Archive for January, 2013

Vine: Data Compression Applied to the Human Experience

Posted on January 28, 2013. Filed under: startups, venture capital |

Some quickly scribbled thoughts on Vine:

1)   for those who think it’s a flash in the pan, think again, here to stay, and maybe as important to Twitter as Youtube was to Google

2)   the amount of information transmittable in a Vine feels higher than any other unit of shareable data that exists…period.  At it’s core, vine feels like a data compression technology where the human eye/brain can read compressed format…the time that lapses inbetween shots is extraneous and unneeded in the creators story…by editing in the content creation flow, a user can tell an hour long story in six seconds if she chooses the right frames/sign posts to capture

3)   There seem to be two primary applications of this compression technology…one is a horizontal view into a single moment and the second is a linear view through time across moments…the first does not leverage vine’s unique compression capability nearly as well as the second.  Sure, you can fit more of the story about what’s going on in a given moment in your environment if you can stitch together multiple images of every angle and dimension of your surroundings…but the result is maybe a 2/1 compressed view of a 360 degree 6 second video clip…the second, however, is staggering…if a photo answers the question “what were you doing at a point in time” vine answers the question “what were you doing through time?”

4)   I think our minds are wired to make inferences and fill in the blanks of what occurred between frames within vine…and a shared context and brain function between the viewer and creator of the vine enables the creator to tell a full story while skipping the “assumed” details…it’s as though the recipient of a vine has cached a local copy of the human experience in their own brain, and thus only needs to “pull down” and “stream” the dynamic stuff that is changing based on the creator’s individual experience

5)   The aggregations of the vineapp that have been popping up like: and are fascinating.  They are the window into human experience that I wanted chatroulette to be, and that Youtube bills itself as when highly edited and culled down into fundamental moments…the amount of nuanced human experience consumable per second within these aggregations is so large and dense…I almost believe if I stare long enough I will see the world in it’s entirety from every perspective of the 7 Billion node network of biological sensors (people) using machine sensors (video) to document time and space.

6)   I think the app poses as great or greater a threat to text than it does to photos…this is not an instagram killer…vine’s don’t capture beautiful moments…this is a tumblr/wordpress killer…vine’s tell stories in a way that text/image publishing platforms do…only they are much more efficient and lower commit for the publisher…

7)   I’m not sure how defensible the start/stop mechanic is on the video tool, but what’s lost in defensibility is gained in distribution through twitter…will be interesting to see how Youtube responds…will they make an app that’s focused on the creation side of the video experience…will it use the same mechanic?

8)   If the tweet lowered the commitment to create textual content and created a new sphere of publishers not seen by blogging platfroms, the vine feels like a similar disruption to traditional video capture/publishing

9)   Vine = data compression of human experience into a shareable and consumable unit that vastly increases the volume of transmittable information consumable by a human in a unit of time

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Watching stars fall

Posted on January 26, 2013. Filed under: startups, venture capital |

Oft covered is the guy who ascends through professional rungs, leaping road blocks, defying statistics…he is an outlier, he is romanticized, he is something slightly more than human but not quite divine…the rise of a star is an intoxicating story and object of observation.  A young phenom starts scoring 40 points a game in highschool…fascinating…a hedge fund manager puts up 80% annual returns…fascinating…a little girl starts beating grand masters in chess…fascinating

But like the rise, the fall has always been fascinating to me.  Lance Armstrong drops from world inspiration to nothing overnight.  Steve Cohen from wall st god to alleged cheat…fascinating…  I used to work at a place where the “smartest guy in the room” ran conversations, passed judgment on all, and was respected as the self-appointed “golden boy” of the firm…I remember reading recently of his “departure” from said firm…his wandering around without a home…and ultimate acceptance of a much less prestigious gig than the one he had obviously been pushed out of…I thought to myself…god that is sweet…I’ve watched countless high-flying founders turn their nose up at the world, only to have the rug pulled out from under them 12 months later…the rise is inspirational and the fall is cautionary…the fall is what happens when you lose site of your pre-rise self…when you start to believe you are above the law, or the rules, or other people…personally, I LOVE watching the fall.  If the rise and the fall were on tv at the same time, I’d DVR the rise, and watch the fall live…there is a justice in the fall that is just too good to turn away from…the fall is statistics catching up with you when you forgot that the longer you live, the less likely you are to defy them…there is something so beautiful about the guy who stopped being friend to man…sitting on his living room floor…alone…shamed and shocked…not having a man to call…out of moves…forced to begin again…in a place even lower than where his previous ascent begun.

How a man who has fallen rises again…if he rises again…is much less documented than the initial rise or fall…my guess is because after the fall…a man realizes that the rise and the power and the success meant nothing in and of itself…that the contextual pinnacle that he so proudly and arrogantly sat atop lacked the human foundation that he needed when it all disappeared…so to rise again did not mean bright lights and big bank accounts…but perhaps rather ordinary relationships and ordinary living…which is not a very media worthy resurgence…or maybe after a fall…one who has risen learns to fear the fall…fear the shame of falling again…and thus goes through a second ascent more discretely and tastefully than the prior…I don’t know…but I do love the fall.  It may be that those who do not fear it, acting wrecklessly in their pursuit and preservation of the apex, are in fact more likely to reach said apex…but I will stick with my fear…or perhaps I should say respect…of the fragility behind any state that is comfortable or enjoyed…that which we take for granted or as a given…is not…and while 99% of the days you wake up…things might go as you’ve become accustomed for them to go…keep waking up…and living more days…and the rake will catch up with you…push your whole stack in, (emotional, financial, social, or otherwise), leave it hanging there, in the middle of the table, as you hobnob with the other players and slurp down the “free drinks”…and one of these days your aces will get cracked…OR…maintain the mindset that no matter how big your proverbial stack gets…the rake is the rake, and you are as susceptible to it as the small stack to your left…and you will enjoy a life with small stumbles instead of 1000 ft cliffs…god I love the fall…life’s rake against those who rose without moral fiber, self awareness, and personal character.

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The crumbling network of startupland

Posted on January 23, 2013. Filed under: startups, venture capital |

Lately I’ve been wondering if the startup community is becoming less connected than it once was. It certainly feels like the network is being diluted, and also that the average strength of connection between all nodes in the network is lessening…the primary culprit that is disconnecting us is sheer size…it is not surprising that as a network grows, the strength of connection between nodes dilutes…typically when this happens in an online network, the product and use case of the application which defined a network evolves…twitter isn’t what it used to be (heavier emphasis on content distribution away from multi-person conversation around content), Facebook isn’t what it used to be (pushed downstack to infrastructure layer, pushed experience into 3rd party environments), I never knew exactly what Linkedin was, but you get the idea…

So if the startup ecosystem is a network, and the volume of nodes in the network is pushing the limits of the original “application” which created it (building real technology companies)…it begs the question…must we let the initial application go and accept the new reality of the network?  My guess is yes…where the new reality is a maturing and fragmented market where innovation and creation happens more in vertical silos (industries) than in a horizontal community within one vertical (technology)…or said another way…if technology has largely eaten the world by now…it’s no longer technology that defines starting up…it’s now fashion, or auto, or finance, or foodstuffs, now tech-enabled, spawning industry specific community that is tighter nit and adequately intelligent to support innovation and starting up?

And what happens to the core users, who liked the first application and built relationships and behaviors before the network got too big?  I think they break off and find a new home for their network (see Branch re Twitter, Instagram re: FB), etc…so where do we go, who talked and learned together before a world with infinite content and blog posts and a sea of faceless seed funded founders?  Where do we find ourselves and begin to learn again together?  Someplace smaller?  Someplace with a higher barrier to entry…some place where the technology and challenges are harder… Maybe…it’s as though the infrastructure of coworking spaces, accelerators, public forums, and even capital…all the things that supported us and helped us form community when we were unnetworked…are the very places we can’t go anymore to find what we had…either the network has to contract or shard…wonder which will happen first

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When Founders Melt

Posted on January 8, 2013. Filed under: startups, venture capital |

Between my own experiences, those of my friends, and those of founders who I have invested in, I have seen many startups go through difficult times.  A product flops…a cofounder leaves…the company gets sued…a financing falls apart…an acquisition falls apart…an api gets cut off…the money is running out…the money ran out…

In these times, if you are a founder, shit gets very dark.  More often than not, you start to worry about your team.  You worry about your employees losing faith in the company.  You worry about your investors.  It becomes hard to answer that question from the market and your friends: “how are things going?”  Between the social pressure, self inflicted pressure, investor pressure, and market pressure getting out of bed in the morning is not pleasant.  In my experience, there are two states a founder can exist in when such a situation arises: 1) depressed/stressed/exhausted and 2) melting.

Both blow, but the single greatest predictor of a company’s demise or resurrection is which of these two states a founder is in during the time of duress.  As an investor when I’m asked to bridge through this period, as a friend when I’m asked if it’s worth fighting through, and as myself when I look to calibrate how I’m dealing…the question I always ask is “is the founder melting?”  Once you’re melting, it’s over…there’s no coming back, no bridge will help, no new product effort matters…your going one direction and that’s down the drain.  You know you are melting when you start lying to people…you know you are melting when you lose confidence in your decision making…you know you are melting when you are pretending to execute as opposed to executing…you are a shell of yourself…the outside remains solid, but the inside is soup.

If you are melting, don’t ask for the bridge.  If you are melting don’t ask for your employees’ continued loyalty.  If you are melting don’t tell your family it’s going to be ok.  Be responsible, recognize that you need to exit this situation, and preserve your relationships with your team and investors, do right by them…

More importantly, however, is not to melt.  I know it sounds absurd, to ask someone who is depressed/stressed/exhausted to hold it together…but that’s the job of a founder.  Even when it appears that you have no outs left and no moves to make…the one move that you can always make as a founder is to keep your proverbial cool…to not melt.

There is a reason airline safety demonstrations always instruct parents to place the mask over their own nose and mouth, before helping secure the mask on dependents.  Leader has to stay coherent for anyone to survive. Your first move as a founder is keep yourself alive and functional…if you melt…company is gonzo…Do whatever it takes to keep below melting temperature…don’t just stare at a screen, hoping things will change…go to the movies, go on a date, talk to a shrink, open up to a friend, or advisor, or spouse, go on a week long hike in the mountains if that’s what it takes, whatever it is you need to do to remain in solid form…do it. When founders melt, a small hole forms in the trough of sorrow, and the team and investors and product and company drain out the bottom into oblivion…stay cool

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A Human Foundation

Posted on January 3, 2013. Filed under: startups, venture capital |

Sometimes I write a tweet and immediately realize that there is more to be said on the subject than can fit in said format.  Today, I was sitting in the sun, on the back porch of a rental house on the coast of Uruguay, and I was reflecting on my hopes and ambitions for the year.  Many of them were personal or existential in nature, and of course, some were professional.

I tweeted: “In 2013 my professional goals are all around people I want to work with and not at all around traditional biz metrics. Team is everything.”

It’s strange, because I have been engaged in the same practice of delineating and ruthlessly chasing down annual goals for at least the last 5 years, and usually the professional ones orient around big, visible metrics (i.e. raise $5M, build a product that reaches a million people, become a partner in a venture firm, learn how to code, etc…).  This year was different.  My ambitions were a reflection of maturation in my thinking this time around… 2013 will be strictly foundational for me, in what I feel in my heart to be a coming 5-10 year journey.  I literally do not give a shit about any traditional milestones…when I think about what I want out of this year professionally…my mind visually wanders to the faces of the people who I admire and with whom I have rewarding and rich interactions.  What you come to realize if you’ve built one or two startups is that most business metrics and milestones are simply reflections of a team’s capacity…unless you royally fuck something up, when you assemble thoughtful, ambitious, ethical, humble, deeply intelligent people around a sound yet flexible direction, milestones and metrics follow.

So yea, it’s cool that metrics follow excellent teams, but metrics are not the root of my 2013 goals.  It’s something deeper than that.  Interacting with people takes a tremendous amount of energy…and for me…that is probably more true than for many others.  I spend a lot of time alone, I like thinking through work and life, almost as a mediation, without conversation…so when I do engage people (which at work is often, obviously), I put a lot of myself into those conversations and meetings.  My hope is that what I put in is only a small fraction of what comes out, and for that equation to hold, I absolutely need to work with additive contributors.  Further, I want that equation to hold for any interaction between two members of our team.  If an interaction simply yields the aggregate of what both parties invest, there is no hope for exponential yield…

So people are at the center of my 2013 goals because the people I want to work with will be good for business…no doubt…but it’s even broader than that.  What you come to realize in entrepreneurship is that work is life, and it’s always going to be that way.  Who you spend your life with is on the short list of important decisions that you actually get to make. Spending your life with people you respect and love and with whom you share values trumps any joy that will come from success in business alone.  I see miserable successes everyday and guess what…I’m not gonna be one of them.  2013 will be the year we assemble a group of people who will define my day to day and my future…it’s so important that I get it right…and it is my singular focus

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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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