Archives for June 2011

The Overture

Approaching and starting a conversation with a stranger is never entirely comfortable.  When it is at an event specifically billed as a mixer for different constituencies to access each other, it can be especially awkward (e.g. entrepreneurs to meet investors).  Even people with the best of intentions can have their guard up, make unfair assumptions, or slip into stereotyped roles. When you think about the fears and motivations in play, this is no surprise.  In the entrepreneur/investor context, the investor is afraid of being trapped for an excessive period of time in an awkward conversation where they have no interest in the subject, and to escape, will be forced to say something that might come across as hurtful, disrespectful or rude.  The entrepreneur is worried about getting and keeping the investor’s attention, laying their story out in a cogent way, and looking down the barrel of almost certain rejection.  Eyes dart, brows furrow, sweat beads, minds race.  Nobody sets out to be an oaf, but it seems to happen anyway. 

I was struck, at just such an event tonight, by the huge difference basic people skills and manners can make in terms of an entrepreneur’s overall effectiveness in this setting.

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Photo from the New York Times


I’ve never been big on crowds (or traffic for that matter – just ask my wife), but I am a big fan of crowdsourcing.  In my view, crowdsourcing has the power to catalyze very significant and positive change in the way society and business works.  There has been a great deal written about this subject in the few short years since Jeff Howe first coined the term in his 2006 Wired Magazine article “The Rise of Crowdsourcing,” including a great book by Jeff himself (“CrowdSourcing: Why the Power of the Crowd is Driving the Future of Business“), James Surowiecki’s seminal “The Wisdom of Crowds,” Don Tapscott’s “Wikinomics: How Mass Collaboration Changes Everything,” and some of the work done on one of my particular fascinations, prediction markets.

This is an area I follow (both out of curiosity and as an investment focus), and a topic I look forward to writing more about at some point, but what brings it to mind today is the juxtaposition of two recent events.

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Pick Your Founder/Co-Investors Carefully & Reflections on the Nature of Entrepreneurs [Updated]

[See Update below regarding Groupon’s IPO Crisis]

I know Charlie Sheen tried to redefine “winning” earlier this year but I’d like my say as well.  Fortune just published a really excellent piece of reporting by Kevin Kelleher on Groupon co-founder Eric Lefkofsky called The Checkered Past of Groupon’s Chairman.  Kind of a scary story, really.  Lefkofsky comes off looking very dodgy, which is quite troublesome when you consider that main street America is currently being sold a gazzillion dollars worth of stock in his company by Wall Street.

Kelleher takes a walk through Lefkofsky’s history and finds a very disturbing pattern which he summarizes as follows:

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RSA: This Just Keeps Getting Worse

Back in March when I posted about the RSA snafu], I was kind of harsh, because I was worried that this was going to turn into a really big mess.  It sure seems to be turning out that way.  Here’s a few recent headlines for those who have not been following the story:

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Should I Wait For A Technical Co-Founder?

Should I wait to find a technical co-founder or get started with a free-lance resource?  Do I need a technical co-founder before I go out to raise money for my start-up?  I’ve been asked about this enough to merit a post.  Not sure there is one right answer, but here’s what I know.  While an entrepreneur isn’t required by any law of nature to get a technical co-founder before seeking funding, it is safe to say that for most companies in the tech space, it would be “very much preferred” by the typical investor.

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When Everybody Wins

Gotta love when everybody wins.  I finally got around to trying the optical character recognition (OCR) engine recently built into Google Docs, and I have to say, I am pretty impressed.  It’s not perfect, but its GOOD ENOUGH to turn the text in any scan or PDF or photo into editable text.  Some editing and clean-up is required, but it beats re-typing the whole document.

Little miracles like this always make me stand back and contemplate the forces that conspired to bring them to me.  In this case we can thank one of the more powerful forces in the universe: the beneficial alignment of interests.

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