venture capital

The path to billions of “programmers”

Posted on April 5, 2017. Filed under: startups, venture capital |

I have always been fascinated by publishing platforms…I love the idea that a new platform or technology has the ability to give a voice to someone…or many people…that previously did not have one. I try to stay very current on the places that people go to express themselves, and I think overall the internet has done a pretty good job of giving everyone and anyone with a computer or camera the ability to publish. It used to be that in order to have a public voice, you needed to be a journalist. The technical requirement to publish was a journalism degree, and therefore the number of people who both had that credential and were able to get a job at a media outlet limited the universe of potential voices in the world. Along came blogging platforms, and all of the sudden you didn’t need to have a journalism degree or a job at a newspaper or magazine, you just needed to know how to write. The universe of voices expanded to maybe anyone with a high school education or liberal arts degree, and all of the sudden we had more public voices in the world. From there, came microblogging, and now you didn’t even have to know how to construct a 3 paragraph essay…if you could assemble a sentence or a tweet, independent of structure…you too could have a voice. In parallel, publishing platforms like instagram and Facebook enabled visual thinkers to express their voice through photos, even if they couldn’t conjure a thought in text. Each time a new platform came along, the schooling and technical writing proficiency required to publish and have a voice declined…until we arrived where we are today, where let’s say a few billion voices have joined a conversation that a few thousand were previously dominating. I had a post a few years ago that described these successive breakthroughs in publishing platforms and their impact on expanding the universe of people with a voice. I visualized each new platform as unlocking a new and larger rung of publishers in a series of expanding concentric circles. There I focussed on the reduced effort that each new platform required to publish, but here I focus on a reduction in required training to publish because I think there’s an important parallel to be drawn between the history of publishing platforms and the current state of programming and software development.

In a sense, programming and publishing an application, be it a website on your own domain, a mobile app in the Appstore, or really any piece of automation is a lot like publishing an article or blogpost. You write within the guidelines of the platform you are writing for, and if you have the background and understanding of the language you are writing in, you can take something that’s in your head and express it externally. When I started working in technology, most of the programmers I knew had formal computer science degrees. If you wanted to write software, you needed a lot of education, and therefore the number of programmers in our world was quite limited. A few years later, there was even a bubble of sorts in aquihires, as demand for people who could write and publish software far exceed those trained in the field. For a host of reasons, not the least of which was the emergence of more flexible programming languages and frameworks like Ruby on Rails, the schooling required to express thoughts as software and applications declined. Today, instead of 4 years at MIT, 3 months at programming bootcamp can land you a job writing software, and certainly provides the basics required to build a basic web application on your own. Advances in modern programming languages and abstractions of knowledge dependent layers in the development stack have played a similar role in programming to advances in blogging and microblogging in the publishing world. As a result, the universe of software publishers has grown, more people can express themselves through software, and the universe of people capable of writing automation has widened…but still the hurdle to express oneself or an idea through software remains too high.

I find myself looking for the platform or technology that is going to meaningfully increase the number of people who can “write software” and I don’t think it’s going to be an educational platform so much as a much more flexible programming language or platform that more closely mirrors and accommodates natural language. I know we are far from it, but when we get to the point where a person can write automation in plain english, we’ll have billions of people writing software much in the same way as we have billions of people publishing thoughts on today’s publishing platforms. What automation we write will look and feel different than what you see in the Appstore today…early hints of this future might exist in platforms like IFTTT and Workflow…but even these environments are quite rigid and lego-like when compared to a free-text box that any liberal arts student could approach. Yesterday I came across this YC company called Algoriz, which positions itself as free-text based algo trading without the need for programmer…in practice I found the tool far from this promise, but in positioning I was captivated by the idea of unlocking a new concentric circle of programmers…even within a tight vertical like trading…and my mind immediately longed for the more generic version of this promise.

When you go down the actual rabbit hole of approaching something like this, you quickly get into concepts of templates and modules and hardcoded mappings vs generic and broad capability…the state of the art ain’t pretty in this domain…but I’m more than ready to talk to anyone who is trying to grow the universe of “automation publishers” less through education and more through advancement at some platform, technology, or even interface layer. Who is taking the requirement to publish software from a 3 month bootcamp to a plain vanilla liberal arts education…and who’s doing it more flexibly than templatey? That’s something I’d like to back…

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Vlog #4: new office, new observations, new data, new constraints

Posted on February 18, 2017. Filed under: startups, venture capital |

Happy Saturday. Here’s a ~25 minute update on what I’ve been thinking about and working on over the past few weeks.  I know that’s a little long, but pour yourself a cup of coffee and just imagine we are having a quick coffee together…Please forgive the slightly congested voice…at least I didn’t sneeze during it. Was worried that might happen 🙂

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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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Life is an experiment

Posted on May 16, 2016. Filed under: startups, venture capital |

Life is an experiment…when I was a bit younger…i lived this way very truly…the world was this fabric that you could touch and bend…and most of what i did…whether professionally, socially, romantically, or otherwise…was try to bend it. I hated the concept of “the path”…I detested highly predictable outcomes and the decisions that would lead to them…all I wanted to do was look at the world as an experiment and fuck with it because I could see it that way, and most other people weren’t trying to. I was not outcome oriented. A successful bend of the fabric, or the discovery of a nuanced wrinkle…these were wins for sure…but not toward any end beyond empirical progress…simply exploring and testing was the reward, and it was everywhere.

When you start to get comfortable in whatever reality you have designed for yourself, you stop trying to bend it. You start to get attached to the notion that one outcome is better than the other…you start to believe that your current understanding or context is better than what might be around the next corner…and this penchant for stability creeps in and starts telling you to run less experiments…or run more outcome oriented experiments…you start to develop a will as to which way you want the experiment to unfold…and maybe you stop taking on experiments that don’t have some purpose beyond a specific desired outcome.

I feel as though I’ve become less plastic..less willing to treat life as an experiment…maybe for good reason…i have all these good things in life that i don’t want to disrupt. I have financial stability from hyperpublic and lerer ventures. I have romantic stability in my soon to be wife. I have social stability with friends i like. I have professional stability accrued over years of hard work and thought…these are all things that make me happy…and if i only run experiments where a likely outcome will strengthen them…there’s a pretty darn good chance that this nice reality will persist…

The problem is…part of my energy…part of what makes me me…comes from instability. I like shaking things up…I like change…and it’s in these changes that i see and love the fabric of the world. I am the deepest expression of myself when I am learning and discovering…when i am touching newness…and I am something less when I am moving through things I’ve seen or done or understood before.

So when life becomes less of an experiment…i become less of myself…or at least the self i feel most connected to.

Things have a way of stacking up…as responsibility and expectations and life cement…and it gets easy not notice as the experiment slows down.

I really want to find this experimental mind again…and not to rip out that which I truly value (my future wife might be freaking out a little while reading this…), but certainly to risk that which i have passively come to accept as real or true.

I used to flee from complacency like it was the devil…these days I walk away from it deliberately like it’s someone i don’t care for…but there’s probably something in between that is a little more me…and i’m really going to try to reconnect with that. If you know me, please help me stay true to this goal.

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Justinkan, Grantcardone, and the voices of Snapchat

Posted on April 28, 2016. Filed under: startups, venture capital |

I spent the day yesterday digging into Snapchat in a pretty deep way. I’ve wanted to do this for a while. One of the most interesting things about Snapchat, is that the user experience completely breaks from all of the conventions that precede it…so really getting into it, and getting the full impact of the experience, requires effort, exploration, and poking around. I’ve been on Snapchat for a very long time, and used it in a pretty superficial way forever…but I’ve always had this feeling like “i’m doing it wrong”…I see a friend use faceswap, or a filter to make lasers come out of their eyes, and I’m too stubborn to admit that I don’t know how to find that in the app. It must be some 3rd party publishing tool they are using? no…you have to long press and hold your thumb down over your face to evoke this hidden feature…somebody has to tell you how to find it…it’s almost a secret…

Even the most fundamental of actions, like finding people to friend or follow on Snapchat is incredibly difficult. I spent a few hours, asking my friends on twitter to send me good accounts, reading lists of “good snappers” to follow, and playing w a 3rd party discovery app called Ghostcodes, trying to build up a good group of people to follow…Why would they make it so hard to find good people…well…for starters this isn’t Twitter…and no matter how much I might want it to be video twitter…it’s not. I think we have a bias when exploring new platforms to bring our habits and expectations with us from the last place we felt at home. I love twitter as a publishing platform (a place where a person can have/express a voice), and there is no question that Snapchat Stories is a new and potentially richer publishing platform…but because I learned to have a voice on Twitter, I keep trying to fit Snapchat into that place where I learned. Here’s where I’m at a disadvantage to the generation who first found their publishing voice on Snapchat. They didn’t bring any bias with them…they learned within the UX and context of Snapchat, how to publish on Snapchat, so their natural instinct is to create and speak in a way that’s native to the platform. One of the first things I considered, was how hard it must be to amass a “following” on Snapchat. Someone like Justin Kan, who has been recognized for creating great content and emerging as in influencer on Snapchat…he must have a fraction of the audience that he does on Twitter…not because he’s better at Twitter than Snapchat, but because it’s so fucking hard to find and follow him on Snapchat. Yes, their are Snapcodes (the weird image/QR code upper right on this page)…but even those are a mystery you have to commit to figure out. I’m pretty tech forward, and only yesterday learned how to properly use them. I was screenshotting Snapcodes for the longest time, and then searching my camera roll in the Snapchat app, to select screenshotted codes to add to my friends list. Turns how, if you just photograph the Snapcode through the Apps camera function, it will auto-friend these people without selecting from camera roll. Where would I have learned that things worked this way? There’s no tutorial, or explanation…and that’s the point. Maybe snapchat doesn’t want to turn into Twitter…maybe they’d prefer your graph of friends/followers to be small, and intimate, and true friends vs followers…maybe Stories aren’t for influencers or publishers…maybe they are for friends and loved ones…or maybe they ARE for influencers and publishers…but only if influencers are willing to play by the rules…which are that the content here is intimate, and raw, and you need to behave like you are speaking to friends, even if you are trying to speak to 1 million of them.

Something interesting I’ve noticed is that the production value of content in my Snapchat feed has risen in the last 6 months or s (if you’ll call it a feed…Stories were very unfeedlike for a while…but with the recent autoplay feature that rolls through all stories without needing to tap, i’d argue that this is now a non-vertical scrolling feed of content). “Production value” is the amount of energy/time/thought/polish/expense that is put into creating content. Blair Witch Project was low production value film. Avatar was a high production value film. Whereas my friends’ stories used to be quick/observational/quirky frames (likely a result of creators who first found their voices on instagram, bringing these habits with them to Snapchat), now my friends are starting to speak into the camera, plan sequenced shots ( a “snapstorm”), and even create art and interstitials between shots in their Stories. This isn’t the poop emoji on a friend’s face anymore…people are trying to say something in this channel now…they are trying to see it while taking advantage of the richer format…they are trying to publish. Interestingly, the ratio of production value to audience is pretty shitty on Snapchat compared to platforms like instagram, twitter, and facebook. It might take me 5 minutes to create something good on Snapchat that only 40 people will see, whereas it might take me 15 seconds to create something good on twitter that 7000 people will see…and still..after a few days getting into it, i’m happy to do it. Why? because it’s fun, and video is richer, and importantly…the environment shapes the content and sets an expectation of levity and fun and rawness that inspires me to make a new style of content that I like and that i’m proud of. All of this is to say that Snapchat stories, while rebuking the legacy of twitter/facebook/instagram at every design turn…is undoubtedly on a course to enable hundreds of millions of voices as it’s users become publishers. I think discovery will get a little easier (as signified by their recent roll out of a url to “addme on Snapchat”, but we’ll probably see some more ground up features designed to make finding voices easier on the platform…one thing you can bet on…is they won’t be the mechanics we’ve seen from other’s in the past…like everything else in the experience, they’ll be original, non-intuitive for migrators from existing platforms, but natural for natives and careful non to disrupt the tone that makes Snapchat content unique.

There’s still a lot that in Snapchat where I still feel an outsider. I know native users are having rich 1-1 chats, acting less as publishers and more as messagers…my limited 1-1 messaging has felt disjointed…a function again, of bringing my expectations from SMS, Facebook, and email. I guess as more of my graph is willing to “relearn” how to message in this channel, volume will pick up, and I’ll get the full experience…but for now I can only look enviously at Olivia’s 10 year old brother who didn’t have to unlearn SMS to enjoy 1-1 messaging in Snapchat.

As an aside, for those who are still feeling a little “outsider,” here is a bit of a cross section of usernames to get you started. not all people who’s Stories i like, but a bunch of the different flavors of publishing that people are doing on the platform:

arnoldschnitzel (feels like you are a perpetual student in his kindergarden cop class)
justinkan (creative content creation/style)
grantcardone (this guy is the worst…but worth seeing just how terrible he is)
man_repeller (professional publisher migrating to snapchat)
micdotcom (professional publisher migrating to snapchat)
rbfishman (lifestyles of the young and handsome socialite/entrepreneur)
yesjulz (party/nightlife)
therealdrmiami (platic surgeon in MIA)
msuster (vc blogger…using it as educational platform)
kimkardashian (celebrity)
djkhaled305 (celebrity)

i don’t have the energy to upload all their snapcodes for you…touche snapchat…

and i’m jordancooper1…but instead of name lookup…maybe be advanced about it, open snapchat, and use the snapchat camera to photograph that weird picture in the upper right on this screen (or screengrab it from mobile and figure out how to add by Snapcode in the settings…)

Have fun.


p.s. i think it would be cool if Snapchat adopted the ghost emoji as a replacement for the @ sign before their user handles. so instead of i’m @jordancooper on twitter…i could be “Ghost on Apple iOS 9.3jordancooper” on Snapchat

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A Viral VC Model

Posted on April 25, 2016. Filed under: startups, venture capital |

I’ve been spending some time thinking about disruptive models in venture capital lately…here’s a little thought experiment:
If you are a founder raising seed capital…while personalities and people deploying capital vary, the product investors are selling (institutional seed capital) is for the most part pretty consistent…money is money. Yes, folks tweak terms so that their product is more or less dilutive, more or less controlling, etc…but standardization of docs and rampant access to capital have kind of leveled out these variables, and really reduced a founders’ choice of provider down to “do i like this person? do i think they can help me? and do i care or do i just need the money and believe they won’t hurt me?” I’ve seen a few interesting wrinkles in the capital structure/vc product that enable different investment approaches on the investor side (i.e. angelist, special purpose vehicles, etc), but most of these variations from the standard don’t dramatically impact founders math or incentive structures when making decisions about with whom to partner.

Something that is pretty clear, is that more and more founders are and want to be investors as well. In 2010, when I first joined Kenny and Ben as a Partner in Lerer Ventures, while simultaneously building Hyperpublic, people really had a hard time understanding how I could or would want to do be an investor and an operator at the same time. Today, you can’t swing a dead cat without hitting a founder/operator who isn’t also a venture partner/advisor/scout/angelist syndicate lead, etc… for some vc related entity. I’m exaggerating a bit, but it’s obviously a thing. Over a 5 or 6 year period, exercising both my investment and operational minds, I found many points where one activity would feed and improve the other…so much so that I don’t think it’s surprising that more operators are looking to get involved in early stage investing while executing on their own endeavors. It’s great data, a great networking platform, and it keeps you creative and broad while your deep into your own endeavor.

What if there was a new VC fund that bent the financial product being offered to you, the perspective founder…let’s call this new fund ViralVC. ViralVC doesn’t exist and I don’t plan to make it exist, but for purposes of this explanation, the pronoun “I” represents the Managing Partner of ViralVC. What if my $200K investment in your company came with a matching $200K check for you to invest in another company? What if taking my investment enabled you to make an investment without risking your own personal capital? If the deal works out, you can keep half the carry and build your credibility and track record as an investor. If the deal doesn’t work out, no worries…make it up to me by crushing it with your own business, which we’re already partnered on by way of my initial investment. I kind of like this idea of every investment a fund makes perpetuating a second investment, and using the initial portfolio of founders/their DNA as the filter for who else is interesting and special and of a similar value set.

Most seed funds hit a point where their partnership doesn’t scale to cover the number of investments they want to make/manage, but what if a portfolio of founders played a more active, yet non-distracting, role in investment identification and management. Theoretically, a seed fund could scale to distribute very large sums of money without bumping up against the constraints of today…I could see a path to deploying funds well beyond the $100M fund size that most seed funds max out at…in fact, i could see a path to responsibly, intelligently, and profitably deploying on the order of billions of dollars of capital into the seed stage asset class, simply by giving every recipient of capital a matching check to invest capital, so long as they agree to shepherd the investment and treat it with care. If you make great initial decisions on where to invest capital and in what founders, and apply a simple rule for portfolio founders like “your matching check is unconditional, so long as I, the managing partner, gets to meet the recipient, and we together agree it is a good investment. if i don’t agree, we don’t invest in this company, but you retain your matching check, go find someone else/better/different.”

It’s not a new idea for seed funds to invest in “connecting founders to each other” or “platform” as a form of scale, but it is new to make founders in your portfolio into investors of your capital, in an unconditional, non-one off way. I think the key would be to build great systems of communication and reporting to mange the network of investments and founders as it scaled beyond the first few generations of investment…and to build a crystal clear and well understood set of values for the community to abide by…so clear that even at large numbers, the group could operate as a cohesive unit to maintain and manage a consistent brand to the market and perspective founders…also key would be to deeply scrutinize the dna of early founders/recipients, knowing that the out years DNA of the portfolio will emanate directly and as much from them as it would from you, the Managing Partner of the fund.

So now, as a founder you could take someone else’s money, or you could take ViralVC’s money that comes with a matching check for you to deploy, significant upset economics, new experience and information, admission into a community of like minded founders, and the ability to give this exact same gift/value proposition you’ve received to whoever you believe in, regardless of how well networked or branded or popular they might be.

Kind of an interesting thought exercise…as ViralVC, you could lose a lot of money quickly executing on this model…but you could also completely upend the seed stage asset class if you did it right…

Come to think of it, what fun is a thought experiment without putting it to the test. I’ve got a $25K angel check for anyone who’s raising. If you earn it, I’ve got another $25K check for you to deploy (you keep 50% of the carry). Any market, any layer in the stack…just be original and genuine and creative and wierd. (put ViralVC in the subject).

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New School Thinkers, Where Are you at?

Posted on January 7, 2015. Filed under: startups, venture capital, wildcard |

Getting old is an interesting thing in startup land. I realized this a few days ago when Forbes 30 under 30 came out and I could finally tweet my hatred of lists like this without any suggestion of my exclusion as the source…because…well…I am not even eligible anymore. In fact, I haven’t been eligible for 2 years at this point. 32 years old is not grey beard territory, but there is now a very defined generation of founders and thinkers in our community that is after mine…that think and behave differently…that make some of my context and assumptions about the world antiquated and non-contemporary. I am certainly a student of technology and social behavior, and I invest quite a bit in staying up on how things are changing, but it doesn’t change the fact, that I now fall more into the category of experienced and biased, than youthful and “temporally native”…if that phrase makes sense.

Anyway, this post is not really about me getting older…it’s actually about my network (that word sort of makes me puke…especially as a verb) getting older. Networks age…and there are some amazing things about this reality, and some shitty things about this reality. The amazing thing about my now-aging network, is that the “kids” i grew up with in startupland, continue to accrue more and more responsibility, more and more influence, and it’s good to be friends and close with people who are leading meaningful companies or initiatives within those companies…my network has many more “decision makers” at increasingly important places than it did when I was 24 and just beginning in this world. The down side of my aging network is that it is harder to find quality thought coming from a super contemporary place…originating in fresh data that is not biased by historical events or previous knowledge. Said another way…most of my “go to” people that I’ll grab a coffee with just to talk about the world and what’s interesting don’t reside within the 22-26 year old, “temporally native” crowd. We have a great little pocket of folks like this here at WildcardMax, and Ryan, and Connor (the Wild Kids if you will) remind me a lot of myself when I started out in startupland…and their thinking inspires and influences me daily…but lately I’ve been feeling like I’d like to invest more heavily in extending my network into this age group…

In my old age, i’ve become very protective of my time…I won’t take or request a meeting with someone new…ever…if there isn’t an explicit purpose for doing so. When I was 24 and someone interesting on twitter says “hey, want to grab a coffee” I think more often then not the answer was yes…and I’d similarly claw to get as many coffees with people who I thought were impressive…with no specific agenda other than “i want to know this person.”

I mentioned previously that my mantra for 2015 is “Effort,” and that mantra I think applies to many different realms…one of which I’ve decided is “building closer relationships with the new kids on the block.” I’m going to try to hang with a few folks from the 22-26 year old crowd every week…no agenda…just talk about the world and what’s happening…and develop some new thought partners to round out my “go to” group. I don’t know that I have a ton to offer…I don’t really want this to be “career advice” or “business pitch” or “job interview” type stuff…I guess I just offer my genuine interest and ideas and willingness to learn and explore any area that matters with anyone smart who wants to spend an hour doing so.

So if you’re part of this “temporally native” crowd and would like to waste an hour with me, I’ve carved out time and would love to do it. Just send me an email to with a link to your online presence so I can do a little research and figure out if we are going to think about interesting things together…

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This isn’t the death of the web, it’s the birth of the native web

Posted on November 25, 2014. Filed under: startups, venture capital, wildcard |

Something interesting happened a few days after we launched Wildcard last week. We released the first ever “native card browser” on November 13th, a serious departure from traditional HTML based web browsers, and 4 days later the Wall Street Journal published an article entitled “The Web is Dying; Apps are Killing it.” This is by no means the first time this concept has been suggested, but the debate flared up in the wake of our launch, with a wave of follow on posts discussing the future of the web and its health as it relates to a mobile first world. I can’t say that Wildcard is responsible for provoking this instantiation of the debate, but I do think our product and message reached the community of folks who are thinking about the future of the web, and the timing/language that flowed through the posts I read suggests to me that Wildcard was present in people’s minds during the conversation.

Two years ago when we started building Wildcard, the debate of native vs web was in a very different place. It was not a forgone conclusion that almost 90% of our internet consumption in 2014 would occur within apps, and a large contingent of “web purists” still held hope that HTML5 would win out over native. At the time we bet on the native ecosystem, but aspired to bring some of the most important properties from the web (like discoverability and sharing/linking) into this new reality. We thought of cards as the native analog to webpages, and didn’t aspire to kill the web, but rather to modernize it into what was clearly a superior user experience on mobile (app/native technology).

I was pleased to see in the most recent wave of this discussion, a general acceptance or recognition that in today’s mobile era, the web as we know it, is pushing down stack to a more infrastructural position that is powering new, native interfaces that are easier to interact with on mobile. I liked the supposition that just because users are interacting with the information from the web in a different interface or format, that does not mean that the web is dead or dying…to me this arc read more like an evolution than than an extinction.

I have largely tried to stay out of this debate, mostly because I am sensitive to my lack of historical context associated with the development and emergence of the desktop web. There are so many smart people who lived through it, who are intimately familiar with it’s definition, properties, and ideals…and my study of the internet really only began in 2005…I feel really confident building what I hope the native web or native internet becomes…but less comfortable pontificating on how that future does or does not jive with the past.

So this is all to say, I was pleased to see thoughtful posts like this and this pushing forward a more flexible and updated definition of “the web” and I hope that Wildcard can play a small part in defining an interaction paradigm that recognizes today’s hardware and context while delivering on some of the things we lost in the migration from the web as we knew it to this more modern, native consumptive pattern.

For ease, i’ve pasted a bunch of the media from this latest conversation:

“The Web is Dying, Apps are Killing It” – WSJ, Chris Mims

“Follow Up: The Soft Bigotry of Low Expectations for the Web” – WSJ, Chris Mims

“The web is alive and well” — Quartz, Zach Seward

“Native Apps Are Part of the Web” — Daring Fireball, John Gruber

“The Web, Still Dying After All These Years” — MG Siegler

“Is the Web Dying, Killed Off by Mobile Apps? It’s Complicated” – GigaOm, Matt Ingram

“The Web is Dying! Wait, How Are You Reading This?” – Slate, Will Oremus

“Rumors of the Internet’s death have been greatly exaggerated” – Daily Dot, Ben Branstetter

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Not Every Datapoint Demands an Insight

Posted on October 28, 2014. Filed under: startups, venture capital |

I read a headline in my twitterfeed just now that said something to the effect of “why twitter’s stock price is trading below it’s ipo value again.” Out of 100 tweets or so i consumed, that information triggered my “signal detector” which is the little voice in my head that says “this new thing might mean something / change something in our overall view of the world.” That detector goes off in my head, conciously…about 25 times a day…it can be triggered by a piece of news, a conversation, or even the expression or aggregate expressions of the strangers that i pass by on the street on my morning walk to work. I think one of the things that makes me weird…that attracts me to weird problems…and potentially isolates me from regular folks is that my detector tends to go off by a set of events and information that are really different than what most people pay attention to. I don’t know why, but it’s always been that way.

As a result, my process of listening to and addressing the information that sets off that trigger is really different from, say, what an equity research analyst or a private equity partner might have. Let’s take the case of that tweet from earlier…my process for analyzing that event was too go to Yahoo Finance. look at the one year stock chart of Twitter, spend about 20 seconds asking myself “is this different from what I expected?” or put another way “does this conflict with my current world view” and if the answer is not “yes, this is unusual”…than i x out of the tab, keep rolling, and don’t think about it anymore…and that’s exactly what I did in the case of that tweet. Now that doesn’t mean that datapoint is gone…it may reemerge sometime in the future, but I never try to force my way to an insight around things that trigger my “signal detector.” I feel like an analyst would sit down, look at this new event, and apply a process that would not be complete until some conclusion was reached…insistent that every new piece of info is some sort of “update to his worldview” but that’s not the way I think about this stuff…most information…i just try to let it wash over me…run somewhere in the background, and then wait for a signal that conflicts with it all to induce an insight or understanding of what’s going on…it’s kind of the opposite of a linear analysis and i think it makes room for a wider top of the funnel when it comes to the types of things that trigger my “signal detector”…

Happy Tuesday

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Creating Fast Moments

Posted on September 10, 2014. Filed under: startups, venture capital, wildcard |

I live for fast moments. The sprint to recruit and close a superstar…that’s a fast moment. The intensity of raising capital…that’s a fast moment…the breakthrough product idea that changes everything…and the week long sprint to get it into production…those are fast moments in the life of a startup. These fast moments are the days and weeks when everyone in the office shares an elevated heartbeat…anticipation becomes palpable and you can begin to vaguely make out the place that was talked about but previously beyond the horizon…

If I go too many days in a row without a fast moment…I start to feel it. Before I think it…before I analyze it…I can literally feel the slowness in a period of time. I get grumpy without being able to articulate why…I get unproductive without being able to articulate why…I just feel the slowness and it literally interrupts whatever I am doing and says “hey…wake the fuck up…we’re not going fast anymore.” It usually takes me about two or three days of unpleasant feeling to realize what’s happening and then I sit down with a stack of white computer paper…i map out everything that is happening both internally at the company and externally in our market…I find the 3 or 4 fast moments that are waiting around the corner for us…and I steer directly into them.

When I was younger, running Hyperpublic…I would literally try to create these fast moments myself… “not moving fast enough? I’m going to go out there into the world…hunt a giant fucking animal…whatever that might mean…and I’m not coming back until I’ve got a carcass to drop in the middle of the office floor.” That kind of works…but there are many more fast moments than a CEO can create on his or her own. We have such a talented group of people building Wildcard…on any given day…any given person is capable of changing the game…now when I map on that stack of white paper…i’m just trying to figure out who is coming up to bat this inning and what type of pitch represents their next fast moment.

The reality is it’s a 9 inning game…in a 162 game season…and some innings are gonna be slow…sometimes we’re going to have to grind out a 0-0 game until the bottom of the 9th…and sometimes we’re going to score 8 runs in the very first inning…I guess I should be more accepting of the slow moments in the season…but I can’t help it…I just love fast moments…and I’m gonna chase them down until the day I stop playing this game.

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When to walk from a deal

Posted on July 15, 2014. Filed under: startups, venture capital |

Negotiating a deal is an exercise in reasonability. As long as the other party continues to be reasonable and as long as you continue to be reasonable, the odds are good that you will get to a deal both are satisfied with. Giving a little and getting a little back and forth are expressions from either side of reasonability. Drawing a hard line in the sand is an unreasonable action unless it is absolutely real and you are prepared to walk if your terms are not met. I have no problem employing this tactic in a negotiation and do it all the time. The good part of this negotiation method is that you can clearly articulate your needs and they are often met. The unpleasant part is that you often have to deal with the pain of walking from something that you genuinely wanted to happen. Even when you sit down rationally and say “this deal doesn’t make sense at any terms beyond x” when you face the operational reality of not doing it there is a cost. You already decided you were willing to incur it when you drew the line in the sand…but it’s unpleasant to pay it nonetheless.

I was having dinner a few weeks ago with a friend 30 years senior to me who runs a company in a very different field from ours, and we were talking about this dynamic of “being willing to walk.” When all posturing is put aside, there exists the point where any CEO/investor/whatever is willing but doesn’t want to walk from a deal they value. I asked him about a big deal he was working on in which he had clear leverage “when it really comes down to it, are you willing to go through the pain in the ass and inefficiency of finding an alternative if they don’t agree?” and his answer was I think what most CEOs feel in these situations…he made a snake like motion with his hands as he said “nooooo….but maybe yes.”

We have this natural instinct to avoid the pain of walking…it’s a more basic instinct…lower level in the emotional stack…if you will…than the optimizing/strategic mind…and there is a dance between this preservation instinct and optimization that is probably healthy. Instinct governs you to be reasonable and work toward a shared goal at the cost of optimization…and the strategic mind is the kill switch that can override preservation instinct when the avoidance of pain has a smaller absolute value than the gain in optimization from walking.

So when do you actually walk from a deal? When your strategic mind tells your preservation instincts to shut the fuck up and go find the better deal that’s out there…

p.s. this post has nothing to do with Wildcard….be cool

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Give it a minute

Posted on July 3, 2014. Filed under: startups, venture capital, wildcard |

On Tuesday night I went for a bike ride with my friend Pierre. He runs a company called Sunrise which I very much admire. We were talking about getting featured by Apple and he had a very astute comment. He said “of course, it’s wonderful, when Apple features you, but no matter how well you do with features in the App store, that is not going to make you successful…building a great product that people value is.” As we drilled down on the “that people value” half of that sentence, he mentioned Evernote as having created and effectively communicated 3 clear pieces of value that it reminds users of every session. I can’t remember them exactly, but it was something like 1) your information everywhere, 2) instant search, 3) easy capture. I may have gotten that a little wrong…i’m not actually an evernote user…but the gist was that Evernote has 3 concrete pieces of value that it’s users know and can clearly articulate as “what Evernote gives them,” and Pierre said every company should be able to articulate those 3 pieces of value. He said, “when you know those 3 things…the product roadmap writes itself.” The more interesting part is that Pierre felt he had only identified 2 at Sunrise, and that the 3rd had not yet been built. I commented that having the patience for the 3rd to present itself in the future is a leap of faith that is required to get to the promised land. I suggested that he had already made the decisions that would determine if Sunrise finds it’s three and becomes the megasuccess he hopes it will…and now all he needs is time for those decisions to play out.

My belief is that the team you assemble in the early days of a company either is or is not capable of building the product that reaches the promised land…and then as a CEO your job is just to create enough time and space for them to realize their potential. People often think that when you make an incredible new hire or bring on someone very special…that the company realizes her gain or value overnight…in reality, I believe that you invest in exceptional people and you don’t yield the results or “the return” on that investment for years. Brilliance takes time to express itself…that 3rd feature or piece of value…that product tweak or insight…that growth feature…or performance shattering technical breakthrough has a gestation period…and it requires an incredible leap of faith on behalf of a CEO or founder to simply be comfortable that the people he or she has assembled are the right people…and that if given enough time and space to express themselves deeply, they will find the promised land for you. There is this fable or false archetype in startupland that the CEO is out in front…leading a team of people in a direction that he or she sees…and that if they find the promised land it is because he navigated them to it…As I mature as a CEO myself, I am increasingly aware that it is actually the team that is out in front…collectively leading smaller interlocking efforts, that in aggregate set the path toward the promised land…and it is the CEO…pulling up the rear…making sure there are no sprained ankles, everyone is properly hydrated, and that with so many people confidently expressing themselves…nobody is breaking from the pack and going in a direction that is at conflict with the whole and the Company’s vision. Maybe this is not everyone’s approach, but at Wildcard I am certain that if we are to achieve our ambitious goals, it will be because we were able to stick around long enough for the people already sitting in this room to fully express their potential.

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Women at Wildcard

Posted on January 8, 2014. Filed under: startups, venture capital, wildcard |

I’ve wanted to write this post for a long time…and every time i sat down to do it…it just didn’t come out right. If you’ve read this blog for a while, you know that I care about the people on our team more than just about any other dimension of Wildcard…more than I care about product…more than I care about fundraising…team is everything. It was true it Hyperpublic and it’s true now. When Hyperpublic was acquired by GRPN, we were 10 people…9 engineers and me…1 first generation immigrant and 9 born Americans…8 caucasions, 1 Asian, 1 African American…1 profesional musician, 1 chef, 1 billiards master, 1 former professor, 1 outdoors enthusiast, 1 fashion efficianado, 1 college drop out, 1 improv master, 1 son of a preacher man, 1 semi-manic tech blogger…and 10 MEN…we had such an amazing and diverse group along so many different axis…except gender…where we were shockingly homogenous.

At Wildcard we are now 10 people as well…6 engineers, 2 designers, 1 ops, and me…guess how many women? Not for a lack of interest and not for a lack of effort…but still the facts are the facts. I have a handful of close female friends in the tech community, and a smaller handful of close female friends in the engineering community in NYC…and over the past few years I have listened carefully as they’ve shared their views on building a multi-gender culture into your startup. Here are a few “near quotes” that I’ve heard that have stuck with me and inform the way we make decisions at Wildcard.

1) “if you get to be too big without bringing on a female employee, it get’s much harder to do so down the road.” The spirit behind this observation is that it can be intimidating for a potential recruit to be “the only woman” on a team of 15 males…obviously that intimidation factor grows when you replace the number 15 with 20, 30, and so on.

2) “It isn’t enough simply to have female employees at your company. You need to have female employees in leadership roles at the company.” The spirit behind this thought is that young ambitious women want to see that your organization is a place where they have the ability to grow and advance into influential roles within the company. If the leadership in the company is uniformally male, that does not set a tone of opportunity within the company.

3) “you’re brand of being badass engineers is too unwelcoming and does not appeal to the female psyche in the same way that it does the male psyche. Consider modifying your tone from working amongst the most badass engineers to working amongst the most intelligent people in NYC. There is nothing wrong with communicating the pedigree and ability of your team, but do it in a more gender neutral way.” I didn’t realize that “badass” was a more male value…but I can see how that is sort of lazy language to articulate how special the human beings at our company are.

4) “Women don’t want to be hired simply because they are women. Nobody wants to feel like the token girl that got the job because your startup needed a woman.” This one is so important because I think I and many startups have fallen victim to the reality that it is difficult to source female candidates for open positions…but when you advertise that you are looking to or excited about bringing that diversity into your culture you set a tone that can unintentionally trigger the above sensitivity. In fact, one of the very reasons for writing this long, verbose post is to say “I’m listening…i’ve been paying attention…i understand many of the gender dynamics that are at play in the startup ecosystem. I don’t have all the answers, but I care…and maybe this post will lead to a change in the complexion of our team and maybe it won’t…but I’ve BEEN listening and I don’t know what else to do to address it other than write out where I am in the process of figuring out how to build the best team of men and women and New York City.

So yea, I know there are more dynamics at play than the ones I’ve articulated, and in some sense I’ve condensed hours of conversation down into a few bullet points, but at least this on paper…this is how I’m thinking about gender at Wildcard…and my and our actions will be in response to these shared observations and any more that people would be willing to share in the comments of this post. Been too frustrated with this challenge for too long not to work through it head on.

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The Day is Upon Us

Posted on January 4, 2014. Filed under: startups, venture capital, wildcard |

As a founder, I am not big on company wide communications. At Wildcard we have a company-wide mailing list called “Family,” but I use it sparingly. If there’s an article that’s interesting or a new person starting soon I’ll fire off a quick note, but beyond that I prefer more personal communications with our crew. This past week, however, I did have an instinct to send a note to our group…New Year’s Eve has a funny way of commanding communication between family members, independent of where on the globe they happen to be.

As I opened my email to send a New Year’s message to our small but growing family, the most surface template that came to mind was something to the effect of “Love you all, 2014 is going to be a big year” or “Love you all…rest up…we are going to crush 2014.” I sat with the draft email open for a few minutes…but with slightly more depth behind my thought, I realized that these messages were empty…and further, not how I really feel about what 2014 holds. The truth is, I have this strong instinct that 2014 is going to be an incredible challenge. The email I would have written if I had more than a sentence or two to explain it, would have began with something like “Love you all, 2014 is going to be fucking hard.”

I am so proud of what we accomplished this past year. We have built incredible technology, assembled one of the most talented teams in New York City, and took what began as an incredibly abstract vision of what the mobile internet could become, and turned it into something real that you can touch and feel that hints at the probability and promise of this future. On one hand, I love where we are sitting…and I know that our investment over the last 12 months will continue to yield into the next 12…but I am acutely aware that what we have done is not enough…that for us to pull off what we aspire to…it will require near flawless execution…continued discipline and vigor…tremendous fortitude and flexibility…and increased emotional composure. In 2014 we will deal with an incredibly dynamic ecosystem of giants, bobbing and weaving through their legs and perhaps securing seats on their shoulders…We will get our first taste of the challenges in mobile distribution…We will most certainly say hello to a few competitors who we don’t yet know about…and we will learn what it’s like to design and develop within an organization that is twice our current size and larger than we ever built at Hyperpublic. We’ll move from developing product beneath the understanding lens of our own team and investors, to building under the judgmental and non-empathetic gaze of the masses…we will receive negative feedback…something we have had very little of to date…some people will hate us…or tell us we are wrong…our small knit community of believers will be drown out by the skeptics…and like every good startup to put product into the world…we will painfully learn how to communicate our message and convert the non-believers…pats on the back will turn to punches in the stomach…intermittantly eased by the deep tissue massages of our small and large victories.

There is a battle upon us…it is one I know how to win…but there is no shortcut…no secret weapon…that allows us or anyone else in our position to escape the hand to hand…in the trenches…ugliness of taking a spot in the world that many don’t know they want you to hold and that some actively know they don’t want you to hold. You might think from my words that I am not looking forward to 2014, but it is just the opposite. This is what we do. It’s why we kept the bar so high on recruiting. It’s why we don’t simply hire talent to fill roles, but rather dynamic athletes…with the mental and emotional strength to walk into this fight every morning…and not let the stomach shots or duress dilute our craft. This is the year I get to see why every hire we made over the past 12 months was so so right and I can’t fucking wait. So yea…you can see why “Love you all, we are going to crush 2014” doesn’t exactly say what I needed to say. Upon reflection, perhaps this message would have been more appropriate:

“Family, I don’t need to tell you how much I love this group of people. You can see my affection and pride every day I walk in the door. I feel deeply privileged to walk into the coming battle with such a fine and honest group of human beings. We are a small but formidable cadre with the skills and shared ambition to win any fight we choose to enter…and believe me, the fight was have chosen will not be without blood and grueling conditions. It is in our composure, sustained confidence and cohesion that we will endure and ultimately persevere against any that are not with us. Stick to our plan, but watch and communicate as the battlefield changes…Fight with humility and integrity and those that sit on the sidelines will eventually join our ranks…we are small but will not be small forever…whether back against the wall or advancing through enemy lines, remember that those that are not with us today, may well be allies tomorrow. It is January 1st, 2014. The day is upon us…”

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Going Uncomfortably Fast

Posted on December 5, 2013. Filed under: startups, venture capital, wildcard |

I didn’t learn a lot of things in my time at GRPN…I was only there 4 months after all…but there are a few tidbits that I picked up that have stuck with me as we forge forward at Wildcard. I remember Andrew Mason visiting the Palo Alto office on more than one occasion…he’d come and address the engineering team, talk about what’s going on in the company…and frankly run damage control as the stock continued to get abused in the public markets. He was actually a wonderful orator and his cadence with the team I found inspiring and emotionally intelligent. Now some of his words may have been lip service, and some may have been genuine, but I remember this one phrase which I may slightly butcher…but it will be with me forever. In describing why things were “breaking” at GRPN he would repeat over and over “We intentionally made the decision in the early days of building that we wanted to go uncomfortably fast…that we liked the feeling of the wheels shaking on their axels as we grow…and it is this commitment to going uncomfortably fast that allowed us to defeat an entire market of ‘me toos’ and get to where we are now.” Now his words were through a lens of the costs and required repairs that come with going uncomfortably fast…but the idea that they deliberately sought to exist in this forward moving state of instability I found fascinating…at my first two startups I had always tried to preserve stability…

As I reflect on his words, they echo a hand that Kenny has always put gently and sometimes more forceabley on my back…pushing me forward…faster than my stomach would intuitively dictate…A common phrase that I hear from Kenny when we talk about Wildcard is “You need to go faster…step on it…now.” I think to myself…we are going fast…faster than I have ever gone before…and yet still…it is not fast enough…we need to be going “uncomfortably fast…” I’ve said before that I think the optimal burn for a startup is the amount that causes a CEO to feel slightly uncomfortable with what he or she is spending…and I think this sentiment applies not only to what you spend, but across all operational metrics and decision making…there is a very fine line between irresponsibility and the optimal angle at which you lean forward in your decisions…and I am forcing myself to live on it…every single day…the crazy part is, even though I feel like I am approaching that line…in reality, I am probably still not even close to it…there is something to pointing your skis straight down the mountain that is actually safer and more optimal than sliding down the double black sideways…but it requires this leap and confidence that you can only gain through a combination of experience and gentle pushes from those that have more than you.

I am grateful to Andrew and Kenny and a few other close friends who gently and not so gently continue to nudge our skis into that optimally uncomfortable position…it’s getting us to places that I’ve never been before 🙂

p.s. if you want to come skiing with us…this is where the lift tickets are sold:

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How I spend my time as a startup CEO

Posted on November 27, 2013. Filed under: startups, venture capital |

Last night I had the following exchange with Semil on twitter:

@jordancooper what does it take to be startup CEO, in first year? can you squeeze it into 140?”

@semil vision, ambition, empathy, discipline, passion, humility, language, listening, hustle, support, great cofounders, special team, love”

I responded in an instant without deep thought or analysis…but those are the ingredients that I guess were top of mind…my gut response. It was an unusual position to find myself in…where someone well respected and authoritative in the startup community was asking me, as a CEO, what I believed it took to be good at my job…embedded in the question was an assumption that…well…I am good at my job. Having been in this seat, now 3 times, this is the first tour I’ve done where I am not constantly defending myself and my worthiness in the seat…that is a huge part of being a founder…and a young founder…simply justifying that you are good enough to warrant the position you’ve assumed…so before going forward…i guess…thanks Semil for believing in me. Anyway, beyond the personal characteristics and components that I find valuable as a startup CEO, I have been spending a lot of time recently thinking about…well…time. How am I spending mine? Is this optimized? Where can I change or improve or shave or reallocate to be more effective as CEO of Wildcard. I go through this process of self analysis every so often…it is usually when my activity is breaking the structure that I had previously put in place…i feel sub-optimization in my body and my mind…I go from energized to exhausted…and from consistently thoughtful and creative to spottily thoughtful and creative if that makes sense…spurts of magic as opposed to flow states…anyway…recently I have been feeling my structure cracking…not yet broken in the sense that things are moving forward and fast…but I can sense that a reflective optimization is on the horizon…

Generally I have two goals as CEO of Wildcard.

1) Support the exceptional people I sit next to everyday in any way I can. This can be in thought, in emotion, in sustenance, in vision…whatever I can do to unblock and unleash the greatness in everyone else…I will do…and the time I spend doing this, weather it manifests in something as mundane as taking out the trash, as substantive as an analytical conversation, or as nuanced as a thoughtfully timed hug…these actions are always optimized and priority..the time I spend thinking about and caring about everybody at Wildcard will never fall to the coming reoptimization.

2) Clear everything else off my plate…every task…every to do…every meeting…every request…and find the time and space to focus on the one thing that will push us forward the fastest and most dramatically…that thing can change from moment to moment…but more realistically it changes from week to week or even month…One month it can be “secure investment,” another month it can be “better define product” and another month it can be “recruit Design Leader”…but generally I find that I can maintain many balls…but really only excel at one important thing at a time…if “excel” or “excellence” is a true requirement of the task at hand. Context switching is a big part of my job…being able to dip in and out of different problems and questions and thoughts…while contributing meaningfully to each….but every switch takes a toll…which is why i try to only switch off the one most important thing when it is in the spirit of supporting someone on our team to achieve their “one most important thing.”

So how do I clear every moment and task that does not fall into one of these two categories and make space to do these things well?

1) extreme honesty and discipline: I say no to a ton of meetings, a ton of emails, a ton of opportunities…with no remorse and sometimes lacking a little bit of social grace (although i try to be human about it). I’ve never had a problem saying no before…it’s a requirement of time optimization.

2) I invest in people who are better than me at everything I do. I constantly look for ways to replace myself…to upgrade in areas where I can push things forward…but not nearly as well as someone better than me…I pay deep attention to my efficiency in all realms…and sense when I am not achieving the desired result in the same amount of time as another could…that is an opportunity to upgrade

3) I force reflection: at least once a week, and often once every few days…no matter how focussed or involved I am in a given task, I force myself to look at my own time and our entire business from a birds eye view…I write out priorities and observations on blank index cards…and I visualize my own and our team’s efforts in semi-real time as opposed to on our traditional 90 day roadmap axis…

4) I walk to and from work every day: I know this sounds like a sub-optimization of time…but in fact it is built in, uninterrupted focus within the chaos of meetings and conversations and inboxes and bullshit…it is a meditation that actually calls less on directed analysis and more on surfacing the things that are “running in the background” of my mind…this is key for me…because awareness of what’s going on can be stifled by concentration and focus…I need space to surface the unsolved…and my walk is that space.

5) I am disciplined about believing in my decisions. I would estimate I make about 10 decisions a day that impact our company…some of them are big…some of them are small…but once they are made, I almost never look back…they will not all be right…often they are…but second guessing or even reexamining in the absence of new information or data is a complete waste of time and energy.

Anyway, I’m sure there are more, and I could go on this track for much longer…but I’ve been writing this post for over 20 minutes now…and I am getting diminishing return on these next minutes…I’ve written to the point where I understand the thought I was trying to explore…time to get back to the “one thing that will push us forward the fastest”…in this case…it’s finding a truly excellent owner of this position and side of our business. Happy Thanksgiving.

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Bitcoin, Taxes, and a Path to the Promised Land

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

Bitcoin is at an all time high today…again…as it was yesterday and the day before and the day before etc…for anyone who owns bitcoin…it’s pretty fucking exciting…so exciting that there’s only one thing that people want to do with their bitcoin: “hold.” Demand for bitcoin is fueled by 3 things:

1) idealism: those that want to believe there is a better way…those that rabidly consume information on the currency..that consider “what if” and are excited enough about a bitcoin future that they participate with their wallets.

2) speculation: curves like the one to the right don’t come along very often…people who own bitcoin as a pure investment are generating returns that you simply cannot find anywhere else…those returns are intoxicating and seductive and lure “double down” behavior…and…investors who generate those type of returns like to brag about it…causing viral spread of bitcoin as an asset allocation.

Screen Shot 2013-11-13 at 6.18.04 PM3) bad action: whether your laundering money, buying illegal goods and services, or trying to cover your tracks for some other reason…in it’s current form, bitcoin offers some cover if you’re transacting in bad faith…

I’ll start with Group 3 and say I’d assume this group is either flat or contracting as a % of volume in the bitcoin market. While providing much of the early liquidity in the bitcoin ecosystem, i believe that the group of bad actors who found this unregulated/unwatched channel is finite in size and a small portion of the overall addressable population/$ volume. So, as the other two groups grow in size…i believe this group will contribute a smaller portion of the volume in the market, and become less influential…further…i believe that the veil of true anonymity is starting to crack in this ecosystem, and when bad guys go down…other bad guys maybe back off…or find some other dark corner to transact in…

Groups 1 and 2 are more interesting to me…and I believe that for bitcoin to become really real…whatever that means…they are both going to have to start doing something that they aren’t really doing right now…and that’s spend. Let’s examine the incentive structure for each and figure out a path to this reality.

For the idealist, why spend?: “it’s simple…until bitcoin starts being exchanged for something other than dollars…the volatility puts your mission in jeopardy…crashes freak people out…some portion of the bitcoin in the world needs to become less liquid than it currently is…it needs to get locked up in places that won’t dump it back to the exchange when large holders sell…it needs to hold it’s value relative to a sweater or a carton of milk and move in value in a non-realtime way…so that when the “smart money” dumps…there is at least a lag in how that carton of milk gets “repriced” in bitcoin…(god i wish i took economics in college…this is straight intuition…but pretty sure it’s right)…until bitcoin goes into “circulation” in a real way…it’s value and legitimacy as a value store hang by a thread…a hope-filled, exciting, logical thread…but a thread none-the-less

For the investor why spend?: This one is trickier…why should I spend $100 worth of bitcoin instead of selling it back to the exchange for $100? Sure…maybe i could save the tiny fee in selling…but 1% or whatever isn’t a good enough reason…it’s still effort to spend my bitcoin…there aren’t very many place to do it…it’s an unfamiliar transaction…i don’t get to realize my gain all at once and see it on paper…it’s just more complicated than why? Well…at the system level, it is clear to me that a bitcoin spent vs sold helps to maintain the value of the remaining bitcoins i hold…but getting investors to think that way either requires them to be moving in volumes that are very large (market moving on their own)…or it requires them to think as a collective or a whole…to act together…that’s a flywheel that seems tough to get spinning…so why? It may be that the answer lies in something much more simple: TAXES.

I’m no accountant…and I’ve asked this question on twitter four or five times with no definitive answer…but I believe that the speculators who are earning insane gains on their bitcoin holding are eventually liable for short or long term capital gains tax when they sell their bitcoin back to the exchange…Short term capital gains in new york city I think can get up to 40% and long term capital gains I think are approaching 26% (inclusive of state and city tax…)…these numbers may be a few points off, but I didn’t feel like wasting the time on research…because in the scope of this argument…all you need to know is that it’s 20-40x the fees that the exchange takes for selling bitcoin back…

So these megagains for speculators are great, but the haircut to get out is quite singificant…unless…as a speculator you achieved liquidity through another means outside of selling…i.e. SPENDING…if you spend your bitcoin with merchants, buying ski jackers, and food, and anything else that you would normally use cash for…I BELIEVE (and please please please) correct me if i’m wrong…that you do not pay any tax on the appreciation of bitcoin currency…in the same way that you aren’t paying taxes on the dollars you hold in your checking account when the US$ rises in value…Getting to enjoy an extra 26-40% of the value you hold in bitcoin is a big fucking reason to spend instead of sell…and if this is true, i believe it’s how bitcoin will begin to circulate at scale…

So…this makes owning the merchant network in this ecosystem a pretty interesting layer…sure…but I think there is an even bigger opportunity as bitcoin matures into something people spend vs. hold…i’ll write about it another time…

oh…and if you own at least one bitcoin and want early access to Wildcard…send me a note with“beta” in the subject to…Wildcard loves bitcoin so much that we’re going to open our doors a little early just to folks in the bitcoin community 🙂

p.s. as with everything i write…if i am understanding something wrong from an accounting or economic theory perspective…please correct me…

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4 things about Bitcoin that make my head spin

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

1) programatic transfer of value based on context or events. that’s just awesome. Naval articulates some of the applications (like his driving in a car example)…quite well here:

2) public log file enables a real time visualization of how value flows between parties…the implications of this on enterprise, real time reporting, etc…are fascinating…for consumers the visualization of where their $ is going is an interesting layer of value to be created…i’m reminded of “where’s George” with perfect visibility…if I’m a “green consumer” I currently have visibility into the first hop of where i allocate my resources…I know I buy “organic” for example from whole foods, but I can’t see the second, third and fourth hops…how is whole foods spending my resource…how did “my bitcoin” end up in Monsanto’s wallet (not the same bitcoin, but you get it) in the 3rd hop when i paid whole foods in the first hop? All of the sudden I can see my influence as a consumer in a fidelity so far beyond what i currently have. How does this change my spending habits? What are the implications of this high fidelity view on political contributions? With fully public transaction logs, all of the sudden my decisions and actions are visible at a system level never before visible…and in doing so resource allocation (or spending) becomes networked in the same way as information sharing or dissemination…the implications of this networked resource allocation are beyond fascinating…the level of efficiency that can come not just within a fiscal context, but all derivative life contexts given the infrastructural position of resource allocation (or spending) in the broader societal system design is incredibly exciting…for this reality to become realized, ironically, the most apparent present day value proposition of pseuodonymity or anonymity must fall to it’s inverse…or radical publicity…metadata and identity appended to transactions and currency is such a powerful thought…and a public log file that is viewable by all is a great platform to enable that type of mechanic.

3) I worry about the next 100 cryptocurrencies to be created and how they impact the value of my bitcoin as an investor. Will one win? Why? Merchant acceptance? Consumer acceptance? Elegance of platform design? Structural innovation? My sense is, like all platforms…they will be disrupted by better mousetraps. What does that mean for a platform so deeply tied to value store?

4) I love the idea that because a digital currency is programmable, rules can be written to structurally ensure that users, merchants, and other participants in the system behave in a way that gives the currency the best liklihood of succeeding and supplanting more traditional value stores. For example, if I determined that a necessary step in the realization of the bitcoin dream was that people started spending it instead of holding or sellling back to the exchange, could i write a rule for my bitcoin as a consumer that says I will pay you merchant x, but I demand (and programtically define) that this coin can not be sold back into the exchange for 180 days…you may transfer it to another merchant directly, but it can’t go back into the exchange…in other words…programmable and contractual are intimately related…and it’s fascinating that i can program a contract into my value store that ensures the value store will not decline (when such contract is implemented at a network scale)…

NOTE: I am still learning about bitcoin. if i am misunderstanding anything or am thinking along axis that are not technically possible within the platform, please correct me…but don’t hate me…just whimsically brainstorming here

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Understanding Snapchat

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

I just came from dinner with my friend Kortina. For those who don’t know him, he started a company called Venmo. If you’ve used the app, you know that he is a “contemporary mobile thinker,” and yet he confessed something to me at dinner which is a sign that we are both getting a little old…he said, “dude, i’ll be honest with you, I don’t even understand Snapchat.” The context was that there was this new generation of users and popular applications to which we recognized we have a harder time relating. At 31 years old, for most of our professional lives we were the generation that the older guys were trying to understand, and mainstream applications spoke to us naturally…but now here was this megasuccess that we had to work…really hard…to understand..something had changed. I confessed that it took me a long time to really “get snapchat”, and by “get it” I mean understand why it was unique or special and how i could be a user that derived pleasure from it…Kortina said, “so you use it? What is it really?” My first reply, for simplicity, was “think of it as the easiest way to video chat on your phone.” His response: “I get that, but is that it? Does the disappearing thing even matter?” I thought for a moment, and then replied “yes…but not in the way that you think. The disappearing content isn’t about changing the nature of the content that you share…it’s not about making things more lewd or dangerous because you know they are going to disappear…that might happen, but I think the impact of the disappearing unit on the uniqueness of the application lies in the relationship that the recipient, not the sender, has with the content. Because the content will disappear, it commands the recipients full attention…knowing that they have one chance to consume it…and perhaps more importantly…the recipient can’t become “attached” to the media in the same way that they can a photo in instagram or facebook for example. there is no deep analysis…no scrutiny…no returning to it…or pining over it…or revisiting it to take another sip of the feeling it gave you the first time you consumed it…and in that ephemerality, in the inability to “attach” to what you receive through snapchat, comes a lightness…and it’s that lightness that is special…it says…this isn’t so fucking important…this isn’t a deep statement…this isn’t a reference point or something for you to really think about…to me the disappearing unit is about levity, not scandal or sex or illicit media that has found it’s share channel…I think the illicit content exists, but it’s not at the core of the innovation i see in the experience.”

So yea…that’s two newly old guys trying real hard to understand the products that matter in today’s world.

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10x improvement

Posted on October 10, 2013. Filed under: startups, venture capital, wildcard |

I spent time this morning with Brian Pokorny.  I always like coming out to the west coast because people here have different language, different frameworks, and different models for how they think about problems and opportunities.  It’s not surprising…while the internet is a global phenomenon, there is a local bias in the data we consume, simply as a function of who we talk to everyday and what they are building and thinking about.  I am intimately familiar with the lessons of the last 500 companies to succeed and fail in New York City, and familiar, but less so, with the stories behind their west coast counterparts.  Today Brian planted a thought in my head, that has stuck.  In discussing our plans for Wildcard, and what an experience might look like that achieved broad adoption, the notion of a “10x improvement” was surfaced.  Brian’s suggestion, which I think I agree with, is that in order for a non-social application (or a “utility”) to penetrate a large amount of consumers, it needs to represent a 10x improvement over existing and entrenched alternatives.  Now I don’t know if it’s 10x, or 9x, or 5x, but the spirit behind it is right.  For people to recognize Wildcards as a better alternative to mobile web pages, the experience needs to be a slap you in the face improvement over similar solutions found in Safari, Chrome, and the distributed forms of those experiences.  That’s a high fucking bar…but I think it’s the right one to try to clear…so what does a 10x improvement mean in the context of Wildcard…I thought about this for a while, and I came to the conclusion that speed is everything.  For Wildcard to win, we need to be able to take actions that require 60 seconds of a user’s time in Safari, and achieve them in 6 through Wildcard.  As crazy as that sounds…I think that is the opportunity we’re chasing…and while a big swing for sure…I think it’s one we can achieve.  There are a lot of different ways to shave 54 seconds off a minute, and we are pushing on all of them…In the course of the conversation, we shared examples of others who pushed on utility innovation, and no doubt the road is littered with $20-70M outcomes that had to fall into a larger distribution platform in order for their innovation to reach many…we referenced those outcomes as “misses,” and thought of ways to avoid such an outcome…there were distribution hacks, indirect product designs that were A to B to C type strategies…but at the end of the day, after thinking through all, I actually believed our best chance at breaking into the Evernote/Dropbox/Google sphere, was to continue to pursue the 10x form of our product…It’s not a new concept that I didn’t understand before…obviously our experience has to crush the shitty mobile web experience currently enjoyed by hundreds of millions today, but thinking through a lens of 10x improvement really isolates the one key thing that will warrant a population’s change in daily behavior…in the case of Wildcard, in a world with load times, and errant clicks, and inefficient attempts at known desktop behaviors…we will strive to make your interaction with the information and actions of the internet 10x faster than this clumsy bullshit you are using today.

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    I’m a NYC based entrepreneur. I think there is one metric that can be used to measure the value of a human life and that’s impact. How did you change things? How many people did you touch? How different is the world because you lived in it and how positive was the change that you affected? (p.s. i don’t use spell check…deal with it) You can email me at


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