Archive for August, 2012

What’s Next?

Posted on August 29, 2012. Filed under: Uncategorized |

I was walking on the beach today, as I have done almost every day for the last week and a half, and as usual, over the sounds of crashing waves, the mind wanders to one of 3 or 4 topics that are not fully resolved in my mind.  Today and in general I have been grappling with the question of “what’s next?”  There have only been a few times in my life where I have stared at a blank slate and agonized over what to draw.  When I left General Catalyst to start my first company the slate was not blank.  Even before I knew what I would build, I knew the next step was to build something, and that was direction enough. I had such a chip on my shoulder after GC decided not to blank check invest in me as a founder that I had rocket fuel in the tank driving me toward entrepreneurship right out of the gate.  That endeavor was less about what I was going to build and more about becoming an entrepreneur…one of the many lessons I learned from that failed experience was that all the will in the world to start something is not enough to succeed at building something.

Fast forward about a year and half, I had just shutdown my first company, lost 50% of my investors’ money, returned the other half…and again…I faced a blank slate.  This time I wasn’t so sure I would build again.  Maybe I was supposed to be an investor? Maybe I was better at that? Maybe I was supposed to build again…but what?  Would I be able to raise capital again even though I lost money for investors? Was I emotionally ready to jump back in or did I want the safety of sitting behind some Sandhill desk, working hard, but working for someone else…not putting my identity and name on the line…collecting a cushy salary and waxing philosophical…

In making the “what’s next” decision in the face of a blank slate, I created a new set of filters…they were different than the first time I decided to start a company.  I had already been a CEO and gone through the process of raising money, building a product (sort of), managing a board etc…so just those activities didn’t feel like enough anymore…what I would build had to satisfy a more rigid set of filters.  Industry became much more important to me having flamed out in a market that I didn’t understand and never really figured out.  Team chemistry and DNA was a much deeper focus. Ability to generate revenue immediately was a new filter (b/c I wasn’t sure I’d be able to raise capital without traction now, and I was basically out of $ and living pretty poorly), social proximity to the value chain was a filter (or more broadly “actionability”)…and so on and so on.

I kept a spreadsheet where I power ranked all of my ideas by an aggregate of these various filters…and ultimately decided to jump back in and build what became Hyperpublic.

Now again, I find myself facing the blank slate. In many ways, it is blanker than ever before.  More is possible, less constraints, and more knowledge/domain expertise.  I have batted around a bunch of half baked shit over the past few months…not jumping into the blank slate fully…mostly because I knew it would be healthy and valuable to heal and recover from a hell of a battle with HP.  As the summer winds to an end and I walk along the beach, I have begun to bring some real process back into “what’s next?”  I always keep an ideas spreadsheet, but today on the beach I realized something that was causing me great angst.  I haven’t been able to build real conviction around a new goal/direction, and I realized it is because I haven’t built new filters…new to fit a new context…I am very gut driven, and my gut has held me back from many potential directions over the past few months…but that is just intuition listening to new filters that the mind has not properly articulated or realized.

Today I isolated the first major new filter that a new company must satisfy.  I made a new spreadsheet. Many of the filter columns are the same as before, but I added a box: “Would I be happy living in this company for the next 10 years (Y/N)?  This is not will this be successful or can we make money or can we do it or is this the direction the market is going or anything else like that.  This is, “change your focal length, don’t build to sell, forget about following your passion, passion is powerful, but this is will you be happy and comfortable in this space building this thing with this impact and mission, because once you push your stack in, it’s for the long haul. Reality changing innovation takes a long time to come to fruition.  The larger the vision, the longer the focal length and time it takes to get there.  Are you patient enough?  Can you live in this new vision and company for a long time, without getting bored or antsy?  Can you build a life and a family and identity around this new company? Is it sustainable, not just as a company, but as your company?”

It is a tremendously unforgiving filter, but it is now defined, and into the Fall we hurl, head first, and for the first time not angry or defensive, not with any chip on the shoulder, but wrought with anticipation, excitement, and a sense of pace…no need to frontload the conversion of ambition into action and energy. What does a company look like where we amortize our ambition and energy over a longer term horizon…still acting with urgency in the throws of the fight, but having bitch slapped the shit filter that is “satisfies my fear/insecurity of failure (Y/N)” so far down that it can only be heard on a day when the ocean is still and not a single wave crashes as we walk on the beach, contemplating what’s next.

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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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