Archive for December, 2012

Devastating Pain

Posted on December 19, 2012. Filed under: Uncategorized |

I stare at the white box, curser flashing in my face.  Scrolling through an index of recent observations…trying to pick out unique thoughts, pointed words, and determining what/if any of the days experiences are worth sharing with the twitterverse.  I consider my agendas…what I want to communicate to the world…in this case my professional world…and the cursor continues to blink…I keep things tight at the moment….bite my lip and sit out of the mobile web conversation…bite my lip and don’t rail the arrogant VC that presumes I want his money (a presumption that couldn’t be further from the truth)…wrapped up in this self involved process of strategic content creation…as I replay the index, and tire of the mundane, or already said…I glance to the right of this empty white box, and see Eghosa’s tweet in which he admits he has wept…a rare display of emotion in a usually strategic feed of self-advancements and clever quips…click through to the words of a mother who has lost her 6 year old Noah…and sure enough, I well up myself.  I am not a parent.  The loss of a child is not a pain I immediately understand. Her words bring me into the pain. I have thought about the massacre in Newtown on a number of different levels…I have been involved in conversations around policy and action…but only in reading the words of a mother, speaking to her slain son…do I begin to feel Newtown.  I am so sad.  My heart aches…my agenda for creating this content is base…it stems from a need to share with you the fact that I am human…to revel in humanity…to trump professional agendas and express a sense of connection to Noah and his mom, and you, and every other being on this earth.  We advance products that strive to connect all human beings on earth.  We laud Facebook for connected a billion people together partially because of the beautiful visualization of humanity it provides.  It seems as though we should attack products that rip us apart with the same force and energy.  Demandaplan is a good place to start:  

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The Edge

Posted on December 8, 2012. Filed under: Hyperpublic, startups, venture capital |

The edge: the edge is a character trait, type of intelligence, and behavioral style that optimizes for the self irrespective of, but not necessarily at odds with, collective interests.

The edge, or an edge, is not unique to some, but rather present in all…it is a base level intelligence that is responsible for calculating toward optimal outcomes for the individual…what is variable is a higher order function which is an individuals choice of how influential the edge is in how she carries herself in a given setting.  Also variable is the strength of this intelligence…some people are extremely tuned to how their own and others’ actions impact their personal satisfaction…they tend to also be extremely tuned to the presence of edge in those around them…they detect when another is acting from “the edge” and instinctually calculate if the other’s intention is good, bad, or neutral for them…if one chooses to be ruled by the edge, that calculation is immediately followed by the action most likely to minimize adverse impact on one’s self interest.

Ok, sorry for the abstract description, but I wanted to really get across what the edge is.  Some more visible manifestations of the edge, or related real world examples might be seen in, for example, styles of poker.  He who plays extremely tight, with perfect calculation, and optimizes for each individual hand, likely has a strong expression of “the edge.”  He who plays loosely, chats with the table, makes some friends, makes a couple calls for the fun of it, may either not have as developed an edge, or may have made the higher order decision not to be ruled at the action layer by it.  Now, a few things worth pointing out.  The edge player does not necessarily win against a non-edge player…each player has a style that works for them…in the short term, or on a given hand, I’d put my money behind an edge player if I had to bet…but over the life of a game, or many games, the same does not hold…I say this because persistent self optimization is not necessarily the most effective path to overall optimization.

Last night I was talking to a close friend and former Hyperpublic engineer, Eric Tang, about the role of “the edge” in business…and more broadly how to carry yourself in a professional and startup setting.  We talked about a mutual friend who we agreed is incredibly smart and competent.  This friend has ambitions of starting a company one day, and I said “he will be amazing…the only thing that might get in his way is his edge.”  Eric’s response was sort of confused…he viewed the edge to be a powerful tool (which it is) in carving one’s way through startupland…but I explained that in my experience, early startup environments are often to fragile and vulnerable to support a heavy-edged leader (and by translation…culture).  I told him, the edge feels like a sword…that you choose to brandish…and more often than not, I prefer to leave it holstered.  I’d much prefer to lead with love and respect and engender a culture that softens the edges of everyone, than allow for an active “dialog of the edges” to emerge within my organization…

I am not saying that an edge is not important, and there is certainly a time and place for fact, when I do brandish said sword, and act under the influence of the edge…I am fucking ruthless about it…but especially now, a little later in my career…I am very careful and conscious about when I choose to use/listen to it.  I have always had a very tuned edge, and when I was younger, not only was I ruled by it, but I couldn’t fathom why anyone, especially in a professional setting, would choose to mute it.  I viewed those who did not act with the sharpest of edges as less sophisticated of shreud…but I was wrong…I attribute much of my current understanding on this subject to Kenny…who you might have heard…has an edge that will cut glass…but his selection of when that edge gets expressed is masterful and nuanced.  Of course, there are those that get far under persistent influence of the edge…but it is not the only way and not long term optimal approach for many.  If you are playing the long game…and by long game I mean lifelong pursuit of excellence in the professional arena…I believe there is more upside in an optimization strategy that checks the edge’s influence over day to day interaction.

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We Can Do Anything

Posted on December 4, 2012. Filed under: Hyperpublic, startups, venture capital |

I don’t know if surprised is the right word…because I’ve now done this enough times to know that nothing is surprising…but amazed certainly seems a fitting alternative.  Amazed that no matter how much things have changed since the last time I did this, some things…that you would think are contextual…are actually constants…each time I start something new…I think I know where I am as a person, I think I know what I have learned…I think I know what I know, I think I know what I care about and what I don’t, and what moves me, and how I want things to be…and I carry that concept of the way things are, quite confidently and assuredly…right up until the moment where I am standing on the diving board, toes hanging over the edge….visualizing my movement though the air, breaking the plane of the water, propelling myself underneath the surface, and ultimately reemerging again…and then, with  a jump…sure enough…it becomes clear that the view from the edge was distorted…and that there are certain dimensions to starting a company that…for lack of a better term…are simply water activated.

Today I am wet…I realize that sounds disgusting…but in the metaphor of diving into the pool, there is no other way to describe it.  That which laid dormant since we sold Hyperpublic to Groupon on February 17th…all which is water activated, seems to have emerged…for good and for bad…I say for good and for bad…because, which will be no surprise to you or anyone reading this blog, this process has inescapable joys and inescapable struggles…there is no “I sold my last company, so this time it will be ‘struggle light’…and there is no ‘I have done this a few times, so this time it won’t be as special’”…in fact…part of what’s special is interacting with and touching the struggles that are constants…the exhileration of a difficult task, the risk in putting yourself out there…the feeling of your heart leaping up into overdrive…inexplicably…when the calendar reminder tells you “10 minutes to game time.”  These are phenomena that no entrepreneur, independent of their past experiences and successes/failures, can…or even wants to…escape…these are the thrills and anxieties of being in the game…and it is a feeling more alive than I can describe.

I was talking to a friend yesterday who is not part of this world and he asked me to share with him “what is it?” “what is this feeling that has you jumping out of your seat?”…he literally couldn’t understand the speed of my energy and wanted me to articulate and share it with him…I thought for a moment, and really tried to isolate what it was that I was experiencing…and the only words I could find…which I think are the right words, were “We can do anything”

the belief and exploration and testing and celebration of this principle is at the core of my joy and why I love to start companies.

A note on team:  if you want to come on this journey…and explore this principle…if you’ve ever read this blog and thought “that dude would be cool to work with”…you are invited.…I speak from experience when I say it will be fulfilling and exciting and so so so hard…senior and junior, all skills…problems will be engineering and design intensive.  The bar is excellence…tough to join, once in, you will enjoy the company of people who share your aptitude, ambition, curiosity, ethics, and general dopeness.  If we do it right, you will not be the best on this team, but you will be on the best team…which is way more fun.


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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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