Brad Feld

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My Relationship With Apple Is Like My Relationship With The Republican Party

Aug 28, 2008
Category Technology

Scott Converse has a wonderful post up titled Is Apple a Republican?  After reading it, I pondered my relationship with Apple and realized that it is just like my relationship with the Republican Party – there are some things that theoretically appeal to me, but endless deal breakers that push me away and head fakes that leave me cynical.

If you are a long time reader of this blog, you know that every six months or so I try again.  I go to the Apple store and buy whatever shiny new Mac toy there is.  A G5 – yeah.  A MacBook Pro.  Sure.  An iPhone – definitely.  A MacBook Air.  Yeah, this will be the one.  After tens of thousands of dollars spent on Apple products, the only three I am using today are my Apple 30" Cinema Displays (I love them), my G5 in my office (which I’m running Vista on), and my iPhone 3G (which has now lasted three weeks notwithstanding the endless dropped calls and lack of Outlook Task synchronization.)

The Republicans promise me smaller government.  Oops.  Better fiscal policy (e.g. no deficits) – double oops.  Distribution of power to state and local government.  Um, yeah.  Equality for all.  Patriot act, immigration policy, wars, anyone.  The list goes on.  I’ve always described myself as "conservative fiscal policy, liberal social policy" where theoretically a "moderate Republican approach" would work for me. 

Wrong.  The big deal breaker for me is abortion.  I couldn’t ever vote for a pro-life president.  Stay with me, you’ll get the Apple analogy soon.  There are plenty of others – war, immigration, protectionism, religion – but I still fantasize about that enlightened "conservative fiscal policy, liberal social policy."

Ironically, my friends the Democrats have always had the liberal social policy down and now appear to have a much better handle on the conservative fiscal policy side of it.  I was a Reagan youth, but have voted Democrat ever since.  And while many think I’m a hard core Democrat, I’m actually an Independent.

About the time I voted for Reagan, I had an original Mac.  My first computer was an Apple II.  I even had an Apple III for a while.  My Mac had one floppy drive and 128k.  I loved it even though it was basically useless.  When I got my first IBM PC (two floppy disk drives, 64k) and started writing software on it (and making money with it) I became a PC / Microsoft user.  My Apple fantasies continued unabated – every few years I’d buy another one and end up discarding it after a few weeks to go back to my PC.  There were always "deal breakers."

The deal breaker for me with Apple for the past few years has been Microsoft Exchange support.  Entourage 2004 was so inadequate that it never became an option for me and Entourage 2008 disappointed me so much that I punted.  I don’t really want to run Entourage – I want native Exchange support in all the Mac products.  ActiveSync anyone?

I tried with the first iPhone – I really wanted to like it – but it just didn’t get there for me.  Remarkably, after resisting for many years, Apple finally licensed ActiveSync and integrated it into the iPhone 2.0 software.  Voila – I dumped my Dash and am still using my iPhone 3G several weeks later.

But – Apple forgot one thing.  Tasks.  Apple syncs Mail and Calendar with Exchange, but not Tasks.  For anyone that is a hard core Outlook user (like me) that manages to a zero inbox, Tasks are important.  It’s kind of like being pro-choice but being against birth control.  Weird.  Limiting.  And intensely frustrating.

Third party apps are starting to appear that try to sync Tasks, but they are all weak.  KeyTasks from  Chapura seems to come the closest so far, but it’s not server side sync (with Exchange) – you have to have a client side agent running.  And of course, it doesn’t have categories ("Category support coming soon.")

Theoretically wonderful, but always comes up short with a deal breaker.  We didn’t even get into religion yet, but ponder that as you think about the Cult of Mac vs. the PC / Microsoft. 

I definitely have too much politics on the brain.  I can’t wait until 2009.