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

Last week tr.im 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 tr.im 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 (bit.ly) 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 tr.im in my Twitterstream.  Tech Zing is hosted by Justin Vincent & Jason Roberts and I've never heard of any of them before the tr.im 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 tr.im....
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 - bit.ly 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 mail.com, founding CTO of myinternet.com, founded a domain portfolio company and currently founder of Nambu.

VMware to Acquire SpringSource for approx $420 Million

"VMware will acquire SpringSource for approximately $362 million in cash and equity plus the assumption of approximately $58 million of unvested stock and options. The acquisition has been approved by SpringSource's stockholders and is expected to close in the third quarter of 2009, subject to customary closing conditions."


[Sent from my iPhone 3GS]

via @techcruch "There’s a large uproar right now following Tr.im’s demise on whether or not anyone should actually be using URL-shorteners just in case something like this happens."

There’s a large uproar right now following Tr.im’s demise on whether or not anyone should actually be using URL-shorteners just in case something like this happens. [...snip...] But an archive of these links that is maintained outside any one service could help put people’s minds at ease.

Yes, I was a tr.im user. It was a great service and now they're holding my links hostage because they could not figure out how to monetize the service. Hopefully a company like bit.ly will step up and pony up enough ransom to free them. Aaahhh perhaps that is the URL shortener industry's new monetization approach. Get competitors to buy you out if your shutdown threatens credibility of the entire sector...

Facebook Acquires FriendFeed (only 12 Employees!)

FriendFeed is based in Mountain View, Calif. and has 12 employees.

The most interesting point, for me, is that FriendFeed has only 12 employees! I know I shouldn't be supprised in this new age of small startups that stay small, but the site just oozed polish, features and performance. I expected them to at least break 40 employees. Kudo's to those guys and I hope they got some good cash in the deal.