The Gmail Hoody: Breaking down offline communication dropoff

Posted on November 9, 2009. Filed under: Uncategorized | Tags: , , |

Spectrum of commitment in communication: It is a lot easier to observe than it is to lock eyes.  It is a lot easier to lock eyes than it is to smile.  It is a lot easier to smile than it is to wave.  It is a lot easier to wave than it is to say hi.

Note:  sorry in advance for the first paragraph below, but push through…you’ll see the point

Each step in the above spectrum requires an increased amount of commitment when interacting with a stranger.  The spectrum begins with a observation, which is a complete lack of communication.  There is minimal social risk to engaging in this behavior with a stranger, short of getting noticed.  If the average new yorker comes into physical proximity with 10,000 people in one day, they might engage in this level of interaction with up to 75% of them.  As you progress along the spectrum, to eye contact, the percentage declines significantly.  When our new yorker makes eye contact, they first take the plunge from an absence of communication into the world of non-verbal communication.  The significant event being a bidirectional interaction.  Even within eye contact exists a sub-spectrum defined by duration of connection…a staring contest is much greater commitment than an immediate aversion of the eyes upon contact).  From eye contact, the leap to smile is even more rare. It exposes the smiler to potential rejection, along with the wave, which is marked by an even greater commitment as it increases the likelihood that such rejection will be noticed by others.  Between a wave and the utterance of a word to a stranger exists a grand canyon of commitment, and therein lies the inefficiency of communication within a local environment.  Online retailers measure a customer’s commitment to them in terms of “drop off.”  If 100 people come to Amazon’s home page, only 50 click on a product, and only 25 reach the check out screen, and only 10 enter all of their credit card information and complete a transaction.  At each step some people “drop off.” Each step in the spectrum from observation to verbal communication represents a point of drop off as well.

While the volume (let’s say volume = richness x duration) of communication with strangers is extremely low in the physical world, it is growing, i’ll guess exponentially, in the digital world.  By reducing the commitment required to engage another person, largely due to reduction in the possibility of physical harm as an outcome, interaction with strangers is extremely common in an online environment (blog comments, craigslist sales, twitter interactions, etc…), yet extremely uncommon in an offline environment.  The downside of this disparity is that we are throwing away valuable non-verbal data that should be a leading indicator of richness of interaction.  Aside: If you wanted to get really heady, you could say that the goal of maximizing volume of communication is a furtherance of our species from an evolutionary standpoint in so far as increased communication equals increased rate or reproduction.

Let’s take the example of an uncrowded subway car from soho to park slope in brooklyn.


2 men in suits reading the WSJ

2 women with strollers

1 hipster with skinny jeans and a mustache

1 single girl listening to her ipod

If you had three separate rooms, and you were going to place 2 occupants of this car in each room with the goal of maximizing the volume of communication (as measured by richness and duration in the present as well as any future communication between occupants), who would you put in a room together?  Obviously, the two guys reading the WSJ are going together, the two moms are going together, and the two young singles are going together, right?  If we were in the online world, that’s how they would be paired: the two WSJ guys might interact in a forum on the WSJ website, the two moms may exchange parenting tips at, and the singles might flirt on Facebook

BUT, what the online environment does not account for, is that the girl listening to her ipod has been smiling at one of the guys reading the WSJ for 5 stops, and he is smiling back, and they are both carrying bags from TheStrand used bookstore (and they happen to be soul mates)…but what happens today?…the guy gets to his stop, he looks at the girl one last time, and gets off, never to see her again…why? because almost everyone “drops off” in that leap from non-verbal to verbal communication.  The solution that seems natural, which some location based services companies are going after, is to add a digital layer, on top of this physical layer, and enable strangers to interact non-verbally (but much more richly than smiles and body language) through the use of text based communication.  In this case, text based communication (IM/direct message/text/email) is the bridge between non-verbal and verbal communication within a physical proximity.  The problem, however, is that the requirements from a network effect perspective are so great, that these two soul mates don’t stand a snowballs chance in hell of realizing their life together (which would result in the maximum net volume of communication possible in the subway car).  Some sort of near field communication technology, where you can point and aim texGmail hoodytual messages to strangers in a physical proximity would be rad, but in the meantime, I decided to run a little experiment to see if I couldn’t lower the “drop off” by converting my physical proximity strangers into the safer world of online communication.  I present to you, my Gmail hoody.  I have worn it about 5 times, and every time, I have gotten at least one email from a stranger.  What’s more, simply by signaling that I am open to communication, 3-4 strangers per day approach me and engage in verbal communication (i.e. is that your real email? etc… etc…).  Obviously, people are not going to walk around displaying their digital identities on their clothes everyday, but I think the potential for display of online identities based on real world physical proximity has some real room for improvement… If you want to make your own Gmail hoody, I recommend this place in DUMBO

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Idea, Execution…and Gumption

Posted on November 5, 2009. Filed under: Uncategorized | Tags: , |

It’s 10:43pm.  A former colleague of mine is sitting across the table from me in the Think Coffee on Mercer and West 4th Street.  We’ll call him Jim (for privacy’s sake).  The rings under his eyes are visible.  He hasn’t cracked a smile in two hours, and he can’t get onto the internet.  My man is beat.  To understand the gravity of his situation, perhaps it would be helpful to share a little context on the events leading up to this evening.   If I look at the economic trajectory of his 30 years on this planet, it would look something like the letter n.  He came from nothing and clawed his way to a prestigious undergraduate degree, a high paying job on wall street, a fund of funds career, and a stint at a top tier venture capital firm.  He is a worker and always has been.  By the time I met Jim at General Catalyst Partners, he had worked over 25 jobs, ranging from waiter, to beer guy for the Arizona Diamondbacks, and everything in between.   I watched this guy support himself, his older brother, and his mother, quietly and selflessly, and it was clear that he had been doing it for a long time.  So General Catalyst was the arch at the top of out letter n, but not without a fair bit of spilled sweat.

Fast forward to the sharp little point on the bottom right of our n.  Tens of thousands of dollars in debt, cancelled a first date with one of the most beautiful women I’ve ever seen because he couldn’t buy her a drink, and you might ask yourself how did he get here only 18 months.  Drug addiction? Gambling problem? Unexpected child?  Nope…entrepreneurship.  He has been financing a relatively involved software build on savings, and credit cards, and a bit of friends and family money.

So, to the present.  You might think the dark rings under his eyes are attributable to the countless hours an entrepreneur must spend creating something from nothing.  And no doubt, those hours are adding up, but these rings are dark.  Why?  Because Jim just took a full time wait job, on top of his full time Founder job, less then a month from his product launch.  He doesn’t have another choice, New York is an expensive place to live while your bootstrapping something.  Jim could break, and get a job that pays $200,000 tomorrow, instead of running himself ragged like this, but he is driven by a burning desire to fix a problem that needs fixing.  It has consumed him to the point where he has sacrificed his wealth, his health, and any sembilence of a personal life for his company, and in 3 weeks he’s going to get to see the flop.

I wrote yesterday about the qualities Michael Jackson embodies that I wish for in a VP of Product, and today I put forth Jim as an example of what I look for in a founder, or a co-founder for that matter.  With the last company I started, I picked my co-founder almost entirely on character (and of course competence and intelligence), because starting a company is fucking hard.  You need to run through wall, after wall, after wall, and keep on running, no matter how hard it gets.  People often site idea and execution as the two factors that dictate the success or failure of a startup.  Perhaps I’ll tack on gumption as a third, and say if you have the drive of my buddy Jim (and you’re the MJ of consumer internet products)…holler, I’m working on something kickass…

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Michael Jackson: VP of Product

Posted on November 4, 2009. Filed under: startups, Uncategorized | Tags: , , |

There is this illusive animal in startup land that every consumer facing internet company is searching for.  The mystical VP of Product, who has such a profound understanding of how the consumer will perceive your value proposition that they can sculpt a user experience to perfectly achieve the desired behavior and interaction.  Ask any venture capitalist what is the hardest position to fill with A-level talent, and they will speak of this unicorn hire. As I develop my own sense for what I am looking for in a product hire, I find myself strangely attracted to…Michael Jackson?

Despite a true sense of ambivalence toward the King of Pop and his recent departure, last night I went to see This Is It.  For those who haven’t seen it, the film documents MJ’s preparation and rehearsal leading up to what was supposed to be his sold out comeback tour after 10 years in hiding.  I guess I was expecting to watch a two hour window into the disturbing train wreck that was Michael’s life, but what I saw was a professional with amazing product vision and a maniacal focus on perfect execution.  It is apparent that he was able to experience his own product through the lens of his consumer (in this case ticket holders).  More impressive, was that he was able to drop in and out of that lens during his rehearsal (product development) and modify his product in real time without any user feedback (audience response).  It was as though he was experiencing his own product as he was creating it, with a preternatural understanding of how seemingly minor modifications would mean all the difference between a good user experience and the best user experience his consumer never expected.  This type of intuition is an intangible which is challenging to identify in an unproven product hire, but I think it is the “magic” from a talent perspective.

But talent alone is not enough to win on a product level.  Knowing nothing outside of this film, my guess is that the success of MJ’s product (measured strictly by impact, not dollars, although there were plenty) was as much a function of his motivation as it was of his talent.  Why did he care so much about creating this perfect product?  The tour was already sold out, he had nothing left to prove on a professional level, and he couldn’t possibly attain any greater fame.  Rather, his pursuit of perfection seemed to be entirely organic, motivated by a genuine desire to delight his audience.  This is what I dream about in a product person…Someone who gets off on getting our users off.

Lastly, I was amazed by the infrastructure that Jackson’s creative partner and stage director, Kenny Ortega, built around his product luminary.  For purposes of this startup analogy, we’ll call Kenny the CEO of the “This is It” tour, which would have been a $80M+ revenue enterprise just on London ticket sales.  Ortega’s entire function, in coordinating and managing what I’ll estimate to be about 100 contributors to the production (employees), was to eliminate the friction in Michael’s translation of his vision into an actual product.  Perhaps the lesson to take from this is that a great consumer company is built on the back of a great product.  Marketing, Bus Dev, Sales, Fundraising, and every other function deserve strong, but supporting roles.

So yea, if you’re the MJ of consumer internet products…holler, I’m working on something kickass.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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