Archive for May, 2013

In response to @aweissman on “interestingness”

Posted on May 29, 2013. Filed under: Uncategorized |

My friend Andy Weissman wrote a post today entitled “Interestingness.”  Despite voicing a very different perspective than my own on the subject, it’s one of my favorite blog posts of the year, and you should read it.   In it, he explores our tendency to be obsessed with greatness.  It’s very nuanced, and identifies the relationship between “great” outliers  who now, in a media age, are so visible to us, and the questions one asks themselves about purpose and role in life.  His message is that not everyone needs to be exceptional, and that when traditional concepts of greatness are not “within grasp”, we needn’t obsess over achieving something held only by scarce outliers who simply appear less scarce in today’s world.  I think I got that right, but read the post and then come back…it’s too hard to encapsulate.

Ok, welcome back.  So I’d like to explore the concept of “greatness” for a minute.  About 6 months ago, I sat on the corner watching a ten year old boy play what I can only assume was concert level piano for a sea of agape mouths…it was simply awe inspiring…after each song, droves of passers by dropped dollars into a hat and I thought to myself…”wow, that is a truly deep expression of human life.”  Around the same time, I had been grappling with concepts of energy and the universe…general what are we and where do we come from type questions…and it occurred to me that every human being is an expression of the same fundamental “thing.”  You could define that thing however you want…you could say we are all expressions of carbon and other elements in composite, or you could say we are all expressions of the same energy or source, or we are all expressions of god…whatever your affiliation or predilection, we can agree that a human being is a human being, derived from the same source, and simply expressed differently at the “phenotypic” layer…When I close my eyes, and try to see that “source” it generally renders to me as a composite of some sort…in the same way that black is the absence of light and white is all the spectra of light combined…the thing that we are all derived from feels like a combination of every spectra of humanity or life….it is an aggregate, that when expressed in an individual manifests with uneven distribution between each ray in the spectrum…at a crude level this 10 year old boy that I saw in union square was handed a full sliver of musical flow…deeply connected to the “musical pattern or ray” in our source…and perhaps less connected to the ray of love or physical movement (i.e. athleticism), or any other piece of the spectrum.  In Andy’s model, this child is an “outlier” or embodies “greatness.”

In my model, he is simply the deep expression of a single facet of a very broad spectrum of human energy.  Most people…are more blends…a blend expresses all the elements of the spectrum in a more even distribution…Andy would call a blend “normal.”  They are no weaker an aggregate expression…I believe, rather they are equal…but without some outsized sliver of the source…or an uneven distribution…the source or “where we came from” is less visible.

So now we have a new model for expressions of human life, even and uneven distributions, and we understand that outliers show a particularly deep expression of an aggregate composite that we all are derived from…but why were people putting money in the hat?  This is where things got interesting to me…I realized that we revel and envy in these deep expressions because they make “the thing we all come from”…weather that’s our humanity, or life, or energy, or god or whatever…more visible in day to day…deep expressions of life remind us what we, ourselves are…what we all have the capacity to do or be…if even we were only dealt a small sliver of the thing we look at and envy or admire…we, as a society and a species, reward these deep expressions of ourselves, these visible reminders of who we are…with resource…with money…we want them to live…we want them to excel…to become even more visible…we want them to remind everyone else what they remind us…that we come from an amazing and shared place…weather a rock star, a performance athlete, an inventor, or a painter…we as a group, systematically sustain the deep expressions, elevate them…in a way that we do not sustain blends…it’s harder to see ourselves in a blend…no piece of the composite is super visible to relate to…we need to work harder to see what we share…or to see ourselves in a blend…even though they come from the same exact place as did the deep expression…

So do we all need to be “great”…I think not…a blend is as “complete” as a “deep and unevenly distributed expression”…but I like to think that life is an exploration…and we know not what pieces of the spectrum we were dished in outsized distribution….and discovery and self discovery to find the parts of the source that we can channel and harness is a life long and worthy pursuit….envying the “outliers” and trying to be them when you’re not is a fools game…discovering weather you might be a different type of outlier…a unique expression of something…I like that as a pursuit…my response to Andy would be “there are a lot of rays in a blend…make sure you explore them all in yourself before throwing in the towel on “greatness.”

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Two Ways to Stay Cool When Stressed

Posted on May 20, 2013. Filed under: startups, venture capital |

I used to be pretty bad at dealing with stress and pressure.  Things would get heavy and I’d agonize to the point of physical detriment.  Over the past five or six years I’ve become really good at operating through high stress environments.  I was recently talking to a stressed out friend about what I do to deal with the pressures of building a startup and I think it really comes down to two related practices:

1)   When things get heavy, be sure to find yourself.  I know that might sound a little strange, but pressure can come from two places. Either external forces are pushing on you or you are pushing on yourself…regardless of the source, stepping outside of those two voices and finding the mind that is with you regardless of context is where to begin any stressful day.  Meditation has become an amazing tool for me to return to myself every morning…but it’s not always easy.  The main idea is when you are yourself, acting naturally, and not forcing things, you are at your maximum capability to address any contextual situation…pressure and context are ephemeral…treating them such is the best way to move through them.

2)   Remind yourself that you are capable. It is one thing to believe that you can solve a contextual problem or challenge.  You can stare at something that isn’t working or is disappointing and say…”if I analyze this situation, there is a way out…”  That works sometimes…especially if there is a visible path to somewhere different…but I think that’s more of a band-aid approach…sometimes there will not be a very visible path…it seems stupid, but sometimes I just say to myself “dude, you are good at this…don’t sweat this moment.”  It’s hard to have and believe that dialog with yourself if things aren’t swinging your direction.  Lot’s of people rely on friends or mentors to provide that voice and reassure from afar…but if you can get to a point where you can find yourself and your base self is confident and a believer in you…steps 1 and 2 together tend to put stress in it’s place.

So that’s pretty much it.  Took me years to find these two practices…and I’m not always able to implement them…but they’ve been helpful to me and I hope they are helpful to you.

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When I’m Creating…

Posted on May 6, 2013. Filed under: startups, venture capital |

Today I got an email today from a girl I used to date in college.  Interestingly, she knew me when I was a very different person than I am today.  I hadn’t found most of the things that have now become deeply important to me.  I guess you could say I was “unformed.”  Anyway, she sent me a note today and asked me “how’s the new venture going?”  We’ve stayed in touch periodically over the years, and she knows that I now build technology companies.  My response took 3 seconds to write, and as soon as it was on paper, I realized how true it really was.  I said “new venture is going great…fun to be creating again…this is when I’m happiest.”

I’ve never really articulated that before.  There are so many factors that drove me to start another company…frankly not all of them were about optimizing for my happiness…but it is true, that when I am creating, I am happy.  You build a startup to change the world.  You build with a mission in your heart much bigger than “personal happiness”. You build with the interests of your entire team and the entire world in your mind.  So many reasons why doing this makes sense….but it is a wonderful cherry on top…one which I would not require in order to continue down this path…but a cherry none the less, that when I’m creating I’m in my happy place.

I’m not sure what I will do when I get too tired to create like this anymore.  I’d imagine creating children and a family will feed this same need.  But I can’t paint and I can’t play the guitar…so for at least the foreseeable future it seems that creating technology companies with people that I love will be what keeps me smiling.

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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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