What Really Happens When You Fail in Startupland

Posted on February 13, 2013. Filed under: Hyperpublic, startups, venture capital |

This is not going to be an easy topic to talk about, but it needs to be said.  This post is about failure, the way we talk about it in the startup world, and the disparity between the way we talk about it and the way it is.

The party line on failure, if you talk to anybody in the venture world specifically, is that “failure is a badge of honor” or at the very least, “there is nothing wrong with trying and failing.”  This is the line that we tell young founders to encourage them to jump in and take risks.  This is the line that we tell the world so that we appear genteel, respectful of the risks that people take, and admiring of their willingness to risk everything.  It is a pom pom we wave when we are trying to say “we love entrepreneurs and admire their boldness.”

The truth is, and I am speaking from an investor’s standpoint here, we want to believe that we live the reality of this party line.  We want to believe when we lose money with a founder that that loss has no impact on our feelings toward this person…but if I am really honest about it, and I look at empirical data…the party line and the reality don’t always line up.

The truth is, when you fail, your investors tend to have a bad taste in their mouths.  Nobody likes to lose money. Nobody likes to be wrong.  Nobody likes to sit in that space that isn’t so happy…and unfortunately for a founder, his person at the point of failure is an embodiment of many things that nobody likes.  Now sure, an investor doesn’t dislike the founder himself.  If the founder does right and doesn’t succeed, there is no “black ball”, or malevolent desires on behalf of an investor…but I’d be lying if I said there isn’t a slight tinge on that relationship…and unfortunately, in this world, a slight tinge is all the friction necessary to turn momentum into something less.  Note: this tinge is not permanent, and it is not insurmountable…but coming off a failure…you are only as good as your next act…and weather we say it openly or not, clawing your way to the next act, you are starting not at neutral or positive, but with a headwind.

I’ll give the example of my own experience as a founder.  My first company, I raised about $600K.  I operated for a year, failed, and returned about 50% of the capital I raised.  I felt terrible.  Everyone said I did the right thing returning the capital, that I was a standup guy for doing it, but still I lost them money.  Nobody turned their back on me, once the company wound down…but they just weren’t leaning into investing more time and energy on me.  When I went to raise money for my second company, Hyperpublic, weather I asked them or not, not a single investor in my first company invested in my second.  Just gives you a sense of the increased friction you face, coming off a failure.  Sure I was able to raise money from new investors, but I had to answer the question “is so and so from your last company investing?”  and so on.  New investors call old investors and say “What do you think of Jordan?”  Of course, again, investors who lose $ with you don’t “blackball” you, so they say “stand up guy, did the right thing, etc…” but still their signal of not reaching out to put $ into the next thing becomes something a founder has to overcome.

Now, let me show you how powerful the mental impact of a failed venture can be on a relationship.  When I started Hyperpublic, I felt so bad about losing my previous investors’ money, that I cut all of those angels a piece of equity in the cap table of Hyperpublic.  It was free, they didn’t know how much they had, but they signed a piece of paper, that to them was a nice gesture, but still probably worth very little. In their minds they owned a piece of a new thing with an unproven and recently failed person.  Fast forward a few years, I sell Hyperpublic to Groupon, and get to send an email to each of these angels saying “you thought I lost half your money, turns out I doubled your money. Here’s the check.”  Again everyone appreciative.  But now, if I am really honest about it, I only have real relationships with two of the seven or eight investors who lived three years thinking I failed and lost their $.

I listen to the way investors I interact with on a daily basis, from all different funds east and west, talk about their “losers” or the ones that didn’t work out…and it is always the same…a muted expression of disappointment, and slight negative tinge…not a condemnation by any stretch, but we have to be honest about the realities of failure.  It is ok, but it’s a black mark that you have to work your ass off to wash away.  Coming off failure, you are only as good as your present and future.  That’s the reality of the market.  I don’t want it to be this way, but even the most accomplished of people cool off when things go south…which means if you haven’t proved anything, and you fail, you really cool off…only way to heat back up is to earn it back through hard work and new success.

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When the wise thinks himself wise

Posted on February 11, 2013. Filed under: startups, venture capital |

Earlier today Chris Dixon dropped a nice excerpt from “The Principles of Psychology” by William James. The entire excerpt can be read here, but I absolutely loved the following thought :

“As the art of reading after a certain stage in one’s education is the art of skipping, so the art of being wise is the art of knowing what to overlook.”

That is a very powerful concept that I hadn’t fully articulated but have definitely been living as I begin to build the mobile web I want to see in the world.  Said another way, knowing what NOT to focus on at various stages in a company’s development can be as important as knowing what needs focus.  I have actually been pretty dogmatic about focus this time around.  I guess you could say, I’m feeling sort of wise.  I’ve now been through this phase in building a company three times, and I’ve seen this stage in company development at least 5000 times more.

I sat down last week to write a 90 day plan for what we needed to do as a team and as a company…and it took me about 30 minutes to lay out what I’ll call an A- plan.  A few years ago, it would have taken me 6 months to even figure out that I needed to develop a 90 day plan, and the amount of ridiculous crap that would have been in it would have been immense.  So my plan was an A-, and I knew that it would take some more thought and discussion with our team before it got to an A, but I was feeling pretty wise indeed, knowing that there was nothing on that paper that the wise man would or should overlook…but what I learned a few hours later, was that I had gone a little heavy on the “wise whiteout.”

That night I went to a sushi dinner with a dude who I have come to see great wisdom in.  I told him, “this is my 90 day plan, not my big vision of where we’re going, I just want to focus on ops and see if there’s anything you’d be doing differently”  I would have preferred to have my plan at an A, as this dude’s time is scarce, but our meeting ended up being a few days earlier than I had anticipated, so I just dropped in where I was in thought.  I went into the dinner hard pressed to add any major initiatives to the plan (as it was already quite ambitious), but left feeling a gaping weakness in what I had been thinking.  My friend rightly suggested that I had designed a 90 day plan that overlooked one of the hardest parts of our effort.  I wanted to keep the scope of our first build manageable and known.  I didn’t want to commit to a messy challenge, knowing that it might turn my 90 day plan into a 120 or 150 day plan, and so I had “wisely” chosen to overlook it until a time when I either had the resources or gun at my head to address it.

Turns out I thought myself too wise.  Under the guise of wisdom, I gave myself the license to overlook a key element of the company we are trying to build…while maybe not solvable in 90 days, it was certainly attackable…and further…the commitment to attack it will be a key influence in the early DNA and culture of our company….and thus my response to Chris’ post was a retweet with warning: “True but dangerous when the wise thinks himself wise”

 The lesson: wisdom is a spectrum, no matter where you are on it, seek out the wise and they will pull you closer to their end 

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Bad Asses Make Peace with Unanswered Questions

Posted on February 7, 2013. Filed under: startups, venture capital |

As I walked to work this morning, I found myself extremely aware of how wound up I am in moving forward on our new mobile web endeavor.  I found myself hurrying.  Hurrying to shorten my morning routine at home, hurrying to make progress on product design and definition…hurrying to get administrative tasks done…and if I had to take a step back and examine the hurry more holistically…it’s really a hurry to answer all the unanswered questions between today and the future I want to build into the world.  At Hyperpublic I lived hurrying for two years…a founder is never satisfied as long as questions are outstanding…but the question I arrived at today, which I already knew the answer to, I just hadn’t articulated it in my mind, is as follows: “Is hurrying a necessary state of mind for a startup to succeed?”

There is no doubt, when a tone of hurry is introduced into a founder’s mind, and by extension a team’s mind and culture, things get done.  We see founders all the time setting artificial deadlines, things to run at…as though creating a sense of urgency is a necessary catalyst to stretch a team to produce.  Urgency is real, and sometimes a deadline is the difference between getting a deal and not.  Sometimes, when building a startup, you have to be in a hurry or someone else comes along and eats your lunch.  But there is a difference between recognizing moments when we are in a hurry, and creating a culture where the only way to find the finish line is to live and work in a state of perpetual hurry.  It doesn’t take a rocket scientist to know that running a marathon is not simply a consecutive set of strung together sprints…but there is more to this question than just strategic pacing.

Hurrying can be at odds with thoughtfulness, happiness, health, etc…I have seen some repeat-founders, in recognition of this truth, slow down too much.  Having isolated the truth, that hurrying is not the way to win a marathon, they attempt to create a new culture and personal lifestyle that takes urgency out of a startup’s culture…often these repeat founders have had a success in the past, and now in their wisdom, they say “this time, it’s important to be as zen as I was in that lovely 12 month break between gigs, so this is what our new culture looks like.”  Almost invariably, those founders either fail in the new endeavor or realize they swung the pendulum too far, that they lost a full cycle of development and progress, and now it’s time to “get serious and buckle down”…at which point they inject hurry into a culture that isn’t as ready to accept it.

On the other end of the spectrum, I have seen young first time founders hurry the entire way through and either succeed wildly or burn out while running at the finish line.  I think you get to do this once, and only once, in your life.  I have never seen a repeat founder attempt to sprint wire-to-wire the second or third time around.

So where does that leave me?  Sort of retraining myself…My mind and my body recognize this period of deep uncertainty/opportunity as a state where we hurry to answer the unanswered…we’ve been here before…and when we hurried we did well…so I wake up and instinctually I am hurrying…taking deep hacks at the unknown…but as I walk through my day…my experience and rational is talking to my mind and body and saying, “dude, chill the fuck out.  You are not in a hurry right this second.  You are not going to lose this market if you enter a week later.  In fact, you don’t even know yet if your timing is 6 months early or 6 months later than optimal. You haven’t raised capital and you don’t have any burn…time is not running out, it is just beginning.  THESE UNANSWERED QUESTIONS THAT YOU ARE ATTACKING LIKE CANCER WILL GET ANSWERED OVER THE NEXT 5-10 YEARS. STOP TRYING TO ANSWER THEM ALL TODAY.

So the CAPITAL LETTERS in my head are my experience yelling at my founding instincts…saying “you asked to be in this ocean of unknowns…I told you how nice it was to chill on the beach and let the world pat you on the back…and you just couldn’t let us graduate into the life of a non-hurried venture capitalist…waiting for other people to answer the unanswered for you…FINE…we’re back…answering the future ourselves…and making up the answers where no answers exist…I accept this, but remember you are a mother fucking bad ass, don’t act like a fucking kid.”

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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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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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Mobile Distribution Hack

Posted on November 19, 2012. Filed under: startups, venture capital |

So here’s what I was thinking about yesterday.  It is no secret that distribution in the mobile ecosystem is FUCKED.  I complain about it in tweets at least once a month.  No matter which way you slice it, getting people to download your app, even if your app is dope, is really freaking hard.  As was the case 24 months ago, today there are still very few channels by which you can acquire new customers.  The fact that “get featured in the app store” is the number one method for building a native user base is completely absurd. Even if you can get people to “share” in your app, a deep link into the app store just sucks. The drop off is huge. Signing in and installing something before a user gets any value is completely contrary to the way users have become accustomed to acting on the web.  It’s the equivalent of forcing registration in a web app before delivering any value to the user. Imagine if Yelp made you register before you got to read reviews on their site…just doesn’t work.  There is this big step in the funnel from when a user is exposed to a brand to when they commit to it that is simply missing from the native mobile ecosystem.  It’s so bad, that if I had a mobile app that I was trying to spread, I would drive recipients of any share experience to a web based UX where they could interact with my application in a non-native environment…I’d try to win them there…and then attempt to convert my web users to native mobile users down the line…

Anyway, these problems got me thinking…if everyone gets a small install base out of the gate, and then struggles to grow it organically or socially the way they would a web app, that must mean there are A TON of “walking dead” apps.  You’ve heard of “walking dead VC’s” that still exist and have a brand but don’t do anything and don’t die…”walking dead apps” are apps that have install bases of between 10,000 and 100,000 but no growth and declining engagement.  These apps will never be meaningful companies, will never make any money, and at some point I’d imagine they just disappear.  BUT, one thing walking dead apps have is a footprint…small but valuable real estate on a user’s phone.  Granted the user probably doesn’t engage with their app, but they probably haven’t deleted it either…so how much is that footprint worth?  Well…if apps like Groupon or Zynga are willing to pay $5 an install, that would mean a crappy app with 10K downloads is sitting on $50,000 in IOS real estate.  What if…theoretically, there were a way for GRPN to buy “crappy app” for $2 an installed user, replace crappy app client side code with GRPN client side code in an “update”, send an email or push from crappy app to userbase saying “crappy app is now GRPN, check out the app already on your phone”…and then GRPN converts some % of crappy app’s users to GRPN mobile installed users?  I realize the mechanics of this sound ugly…but if someone were to come along and buy lots of crappy apps, put them together in one network, build a large installed footprint, and then sell the real estate plus “services to facilitate and optimize transition/conversion” from crappy apps to “buyer’s apps” …that might be kind of interesting…or better yet, what if someone built a marketplace where crappy apps could list themselves, there install bases, their recent active user base, and there category…and buyers could come along and intead of buying ads inside mobile apps that drive to deep links, they could buy blocks of installed real estate on mobile devices…then crappy apps would have someplace to monetize their now worthless apps, which would lead to more apps being built, which would be good for the ecosystem and Apple actually, and successful apps would have a channel where they could spend $ to effectively acquire IOS real estate.  I realize there are tons of problems with this (Apple’s hissy fit being the primary)…but I’m interested in the idea of fledgling native apps selling installed real estate instead of adspace within their apps.  Give em’ a performance based kicker on successful transition of installed base to “buyer’s app,” unlock more value for those who have been punished by the distribution wall of death…just a rant born out of frustration with the state of the state

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on an inspired day

Posted on November 2, 2012. Filed under: startups, venture capital |

I sat on a stoop beneath a statue in a circle and read a note from a boy about to become founder.

I looked in his eye at the passion and hunger, I remembered the time I dove in myself.

I envied the pain that would come with his journey and listened as he spoke of what was ahead.

I cautioned and warned to make sure he was ready, and embraced his journey as though it was mine.

We sat in the sun and watched life for an hour, then parted to move into the future.

He boarded the subway, wrought with anticipation.

I boarded a treadmill to burn off my laze.

I thought of the question I always come back to, and let it simmer amidst the sea of perfect asses.

I walked into J crew, to replace soiled clothing. A refugee for a moment from minor inconvenience.

I have moved to all black, for it is more simple, and fashion was never my strength anyway.

I sit in the dark, screen glows in my face. The page was once blank, now covered in words

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Posted on October 17, 2012. Filed under: startups, venture capital |

Vision fascinates me.  It is what I focus on when considering investment in a founder and it is my primary competency as a founder.  No startup realm is cut and dry, but within the dimensions of a startup, vision is by my own admission most nebulous, fleeting and difficult to measure.  After about a year building our team at Hyperpublic, we got pretty good at measuring engineering talent.  Our interview process was a series of meetings and conversations, as well as a technical test.  There is, however, no test for measuring vision.  One reason why “visionary talent” is difficult to assess is because it is not “evenly distributed” between the near and distant future.  Said another way, a founder may have strength within a certain focal length (i.e. near term vs long term), but weakness at a different length.

Near Term Vision

Some people “see” the present very clearly.  This is near term vision.  “Today” expires before a thought or decision can manifest, so let’s say the window of value for a founder with strong near term vision, is defined as tomorrow through 90 days.  Near term vision is easier to calibrate than long term vision, for no other reason than a founder’s current product is a manifestation of her near term vision.  How well she sees today is translated into a solution that she builds which, if her near term vision is strong, is consistent with the current state of today/the market/the user/the problem.  The founder archetype who builds to solve the problem that she has today, or to scratch her own itch, or who begins with a simple feature and develops a startup around it, I believe has a more developed near term lens. This is not to say she lacks in the medium to long distance view, but she tends not to lack in her view of the present and near future.  If her product does not build traction, or clearly violates some truth or realty in the present, that is a reasonable sign that her near term vision is not extremely developed.

Medium Term Vision

Push out beyond the tomorrow, or the 90 day window, and vision becomes harder to measure.  There is no tangible manifestation of the way a founder sees the world unfolding…short of her plan.  Now this plan is not just a product roadmap, it is also a company roadmap.  The medium term we can define as 90 days – 12 months.  In measuring medium term vision, the conversation must orient around not just current product extensions, but also company positioning.  Does the founder have a sense not just of how things exist in current form (user preference, consumer behavior, market behavior, etc), but also the direction or change that is occurring or happening to the present.  Directionally, is a set of characteristics or phenomena moving toward or away from a given point? What dimensions or aspects of her product will be successful as the phenomena moves on that more macro curve and what will become stale or irrelevant. What are competitors and tangentially related companies building and how will their evolution change both her user’s thought/behavior as well as her future user’s thought and behavior (I use “user” interchangeably with “customer” and recognize that this principle applies to non-consumer facing companies as well)?  A founder with strong medium term vision can see and articulate the “bridge” between where she is today and where she will be in a year. She is able to define a plan based on let’s call it “one round of financing” (or 12 months) that does not violate directional changes in the market and population, so as to ensure that she is as relevant or more relevant in one year than she is in the present.  Medium term vision is essential to interaction with the capital markets and the M&A markets who tend to measure not just the value of a startup to the present market, but the expected value of that startup down the road.

Long Term Vision

Long term vision is closest to my heart and hardest to calibrate.  In long term vision, metrics and heuristics cross the chasm from logical to spiritual.  The inputs that influence a founders view of the future when we look, say 5 years out, are nuanced and often inarticulable.  Often these inputs, while real, and definitely consumed and processed by a founder, get rolled up into justifications around “feeling”, “gut”, and belief.  The founder with true long term vision both consciously and unconsciously consumes and processes signal from the population and market that most will not process for years to come.  Medium term trends will bring this signal to the forefront of market consciousness on the ascribed timelines, but the founder with developed long term vision has a jump.  Excellence in this realm can be particularly hard to identify, as the timeline of relevance is long enough that any articulation of long term vision can and often will violate near and even medium term realities.  A founder with conviction In their long term vision can ignore and disregard the very signal that is driving the rest of the market.  Once Joel Cutler described to me a founder that “can see around corners.”  It is a phrase that has stuck with me.  The long term thinker’s life is not easy.  Communicating the future to the present and medium term thinkers can be exhausting and challenging and isolating.  But she who sees around the 5 year corner, if competent but not necessarily excellent in the near and medium term, takes all.

Often, the founder with true long term vision makes up for the disconnect between her vision and the present with passion.  She must amass resource not around the solution she has in hand, but around a persuasion of all that she correctly sees something invisible….and the challenge of anyone who might hitch their wagon to this founder (be it a challenge to a recruit, or investor, or partner, or lover) is to identify who amongst the snake oil salesmen is actually the prophet.

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Thoughts From the Dugout of Team Suffering

Posted on September 30, 2012. Filed under: Hyperpublic, startups, venture capital |

Last night I went to a party where I ran into Adam Rich.  Adam is co-founder of Thrillist and runs the editorial side of their business.  I went over to say hi to him, and after some friendly chatter, he mentioned that he’s been reading my tweets and that he’s been enjoying them…he said “they’re good…but they’ve been better.”  I realize how absurd this sounds to be discussing seriously…and it was a joke…but it was serious too.  “My tweets” in this conversation was a euphemism for public voice, and encompassed in his statement was an indication that my blog isn’t as interesting to him as it used to be.  I asked him, “what’s missing?” and his response was “you.”  He said anyone who reads my blog could and also probably does read Business Insider, etc…so he doesn’t need analysis on the market, or trends or how to xx …he said anyone can write that and there is a surplus of places to find it.  I thought for a moment, and frankly agreed.

It hasn’t always been this way, but it is now.  Startup content is a saturated market.  It used to be that Fred Wilson or Chris Dixon would write about term sheets or fundraising or distribution or whatever, and because this knowledge was previously inaccessible to young and first time founders, it was enough and extremely compelling to shine light on these subjects.  When I started writing this blog, I did the same…I’d find areas that Fred and Chris hadn’t covered and I’d write about them.

Mixed in with the inside baseball of startups and venture capital, I used to write a lot about my personal journey and feelings and experiences as I navigated life as an entrepreneur (I think this is the “you” that Adam was referencing)…I was not shy about sitting down to this computer, saying “how do you feel write now?” and then writing 3 paragraphs about the day’s stress and hopefully some solution I had hacked together to resolve or at least live through it.  This was easy content for me to write because it was me and every other kid hustling his ass off in the same boat, just trying to survive and snatch some small victories from the “other guys.”

So who were the “other guys?”  They were fancy VC’s, successful entrepreneurs, market incumbents, and generally anyone who was up high, looking down at all of us…doubting us…comfy and cozy in their fucking mansions and fancy cars…getting in our way and frankly not empathizing with our day to day struggles…they were the guys who forgot that they were once like us…they were the guys who would never let you know that they put their pants on one leg at a time…guys like this. my blog was in many ways a rebellion against anyone who was not on our team.  Our team was comprised of the unproven, the hungry, the uncomfortable, the underdogs…frankly our team was “team suffering.”

Wins on “team suffering” were also not hard to articulate or write about.  When you posted for a month about how you can’t sleep because of what this life is doing to you, and then you finally win a deal or get some funding or whatever, the market roots for you.  They champion you.  They have seen and read your pain, and know you are not an “other guy” and they want you to win…in both adversity and victory, as long as you are on “team suffering” the market supports you.  This support fueled me and also kept my spirits high.  Instead of looking for support from my family or friends, I really looked to “team suffering” to help me through startup life.  I felt a sense of belonging and deep community here, and the more I shared, the more people would emerge and express empathy, compassion, and frankly affection.  I deeply valued my position on “team suffering” and felt lucky that on occasion, through this blog, I could act as a megaphone for what my peers and friends were experiencing.

Which brings me back to Adam’s comment that what my blog is missing is “[me]”.  I hear that, and I agree.  The reality is that I’m not suffering right now.  My challenges, while real, will not resound with the community that I have long and continue to feel a part of.  They are not the daily struggles of “team suffering”…and I will not amplify the voice of “the other guys” because I fucking hate them.  So I’m kind of voiceless until I start making life hard again…which I’m working on…

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My Ambitions

Posted on September 25, 2012. Filed under: startups, venture capital |

Paul Graham recently wrote: “[a startup] is at first is no more than a declaration of one’s ambitions.”

My ambition is global in scale, but the inverse in culture. On one hand, I am obsessed with the human population as a system. I despise the concept of borders and the segmentation of our population by arbitrary lines on a map. I do not value what is near over what is far away, and I aspire to build a business that directly or indirectly reminds people that we are one. Jack Dorsey recently quoted William Gibson in saying: “the future has already arrived, it’s just not evenly distributed yet. So our job as founders, as entrepreneurs…is to distribute the future that’s already here…and to do so as quickly as possible with the right amount of purpose and right amount of values” In the future I see, there is only one country. It is earth. Language as a barrier is nothing more than an absurdity. Physical distance as a barrier is nothing more than absurdity. I want to pull people into a future where we value a human life and experience equally, independent of our social of physical proximity to it. There are many ways to destroy the distance between people. The most visible leaps in this arena seem to exist in the networked communication between individuals. Whether the telephone, the internet, the Facebook (see how I did that.. ha), or the Twitter…step function changes in the way people communicate are narrowing the chasm between distant individuals, and more profoundly, amending the young individuals’ concept of self as distinct from another, whether that other be local or international. These are beautiful and evolutionarily significant efforts to pull our population into the future. There are, however, many other forms that this progress can take. A product or service that achieves global penetration shows the world common experience, despite our differences. There is something about McDonalds at the end of the earth that reminds us that we are far away, but the same. A beautiful vision that isolates some facet of humanity or human experience, and displays it back to the user or consumer, can speed our acceleration to a single networked system. An airline, or cruise ship operator, that enables us to break through physical deterrents, to interact with the previously separate, again pulls us into the future I see. My ambition is along these lines. There is value in achieving this phenomenon domestically, in showing the farmer in Indiana his sameness to the ballerina in New York City…but my ambition is bigger… it is global.

When I say my ambition is the inverse in culture, I mean it. The inverse of global is local, and the extreme of local is self. Inbetween local and self (so perhaps not the true inverse) is family, and that is how I want to live my days. A family irrationally values its members over all else. It does not recognize someone socially or physically distant as equal. It is an irrational allegiance and loyalty and love and respect for a small and distinct group…it does not scale. At Hyperpublic our culture was family. We were only 10 people when we were acquired by Groupon and I loved spending the majority of my hours with our family. So my ambition is to do the impossible. To build a culture of family into a business that scales globally. Like everything else in my life, in business I admire and envy paradox. And so, in my new startup, which is a tiny little baby, virtually undefined, I endeavor to build this paradox. That’s as far as I’ve gotten (well maybe a little further), but these are my ambitions, clearly stated, and now, at least according to PG, I am a startup.

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7 thoughts about sensors

Posted on September 17, 2012. Filed under: startups, venture capital |

So…here are a few thoughts about the sensor market:

1) sensors that track human behavior are pretty boring. You can put it them in a wristband, or a shoe, or a phone, or a necklace but fundamentally there is only so much you can do with the information of how many steps I take and what direction I am going. Accelerometer, altimeter, pedometer…all pretty boring no matter how an application wraps the information. There is a reason that the output of these sensors has stopped at the visualization layer, and not really broken into intelligence…it’s because that shit is not very meaningful…in a vacuum at least.

2) Sensors that track things are fascinating but early: You can put them in your home, you can put them on your garage door, you can put them on your pill bottle, or your tooth brush, or your car, etc…and they can tell you what’s going on with any given thing. Is it getting hot, is it getting cold, is it on, is it off, is it moving or stationary, etc, etc., etc. Here the applications can become more interesting…but there are challenges abound. Size, cost, form, connectivity protocol, and very importantly distribution and the related network requirements for truly meaningful aplications all hamper what we can loosely refer to as “the internet of things”

3) Sensors that track things do not share a standard protocol but there aint gonna be twelve base stations in my house, so something is gonna have to give on data portability at the API/cloud layer…but none of this is defined and its hard to see a software application being built independent of the hardware layer due to lack of penetration in the short run…so it seems like a long slug to be the centralized consumptive/intelligence layer in the near term…unless…you are the incumbent/enterprise…which brings me to #4

4) In the near term, dense sensor distribution seems more plausible through the large OEM than direct to consumer…but…the General Electrics and Time Warners of the world that are positioned to scale distribution of the base station and/or the connected things both lack the critical software application DNA to complete the picture at the consumer layer…

5) so fuck, where is the opportunity? For one, I think you could build a nice little business providing turnkey sensor/software solutions to large OEMs…but boy will that be a bitch of a sales cycle…regardless, I think you could do it for them…probably through a lens of analytics…it’s not enough to promise the OEM’s better user experience for their customers…I think the sale looks something like “you sell 2 million blenders a year, and the second they leave the shelf at Walmart, they go dark and you have no idea what usage and performance look like until some small portion of the user base tries to return it or replace it…by letting us connect all of your things with sensors that talk to a base station and ultimately the cloud, we can give you insight that will inform your product development and marketing decisions in a much more intelligent way.” In software and application development, we get amazing, near real time analytics on what people are doing with our products…and OEM manufacturing should step into the 21st century product development cycle…I think.

6) But…#5 is not for everyone…so what else can we do today? I believe the holy grail lies not in the internet of things alone, nor in wearable technology and sensors alone, but rather in the interaction between these two types of sensor systems…It is in the combination of what we are doing and what our things are doing that we find the raw inputs necessary to build true intelligence atop physical sensors…I cannot see any alternative today other than an attempt to turn the mobile device into a base station for physically distributed sensors on things…and somehow figure out your way around power requirements, etc…I’d like to build a Mophie that interacts with very cheap sensors on everything I own and use…but that is very challenging…and goddam it, every layer you’d like to play at to get to the holy grail is a capital investment in the tens and likely hundreds of millions of dollars

7) Which leaves us at the layer of end to end, software/hardware solutions in a specific vertical with real world utility value in the near term and a flexible path and position to platform or horizontal consumptive layer as hundreds of companies attempt to build out these networks…most will fail, but infrastructure, density, and standards will emerge…and if you are in the game with a real business and domain expertise over the next 10 years with a brand and one if not a few end to end vertical solutions in the space…maybe…just maybe…you get to take the whole enchilada?

If anyone has opinions, please share…but that’s kind of how it looks to me

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The Health of Our Ecosystem

Posted on September 11, 2012. Filed under: startups, venture capital |

For the last six years I have been a member of the startup and venture capital community.  There are many participants in this community.  Some skew toward action and definition of the community, some toward observation and commentary, and some toward follower/trend amplification.

The Actor: the actor is most important. His/Her decisions become reality.  They build a product.  They sell a product. They sell a company. They defeat an incumbent. The Actor is in the game. Making the play.  There are many different types of actors.  The main segmentation I would propose is based on the genesis of their actions.  Many actors are influenced by competitors, or investors, or press, but the purest actor…the one that matters the most, acts from intuition and an internal calling that is insulated but aware of these many influences. I’ll come back to the Actor, but for now, think Actor = On the ground, doer.

The Observer/Commentator: The Observer/Commentator watches the startup ecosystem as a anthropologic activity.  Many Actors are not observer/commentators and don’t give a shit what direction the ecosystem is going in.  Financing trends, bad behavior, the interaction between engineers and business people, the democratization of application development…none of that matters to many actors…often Actors are laser focused.  They don’t need to opine, they don’t tweet, and they don’t consume the commentary of the ecosystem.  And that’s all good.  On the other end of the spectrum, there are Observers / Commentators who don’t Act at all…the Press is the most salient example, but there are also some others who live and breath the conversation without any Doing.  And then there are the in-betweens. Sort of player/coach types if you will.  On the ground, Acting, trying to make moves, but watching and commenting as they go.  Dixon, Vacanti, etc.

The Follower/Amplifier: I have never been a fan of trend amplification, but it has it’s roll.  One brilliant actor does something incredible, and the amplifiers make sure it is noticed.  Some Actors are Follower/Amplifiers, Some Observer/Commentators are Follower/Amplifiers, and then there are many hangers on who are nothing more than Follower/Amplifiers.  The Follower/Amplifier listens to the Observer/Commentator and just echoes whatever direction the ecosystem’s sentiment is moving in.  They can echo that sentiment in words, or companies, or opinions, or spread…they are simply the megaphone that talks to the ecosystem and those outside of it.

I break out these three groups of participants for a reason.  As I said, I have only been in this business for six years, but in that time I’ve enjoyed being an Observer as well as an Actor.  The two are intimately tied for me…which was never a problem so long as I “observed” a healthy ecosystem….somewhere along the way over the past 6 months or so…I increasingly worried about the direction and health of the ecosystem. I’ve voiced that sentiment many times on this blog, trying to Commentate where I could, and hopefully contribute to it’s health, but a few months ago I began to worry so much that it began to change my behavior as an Actor…I became uninspired. It took me a while to really see this, but I think a big part of my challenge was simply in wading through the noise of the Follower/Amplifiers.  They have always been around, I’ve always been pretty good at cutting through their effect, but one of the major macro trends that we experienced as an ecosystem over the last two years as an unhealthy shift in the ratio of Actors to Follower/Amplifiers.  Basically the market was flooded with a group of entrants, disguised as Actors, who by definition and character are in fact Follower/Amplifiers…in this case the entrance itself was following a trend to entrepreneurship and startups resultant from some broader Macro themes and a potentially irresponsible Commentating effort by the Press in a time where our ecosystem was a lone bright spot in a bleak broader economic landscape…

So anyway, the noise got so loud, because of this unusual Amplifier volume, that it became hard to see the thing that really inspired me and made me want to be a part of this ecosystem.  The pure actor, the one acting from within, who shared the values and motivations that I had developed through a genuine adoration and infatuation with the entrepreneurial process and life, became nearly invisible in the sea of noise.  I worried that the ecosystem that I loved was gone forever…

But that was naïve…the very nature of the Actor is that they are immune to the noise. The pure Actor innovates, and pushes, and breaks through the noise.  They rise above, and as sure as the sun rises, they will continue to enter the ecosystem…noise or no noise.  I realized that their voice was not gone or absent, just masked.  This was not a supply problem, but a discovery problem.  It became difficult to discover inspiring people…it used to be that you couldn’t walk 10 feet in this world without tripping over one.

But I am happy to report that the Actors are alive and well.  I have met some new ones…brand new entrants…spinning almost on their own axis…a sub-ecosystem if you will…in some cases an ecosystem of one…but they are familiar, and remind me of what I love and fell in love with when I joined this community six years ago.

As things cool off, the Follower/Amplifiers begin to shut the fuck up, and if you put your ear very very close to the ecosystem, you can make out the voice of the pure Actor…and soon the Observer/Commentator will hear it…a familiar drum beat that was muted by the noise, and they will report as it is and the remaining Amplifiers will Amplify and the ecosystem will know…that it is once again healthy.

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Sharing platforms punch inner monologue in the face

Posted on August 23, 2012. Filed under: startups, venture capital |

It used to be that when we had a thought or observation, that internal voice that hashed it out was talking to ourselves…and then mobile phones came along and all of the sudden that voice started talking to other people…the question I have, is how does that change/affect our personalities and thought quality. If we are no longer reflecting and thinking, but rather the first lens through which we look at an observation is publishing…are we becoming less thoughtful…do ideas and thoughts that are not “fit to print” take a backseat to what others will appreciate and like. Is our desire to feel connected so strong that we are losing the connection and conversation with ourselves?

you have all felt it.  you have a thought and it comes out of your mind in tweet form. there is an audience from it’s conception. i know what’s gained, but what is lost when thought and share merge neurally? In some ways, the self becomes a 3rd party, living and processing experience through an internal dialogue which is less intimate than that of generations past.

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Winning is not a goal worth setting

Posted on August 12, 2012. Filed under: startups, venture capital |

To win is not a goal worth setting.  There is no depth to the pursuit of victory. No purpose.  I do not deny the motivational power of competition, but as an entity it is surface level and temporal.  Victory is the result, but not the purpose.  If you are not driven by something deeper than competition, with victory will come emptiness…guaranteed.  So what do you do in the emptiness but ask why?  I believe competition and the will to win is a meaningful accelerant to a well-defined goal, but it is a crutch…an aid to an inner drive that is less developed than it could be.  If you see me and you want to beat me, I get it…but you are delusional if you think surpassing me is going to fill the emptiness in yourself.  Both victory and defeat are mirrors…but see your self without either…and perpetually…that is truly a goal worth achieving.

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Inorganic “Acceleration” is the Pits

Posted on August 6, 2012. Filed under: startups, venture capital |

There are many different styles to doing business…one of the pluses and minuses of joining an accelerator as a first time founder is that you are coached to adopt the style/playbook of that accelerator.  For a segment of any class or batch, the “YC” playbook or the “Techstars” playbook is a good fit.  Founders, if left to their own devices, would probably gravitate and ultimately arrive at a similar style of interaction independent of the accelerator, and the program, as it should, literally “accelerates” their journey to where they were naturally and organically headed…in this case, the value of participation is clear and the costs are minimal.  For another segment of the class, however, the “playbook” and “culture” of the accelerator (while successful for many) is at odds with the natural disposition of a founding team.  In such cases, people who would never fit the “YC/Techstars/Dreamit” archetype, attempt and are encouraged to emulate it, which causes a dissonance that I believe is detrimental to that startup’s trajectory (NOTE: each program has it’s own very distinct archetype).  If an accelerator does a good job in the selection process, and I am guessing they use “likelihood of fitting the mold” as an important heuristic, there are not to many square peg round hole situations…but the burden should not lay solely on the accelerators to find this chemistry.

Selection processes are short and imperfect…the decision to apply can be longer and more perfect.  Having the self-awareness to say “this accelerator is famous and big companies have come out of it, but I am not a ‘Techstars founder’ or a ‘YC founder’” is an amazing realization.  Some people treat starting up as sport, some delight in smoke and mirrors, some approach the challenge with reclusion and isolation, some take the tact of honesty and genuineness…I can list a litany of companies that have begun and succeeded with each approach, but can list very few that have won by adopting a cadence that is at odds with a founder’s natural disposition and DNA…You can fake the funk for 10 weeks, but not 10 years…and unfortunately it takes many longer than a seed round’s runway to realize that they aren’t building from their natural and organic disposition, but rather from the disposition of another.  When starting out, everybody is clawing for momentum…for a platform…any platform that will propel them out of the noise and into the game…in youth and inexperience, flexibility is an asset and malleability is a dagger.  I can see it in a young founder’s eyes when they are executing on a plan and character that is not their own.  There is a discomfort that they have been told to ignore…somehow convinced that that pit in their stomach is fear that they must overcome…when it is not fear at all that makes them uneasy…it is an awareness that they are acting at odds with their disposition.  Not everyone is meant to be calculating, not everyone is meant to be “product-obsessed,” and not everyone is comfortable walking the line between deception and sales…there are too many successes that have been built from a voice that lies deep within the self…amplified without compromise or adoption of “known archetypes and tactics…” If you see the program and it is you…apply…if you see yourself and it is not the program…do it your way and model after those who have done the same.

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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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