Archive for September, 2013

an unorthodox walk home

Posted on September 26, 2013. Filed under: Uncategorized |

i watched them dance, wild and boisterous, a never ending huddle of black brimmed hats and curling facial hair falling off their the middle of the sidewalk…they chanted, and roared, in ebbs and flows and just as it quieted and appeared to settle, the energy would swell again to a roar. I have seen this energy more than once before…Jewish males only, intoxicated, dancing with vigor in the face of apparent constraints. A young man approached…noticing my noticing…”Are you Jewish”…”yes”…. “come dance with us”. I respectfully declined, but did not shut him out. He spoke of the events that had elicited such celebration… “This is the evening we dance to celebrate god giving us the torah…on all other days we study the torah because the torah is an academic document…but today we dance because…you see…everyone learns differently…you might be smarter than me…and understand the torah differently than me…but everybody has two legs and can dance, so we dance tonight so that everyone can experience the torah the same…to be equal.” I silently rifled through the obvious contradictions before me…but i looked in his eyes…he was young, not the old guard…but my contemporary…genuine in his belief and intention. Again, he invited me to dance with the group, to similarly experience the torah with him…I answered, “I will not go and dance over there, or say a prayer with all of you, but I will dance with you right here in this spot if you want to dance with me”…i agreed to dance not because I felt like a jew, but because his purpose was inclusivity, be it heavily bounded and objectively limited. He put his arms on my arms…a jolt of energy flowed through my heart, we danced…a connection made, that transcended his faith and my lack thereof…and I walked in the night, connected to him, that has chosen my opposite, as I am connected to all.

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Running Wild

Posted on September 24, 2013. Filed under: startups, venture capital, wildcard |

We’re growing at Wildcard. Semil wrote a nice Techcrunch post on mobile cards over the weekend that kindly mentioned Wildcard as a thought leader in this realm. The article mentioned my name specifically, which was cool, but my knee jerk was that there are names at this Company that don’t get mentioned nearly enough. I thought I’d take a minute to introduce you to the special group of people that have come together around our mission of replacing the internet in your phone.

Doug Petkanics: Cofounder and VP Engineering. Previous: UPenn Engineering, Y-Combinator, Frogmetrics, Hyperpublic, Groupon

Eric Tang: Cofounder and CTO. Previous: Carnegie Mellon Engineering, NextJump, Clickable, Hyperpublic, Groupon

Erik Nygren: Senior Engineer. Previous: Stanford Engineering, cofounder/CTO Atma Tech (Acq by Skimlinks ), Skimlinks

Chris Muir: Ops. Previous: Williams College, Goldman Sachs, Hyperpublic, Groupon

Khoi Vinh: Interim Design Lead and Advisor. Previous: Design Director New York Times, Cofounder Mixel (acq Etsy), Etsy

Tom Pinckney: Advisor. Previous: MIT Engineering, Site Advisor, mcafee, Hunch, Ebay

Abhishek Gupta: Advisor. Previous: Georgia Tech, Lead Designer at Lumosity

Joel Cutler: Board Member. General Catalyst: Investor in AirBnB, Kayak (cofounder), Warby Parker, Groupme

Ken Lerer: Godfather. Lerer Ventures, Huffington Post, Betaworks, Hyperpublic board member

Dean Cooney: Product Intern. Previous: U Chicago Engineering, KitchenSurfing, General Assembly

Jared Hecht: Investor. Previous: Tumblr, Founder of Groupme (acq: Skype), Skype

Steve Martocci: Investor. Previous: Gilt, Founder of Groupme (acq: Skype), Skype

SV Angel: Investor in Twitter, Pinterest, Google. Previous backer of Hyperpublic

Jordy Levy: Softbank. Investor in OMGPOP, Buddy Media, Hyperpublic board member

David Tisch: Investor in Vine, Fab, Groupme

You???: email when you are ready to sit side by side with these people. It’s a pretty special group.

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Two Minds

Posted on September 18, 2013. Filed under: startups, venture capital |

I talked with a friend recently who is self-defined as a “creative.” He lives product. He thinks about people. He approaches every interaction as a human being first, and a business man a distant second. He hates paperwork. He hates contracts. He hates thinking with the part of his brain that calculates…he wants to take people at face value. He hates deals. He hates strategic thinking…he just wants to create and connect with people…both through his product and through his real life interactions. He is sensitive…

There is something very pure about this mind…something that doesn’t “take,” that isn’t transactional…that is how you would want a friend to be when interacting with you. My friend that I mention is on one end of a spectrum that I could call the empathy-ruthlessness spectrum. I have this mind that he expresses so fully…it leads me at times…but I am not as pure an expression of it as he.

The other mind…the ruthless mind…is also very present in our world. Just as we praise the pure creator…much praise is given to the pure executor. You may have heard the phrase “he’s an absolute killer” when discussing a founder that get’s shit done at all costs…the killer exercises his strategic mind…he dehumanizes the people behind his business interactions. He acts on perfect logic. He moves through people to get to his goal, and as long as he acts in accord with proper business logic, he is true to himself. He is not amoral, although there is a degenerative form of him that can be…he is simply mechanical. In fact he can be perfectly moral…extremely disciplined when it comes to behaving on the right side of ethical lines…but as long as he exists within them…any decision that is to teh advantage of his business or enterprise is the correct one and will be made. He presumes that everyone else acts the same, he anticipates and analyzes the intention of all those around him…he is Machiavelli. I have this mind as well.

If you were to put these two minds at either end of the empathy-ruthlessness spectrum…I believe most fall somewhere in the middle. Personally, I don’t feel that I am in the middle, but rather I jump from one end of the spectrum, over the middle, to the other…depending on the context of a given moment. I have deep, deep expressions of both minds…which has conflicted me for as along as I can remember…both minds can be so powerful in making progress and living the life you are trying to carve out for yourself…what I have learned with age and experience, is that the empathetic mind is beautiful, the ruthless mind is ugly, and both can be necessary when interacting with a world that is made up of people ruled by both. I try to exist in the beautiful as much as possible. and sometimes it takes the help of a another to remind me when I fall too deep into the ruthless. There are…however…times where living exclusively in the empathetic mind can be detrimental…I wish you could make it through a venture financing without exercising the ruthless mind…at least a little…but you can’t. At some point, when the rubber hits the road, and you move from product and love and relationships and communication to hard numbers, cap tables, and liquidation preferences…it does not benefit you to remain empathetic…even the purest of heart on the other side is excercising something other than pure empathy…there is self interest…business interest…and it is a function of the choice we have made to create within the business realm…as opposed to the arts, or the literary…or the natural…that we must deviate from the precipice of the empathetic mind, on occasion, to move through it. It hurts my heart to live in this reality but we must.

Only recently have I realized that one of the few pieces of true value that I try to share with my friends and founders that I have been lucky enough to invest in over the years is that I can move between these two minds seamlessly, and yet am governed at my core by the empathetic…it is often helpful to analyze the world through the ruthless mind, but communicate the conclusions with a compass  that’s true north is empathy.

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Cards, Cards, Cards…

Posted on September 12, 2013. Filed under: startups, venture capital, wildcard |

About 2 months ago, I sat down to breakfast with Joel Cutler to discuss our vision for a card based mobile internet. Joel sits on our board. I wouldn’t call him a design thinker and I wouldn’t call him a technical thinker, but I would call him a consumer thinker. He’s invested in Kayak, AirBnb, Warby Parker, Groupme, and a handful of other products that consumers love. The breakfast was sort of a brain dump…and in the late innings of our conversation, he said “who else is thinking this way?…I don’t hear a lot of people talking about cards…are you sure you want to push your stack behind this trend?” I thought for a moment, and admitted that not a lot of people were thinking and talking in our direction. I answered his question: “Google, Twitter, Yandex, John Lilly…that’s kind of it.” Fast forward two months and cards have become a very contemporary topic. The market is wizening up to SOME of the thinking that went into the Wildcard thesis…I’ve started to get emails to the tune of “what should we be doing with cards?” or linking to some article that someone wrote about cards as a trend. Chris Dixon tweets about the potential of cards as a fundamental shift in mobile and it gets retweeted a hundred times with super active conversation and response…buzz builds…I walk into the office at Lerer Ventures and Max Stoller tells me I am “so lucky that the card trend is picking up steam,” as though it was some kind of coincidence that we were building Wildcard 6 months before it entered the spotlight…I smiled at Max and said…yea “super lucky.”

I sent a note to our team late last week, that I fully believe, which is that “this is ours…it’s here for the taking…we have a head start, and it’s ours to lose. We are 10% away from owning this fundamental shift…and our job is to evolve into the dead center of this emergent movement.” Sometimes people ask what I do everyday as CEO of our company…I try to explain what “positioning a company” means and it’s a very hard thing to describe…it’s not vision…that is something separate…it’s more of a fine tuning effort…if you’ve ever tried to put an umbrella through the center of an outdoor table….and aimed it at the female piece in the center of the base…that’s what I’m doing here at Wildcard right now…I’ve got the piece, i know it fits…and i’m just gently hovering it over the target, making sure it’s aligned before I drop the full weight and release my tight grip…It’s not always like this…more often than not, as a CEO you are doing all the other shit…picking the umbrella, deciding if you even want a table on the deck, selecting a color, anticipating the weather, fixing the broken spoke, etc, etc, etc…but we have a real chance of dining in perfect shade right now…and I am so pumped about that. Now of course…the wind is gonna blow, and the seasons are gonna change, and we’ll have to evolve our strategy to maintain a pleasant dining experience, but at current course this is one of the most interesting places you could possibly be working right now…if you want to learn more about cards, come visit our new offices at 197 Grand St. We’re growing…

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California Dreams

Posted on September 1, 2013. Filed under: Uncategorized |

I’m sitting on the plane home from Los Angeles. It’s the 1:35 Virgin America flight into JFK. Through an unusual set of circumstances I was able to change from the redeye to this flight while picking up a $500 credit and an upgrade to first class along the way. Nothing is usual about this moment. For starters, I wasn’t supposed to be in LA this weekend, but I was. Further, Jason Schwarzman, of Rushmore and Garden State fame is sitting across the aisle from me. Lastly, the woman to my right I have seen before. In the terminal…i noticed her…perfect style, unusual grace…yet she was unpackaging a newly purchased set of DJ style over-ear headphones…I remember thinking…still my heart…behold this dichotomous being…I was captivated, and here she is, to my right…acutely aware that she has captured my heart. She flips through the Times that she picked up for this flight…she has noticed that I am doing the same. It warms my heart that she starts with the Cover section…neglecting Style which she could have easily chosen…this is a woman of substance I think…this is a woman who I want to know. She wears two rings on her wedding finger…at first glance I dismay, but there is something not normal…I look again, and this is not a wedding ring at all…a large blue stone graces the finger…a mere tenant of the precious real estate she dons…I wasn’t supposed to be here, but I am. What is Schwarzman doing on my plane? Who is this first class woman with contemporary audiological taste?

Dare she be from the land of LA? My crush, star crossed, by 3000 miles and a cultural chasm more narrow than I had believed…but there is something about her…something different than  the sea of relaxed souls that I had encountered in my brief Venice stay…she is focussed…working…there is a seriousness and ambition in her movement…something native to me, and seemingly absent in venice…why is she here? is she traveling for work? successful is sexy…and she is both.

Black jeans and a Knicks shirt…it would be a sad outfit to meet the woman of my dreams if it wasn’t also one of my most “put together”…too much time living in a land of peter pans…where corporations scale and lionize a culture of childhood…where video games and candy affirm engineers’ instincts that they need not be LA…and here I sit, somewhere in between…the Priority on my boarding pass perhaps giving me a pass on the sophistication my friend here has obviously amassed.

And what to do? …my heart beats…if only she is traveling to the west village as well…i might ferry her in a cab to a life that diverges…2A…dammit…it seemed perfect 6 hours ago…but now I am stuck, just one seat off from conversational range…an oblivious asian man separates me from realizing this dream…this whimsical…faithful…half invented dream…that coincidence has dropped me in the lap of my love…on this flight from LA…that I wasn’t supposed to take…alongside the king of coincidence himself.

The only thing to do is send her this note…this real time missed connection…or disconnection…as the case may be…and if she dares…if she believes, she’ll write back with her version of perceived destiny.

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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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