Archive for October, 2016

The nuances of a livestream

Posted on October 31, 2016. Filed under: startups, venture capital |

img_7367Last week I livestreamed my lunch on Facebook…roughly 60 friends joined me as I ate alone in Abington Sq Park, and another hundred or so probably watched a recording of the live lunch that I published to Facebook after the session ended. My sister emailed me the next day and asked if I wanted to meet for lunch because “I seemed kind of lonely on my FB Live lunch.” I tried to explain that I wasn’t lonely at all, that live video is a thing now, and I was experimenting with a new publishing medium…but even after more explanation of the live streaming dynamics in China, why I was doing it, how people are making money doing it, etc…I’m not sure she’s totally on board.

Beyond FB, I’ve spent a time on some of the other livestreaming platforms, both watching the broadcast use case, but also getting a little more familiar with the more nuanced social dynamics at play…and while I understand the power of treating Live as a media opportunity, and why traditional publishers and fast following (or maybe now fast leading) influencers are trying to use it to connect with and grow their audiences, i think for everyday folks there are some more interesting opportunities that Live affords.

As I sat in the park, eating while trying to hold a steady camera in front of my face, I was actually reminded of the most interesting and gripping attribute of my experience in Virtual Reality. In VR, the killer experience for me is “presence.” I’ll define presence as “a feeling of really being there,” and if with others, social presence would be “a feeling of really being there with others who are really there.” In even the most elementary of chat applications in VR (i think v-time is the one I used most), I felt that I was actually with whoever I shared a virtual room with…in a way that most aysnch or near real time experiences, never really achieved. As I streamed live during lunch, while the experience of interacting with those who joined my stream was still quite clunky (comments in 2-way communication in FB Live needs a serious UX overhaul), I did feel a sense of presence and togetherness that certainly doesn’t materialize through any other publishing platform I’ve used to date. Interestingly, when contrasted with say Facetime (which is 1-1), the feeling of streaming to many with lower commitment and expectation of dedicated attention, actually INCREASED the sense of presence I experienced at lunch. With Live, there’s an ability to “be” in whatever environment your in…to remain one foot in the real world…not sucked into the screen completely in the way Facetime requires…and somehow that “being” and “being with yourself” while “being with others” makes for a more realistic and true sense of presence than simply “communicating” through an app like Facetime…there’s a difference between being and communicating…and Live is this weird and perhaps beautiful mix of the two.

From far away I looked at FB Live as just another place to broadcast, but up close it appears to be a place to feel connected, to fight lonliness, to be present with your friends, and maybe even to broadcast your availability (whether in person or virtually) without the stigma of a status update that says “anyone want to go to the movies?”

In some sense, if FB status update is saying “what’s on your mind?” and a Tweet is saying “what’s happening?”, a live stream might be saying “I’m here, I’m present” and the use cases that emanate from that statement push well beyond “listen to what I have to say” into “I am available to talk,” “I am free to meet,” “Let’s be together,”…i guess maybe what i’m saying is that livestreaming feels as much an invitation as it does a statement…and that’s unique in a publishing platform.

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Psychopaths in Startupland

Posted on October 24, 2016. Filed under: Uncategorized |

He looked me dead in the eye and told me that his recently launched app with 1200 installs would have millions of users and be raising $30M on $125M pre within the year, and that he expected to exit in 18 months for hundreds of millions of dollars. He was raising $2M on $32 pre, after having drip raised $12M at successively higher valuations from “high net worth” individuals, and every piece of “value” that he could articulate was “happening next month” or “in late stage discussions with senior executives representing a potential xx.”

I have never understood the person who can look you dead in the eye and lie in a business setting. I know they exist. There are cons and frauds everywhere who maybe tell the same lie so often they begin to believe it, or I don’t know what, but for every overt con or fraud, there are 10 founders out there overrepresenting themselves or their opportunity, intentionally, albeit in less extreme form. On some level the market rewards misrepresentation and deception…which is a total bummer.

I read this tweet recently referencing Chamath from Social Capital…which read “Before @chamath invests in a co., he asks himself, “Is the CEO a psychopath?” If so it’s a buy.” I was so taken back by it, because 1) I think Social Capital is a very interesting fund and have enjoyed reading and listening to their thinking over the past few years (especially because so much of what they preach is about leveling the world’s playing field for the underrepresented and disadvantaged), and 2) because only a psychopath could make a statement like this…and I didn’t think Chamath was psychopath (i hope he’s not, and that this quote was taken our of context, or perhaps just not fully thought through or articulated). But how many psychopath’s walk amongst us? I believe it’s the same impaired empathy and remorse characteristic of a pyschopath that enables a founder to look another human in the eye and defraud or intentionally mislead them for gain. What Chamath identifies, I fear correctly, is that this is a behavior and characteristic that can lead to tremendous success and gain. Just as my friend in the first paragraph had amassed $10M doing this, many have gone on to amass hundreds of millions, if not billions the same way. Some of these psychopaths eventually are exposed…and they end up going to jail or paying steep fines (Madoff, tons of hedge fund magnates, Worldcom, etc. etc.), but many are not, and eventually become legitimized in their success…and their lack of empathy and remorse may not manifest in the form of deception or even breaking the law…but their ability to make decisions for their own and their shareholders gain, without consideration for their customers, employees, partners, or anyone else who is in the way of success is a trait that I fear the ruthless in startupland have come to revere and select for.

I have zero interest in working with the guy in the first paragraph (even if by some grace of god they do go on to make tremendous amounts of money) and I have zero interest in funding any other psychopath for that matter. We have a responsibility as investors to return capital to our LPs, but we have a greater responsibility to our species not to enable those who lack empathy and who will win at ANY cost. This is a moral case for demanding character and ethics in the founders that you back. But as data becomes more abundant, and as it becomes harder for pyschopaths to hide behind shiny magazine cover veneers, there is increasingly a business case as well. I doubt the board members who invested in Theranos and RadiumOne are very happy with their outcomes…and more and more I see public figures and leaders having to reckon with the immoral decisions they make along the way. Going forward, investing in psychopaths will be an expensive strategy (note: i am aware that VC is hits driven business, power law, blah blah blah…but i’ve seen billionaires live like they’ve won for seven or eight decades only to end their life in disgrace with nothing…funding psychopath’s is shortsighted).

I cannot be anything but genuine and honest…it makes me a shitty salesmen…and it always has…but i’d rather be a shitty salesmen than a fraud or a psychopath…and I will only ever back those who I believe have the capacity for empathy and remorse…no matter how much of a “killer” they might be.

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A Break from the Dividing Noise

Posted on October 20, 2016. Filed under: Uncategorized |

Today i spent the morning volunteering in a low income neighborhood in the Bronx. I have some time on my hands these days, and I figured there is absolutely no excuse not to use some of it for good. I wouldn’t call the place where we volunteered a shelter because nobody sleeps there, I don’t think, but it was a facility that offered meals and haircuts and showers and clothes to folks who obviously appreciated all those services. I went with my friend Pierre and we were both assigned to unpack and fold donated clothing alongside two regulars at the facility, Norma and Anne. They were both in their 50s or 60s, lived close by and were members of the community we were serving.

I felt a sense of connection with both Norma and Anne, and a number of the guests who stopped into our room to “shop” for new outfits. I have donated clothes many many times, but never really seen what happens to them on the other end. Our process for distribution was too rip open dozens of giant garbage bags that crowded the floor space in the room, discard any and all clothing that wasn’t in good enough shape for you or I to wear. “If it’s not good enough for us, it’s not good enough for them” Norma proclaimed. Once QA’d, wed fold and sort by size, and do our best to separate things out onto the gender appropriate shelving within categories like “long sleeve womens” and “girls jackets.” The system thinker in me initially agonized over the inefficiencies in our process…but this was Norma’s process…she ran the show…and not only was there not really room for suggestions…it wasn’t really about maxing out on efficiency.

Yes, we wanted to do our best to find the right clothes for the right people, but the conversation, and the connection, and the expression of both support, gratitude, and community were as, if not more, central to the guest experience. There was something about the relationship between this facility and it’s guests that felt very grounding and consistent and regular…in people’s lives who i’m sure face many destabalizing forces. Even though technically we were volunteering or giving, it was without a doubt a privilege to be invited and welcomed into this community…and for that I am grateful.

I know I just dropped in for a day, and it’s difficult not to sound cliche’d when you are a privileged white male reflecting on your morning of travel uptown to volunteer, but I am consistently amazed and inspired by all which is consistent across seemingly very different slices of humanity. All I hear all day long is politicians slicing us into separate groups and demographics and buckets…and i’m tired of it…we are so much more the same than we are different…today was a welcome reminder of that for me.


this is where we went if you are interested in learning more:

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On Angst and Intention

Posted on October 18, 2016. Filed under: Uncategorized |

I have often feared that I am only capable of creating great work in periods of deep angst. I do not want to believe this…in fact I refuse to believe it…but the empirical evidence is hard to ignore…and I know that I am not alone in using angst as an accelerant to achievement.

Angst is an unwillingness to accept where you are in the present. It doesn’t have to be perfectly specific or defined. you can experience angst around your finances, your romantic situation, your geography, your social status, or anything else that is core to your experience but not acceptable to you.

Angst can be an incredibly potent accelerant to work…i think this happens when you are able to sell yourself the promise that a specific effort or body of work, if done well, will change that which you are unwilling to accept in the present. For example, if I had deep angst around my finances, and believed that building a valuable startup could alleviate my lack of money, I could use that angst to find a level of motivation and even superhuman effort and thought that otherwise might not be available to me in building my startup.

Starting out in startupland I think I carried the angst that many young founders do, which was a built up unwillingness to accept the reality of people discounting me and my thinking. I had so many “crazy ideas” that were uninteresting to the Goldman Sachs crowd coming out of college…and I was so tired of not being seen for my creativity…that I simply refused to let those people less creative than me discount my thinking and contribution any longer. That…along with i’m sure plenty of other insecurities and dissatisfactions…created this pure unwillingness to accept the present in my life and propelled me into a period of what I view to be some of my best work and thought. Failing in my first startup…only fueled me deeper…and going into Hyperpublic and the beginning of Lerer Ventures…i was anything but stable…i was an angst filled…fuck you world…hungry mother fucker that simply would not take no for an answer…and not allow anyone or anything to get in my way of changing the present.

That worked…in the sense that I created a great body of work in that period of my life…and it didn’t work in the sense that I was living like a psychopath, completely imbalanced and in a state that was totally unsustainable on any long term horizion…

When I sold Hyperpublic and when Lerer Ventures became successful…I think I lost most of that youthful angst…For the first time I had money of my own, some level of success and respect even amongst the goldman sachs crowd that had previously discounted me…and for the first time in my professional career I didn’t completely reject where I was in life. Of course I maintained goals, and set new ones, and wanted to move forward…as I still do…but there wasn’t thas same rage-filled rocketfuel attached to my work that angst had once provided.

In it’s place, intuitively, I slotted in intention. For the purposes of this essay, I’ll say that intention is an unwillingness to accept the present state of the world (as opposed to your world). Intention is more purposeful…deeper…and considered than angst. One can still be willing to accept their own present while holding intention for what they want of the future…After Hyperpublic, I knew that I should be looking for more considered purpose than just the frenetic struggle to break free from the present.

What I learned, however, is that intention…at least in the form that I developed it…is a very different and for me less potent accelerant than angst…it’s a slower drip…not quite the headspinning, blinders on, kill a baby chic if you have to drug…and that has both it’s benefits and it’s drawbacks when compared with angst. Intention applied to work allows space for relationships, family, and the many facets of life that an angst filled psycho (i.e. me in my early-mid 20s) might backburner in the heat of the fight…it allows for measured progress in a direction of purpose…while maintaining some level of humanity…and that IS sustainable over long periods of time (i.e. life)…

what intention does not do…at least not yet for me…is consume to the point of a neverending dialogue with one’s work. Intention is not an “every waking moment” motivant…or at least it hasn’t been for me. You can turn it off when you need to…and the upside is that that’s healthy…and the downside is that some of the waking moments that get cut out are the deepest and and most brilliant ones…the game changers…the “no normal person would have taken this idea this far down the rabbit hole…and therein lies the opportunity…type moments.”

I very much miss the angst driven rabbit holes of my early professoinal life…BUT…BUT…I refuse to give into my fear that angst is required to create a great body of work…I believe that intention CAN be as powerful…i just don’t believe I’ve found the right way to harness it…my first startup where i tried to combine angst and business sucked (untitled partners)…then I learned how they worked together and things got pretty good (hyperpublic and lerer ventures)…my first startup where I gave up angst and tried to combine intention and business (wildcard) didn’t suck…but it was not my greatest work either. I think I’ll be able to take what I learned and I think things will get pretty good in this new intention based setup…it’s just gonna take more than one try to nail it…but I believe that when I do, another great body of work will follow.

I’ll invest in an angst driven founder all day long…I’ve been one…and I know what can come from that recipe…AND i’ll invest in an intention driven founder all day long…angst or intention…they are both forms of unwillingness…one an unwillingness to accept where you are…the other an unwillingness to accept where the world is…it’s whatever is inbetween…a lack of unwillingness…that I think spells disaster…one form is selfish…the other selfless…i think the first is easier to see…easier to harness…and easier to burn out…while the second requires a level of empathy and internalization of the external that takes time to develop and master. I will pursue it.

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Balance and Kindness

Posted on October 10, 2016. Filed under: Uncategorized |

Sometimes at the beginning of a yoga class, the teacher will ask you to set an intention for the class. An intention is a word or goal or reason why you showed up today…and it’s usually something that you want to connect more deeply to. It could be a person who needs some good vibes, or an element you need to be more present in your own life…really anything you want to put energy toward.

Often times when I go to yoga, it’s because I feel out of whack. It’s not necessarily about stress, but when life spins me up, i’ve found yoga a way to hit reset. I first discovered it when I was an Analyst in investment banking right out of college. My days and nights were blurring together, I was dreaming in excel spreadsheets, and I found this studio on my walk from the subway to the office that I decided to stop into one day. While my job owned me 23 hours a day, yoga became an hour that was free of any context other than my mind and my body working together, with complete inward focus.

These days I go to yoga about once a week…sometimes less, but always when I am feeling like I need to reconnect. Last night, I set two intentions for my class: Balance and Kindness.

Balance is something I am always seeking. After an 8 hour hike up the Algonquin and Iriqous high peaks of the Adirondacks, my body was hurting and in need of adjustment and rebalancing…but also during this period of professional evolution…I sought to level my head and find mental balance as well.

Kindness, on the other hand, is not something I think about on a daily basis. It’s a value that I admire, and one that I aspire to…but one that…for me…can sometimes fall by the wayside in the name of efficiency, shrewd decision making, and rational execution. Of course, I’m rarely mean…but true kindness is something that I’d like to be higher up in my emotional stack.

I’ve reflected quite a bit on the last year and half of Wildcard…it was a period with some ups, but a lot of downs…it was highly stressful and as I look back on some of my conversations with friends, teammates, and others…i find myself wishing that I had better maintained my kindness through it all. It’s easier to see it when you step away, and easy to lose it when your thrown back into the next melee…but nonetheless, it’s a value I thought worthy of my intention last night.

P.S. I’ve been infrequent in my blogposts lately…but i’ve recommitted to writing regularly…so even though I feel that in today’s low attention world, people don’t really take the time to read long form blogposts…it’s how I like to organize my thinking…so I’m gonna keep doing it.

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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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