Brad Feld

Month: April 2008

Wesley Snipes apparently got a three year sentence for tax evasion this week.  At least he’s pretty good at Karate and Kung Fu – I expect that will come in handy if he ends up serving the sentence.  Apparently the message being delivered is "pay your taxes".


There’s a rumor going around that Salesforce.com is switching all of its 4000 employees over to Macs.  If so, this will be the first high profile complete Windows to Mac enterprise defection that I’ve heard of recently (I’m sure there are others, but they haven’t been high profile or big enough to catch my attention.)

For several months, I’ve been suggesting that when larger (great than 2,500 employee) companies start defecting en masse (e.g. the entire company) to Macs, it will signal another potential tectonic shift (and opportunity) in the software business.

Unless you are a browser centric company, it’s still really challenging to fully integrate Windows and Macs in one environment.  It can be done (we do it – even at a 12 person company) but it’s grody and the Mac users are always on the short end of things.  This isn’t new – it’s been going on since the last real attempted foray into the Mac into enterprise in the late 1980’s.

But the pressure on Microsoft and the market dynamics, especially among younger users, seems different to me this time.  I’ve tried to switch to a Mac several times and given up each time because of application integration – in my case Exchange (mail, shared calendar, and tasks), SharePoint, and my cell phone integration with Exchange.  I’ve tried a bunch of different approaches – none of them really worked short of dumping the Microsoft apps and switching to something different which I’m not willing to do – yet.

Some of my daily world is comfortably cross-platform (Firefox, Skype, Trillian, and all the NewsGator stuff I use) and does the "right thing" synchronizing data in the cloud.  But enough isn’t that I just can’t seem to make the switch.

Apple’s finally licensing Microsoft’s ActiveSync and incorporating it into the iPhone will probably get me to switch to an iPhone (from my Tmobile Dash) – assuming the Exchange integration is complete (mail + calendar + address book + tasks).  If Entourage 2008 had an equivalent level of integration with Exchange (or the Apple mail / calendar / contact apps incorporated ActiveSync) I’d try again on the Mac.

Yes – I know I can use Fusion or Parallels – I’ve tried – they just aren’t satisfying enough.  I also know we can throw out all of our Microsoft stuff and switch over to Google Apps or something else – we’ve got to much of an infrastructure investment – even at 12 people – to bother with that at this point (imagine if we were 4,000 people!)

But – it feels like another wave is about to break on us and the chance of a broad change will once again be in our (and Microsoft’s) face.  Microsoft can play offense or defense here – all of the Live Mesh stuff from last week is offense and I’m glad to see it from my friends in Redmond.

I think all of this tension, pressure, and change is good because I want to see (and participate) in more innovation.  More, more, more.  Of course, this won’t really matter much next week since it’s likely going to be all about Microsoft and Yahoo.


At the end of every board meeting I’m a part of we have a closed session.  This is a session that includes only the board members.  All of the boards I’m on include the CEO as a board member so the CEO is part of the closed session.  If there are multiple founder / management board members, they attend.  But – no observers and no members of management that aren’t on the board.

I was on a board call yesterday that was confusing.  The company is doing well, the management team is very solid and stable, and the board packages are comprehensive and transparent.  I’ve worked with the CEO for a long time and we rarely have any misunderstandings (we have plenty of disagreements, but we know how to talk through them.)  The company is mature enough that we’ve shifted into an eight per year board meeting tempo; two meetings a quarter – one in person that is usually deeper and strategic; one by phone that is an update call.

When I got back from vacation on Wednesday, I read the board package.  No surprises.  There are no strategic activities going on for the company (no fundraising, no M&A, nothing "fancy") – just strong and steady execution.  The tempo of the call started off a little odd – the CEO brought up some forward looking concerns of his.  While he was describing them, I was having a hard time connecting what he was saying to the board package I had just read.  As we went through the management team review of the business, I got even more confused as many of the tactical things we had discussed at the previous meeting had been done well and everyone sounded upbeat, although appropriately cautious.  The CEO highlighted a few more concerns of his and then asked an open ended question – something like "what do you guys think?"

We were all on the phone so it was hard to read any nuance.  I expressed my confusion.  I asked a few clarifying questions.  My confusion increased.  Maybe it was jetlag, but my brain was just not connecting the dots.  At some point the CEO took us in a different direction to try to address another issue that he was potentially concerned about.  While the issue he raised had some short term issues, he had extrapolated it as a long term trend.  I didn’t agree that it made sense to extrapolate the trend from one data point, made some suggestions, but felt the awkwardness increasing.

We ended the meeting and went into closed session.  We all took a deep breath.  I told the CEO I was confused.  He was confused.  The other board members on the phone were confused.  If we had a giant time machine we would have gone back 60 minutes and started over.  Instead, we had a great ten minute conversation where we realized that we were just talking past each other.  We hit the giant mental reset button and in a few more minutes had recalibrated.

Even though we usually end after the closed session, this time we decided to bring the management team back in to clarify things.  We realized that when we ended the meeting, we had a leadership team that was likely as confused by the meeting as we were.  I imagine there was sixty seconds of discomfort while everyone gathered where they were wondering what was going to happen next.  We had a short reset of the discussion, clarification of what the CEO was really trying to communicate, and reaffirmation that we were on the right track, even though this was a weird and confusing meeting.

I talked to the CEO today just to check in.  We had a good call and we both reaffirmed that all was cool.  He said he’d learned something important – that if he was just going to "think out loud" during a board meeting that he should preface this with a statement indicating this.  I agreed that this was the right conclusion – that I’d much rather he "think out loud" vs. feel compelled to figure it out all.  I also suggested to him that if he thought I was lost in space, he should just hit me over the head with a brick.

I’m really glad we had the institution of the closed session firmly in place for this board.  It gave us room to figure out what was going on, where the miscommunication was, and reset the discussion.  Without it I expect everyone would have scattered to go back to work with their confusion firmly intact.


I just did a search in my address book for someone and came up with the address book entry for someone I know that died last year.

I was sad.  I sat – paralyzed – for thirty seconds struggling to decide whether or not to delete the address book entry. 

I realized this is a great example of an unintended consequence of technology.  I was not particularly close to this person (they were a neighbor of mine) but I flashed back to a walk along our creek that we had one day while scoping out the location for a new gate that Amy and put up in our canyon.  He was a nice but somewhat troubled guy that didn’t live long enough.

Those were memories I probably would have never had again if I hadn’t seen his name in the address book entry. 

I decided not to delete the address book entry.


During my morning routine (90 – 120 minutes of catching up on email, reading my "daily" folder in Firefox, reading my RSS feeds, and blogging) I came across Alex Iskold’s post Faster – Why Constant Stress is Part of Our Future.  It was ironic to me that I read it shortly after posting my last blog about my Q1 vacation.

Alex makes the argument that constant stress is part of our current reality and that it is accelerating.  I don’t buy the argument that it is inevitable – I believe that it is a choice.  And I reject it.

If you knew me in the late 1990’s, you knew that I was always online, always on the phone, always interruptible, always available (except when on an airplane), and constantly traveling all over the place to save the world (or at least my little version of it.)  By the time we hit mid-2000 I was pushing 240 pounds, exhausted, strung out, and almost manic.  One weekend Amy told me she was "done" and when she defined that (e.g. "if you don’t change, I’m out of here") I listened.

Over the next 12 months I rewired all my patterns.  I stopped checking email before I went to bed at night.  I started taking a week off the grid every quarter.  I actually treated the weekends like weekends and had some downtime.  I started running marathons. 

2001 was a brutal year for me.  I helped wind down 10 companies that year.   There was very little about work that was fun.  At one point I was on the boards of four public companies where if you multiplied all of their stock prices together you got a smaller number (e.g. they were all sub-$1 stocks.)

While I put a huge amount of energy into the very unsatisfying work I was doing, I made sure that I carved out time for myself away from work.  I still got worn out periodically, but the stress started to melt away.

As I look back over the past decade, my intensity level hasn’t changed much since the turn of the century.  However, my stress level has changed dramatically.  I reject stress.  While it creeps up on me (and is usually an indication that I am tired and need a break), I make sure that I control (and choose) the pace of my work and life.

You can do this also – if you want to.  Start by taking small steps.  Exercise five days a week for at least thirty minutes.  Turn off your computer at 8pm and don’t look at email until you wake up in the morning.  When you eat dinner – eat – don’t try to do something else (like email) at the same time.  Go to a movie and turn your cell phone off.  Go outside and play with your kids (or your dogs.)  Decide that you aren’t so important that the world can’t wait 24 hours for you – and give yourself a short break.

Reject the inevitability of stress.


My Q1 Vacation in Q2

Apr 25, 2008
Category Books

If you are a loyal reader of this blog, you know that Amy and I take a week completely off the grid every quarter.  Well – I missed my Q1 vacation so we took it early in Q2.  We spent five days on the big island in Hawaii, hosted by college friend David Cowan.  When I was at MIT, David was my best "Harvard friend." (ok – I didn’t have too many, but he was the best.)  Amy and I hadn’t spent an extended period of time with David and his wife Nathalie since the early 1990’s – it was awesome to reconnect.  I assumed that David was in a good mood because we were around, but I’m sure the Tuesday $1.25 billion Bessemer Hat Trick didn’t hurt.

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In addition to being in a splendid place, completely off the grid, hanging out with old friends, running and playing tennis, eating some great food, and sleeping a lot, I read a few books.

Hold Tight: I love Harlan Coben – he’s one of my top five mental floss writers.  Once again, Coben produced a twisted and complex page turner.  He’s becoming a little formulaic, but that’s ok by me since I dig the formula.

Edward R. Murrow and the Birth of Broadcast Journalism (Turning Points in History: Whenever I read a great biography, I think to myself "I should read more biography."  I’m totally on an Ed Murrow kick after watching Good Night, and Good Luck.  The evolution of broadcast journalism is fascinating, especially against the backdrop of the Internet, user generated content, and the transformation of "old" to "new" media that we are currently in the middle of.

Being Human – Human-Computer Interaction in the Year 2000: A puff piece summary from Microsoft from a conference they hosted on HCI in March 2007.  Books like this encourage me that there are massive opportunities in the HCI arena – no new ideas for me, but plenty of support for existing thought vectors.

The Runner: A True Account of the Amazing Lies and Fantastical Adventures of the Ivy League Impostor James Hogue: The subtitle of this book is "A True Account of the Amazing Lies and Fantastical Adventures of the Ivy League Impostor James Hogue."  Whew.  I once had a running coach who ended up in jail for fraud.  This book could have been about him.  It cut a little too close to home.

The Humane Interface: New Directions for Designing Interactive Systems (ACM Press): Jef Raskin created some fundamental innovations in user interfaces and human computer interaction.  Even though this book was written in 2000, it had some superb sections on HCI and several chapters that had entirely new ideas for me when considering how user interfaces work.  A little dated, but good stuff.

Rant: An Oral Biography of Buster Casey.  By far the best of the bunch.  Micah Baldwin dropped this off for me the day before I left for vacation.  He warned me that my brain would explode.  It took about 50 pages to get into the rhythm of the book – once I got into it I could not put it down.  Chuck Palahniuk brought us Fight Club; with Rant he’s brought us Party Crashing (and a rabies epidemic).  Great great stuff.

Ahhhh.  What a nice break.  I’m back in Boulder for a few weeks before my Q2 vacation.


I have a very patterned daily information consumption routine.  The left-most tab in my browser is called "Daily" and contains a set of web sites that I open up each morning and look at as part of my routine.  Recently, Filtrbox – one of the TechStars companies – graduated to be part of this tab.

I try virtually every news alerting system that I come across.  I have a set of about 100 keywords that I track daily – all of the companies we’ve invested in, a number of people that I follow, and a handful of random things I care about.  My current staples are Google Alerts, Yahoo Alerts, and Technorati.  I can only seem to get Google and Yahoo via email, so they show up in my inbox and get moved to my "Daily" email folder (which I read – er – daily.)  Technorati comes via RSS so I read it each morning in FeedDemon.

The vision for Filtrbox when they started at TechStars last summer was to create an integrated single dashboard of all this keyword alert information.  The tagline "more knowledge, less noise" says it all.  My partner Seth Levine and I totally resonated with this – Seth has a great post about Filtrbox up titled Know what you don’t know which addresses how he thinks about the problem and how Filtrbox solves it for him.

For a while I found the Filtrbox data interesting, but not really that additive. In addition, the UI was "ok" but there where lots of little things that slowed me down.  About three months ago I noticed I was finding new information from it that wasn’t appearing in my other keyword searches and that it was streamlining this information in ways that I hadn’t expected, such as eliminating duplicates (e.g. the same alert coming from Google, Yahoo, and Technorati  – which happens many times each day – only appeared one in Filtrbox) and allowing me to filter based on thresholds for each keyword.  In addition, as the UI evolved, I found I was spending less time scanning the alerts and more time clicking through onto the interesting ones.

I hit a tipping point about a month ago where Filtrbox became more useful to me than Google+Yahoo+Technorati.  I haven’t turned off the other alerts yet, but I find that I’m not getting much additional info from them anymore now that I use Filtrbox as my top level sort.

Filtrbox is still in private beta, but if you are interested in playing around with it you can get a golden ticket by clicking on the special magic Brad Feld Filtrbox link.  I’m really proud of Ari Newman, Tom Chikoore, and team.  They have reached the point where their service is very valuable to me and gets noticeably better every single week.


Why Boulder?

Apr 17, 2008
Category Places

My partners Jason Mendelson and Ryan McIntyre have written a long post on the Foundry Group web site titled What We Learned By Moving To BoulderIf you live in Boulder and want to get a view on how they think about this place 18 months after moving here, take a look.  If you aren’t from Boulder and wonder "Why Boulder?" (which is a question I’ve heard over and over again the last dozen years), here is Jason and Ryan’s perspective.  And yes – last winter really sucked.


NewsGator just released the latest version of their Inbox product – their RSS client for Microsoft Outlook.  It’s free.  It’s solid.  It’s full of RSS chocolately goodness.  ReadWriteWeb explains why Inbox 3.0 Brings Better RSS to Outlook.