Smiling is a choice

Posted on January 20, 2017. Filed under: Uncategorized |

Smiling is a choice. I know that sounds strange…i would have previously said a smile is something that happens when you are happy…a result or reaction…to something inbound…but this is not the case. A smile can come from within. You can choose to smile, as a state of mind and as an explicit action…and while it may seem forced at first…if you let it happen…that smile and state of mind can become genuine…simply by letting it.

One of many lessons learned after a month travel through India. I saw smiles in places that would make you cry. I saw joy in places that you would want to change, or “fix,” or improve…and I met so many people who were happy, despite the most challenging of situations, simply because they chose happiness as a life philosophy.

I left New York at the beginning of December relatively down. A body of work I had spent 3 years on had come to an end that I wasn’t proud of. Many of the things that constitute my really really good life seemed mundane and routine. Not only was I not choosing happiness, I was actively punishing myself for not succeeding with Wildcard. Sometimes I can deprive myself of joy because I feel like I don’t deserve to experience it when things aren’t where I want them to be…and wrapping up Wildcard, that was definitely where I was at…

As it turns out, joy is not about deserving it or not…it’s not a result that only materializes when it’s earned or something good happens…it is a frame of mind that you can choose to experience, regardless of context…it is an input to…not an output of…a life well lived.

As I approach this next chapter in life, and start to think about new endeavors, and work, and goals, and all of the things that get me out of bed each morning…knowing that joy is what I will bring to them…as opposed to what will come from them…makes this exploration so much more fun.

I’ll end with an anecdote without analysis, but worth contemplating:

Amongst the many forms of meditation that we touched in India, one of the most surprising and interesting was a Sufist laughing meditation. 15 strangers stood in a circle, and we were instructed to start laughing…at first this was a very uncomfortable ask…initial laughs took the form of “Ha, Ha, Ha..” almost Dr. Evilesque (with all the vilians sitting around that board table in Austin Powers)…minutes passed and the forced laughter begat real laughter…you’d look at other people laughing and you’d start to laugh harder, and that’d make them laugh harder, and fast forward 10 minutes and 15 complete strangers are rolling on the floor in insane, uncontrollable laughter…i laughed harder in that meditation than I have in years…and it all began with a very forced…Ha…Ha…Ha…with a choice…to begin laughing…

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On Snapchat Spectacles

Posted on December 2, 2016. Filed under: Uncategorized |

So…they’re fucking fun. I got my Spectacles 24 hours and 29 minutes ago…at the risk of losing my 1 year warranty by admitting that I bought them off a kid on craigslist as opposed to “from Snap inc. or an authorized retailer,” I will tell you that I contemplated the 10 hour line on 5th avenue for a $140 pair, and then opted for the incredibly honest and kind Ukranian kid from Sheepshead Bay who (although quite tardy) drove his c. 1980 white BMW into the city and delivered a pair for $200…he even taught me how to use them free of charge. Worth it.

After 24 hours with them, here are some thoughts:

1) This review I read in the New York Times did a pretty good job of capturing the functionality and experience of using the glasses. I won’t repeat all that, but the most salient thing I took away from Farhad’s review was that the images captured by Spectacles are more raw and honest then even iPhone Snaps, which in themselves are more raw than the type of video you would deliberately capture with an intention of posting to Facebook or Instagram. Farhad writes:

“The images I snapped with my Specs over Thanksgiving weekend are deeper, more real and more emotionally evocative than most other snapshots I usually shoot. I think this has to do with point of view. When you take a picture with a camera, you are usually cropping an ideal shot that bears little resemblance to what you actually saw. But Specs don’t idealize the present.”

There is not much stabilization in the video that’s captured, the point of view moves as organically and sometimes jerkily as one’s head might, and consuming the videos later on has a different sense of presence then any other film i’ve captured on my phone. Part of this presence comes form the “Snap viewer” for Spectacles content, which allows the iphone screen to “walk around” a circular image captured by the glasses while viewing any rectangle within it, as opposed to simply fitting the film to one prescribed screen size rectangle. It’s closer to a true field of view, and I really like it (note: the video of my day attached to this post, is a proxy for the feeling of viewing the content in Snapchat, but much more limited…you really have to watch the content in the app to get the full experience.

2) So I had that raw and honest expectation going in, and I love that dimension to the content. There is…however a major downside. Yes, you can capture more raw, honest moments…without interupting the experience by putting your phone between you and the world…BUT…when you are wearing Spectacles, now every raw and honest moment becomes an opportunity to capture and share. Partially because the glasses are tinted…there is this feeling like you are always looking through a viewfinder…and you start seeing the world in 10 second video opportunities…your most raw and honest moments become “is this a good snap?” and that’s now somewhat dilutive to real life. The experience of capturing is more present and non-disruptive…but the experience of living becomes more about capturing. Much in the same way that I’ve started to think in 140 characters…where Twitter has literally changed the format of the dialouge in my head…Spectacles started to make me see in Snaps…

3) The decision to make Spectacles sunglasses and not clear glass is not an obvious one, but I am sure quite deliberate. There are clear downsides, most notably that there are many contexts (including the whopper of nighttime) where it is inappropriate to where sunglasses. Sitting indoors at breakfast with friends (at least in NY…LA might be different) only ass holes would keep sunglasses on…going into a museum to view art…sunglasses not ideal…walking down the street at night…all of these opportunities for compelling content creation on Snapchat, the company forwent…but what they gained is likely more important: Spectacles actually look cool when you wear them…whereas Google glass was completely tone def to societal standards…Spectacles thread this perfect needle where they are attractive independent of the tech forward statement one is making…they are not “four eyes” technology…they are “beautiful people” technology…and therefore have an addressable market of all that aspire to be cool…very on brand…worth the lost addressable content when trying to persuade the normals to wear cameras on their faces. (Note: as a non-beautiful person…i considered removing the sunglass lenses alltogether, and just wearing empty frames so that I could use my spectacles all the time…i think they will come out with non-sunglass options if and when the world starts wearing Spectacles en mass)

4) I am super impressed that I don’t need to have my phone nearby to use Spectacles. The glasses have local storage and videos sync over bluetooth or wifi automatically when the phone and glasses are together. It’s fast, surprisingly low impact on my battery, and no content loss or blips…the UX of navigating, editing, and sharing my Spectacles moments inside the Snapchat app could use some refinement…but on the whole it’s very doable.

5) I think V2 Spectacles will definitely have an always on voice interface (I’m guessing there’s a battery constraint, but it’s not like Siri where the machine needs to make a network request to be functional…i think the always on mic listening for a single word can run locally, which should help w battery). Right now you tap a button on the left side of the glasses to begin recording. It’s non-obstrusive, but it’s still an action that interrupts the moment and ties up one of your hands. It’s not as bad as pulling out your phone, but I want to be able to say “Snap this” and have the glasses record without pressing any buttons.

6) Overall, I think Spectacles are a really promising and complete first generation device. My friend Amy (who’s starring in a bunch of these Snaps today) asked what I thought they could be for the company…I started by saying “do you remember the first generation iPod…it’s like that…they’re not ready to be in everyone’s lives yet…but if the company continues to invest in this thought…something really special could materialize.” I sort of backed off that statement after I said it…because I can’t really predict what Snapchat’s ipod to iphone leap might be (maybe contact lenses?), but I think I said it because i’m hopeful and excited and i’ve been waiting for a new piece of technology to truly inspire me in this world of derivatives on derivatives…and these toy glasses have done just that. Thank you Snapchat 🙂

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Honesty is so hot right now

Posted on November 22, 2016. Filed under: Uncategorized |

Just do something honest…it doesn’t even really matter what…just let it be you…authentic…if flawed…but also maybe great…reach deep…beyond what is working for others…beyond what is not working for you that you have somehow rationalized…be genuine…express yourself…neither in the face of, nor in the name of, economics, acceptance, or praise…what is something you can do that is simply true?…unquestionable…once released or completed…what can you look at without hesitation and say “yes…that is me…this is mine…and there is no ambiguity or regret about it.” That thing…or more precisely whatever you connected with to take that step, make that thing, be that thing…that thing is north…it is what gets covered up and obfuscated by keynote speeches, fireside chats, billion dollar deals, fancy invitations, top 10 lists, and manufactured heat…it is what you give up when your confidence is down…it is what you give up to pay your rent…it is what you give up to be understood immediately…to fit into something that sounds clean and attractive over cocktails…it is what gets drowned out by the hype machine, content marketing machine, megaround, marquis hire, ergonomically correct, cold pressed juice, gloss machine…it is the thing that let’s you make it…without faking it till you…nah…actually if you’re faking it…you’re never gonna make it…even if…somehow…you get so good at not being you…that you make some money and fool some people along the way…you will never make it…because you had something better in you…that was really you…that would allow you to live as yourself…without compromise…freely…and successfully…and you gave it all up to make a top 10 list…that somehow will sound and feel less good in a bio that reads “she was named to SA 100’s coolest people in tech” 6 years ago, and now is a product manager at Yahoo. What are you bleeding to express? Try to make money expressing it and the multiples will expand…economic, social, emotional…it is so rare to hit that sweetest of sweet spots where you can just wake up…be you…and let the world reward you for your honesty…but that is where it’s at…and if nobody sees you…for a very long time…that means nothing…as long as you see yourself in what you are doing…all those things that you admire from afar…some of them are for you…and some are not…and the fastest way to figure out which are which is to express yourself as honestly as possible in your work.

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6 Considerations when buying Snapchat stock post-IPO

Posted on November 16, 2016. Filed under: Uncategorized |

1236651_10100129041401796_1838483504_nSnapchat is going public. As far as consumer technology IPOs are concerned, it’s a short list of scaled social applications that have been able to tap the public markets…but those that have, have been generation defining companies, achieving market caps in the tens, if not hundreds of billions of dollars post-IPO. The list is short indeed. It goes: Facebook, Twitter, Linkedin…that’s kind of it (tell me what i’m forgetting, if I have). You can’t swing a dead cat these days without hitting a social app in the Appstore, but those that achieve true, sustaining scale…that capture an enduring relationship with their user base, and that have the potential to say reach billions of people…the air is quite thin. These companies are important because they represent attention…they are part media company, part publishing platform, part social network…they are where large amounts of consumers spend their time, and that time is obviously valuable…to advertisers…to companies…to anyone who wants share of wallet.

Here are some things to think about when considering a purchase of Snapchat stock:

1) Brand: There is a lot to like about Snapchat for a day 1 buyer post-IPO. It is undeniably where the post-FB generation is expressing themselves, communicating, and frankly identifying. The brand is epic…Snapchat can’t make a move that is uncool…and there’s something to be said for that. That was not true of FB, Twitter, or Linkedin…for a long time it was true of Apple (which although not a social application company, is a good example of the power of brand). From an investors standpoint…brand is valuable and difficult to quantify, but assume there’s some upside here relative to what institutional investors are modeling.

2) Growth and user engagement: I haven’t dug into the numbers, but i’m sure they are staggering. As consumer apps go, i’m sure Snapchat will shine on metrics…as far as day 1 investors are concerned, i’d assume that these metrics will be fully recognized and valued by the instiutional money that drives the public markets. Investor have had enough time to understand how to value social applications at this point (which was not the case in the early days of Facebook’s and Twitter’s public lives)…so I’d assume there isn’t a lot of upside in unique understanding of Snapchat metrics…net-net no upside…everyone is going to be looking at the right numbers and understanding them…

3) Except: is Snapchat a social application or a modern day cable company (i.e. a platform where people consume 3rd party content and media)? this is an existential question Twitter has very publicly grappled with in the public markets. Twitter was constantly trying to tell the story of the lurkers and logged out users…consuming media on the platform but not being social…explaining that active users were more than just people who tweeted or even logged in…but the market didn’t know how to evaluate them…and frankly still doesn’t. Snapchat has some elements of this as well…depending on whether you are looking at their chat and user stories features (most valuable), or their Snapchat Discover feature (where publishers like Buzzfeed and ESPN reach Snapchat users)…there are sort of two stories being told. One is “evaluate us on our social activity”, and another is “evaluate us as a pipe for 3rd party content”…and both can be valuable, but only the first can be $400B market cap valuable…even Time Warner Cable is only valued at $68B last i checked…of course there is a symbiosis that social apps and modern cable companies experience…best realized in the form of Facebook today…and there’s a reason that the two go hand in hand…but explaining this nuance to the public markets is difficult…and i view some risk and market acceptance and understanding of “what is snapchat?” should the story evolve, or certain metrics outshine others quarter to quarter…from a day 1 investors standpoint, I don’t think this is an immediate negative…because i think the promise of being the next Facebook is what will drive early speculation in the stock…but 12-24 months out I can see this story being complicated to communicate.

4) On being the next Facebook: This is really where the action will be early ideas. Can Snapchat amass the next 2 Billion people…younger people…not living their lives on Facebook yet or maybe ever…is Snapchat where they will spend a similar amount of time and energy? I see no reason why the answer can’t be yes…and i think that’s the bull case…but there are some existential threats to the bull case that are worth noting…one of the biggest, i believe, is that Snapchat has taken a relatively isolationist approach to building their application and company. They have not opened up to 3rd party development at all so nobody else is (legally) building businesses or apps on top of Snapchat). They have taken a very controlled approach to opening up to outside publishers and content creators. carefully curating who gets to show up in Snapchat discover, and what type of content they can and should create for Snapchat. And they have done nothing to spread their tentacles across the open web. There is no Snapchat like button. No share to Snapchat. No login to this site with your Snapchat account. No oay with Snapchat…Snapchat is not baked into anything else…and very little else is baked into Snapchat. The positive side of this approach is that they have incredible control and stewardship over the Snapchat experience and brand. The product experience is delightful and unadulterated…and that is reflected in the metrics above…the downside is that Snapchat is not infrastructural in nature…it’s not a platform yet…it’s not an ecosystem…and that means it’s easier to rip out and replace in the world as a whole, than say a Facebook was when it IPOd. Now, the network of loyal users…who have built their identities on Snapchat and creating new social graphs there…that is very sticky…but Snapchat has not diversified it’s touch points to the users or enterprise…it is still subject to the ephemeral whims of an increasingly fickle consumer base with increasingly available alternatives coming down the pipe in the form of “the next hot app, that is cooler than Snapchat.” What this means in practice, is that they can’t ever lose their brand voice, and they can’t ever drop the ball on product…and history would say most other consumer applications do one or both of those at points in their life. When Facebook IPOd i used to try to explain to wall st types that they are thinking about FB all wrong…facebook is a piece of societal and enterprise infrastructure, it’s a platform, and that position is why it’s valuable…it’s not just eyeballs…Twitter had the same narrative available to it, and ultimately squandered it (although i believe that it is still available, and the only interesting investor narrative available at this point actually), but Snapchat does not yet have this narrative. Now maybe it will develop it over time…but today…Snapchat kind of is all eyeballs…and that’s not a super secure place to be. for day 1 investors…if you are long term value investor…this is a negative and one that will not be appropriately reflecting in institutional analysis

5) On revenue and financial opportunity: I haven’t dug in deep here. From afar, it seems that Snapchat is taking a pretty bespoke approach to monetization…and it also seems they are heavily inspired and influenced by the cable television model…I think this will evolve as they need to reach a different scale of revenue…so I wouldn’t really look at today’s business model as the one that will get them to a Facebook sized market cap…Facebook itself didn’t come out of the gate with their killer business model at IPO…the App install add didn’t come for 3 or 4 quarters after IPO, but it was obviously the unit and model that changed the trajectory Facebook’s story on Wall St…and Snapchat doesn’t really have an analagous opportunity visible today. There is no self serve, near-infinitely scalable way for Snapchat to make $ that is visible today…Google has this. Facebook has this…and if Snapchat wants to break into that stratosphere from a shear market cap standpoint…it’s going to need to find something similar…the good news: i think it can. the bad news: hard to see Wall st giving credit for that until it materializes…

6) Overall: I think I’m a buyer in Snapchat at any market cap under $40B…if for no other reason, than that there is no other contender to become the next Facebook…but I do not believe they will get there by being isolationist forever…and I see a fair amount of risk as they are pressed to give up some control in exchange for scale, diversification of touch points, monetization, and infrastructural position.

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what it’s like to meditate

Posted on November 15, 2016. Filed under: Uncategorized |

img_7404Alarm goes off…what day is it? is it Sunday…mmm…no it’s Tuesday…get your ass out of bed…we are not going to snooze our way through this transition…it’s just not gonna happen. brushes teeth…showers…i don’t feel like meditating today…no we’re going to meditate today, 20 minutes, before coffee…like we do everyday…because you know we feel so much better and think so much more clearly when we meditate…yea, you’re right…sits on cushions…starts timer…closes eyes…darkness…familiar darkness…what do i hear? cars passing, refrigerator humming…what do i see? white light shining through my eye lids…small specs in a matted dark space that has some volume to it…what do i smell? nothing…mmm…maybe some maple syrup…no idea why…what do i taste? leftover toothpaste…maybe something sour…what do i feel? an itch on my neck…the feeling of the skin on my outer left foot pressed against our hard wood floors…ok…i am present…1, 2, 3, 4, 5, 6, 7, 8, 9, 10…10, 9, 8, 7, 6, 5…i wonder what kenny is doing right now…i miss kenny…4, 3, 2, 1….1, 2, ah, the matte like space looks a little different…3, 4, 5, 6, 7, 8… i really enjoyed my tea with Dearing…yes…he is an unusual guy…i think he’s good though…were my ideas good? are my ideas good? yes…they”re good…some are not correct, but always original…i’m so bored of unoriginal thinking…there are so many funds right now…so many derivative companies…it’s so noisy…are my ideas still valuable? yes? you just need to change your approach…a lot has happened in the market since you thought this way…ok, what’s a new appr…1, 2, 3, 4, 5, 6, 7, 8, 9, 10…10, 9, 8, 7, 6, 5, 4, 3, 2, 1…1, 2, 3, 4…remember Lois Ratner…she drove me to school every day growing up…that was so nice of her…5, 6, 7, 8, 9, 10…10, 9, 8, 7, 6…did she judge me as a child? maybe…i was the whacky one…her kids were much more together every morning…5, 4, 3, 2, 1…1, 2, 3, 4, 5, 6, 7, 8, 9, 10..10, 9, 8…shoulders drop…man…i was holding something that i just let go of…that feels good…7, 6, 5, 4, 3, 2, 1…do i want a job? maybe…but there are so few funds i’d be excited to join…and who knows if they are looking for new partners…probably not…i want to raise a fund..pick my partners…but there are so many fucking funds…does the world need another fund? yes…it just has to be different…that’s doable…i wish it didn’t have to be a seed fund. I’d rather have $300M than $30M…2, 3, 4, 5, 6, 7….chill out…take your time…let the world unfold a bit…you’re going to India…stay loose…it’s not time yet…8, 9, 10…10, 9, 8, 7, 6, 5, 4, 3, 2, 1…1, 2, 3, 4, 5, 6, 7, 8, 9, 10…maybe it’s time to start having coffees…maybe it’s time to let the world know you are ready to hustle…but your vision isn’t baked…and so much of what’s getting backed is completely boring…we need to get our arms around everything interesting…but the world is different…too many companies, raising too many rounds, from too many funds to build the mental map of the market…we need new tools…we need a new framework and process for keeping tabs…we need softwa…2, 3, 4, 5, 6, 7, 8, 9, 10…10, 9, 8, 7, 6, 5, 4, 3, 2, 1…1, 2, 3, 4 5, 6, 7, 8, 9, 10…10, 9, 8, 7, 6, 5, 4, 3, 2, 1…the dark matted space is a different shape…there is a light center in the midst of the darkness…is it someone i have known in the past…is it energy…focus on it…go deeper…it’s gone…2, 3, 4, 5, 6…it’s back…it’s peace…and lightness…and CHIMES…20 minutes…hold onto this lightness…opens eyes…stretches…fills tea pot…walks to front door to pick up the paper…sit’s down to begin day…the world is interesting…and in flux…and i am meant to do something…eyes open..embrace others…feel no shame…smile…let’s write something…

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On Burning Out

Posted on November 5, 2016. Filed under: Uncategorized |

Burn out is a real thing…in startups…it comes from carrying the angst and fear and frustration and hopes and wants of ~20 people for 3+ years. It comes from wanting so bad to fulfill your promise to your team and your investors and your cofounders and your family and your loved ones…it comes from breaking up with early employees who are also burnt out and ready to move on…it comes from a morning metrics reports that slowly turn from exciting to troublesome as 80% of your new users leave you over 30 days…it comes from a concerned phone call from your mom that your product isn’t evolving fast enough…or from a father in law who just can’t seem to get the search result he wants in your app…these little papercuts to your entrepreneurial soul that one by one harden you into the type of person who can execute while being cut…you build up this armor that allows you to walk through your days…but it doesn’t mean the cuts don’t draw blood…they are just internal…and as you bleed inside…to an ultimate outcome (whether that be success or failure)…at some point…you don’t have to execute anymore…and all of the sudden you are left with a body that is full of cuts that need to heal…each cut remains open until you go back to the point in time where it was first drawn…see that you were hurt…and somehow rationally and logically agree with your soul that you are no longer in that place…and that stops the bleeding.

Burnout is when you kept pushing your body and your mind to move forward…into a series of successive cuts…for so long…that you are too damaged to appreciate the pleasure and joy of moving forward at all…it’s like you’ve trained yourself to expect pain from forward movement…and therefore it’s not so much that you fear moving forward…as it is that you revert back to not feeling as you step…and that’s a pretty inertial place to be. Burn out is numbness.

I’ve been burnt out a number of times in my career. I was burnt out after Untitled Partners, I was burnt out after Hyperpublic, and I am slowly unburning out after Wildcard…the shitty part of being burnt out is that it’s hard to get excited…that numbnesss is real…but the good news is that it’s not permanent. Everyday it’s easier to attain glimmers of interest, moments where your heart races as you lock in on new thinking…

It’s not the most sustainable approach to life…to go through these cycles of 2-3 years burning out, 3-6 months unburning out, 2-3 years burning out, etc…you’d like to maintain yourself in a way where you don’t hit burn out…but i’m not sure that’s possible as CEO of a tech startup…at least not for me…having done that 3 times, over 5 products, and 8 years…and having invested in literally hundreds of my peers doing the same…i think if your signing up to start something…your signing up to burn out…and that’s just part of the deal.

Sometimes when burnt out, it can feel like the excitement to move forward may never return…but time and time again it does…so if your feeling burnt out…just know that it’s normal…and that good things are around the corner 🙂

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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: http://www.potsbronx.org/

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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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Free $1B (or maybe $50M) idea: Pryntcoin

Posted on September 12, 2016. Filed under: Uncategorized |

The problem: Printing tickets, articles, documents that require a signature, and whatever else you find on your phone is hard to do. Increasingly we are a mobile first or mobile only society…1099 workers, digital nomads, consultants…tons of people aren’t going to an office everyday that has a printer set up…and nobody outside of maybe AOL’s remaining dial up customers is going to Staples and buying a desktop printer for the home these days…

BUT…sometimes, despite how digital our consumption has become…we need to print shit…and if you’re like me (and i’m a bit ashamed of this)…sometimes we would just prefer to read something when it’s printed…

SO…we still need to print…increasingly we don’t have access to a printer in those times of need…

Solution: Queue…Queue is a printer that follows you wherever you go. Easily print any document or article you find the web directly from your phone, wherever you are. No more going to staples or kinkos…signing in to those shady ass computers…emailing yourself docs and paying $.50 a page plus the half hour it takes dealing with all that crap while trying to shield your eyes from fluorescent overhead lighting.

Product: Queue is actually technically an application that sits on top of Pryntcoin. Pryntcoin is a blockchain enabled protocol for sharing excess printing resource with mobile users wishing to print in their local geography. It is governed by a cryptocurrency who’s protocol defines the economic incentives and rules of engagement for anyone with a printer to earn coin in exchange for printing documents of passers by. It is also the currency by which, you, as a user, can print anything from your phone, to nearby printer without the hassle of kinkos or fedex.

How it works in practice:

Users of Queue (everyday consumers) can add documents or URLs to the print queue via a dedicate Queue mobile app, or via their share sheet in IOS and Android. Much like you can see your printing queue on your desktop machine, the app let’s you visualize your upcoming print jobs and importantly let’s you determine when you want to print them. You can print at any time, regardless of where you are relative to an active Prynter on the network, but the Queue app will also push notify you when you are in the vicinity of a Pryntcoin printer, at which point for a small fee paid in Pryntcoin, you can send your job to a nearby computer and pick it up on the go. You can specify how far you are willing to walk to get your printouts, or…if you are rich…you can specify an incentive, also paid in Pryntcoin, for the printer or a 3rd party person/service to bring that printout to you wherever you are. You can keep sitting on the steps of Union Sq, watching all the skateboarders and thinking of your next great idea, and someone will come and drop said printouts in your lap. Importantly, every Queue printout will have a cover page with Queue branding and a unique QR code which can be scanned at the time of dropoff/pickup as a form of signature written to the blockchain to govern the release of Pryntcoin associated with this printout.

Prynters in the Pryntcoin network:

Anyone with a printer…be it a bodega on the corner, an accountant working out of her home on the second floor of a brownstone in the east village, or a checked out employee working at a law office with tons of printers…can join the Pryntcoin print network in order to earn Pryntcoin in exchange for printing documents. Much like miners dedicate computing resource to earn Bitcoin, printers in the network dedicate excess printing resource in order to earn Pryntcoin. The protocol that governs the Pryntcoin network handles geofencing and indicates to the network who is within the proximity of a Queue user in need, that is eligible for the Pryntjob, and the first printer in the network who claims the job, prints said users documents.

Collateral: importantly…the network must ensure that Queue users and prynters are able to conduct this exchange of value even when they don’t know or trust each other. It is easy to protect a Queue user, simply by saying “funds in a smart contract on the blockchain are not released until the Queue user sends a signature to the chain that they have received the printout. But how do we protect the Prynter from wasting their time and ink and paper if a Queue user requests a job and then flakes before picking it up? Simple…all Queue users must hold and post a small amount of Pryntcoin to the blockchain when requesting jobs…This way, if they send a job that is accepted, but not picked up…the Prynter has the ability to collect collateral held in a contract on the chain. I think dispute resolution would be baked into the protocol such that users of the Queue app agree to use one of the emergent decentralized dispute resolution services to determine dispute outcomes. Regardless, collateral is not released without resolution…and that illiquidity is in and of itself enough friction to prevent frivolous flaky behavior.

In Summary: the Queue app and service becomes more valuable as more Prynters (printing nodes) join the network. Geographic density truly creates the user experience of a mobile user never beeing more than a few blocks from an available low cost printer. Between collateral that incentives users to hold pryntcoin, an economic incentive for idle printers to contribute work to the system, and an underlying coin that can be earned and spent within the context of a real world application…while importantly enabling the transfer of value of a fungable and underutilized asset (printing resource)…Pryntcoin and it’s killer application, Queue, represent a viable crytpocurrency that can cross the chasm from theortically intriguing to actually useful…Should the Prynycoin blockchain successfully bootstrap and achieve reasonable liquidity…the coin could come to be exchanged for many types of real world work beyond printing…most immediately available would be another semi-fungable unit of value in the form of “courier work”…nodes in the system operating to earn pryntcoin in the form of document delivery associated with the Queue application, could soon come to operate as crypto-incented couriers for a variety of last mile physical delivery jobs…the protocol for ensuring document handoff via QR code, baked into the blockchain governance can transcend the print use case…and with printing and delivery under it’s belt as the first to real world use cases for the exchange of value governed by Pryntcoin, pryntcoin will join the ranks of Bitcoin and Etherium as an enduring and long lasting cryptocurrency that enables decentralized applications that seek to enable the masses to exchange assets and labor freely without a central authority taking a cut or determining who can and can’t participate.

Note: if you are cryptographically inclined, and a little bit crazy, and choose to build Pryntcoin and hopefully also the Queue application, please write into the protocol that 10% of all issued Pryntcoins will be allocated to Pryntcoin’s creater: jordan cooper.

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Dummies guide to abstract crytpothinking

Posted on September 9, 2016. Filed under: Uncategorized |

For the past 3-4 months I’ve spent a substantial amount of effort trying to understand the world of cryptocurrency. The most well known cryptocurrency is, of course, Bitcoin, and the underlying technology that powers Bitcoin is known as blockchain. I’m sure for 90% of readers, this is not new information…nor is it probably news that there are newer cryptocurrencies that are being built that leverage blockchain technology, but that have different properties than Bitcoin. You’ve probably even heard of Etherium, and maybe you know that Etherium has acheived a $1B market cap on the promise of making the Blockchain accessable to programmers who wish to build decentralized applications on top of the blockchain without the hassle of bootsrapping a secure blockchain from the ground up. You might know that Bitcoin can be mined in an exchange of computing power for currency…and maybe not know that all cryptocurrencies are not mined, and that mining is just one form of distribution when a new coin or currency is birthed into the world. Mining is a job that creates value for the network, and coin is the reward for those willing to do it. that work let’s those not wishing to work, enjoy the value of the network (in Bitcoin’s case, money transfer), and holder’s of Bitcoin pay for that work, effectively through the acceptance of inflation on their holdings as new coin is issued to miners as they work. Maybe, you have heard of Steem, which created it’s own blockchain and crptocurency that rewards behavior and participation within a Reddit like media application (which is sometimes refferred to as a protocol vs application, although it feels more like an application than a protocol to me). You probably have not heard of Monero, Dash, Maidsafecoin, Lisk, NEM, Emercoin…or any of the other 20 coins that have a marketcaps north of $20M. And you definitely haven’t heard of the next 20 coins that are currently being designed, white papered, tested, and that will ostensibly be issued over the next 12-18 months. I use the terms “coin” and “cryptocurrency” interchangably here…coin is just shorter and simpler to write. There is something happening in this world…and through fits and starts…and mistakes…and hundreds of millions lost and hundreds of millions gained…I do believe we are getting closer to the potential of cryptocurrencies…and i use the plural because it’s not gonna be one to rule them all…i don’t think…but rather many with distinct uses and applications that will likely be transferrable with each other and traditional FIAT currencies to varying degrees of liquidity determined by the protocols that govern them. The state of this ecosystem is still such that white papers and complex, overengineered economic and technical systems must be digested in order to desire participation, but that complexity is slowly being abstracted away into more approachable and visible real world value…and it will continue to do so until coins begin to sneak into mainstream life and the systems that both govern and enable it.

Since Bitcoin captured the attention of the world a few years ago, with skyrocketing appreciation…most folks have scratched there head to bridge the gap from the theoretical promise of the coin, to the actual real world applications it might achieve. With Bitcoin, like most coins on this list, you kind of have trouble answering basic questions like “why is this better than US $?” “Why should I hold it?” “Why should I accept it?”, etc…for a while, when you really boiled it down…you got to ideological arguments around decentralization (which simply means a redistribution of power and control away from centralized intermediaries and incumbents, to “the people” effectively…or the users of a given service or currency). There’s this notion of trust…and the most paranoid of us, who champion decentralization…are circumspect of authorities whom the vast majority of mainstream population choose to trust in exchange for ease of experience. Banking with Bank of America is easy…but ya gotta trust bank of america…paying with US $ is easy, but ya gotta trust the US Government…paying with Bitcoin is a pain in the fucking ass…but you don’t have to trust anyone…and that feels good for a small minority of decentrally minded folks…

I believe that for a coin, or protocol or decentralized application to succeed against it’s centralized and well established counterpart, the mere ideology of decentralization is not enough to overcome the incumbent. Recently, however, I believe we are starting to see glimpses of coins and contemplated applications atop those coins, that don’t simply replace a centralized system with a decentralized alternative, but rather that contemplate a new societal or consumer oriented system that has no centralized counterpart, because it is something that could only exist from the bottom up, but that has not yet materialized, because there was no good way to transfer value between bottom up nodes around a public or shared service until a blockchain based coin enabled that transfer in the absence of trust, but reflective of the incentive structure necessary to harness bottom up work or value contribution around a mainstream life need.

I realize this is quite abstract, but the marriage of value transfer and distributed but well coordinated work or asset contribution by human beings, or in many instances machines owned and paid for by human beings, represents an efficiency in system design on par with the emergence, say, of parallel computing. We will simply be able to do and sustain systems and services via cryptocurrencies that were not possible on existing financial and societal rails.

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Is abundant data redefining morality?

Posted on July 25, 2016. Filed under: Uncategorized |

I am not a political animal, never have been…but this weekend I had a brief chat with a friend who is voting for Hillary Clinton. He said, “I’m doing it, but if you read the report on her private server, it’s really bad…” My response was that I have become a bit jaded i guess, and at this point it is clear to me that 95% of people who reach Hillary’s level of influence, or even a few rungs down on the ladder, have bent the rules one or many times along their path to the top. It’s a bummer to say…but this is not just a political phenomenon. In business as well…most of the billionaires you know or have heard of…at some point along the way…they broke a law, made a questionable call, stabbed someone in the back, or worse…For better or for worse a very reasonable path to amass influence and wealth in modern society is to break the rules…Many of your entrepreneurial heroes, many of your VC crushes…way more people in our own ecosystem than you might at first consider, have done wrong on their path to the top.

Historically, I have reveled in the fall of unethical titans. Maybe it’s a chip on my shoulder…I don’t know…but as the world is filled with more and more information…and as it becomes easier to see a person’s every move, I have come to accept that almost everyone…even “good” people…do “bad” sometimes. We are in this moment of unprecedented visibility into the lives and actions of any individual…be it a police officer, civilian, public official, or CEO…and I think it’s becoming clear that there is a lot more bad behavior in ANY individual’s life, than we were previously willing to admit or wanted to acknowledge.
In a world of top down media and information, it used to be easier to dilute ourselves into believing that the objects of our public affection were ethically perfect and behaviorally consistent…but in today’s world where everything is recorded and everything is findable, it has become very clear that most are not…

Now we could be depressed that our society seemingly rewards questionable ethics and behavioral compromise with power and influence..or…we could redefine our expectations and accept that ethical compromise is the norm amongst those at the top as well as the bottom, and therefore judge it less harshly. I’d like to think that increased transparency in today’s information age will lead to cleaner behavior amongst our leaders, but I fear we are, albeit understandably, moving more in the direction of lowering the bar…

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

I’ve been an American Express card member for over 10 years…over that time I’ve accumulated quite a few rewards points…and this past weekend I decided to spend some for the first time that I can recall. Jetblue has this new Mint service which is their business class seat where you can lie down flat and fully recline. I “bought” two seats with my squirreled away rewards points for Liv and I to take the redeye home from SF last night. I figured we’d save on an extra night in a hotel and still get some sleep if we sprung for the seats that would let us lay down.

As the plane boarded, a guy in his fifties who was probably 6′ 5”, 250 pounds started to antagonize us as we sat in those fancy seats. He said we were too young to sit there, and that we were ugly people…and disgusting people for paying for these seats. I tried to explain that we used miles (not that it was any of his business), but he was visibly angry…and somewhat threatening.

I had the choice to stand up to him and start a fight on an airplane (which was the last thing I wanted to do), or to just quietly ignore him as he continued to be abusive toward us…and I chose the latter. At first i thought he’s probably just drunk, or crazy…but then I realized we were flyinh from SF…where young rich people are obviously taking their tole on the rest of the city and it’s culture, and maybe he really was just fed up with that dynamic.

This guy was upset. He is not alone these days. He was totally wrong…but i couldn’t help but wonder if he was also a little right.

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Exploring the increasingly porous “membrane” btwn Information Technology and Biology

Posted on May 11, 2016. Filed under: Uncategorized |

Becoming technical in a new field requires work. To cross a threshold from “visitor” to “valued contributor” when learning a new discipline like software engineering you have to commit and you have to really want it. When I started working in venture capital 10 years ago, I stuck to consumer facing businesses and business model innovations, because frankly I didn’t have the background to understand technical innovation. At first I was totally cool with that, and I did really well approaching the markets I could immediately understand…you sort of didn’t need to know what was going on underneath the hood in order to evaluate consumer applications, media, marketplaces, etc… at some point if a deal got interesting enough, you’d call a CTO in the portfolio to check the “technical diligence box,” and then keep rolling on a thesis that really had nothing to do with technology itself.

Over time, however, something unexpected happened…I started to fall in love with the systems and principles that underlaid many of the businesses I was thinking about. I sort of fell ass-backwards into what has become a deep passion of mine, and I started to spend time with a different type of thinker than I did at the start…I started asking the “how” questions more and more, and so began my post-graduate education in software engineering, technical thinking, and system design. I was fortunate to have very patient teachers…Doug and Eric especially, but also hundreds of technical founders along the way, who helped to evolve my mindset into what I guess I’d call “full stack thinking,”…where the viability and merit of a decision is influenced by everything from the infrastructural dynamics and technical approach at hand, up through the consumer behavior and ecosystem dynamics in given market. There is a conversation and dialogue between the technical and non-technical dimensions of any opportunity that informs a much more nuanced perspective than is available when looking at a market opportunity through either of these mindsets independently.

As I begin to evaluate new directions to build in with Doug, Eric, some of the areas in which I am most interested, I find myself bumping up against a lack of technical proficiency. It’s not a feeling I’ve had in a while, but frankly a lot of the work being done in IT specifically (the domain we know well) hasn’t really inspired me…it may just be where i’ve looked so far, but the broader market feels super saturated right now, with tons of companies chasing very similar…often, but not always…incremental opportunities. Granted, we did not achieve our goal of building a native internet at Wildcard, and even further granted, we did end up pivoting into a clearly incremental application of our early work (aka from the Native Browser to the Wildcard News app), but nobody will accuse our initial ambition and mission of being incremental or uninspired. We bit of something big and unknown, and came up short, but at least it felt meaningful at the time.

As I look for similarly or more inspiring frontiers to tackle now, I have become somewhat enamored by the increasing permeability of the “membrane” that has long separated information systems from biological systems. More and more our physiological system is being represented and understood digitally, and similarly the principles behind our manipulation and design of digital systems are being applied within the medium of organic matter and specifically DNA. In this arena I don’t yet have an adequate understanding on the bio side to think in the way I have grown to think about opportunity. I crushed AP Bio in high school, and occasionally attended my introductory bio classes in college, but it’s been a while, and there is another layer of understanding that I need to achieve to get further into the world of genetics, bioengineering, etc…Neither Doug nor Eric has any background here, but our deep data engineering DNA (no pun intended) is obviously applicable to this problem space. I think for a while I forgot how serious a commitment it is to become technical in a new field, but I remember all the work it takes, and I’m kind of interested to committing again here. I can’t say that my learning will inform this next business opportunity, or if it will be a much longer road applied at a later date, but I am ready to be a student at the edge of biology and information technology regardless, so I figure worth hanging a shingle…To that end, if you come from a bio background (or even an IT background i guess) and are interested in collaborating at this intersection, come hang with us at our office in soho…we’re excited to learn what you’ve been thinking about and happy to participate and contribute toward flushing out this landscape together. I’m jordan.cooper@gmail.com.

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experiencing loss by not really experiencing it

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

When I was freshman in college my Grandma Norni died. I was extremely close to her. I remember hearing the news, I remember attending her funeral…and most of all I remember the feeling of wanting to cry, but for some reason not being able to. It was a very unsatisfying feeling to know that type of pain, while lacking the ability to access the release of crying…

Fast forward 3 years…normal day at college…I return home to my apartment to find my roommate Tim watching a film with his girlfriend in the living room. I wasn’t gonna tune in in the middle of it, so I just grabbed some food, opened my computer, and started to do my own thing. At some point, I glanced up at the screen, and happened to catch a 60 second scene of a woman in a hospital, deciding whether to take her husband off life support, and something insane happened…i felt this deep sensation come over me and I cried harder than I have ever cried in my life…heaving…couldn’t catch my breath for like 5 minutes….and the whole time Tim and his girlfriend just stared at me like “what the fuck is going on with this dude?”…inbetween gasps i’d belt out “i’m fine, i’m fine”…but it was very bizarre. I wasn’t sad at all…it was totally physical…and I was almost watching myself have this insane reaction to a film and characters that I had no invesment or context around…Something about that scene had tapped or unlocked this very deep pain I had buried somewhere in my brain when my grandma died. It was total catharsis…it stopped…and I just looked at them and was like “sorry…i know that must have been weird…i’m totally fine.” I tried to explain it to them that that release was from her death 3 years ago, but i couldn’t really explain.

Last week I sat down for coffee with one of my board members who has known me for 10 years…he told me he was sorry I had to go through the experience of killing the Wildcard app and letting most of our team go. He’s not the only one…a number of other folks who care about me, have also asked “how are you, how are you doing?” and my honest answer is “i’m really fine.” There’s something not totally right about putting 2.5 years of energy into a product and vision and team, wiping it clean, and then waking up the next day ready to roll…but in some sense that is very much where I am…it’s only when I really think about it, do I realize that I have this weird capacity to stuff painful moments deep down into places that won’t be discovered until 3 years from now when I stumble across some film or song that unlocks them. I feel like I haven’t really gotten to say goodbye to Wildcard, and that I probably won’t get to before diving into the next direction…

Fast forward to today. We have $3M in the bank, our burn is now less than $50K a month, and my mind has already moved on to self-driving cars, and healthcare, neural networks, diagnostics, climate change…and a bunch of new areas that really excite me…i’m reading ferociously, which is how i learn best…i’m starting to feel very creative again…i feel unconstrained…and open…and my mind just doesn’t seem interested in examining the loss…i wish i could tap into my heart and really say goodbye to the Wildcard chapter before letting my brain take me forward so quickly…but I guess I have this tendency, which i’m guessing many founders have, to move through pain quickly…and whether I like it or not, the pain of Wildcard’s end seems to be in the rear view mirror for now.

So yea…I guess this post was about trying to articulate how I’m experiencing loss…trying to find catharsis…trying to answer that question “how are you doing?”…even if the answer is “i’m experiencing loss, by not really experiencing it…”

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Tough but necessary change for Wildcard

Posted on March 16, 2016. Filed under: Uncategorized |

Today is a rough day. After 8 months of building and living Wildcard 2.0 we’ve made the difficult decision to stop supporting the Wildcard 2.0 app. Wildcard has been through a lot of twists and turns over the past 3 years. We initially set out to replace the browser on your phone with a native card based browser. The first year of our company was about building out awesome technical infrastructure and answering questions around what a card was, both technically and from a design standpoint. When we released our first consumer facing product (Wildcard 1.0) it was really a proof of concept of what the web could look like in this new format where you didn’t have to wait for webpages to load. We were really excited about our future. People who cared about design and technology were really excited, and investors were really excited.

We raised our first $3 Million largely on the background of our founding team. We had successfully built and sold Hyperpublic to Groupon, and folks were more than happy to back our team to take on this wildly ambitious goal of replacing the browser on your phone. We raised our $7M Series A round 11 months later on the technical progress we had made toward this goal, and a pretty incredible early demo of the Wildcard 1.0 app. This all happened in year 1.

The second year of Wildcard was about taking this technology to market. Our 1.0 was a great proof of concept, but we had to focus the product on a use case more narrow than the “catch all” of the browser. We didn’t yet support everything a browser could do, so we needed to tighten our experience to something immediately usable to consumers. We zeroed in on news and media, put our heads down, and spent 7 months building Wildcard 2.0.

When we released it, it was the #1 New App of the week in the Appstore. That was helpful, and good for about 90K installs. 3-4 months later, it was named one of Apple’s Best Apps of 2015…good for another 40K-50K installs. With some press hits in between, and all the “influencer word of mouth” you could hope for, all in we’ve amassed a few hundred thousand installs…

Retention is a challenge…and the average app loses 90% of their users in the first 30 days..we did better than average with 2.0, but despite tons of tweaks and awesome product improvements…our growth and retention numbers are simply not good enough for a consumer facing app to be a viable business.

At current burn, Wildcard has a little more than a year of capital in the bank. You don’t have to be a genius to look at our growth curve, look at distribution dynamics in the appstore, and look at the climate that we are going into over the next 12 months to know that we need to make a change, and we need to do it now.

We could continue to improve the app over the next year of runway, but without a monumental home run iteration, my instinct is that there would be virtually no market for our next round of funding and no path to profitability with the numbers we are seeing. This moment requires a more fundamental change in trajectory…something that is going to be painful, but doable with our current capital reserves, and not doable if we delay or don’t act decisively now. We are going to shut down the app and take the company in a new direction. I can’t say much more about what we are going to build next, except that we will put everything we’ve got into it.

This is a really hard day. We are taking the team down in size. A lot of wonderful people who worked their asses off on the Wildcard app are going to need to find new jobs…

I feel terrible that we weren’t able to realize the Wildcard vision as we set it on day 1. We knew it was a homerun swing when we stepped up to the plate…and unfortunately we sort of hit a deep foul ball. Time to regroup, dig in, and get to something special together.

If you have any questions about this step in our company, or if you are curious about our next chapter, i’m jordan.cooper@gmail.com.

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Virtual Assistants as Parallel Human Processors

Posted on February 17, 2016. Filed under: Uncategorized |

I’ve been thinking quite a bit about virtual assistants lately…and the other day i had a notion that the rise of virtual assistants feels in part a response to the growing demands on human beings around information processing. When you are always connected, and there is an ever growing amount of data to be processed, but a limited capacity to do so, physically, something has got to give. In computing, when a server can no longer efficiently process the requested volume of data, what do we do? we spin up another machine and split the work. Of course there are optimizations on that single server, to make it more efficient in handling increased loads, but at some point, it makes more sense to run processing in parallel. I think there is something similar happening in human information processing. The discovery tools have reached some limit of optimization (i.e. the feed, search, etc), and even the size of the informational units has reached a plaeau in processing optimzation (tweets vs blogposts, headlines vs articles, images vs text, things can’t get much smaller/denser, etc)…and there just really isn’t much more room along those axis to help us handle the ever growing body of information that needs to be processed…in the last 10 years we were able to lessen the load by spreading our processing over much more time than was previously available…mobile gave us much more connected time to distribute the information processing over, but now that we are on our phones all of our waking day, we’re running out of processing time to add…hence a general sentiment of “information overload” and “phone addiction” that is becoming mainstream affliction in today’s day and age…so what do we do, when we physically can’t process any more, and we don’t have more time to add, and we’ve done all the mechanical optimizations we can to make the time we’ve got more efficient? We start to think about parallel processing…about spinning up a second machine, or in this case, a second human, to split the load…granted many of these virtual assistants are focussed on task oriented information processing, but in general…we are adding parallel humans to interact with the same mechanical tools we ourselves have access to, in cases where we can no longer eek out gains in a “single server” architecture (i.e. doing it ourselves)…i think this is a trend that will continue, and i’m interested in seeing how higher order information processing, that’s focussed less on completing tasks, and more on augmenting your knowledge and informational awareness via a second human brain, will come into focus over the next 24 months…I think people will increasingly value being able to parallelize their processing….and it will become more common for people to offload even non-intuitive processing tasks if their interface and ux to do so becomes more frictionless. I can, for instance, see a world where people ask a 3rd party to read and monitor their facebook for them…as odd as that sounds…I use that just an example of the broader theme of parallel human processing as an architecture of living in a world of growing available information with limited physical and mechanical processing tools…

weird stuff 🙂

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Beyond Pixels

Posted on January 25, 2016. Filed under: Uncategorized |

Olivia had some work to do yesterday morning, so I decided to walk over to the new Whitney Museum to enjoy Frank Stella’s one man show without the crowds of a normal, non-Jonas impaired, Sunday. I love going to empty museums, especially with large format work like Frank Stella’s. It’s space to think, and be inspired, and yesterday certainly delivered. I lucked out and joined a small free tour, where I learned about Stella’s exploration from the strict constraints of 2 dimensions, to movement and perspective within those dimensions, and then almost an outburst into a 3rd dimension coming off the “canvas.” I could see the design thought behind his work, and it made me want to design something that wasn’t made of pixels. I don’t consider myself a designer, but my days are often intimately tied to design process and thinking. I work closely with our design team and together, alongside engineering, we create a visual, although not-physical, representation of a thought or feeling or intention. As I looked at these incredible works, playing with concepts of symetry and emotion, I thought to myself…I would love to make stuff like this…but I am not a painter, or a welder, or a craftsman…

Interestingly, for the first time in my 33 years going to museums and appreciating art, yesterday the fact that I am not a crafstman did not feel prohibitive to creating art like Stella’s. I’m not a designer or an engineer, but with a great team and a shared vision, we have been able to express a vision together through software at Wildcard. What if I could collaborate with a designer and a craftsman and a welder…could we together capture something unique and physical?…what would the communication be like? How could we develop a shared language to realize something that none of us as individuals could achieve. Without the promise of an enterprise, or a business behind this collaboration, who would want to come together to create a 10 foot physical object that costs thousands of dollars to produce? I don’t know…but it’s not impossible to see that happening …perhaps a pursuit for another day…it sure would be nice to be creative beyond the screen…and I believe the design thinking that we apply in technology could produce some interesting work in a more physical medium. This line between technology and physical art, is in fact blurring when you think about virtual reality and 3D printing…even Stella’s most recent work in the exhibit was designed on a computer and printed in 3D (as opposed to bent from a raw material like metal)…maybe a pipe dream…but maybe something i’ll try one day… Here are a few photos from the exhibit:



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New Release: Wildcard Communities

Posted on November 9, 2015. Filed under: Uncategorized |

Today Wildcard released a new iPhone app called Wildcard Comedy. It’s the first step in an exploration we are calling Wildcard Communities. We’re taking the design, card technology, and curation that made Wildcard one of Apple’s best news apps, and focusing it on content that is meaningful to specific communities.

If you’re an aspiring comic, professional comedian, or pursuing a career in this corner of the arts, Wildcard Comedy will be your go to source for what’s happening in the world of working comedians each day. You’ll be continuously updated on industry-specific news, watch great expressions of the craft, and get the funniest videos, podcasts, and tweets created by your peers and stars, all in single curated news feed.

Wildcard Comedy Logo

The comic community, like many smaller communities, does not have a best in class mobile app for discovering, reading, and watching what’s happening in their world every day. At Wildcard, we believe that one size does not fit all when it comes to the News and Media that matters. Wildcard Communities is about zooming it in from “what’s happening in the world”, to “what’s happening in the Comedic world”…and if successful, potentially what’s happening in the worlds of hundreds of smaller, more focussed communities like Comedy.

Whether it’s through Wildcard Communities, or other initiatives we have in the works, we are committed to giving you perspective on the world at large, but also YOUR world, and we are well on the way to doing so. We have seen a number of companies that we admire take a winning user experience (Stack Overflow, Amino, Reddit, Twitter) and roll it out on a community by community basis, and we think Wildcard has the potential to do the same as the information source of choice for these smaller groups.

We’ll report back in 60 days and either replicate this model in more communities, modify it, roll the parts that work into the core Wildcard experience, or completely move on if we are way wrong…Should be a fun couple of months 🙂

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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 Jordan.Cooper@gmail.com (p.s. i don’t use spell check…deal with it)


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