Eric Woodward and - A small study in Entrepreneuring...

Last week shutdown and hit the twitterverse from just below the surface of the Social Networking1 space like a Jellyfish sting.  This is not the first internet startup to shutdown.  There are many large and small that shutdown or are acquired and eventually whither and die of neglect.   Eric Woodward's was a popular url shortening service and one that I used on a fairly regular basis.  It had some nice features, but the "url shortening" space has become crowded with competitors of late.  Twitter, a thousand pound gorilla in the social networking space anointed one ( the url shortener for Twitter and Eric saw this as the checkered flag in the race.

As interesting as the underlying issues are regarding url shorteners, I became much more interested in the Entrepreneurial aspects of the story after I stumbled across the Tech Zing podcast about in my Twitterstream.  Tech Zing is hosted by Justin Vincent & Jason Roberts and I've never heard of any of them before the event.  Ever the willing spectator for war stories and train wrecks I decided to give it a listen.   What I heard was a level headed serial entrepreneur2 discuss the realities of a startup.  It took me back to my days in start-ups.  No I am not an entrepreneur myself, just one of those breed that is recruited by entrepreneurs to realize their goals.  I lived through a few startups during the internet boom bust cycle (Viant, 12 Entrepreneuring & Linx LLC) and I can identify with Eric and the choices that all real entrepreneurs must make.  Those choices my include shutting down a business and cutting your loses.

Listen to techZing! 13 for Eric's story. [Note: Some of the questions from Justin and Jason are naive and cringe inducing but hang in there and listen to the entire podcast for Eric's pearls of experience.]

Some interesting points of discussion:

  5:50 - "Developing a small piece of software and selling it for a nominal amount of money is just not interesting to me..."
            Classic 2.0 business model... scale first layer in services later.
  9:00 - Trouble with outsourcing
13:20 - Rock Star developer vs. good teams
17:20 - I didn't start out to build
22:00 - Loosing control of the process...
23:50 - Becoming the poster child for "Link Rot", "But it's not really in my DNA to hand my competitor my product for free"
24:20 - as the insider and the nature and reality of competition
33:00 - Surprised by the reaction
43:20 - Everybody know the internet only has 3 business models
53:00 - Eric's background

1. "Social Networking",  "Microblogging"... Whatever you call the space that Twitter, Facebook, Friendfeed, et al are in.
2. Eric founded an early ISP in Canada, founding CTO of, founding CTO of, founded a domain portfolio company and currently founder of Nambu.

(via @dhh) on FLOSS "Screw 'Release early, release often'..."

It's always great to listen to someone with big opinions and an ego to match... David seems like a hell of a smart guy and has created something incredibly compelling with Ruby on Rails.
(via @dhh) on FLOSS "Screw 'Release early, release often'... I'm going to polish the hell out of this thing! I'm going to write the documentation.  I'm going to build up some marketing intensity around it.  I'm going to do all these things that open source projects  do not..."
This episode of FLOSS  (FLOSS WEEKLY 79: David heinemeier Hansson(link below) is a must listen and if you have the chance you should catch David Henemeier Hansson when he speaks at any conference.  I caught him at a local conference in NYC and he was very informative and entertaing. 
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[Sent from my iPhone 3GS]