIT, all buildings are known by number (E53, 16, 4) and rooms are correspondingly numbered (E53–301, 16–134, 4–104 – several of the more famous ones are 26–100 and 10–250.)  After wandering the halls for seven years, I don’t know the actual name of a single building or classroom (other than the Green Building), but could find my way around blindfolded if you gave me a number.  Given the culture of MIT, the building that my bathroom would be in would first be known as Building X (90% of the people), then as “The Feld Bathroom Building” (9% of the people), and finally by the actual name associated by whoever gave the $20m+ naming gift (1%).  Oops.

Since moving to Boulder, I’ve been involved in several programs at CU Boulder.  My most significant engagement is with NCWIT (the National Center for Women & Information Technology) where I’m chairman.  It has been an awesome experience and is now housed in one of the newest buildings on CU’s campus – the ATLAS Center.

I was in a meeting with John Bennett, the new president of the ATLAS Institute (ATLAS stands for “Alliance for Technology, Learning, and Society) a few weeks ago.  We were talking about NCWIT and a few other ATLAS related things and the MIT bathroom story came up.  John said “I’d be delighted for you to sponsor a bathroom at ATLAS.”  We quickly came to a price for a gift with one condition – that I got to put a plaque up on the wall outside the bathroom with a quote on it that pertains to entrepreneurship.

So – I’m asking for your help.  I’ve come up with a few quotes – none of which I’m happy with yet.  An example is “The Best Ideas Often Come At Inconvenient Times – Don’t Ever Close Your Mind To Them.”  I’m shooting for something that combines entrepreneurship, bathrooms, and the various things people do in bathrooms and is witty while not being obscene or grotesque.

Please comment freely.  Who knows, maybe your name will end up on the plaque also.

I had breakfast with Matt Blumberg – the CEO of Return Path – yesterday.  I’ve worked with Matt for at least six years and love the way his brain works.  During my frustrating quest for the best chocolate croissant in Boulder (so far all of the ones I’ve found appear to be exactly the same – I’m guessing there is one chocolate croissant distributor in town) we talked some about “collaboration.”

Matt has been writing a book (actually – a series of blog posts) on collaboration titled Collaboration is Hard.  So far there are three parts: 1, 2, and 3.  Matt goes deep on how he thinks about this as a CEO and how they approach this at Return Path. 

We must be getting to the end of the summer – I’m starting to see more deep, thoughtful, reflective blog posts in my feed reader each morning vs. the typical “news” or “repost” type of stuff (although I recognize the irony that my two posts this morning have been “hey – read that other guy” type of things.)  Time for a run – maybe I’ll come up with something creative on my own.

My friends Larry and Pat Nelson of w3w3.com interviewed me last week.  The word of the interview appears to be “significant.”  Feel free to play bozo bingo and count the number of times I refer to something as significant. 

I covered a bunch of stuff – exits, “web 2.0 or whatever”, several TechStars companies, Facebook, and Donkey Kong.  Even David thought is was great (but was it significant?)

Andrew Hyde – a new friend and the creator of Startup Weekend – has a great post up today that all entrepreneurs should read for that warm moment of identification and inspiration. 

It starts off with “I look a drink of my coffee this morning, took a breath, closed my eyes and had a nice moment. Things are going well, really well. Unbelievable fairy tale well. “  And it gets better.  Andrew has a beautiful rant on the “state between broke and funded” that describes the adventure he’s on.

My partner Seth Levine has written an excellent summary of Startup Weekend.  It’s hard for me to fathom that it happened merely a week ago.  As I sit here early this Sunday morning getting ready for a long run into town, I’m wondering how many of the 70 or so people involved with Startup Weekend are still chanting “VoSnap” every hour.  Upon reflection, while the product didn’t ship at the end of the weekend (and still hasn’t – although I’ve seen a working version and it’s pretty cool for a weekend’s worth of work) I think the weekend was a massive success.  I viewed it as a sociological experiment that I’d participate again in a heartbeat.