venture capital

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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Running Wild

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

David Tisch: Investor in Vine, Fab, Groupme

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

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Two Minds

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

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

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

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

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

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

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Cards, Cards, Cards…

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

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

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

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Everybody Close Your Eyes

Posted on August 22, 2013. Filed under: startups, venture capital, wildcard |

Yesterday I had breakfast with one of our investors who I’ve known for a long time.  He had read my blog recently and was really excited about the future we are crafting at Wildcard.  I thanked him for his supportive words, but pushed him for harsher criticism.  I said “what are we doing wrong?  What would you be doing differently based on what you know?”  His answer was something I had not considered and it was deeply insightful.  He said “I really like the early voice you’ve established to communicate your view of the future…but don’t tell people what the future is going to be…rather invite them to help you define it together.”

This advice touches on a very subtle nuance around balancing vision and cooperation.  When I close my eyes, I see a future on mobile that is better than what we’ve got today…and everyday I come into work and try to find better language to describe it, and refine it, and bring it into reality…sometimes, when you spend all day willing something into existence, it becomes easy to become attached to the thing you see when you close your eyes…in reality, I think the process of getting to an optimal future is about making a contribution…sharing your version of the way it could be, and then listening to what others who long for an optimal future see when they close their eyes.  It’s in this dialog, that we can collectively shape something meaningful.  There is something to be said for conviction and resolve…and I do not suffer from a lack of that for sure…but Joel reminded me that if we are going to get to a mobile internet experience that is not just on par, but better than that of the desktop web…it’s going to be through a conversation with everyone who cares…

I’ll keep beating the drum for a web of cards, and the convergence of native and web on mobile…for a hybrid future, where selfishly and benevolently Wildcard will play a pioneering role, but I can’t wait to listen to the beats of thousands of other drums…may we find a rhythm together that is sweet to 14 Billion ears…

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Visualizing the seat you want

Posted on August 11, 2013. Filed under: startups, venture capital, wildcard |

Friday night I had dinner with close friends who were in town after a few months on the road. While we were waiting for dinner to be served, the subject of Wildcard came up. After explaining what we are working on (which is always fun and interesting, especially to a non-tech crowd), my friend Jess asked me what my goal for the company was. She said “Are you gonna try to sell it to Google or someone like you did last time?” She saw how cool that experience was for us…I guess it’s sort of natural to assume that we would want to do that again…

Instead, I explained that my goal was to become a Google, or Amazon, or something of that magnitude.  Like all good friends would, she accepted that goal as possible, without doubt or hesitation (thanks Jess). As we talked through what that might look like, I admitted that I was having a hard time visualizing a future where Wildcard was, in fact, a company with tens of thousands of employees and global impact/reach. I explained that it wasn’t hard for me to visualize our product on that scale of influence/import, but rather it was hard to visualize myself running a company like that.

For my entire career, I have always paid very close attention to the traits and characteristics of people in positions that I aspired to have. At General Catalyst Partners, I had 4 or 5 models of what General Partners at a top tier VC “looked like.” If I wanted to become one, I had some kind of picture in my head of what that was, and therefore I could see my path to attaining it, and also what I looked like in the seat. Sure enough, I became a General Partner at Lerer Ventures, and I think I behave sort of as I pictured I would even back then. When I was preparing to become an entrepreneur, I talked to thousands of early stage founders…again, built the model in my head of “what that looked like,” and then it became easier to see myself in the seat. Once you can see a picture of yourself in the seat…it’s not so hard to execute toward that reality. As Hyperpublic grew, I had models of my peers as well as CEO’s who were two, three, four years ahead of me…I saw our path to twenty people, and probably even 40 or 50, and I could visualize myself  in that reality.

With a goal like becoming the next Google or Amazon, I must admit I don’t have very many first hand accounts to look at…it’s hard to build the model of what “that seat” looks like. I spent a few months at GRPN post acquisition, and caught a couple glimpses of Andrew Mason in action…so I guess that’s a little input, but I’ve never really worked at a giant company, and have had very little interaction with those who run them. An email here and there, or time spent with former captains of these types of companies, for sure…but no real, first hand, “this is what the person looks like who started and is running this mega-company.” It’s a bit of a blind spot for me that I’m going to have to work on, as someone who gets places much faster when I can visualize them and then make them real.

I suppose there is something to growing into that seat organically…and I think all those who are in it, must have done so their own way…but organic matter grows faster when atop a scaffolding that provides structure. I’m not quite sure how I’m going to attain this scaffolding (good thing, we’ve got quite some time before it becomes necessary), but this is a bit of a strange feeling not having a visualization to run at of the seat I want. Maybe the first time in my life where I can’t clearly see exactly what I want to become. I guess that’s a sign that we’re shooting appropriately high.

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Bootstrapping to an A round isn’t all roses

Posted on July 16, 2013. Filed under: venture capital |

There is a common adage amongst startup veterans that goes something like “bootstrap as long as possible before taking venture capital.”  The thinking behind this approach is that the early days of developing a company are where you can build a ton of value, so that when you absolutely need the cash, it will not be nearly as dilutive as if you had raised money earlier.  I think there’s a secondary current behind these words that suggests that early stage execution in the absence of investor meddling is somehow a recipe for greater efficiency.

The first reason makes sense.  The second I don’t personally buy, but some founders have a chip on their shoulder I guess…and to each their own.  Often bootstrapping is not an option…and for many early companies, a seed round or angel round is the only way to make an idea into anything more than an idea…

Early in our development of Coopkanics we made the decision that we would like to bootstrap until we had made enough progress to skip a seed round and go right to raising a Series A.  We worked without pay or any resources for about 6 months, and then closed a $3 Million Series A round about two weeks ago.  That financing, was, in fact more money at a higher price than we would have been able to get had we raised shortly after coming together back in January…the plan worked…BUT, it was not without sacrifice.

Fortunately, our core team was capable of engineering anything that we wanted to build, which allowed us to develop unique technology without hiring any employees, but our rate of development was what I’d call “slow and steady.”  This is not a rate that we were used to.  Eric will kill me for saying that, as he put up a herculean effort to get to where we are in the timeframe that we did, but objectively, having built deep technology with a team of 10 at Hyperpublic, as contrasted with a team of 3 at Coopkanics, as you might imagine, things moved slower…it was fine, we weren’t burning any cash, and our market is so far out that there is no saying that entering it a few months later as opposed to earlier is good or bad, but still…it took us longer to answer questions and assumptions than it would have had we raised a seed round in January.  I expected that slower pace going in…well worth the tradeoff along this axis.

What I didn’t account for that we are just brushing off as a company, was the impact that sustained bootstrapping has on the mindset and culture of a startup…there is something to being tough and hunkering down…the Spartan culture created an insanely effective war machine after all…but being a Spartan probably wasn’t super enjoyable day to day…The week we closed our round, we went out for a team lunch and for the first time when that check came, it was “on the company.”  I know that sounds trivial, but the lightness of that gesture in contrast to the Spartan battle we’d been fighting, really highlighted some of the more intangible implications of bootstrapping to an A round.  The heaviness of being cash constrained, of skimping on office supplies, of going head down and suffering for the reward of a better round in some ways translated into this culture of mental toughness…it was almost as though in this period, we wouldn’t allow ourselves to smile…this period was not a time for comfort and joy, but rather a time to sweat it out…and although not explicitly, and although completely rational, this mindset wears on folks after a while…how can we have fun in this Spartan stage? The only thing that was going to get us out of it was hard work and discipline…and so we adopted a culture that lacked the lightness you might find in a more normal startup environment.  Luckily for us, we were able to rest on our extremely tight bond and past experience managing the “hard days” at Hyperpublic…but we are still undoing some of that Spartan influence weeks after capital breathed new oxygen into the company.  There is this feeling of “oh yea, I can go enjoy my softball game without impacting our army’s integrity…oh yea, I can joke around and laugh while we’re doing this…I can invest in culture without every minute going toward production…I can smile.”

The other day after reading Andy Dunn’s essay on the “hard days” at Bonobos I thought to myself: “So much of being a successful founder has to do with a person’s ability to execute when the smiles are few and far between…there is something to how effective you can be in your debilitated form…”  I won’t say that bootstrap mode was debilitating, but smiles started to spread out…

So anyway, I am proud that we had the toughness and discipline to execute on this Spartan strategy, but if I could do it again, I would go in knowing that the corners you cut are felt, no matter how tough or capable you think you are.  It’s not about dollars and cents, but about the mindset of conscious deprivation and what that does to the collective mindset of a small founding team…

Pretty happy to be out of bootstrap mode.  Feels good to let a smile slip here and there.

Leonidas might not approve, but I was always more of an Achilles anyway J


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Two Ways to Stay Cool When Stressed

Posted on May 20, 2013. Filed under: startups, venture capital |

I used to be pretty bad at dealing with stress and pressure.  Things would get heavy and I’d agonize to the point of physical detriment.  Over the past five or six years I’ve become really good at operating through high stress environments.  I was recently talking to a stressed out friend about what I do to deal with the pressures of building a startup and I think it really comes down to two related practices:

1)   When things get heavy, be sure to find yourself.  I know that might sound a little strange, but pressure can come from two places. Either external forces are pushing on you or you are pushing on yourself…regardless of the source, stepping outside of those two voices and finding the mind that is with you regardless of context is where to begin any stressful day.  Meditation has become an amazing tool for me to return to myself every morning…but it’s not always easy.  The main idea is when you are yourself, acting naturally, and not forcing things, you are at your maximum capability to address any contextual situation…pressure and context are ephemeral…treating them such is the best way to move through them.

2)   Remind yourself that you are capable. It is one thing to believe that you can solve a contextual problem or challenge.  You can stare at something that isn’t working or is disappointing and say…”if I analyze this situation, there is a way out…”  That works sometimes…especially if there is a visible path to somewhere different…but I think that’s more of a band-aid approach…sometimes there will not be a very visible path…it seems stupid, but sometimes I just say to myself “dude, you are good at this…don’t sweat this moment.”  It’s hard to have and believe that dialog with yourself if things aren’t swinging your direction.  Lot’s of people rely on friends or mentors to provide that voice and reassure from afar…but if you can get to a point where you can find yourself and your base self is confident and a believer in you…steps 1 and 2 together tend to put stress in it’s place.

So that’s pretty much it.  Took me years to find these two practices…and I’m not always able to implement them…but they’ve been helpful to me and I hope they are helpful to you.

IMG_4541 (1)

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When I’m Creating…

Posted on May 6, 2013. Filed under: startups, venture capital |

Today I got an email today from a girl I used to date in college.  Interestingly, she knew me when I was a very different person than I am today.  I hadn’t found most of the things that have now become deeply important to me.  I guess you could say I was “unformed.”  Anyway, she sent me a note today and asked me “how’s the new venture going?”  We’ve stayed in touch periodically over the years, and she knows that I now build technology companies.  My response took 3 seconds to write, and as soon as it was on paper, I realized how true it really was.  I said “new venture is going great…fun to be creating again…this is when I’m happiest.”

I’ve never really articulated that before.  There are so many factors that drove me to start another company…frankly not all of them were about optimizing for my happiness…but it is true, that when I am creating, I am happy.  You build a startup to change the world.  You build with a mission in your heart much bigger than “personal happiness”. You build with the interests of your entire team and the entire world in your mind.  So many reasons why doing this makes sense….but it is a wonderful cherry on top…one which I would not require in order to continue down this path…but a cherry none the less, that when I’m creating I’m in my happy place.

I’m not sure what I will do when I get too tired to create like this anymore.  I’d imagine creating children and a family will feed this same need.  But I can’t paint and I can’t play the guitar…so for at least the foreseeable future it seems that creating technology companies with people that I love will be what keeps me smiling.

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Right Hand Intern/Apprenticeship

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

If you are a reader of this blog, you likely know by now that Doug, Eric, and I have been cooking on a new startup for the past few months.  We’ve arrived at a stage where I am ready to bring on someone to help me be a more effective CEO.  I had this “right hand” relationship with a very talented MBA student while running Hyperpublic and I’ve learned that I like working alongside a right hand guy/gal.  The only reason to take this gig is to get a crash course in startup operations, strategy and company building.  We have been bootsrapping. There’s no cash to be had, so you have to really want to learn and be a part of the earliest stages of building a technology company.  For the right person, this is your window into the “how to build a successful company playbook.” My goal will be to hand you the bottom 10% of work that I do as CEO, and to share with you my process and thinking around the other 90%.  I will invest heavily in mentorship and guidance, and I will expect you to invest heavily and getting shit done.  This is a job for someone who takes deep pride in EVERY single thing they do.  There will be a lot of small jobs. A lot of unsexy work…and some really important, very sexy work… I envision this being a sort of 2-3 month gig.  At the end, my hope is that you will go on to start your first company, with a playbook and model for early stage execution in your head and a network/platform within the technology community to succeed.   It may be that you fall in love with our company and we evolve to a point where there is a full time role for you here, but that is not why you take this opportunity.

The ideal candidate

–       you were born with your sleeves rolled up

–       you might be trying to move from another industry into the tech/startup world (my last right hand guy came from Goldman Sachs)

–       you are the hardest working person you know

–       you are a self starter who can get things done without a lot of direction or help

–       you might have an MBA, but one is not required

–       operations, execution and project management excite you

–       you have deep attention to detail

–       you like research and analytical thinking

–       you are upset by the experience of using the internet on your phone

What you’ll get

–       a ground floor seat on our rocket ship

–       I’ll teach you everything I possibly can

–       You’ll spend your days sitting next to some of the brightest minds in our industry

Commitment: 4-5 days per week, 2-3 month gig

Start Date: ASAP

Send resume / relevant web links to: (put Intern/Apprenticeship in subject line pls)

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Flow State

Posted on April 15, 2013. Filed under: startups, venture capital |

Lately I’ve been thinking about flow state.  For a Wikipedia definition of flow state, click here.  In my mind, flow state transcends any specific activity or task.  There is a more generalized form of effortlessness that a person can carry from one task to the next..from one realm of life to another.  At the core of flow state I believe is a surrender…A few years ago I wrote this post about dropping into the zone…at the time I was just discovering and getting to know this state of mind…I was so excited by it that I kept trying to “hack” my way back…actively constructing reminders and triggers that would keep me in an unconscious state of flow.  More recently, however, it is clear to me that surrender is much more powerful than control in the pursuit of flow state.

I was riding the subway the other day and I saw an advertisement for a casino in Rockaway Beach.  Two large red dice tumbled almost out of the poster, rolling in my direction.  I was reminded of my days as a college student when I could not get enough of gambling…it wasn’t about winning or losing, although of course I loved to win…rather it was about dropping into this zone of chance, playing games in my head, trying to become one with the game, see around corners…literally to participate in this perfect rule of chance that I could not influence but could act in.  There was a meditation in the turn of a roulette wheel or the flip of a blackjack shoe that I craved…To gamble was to surrender completely to the forces of chance…to a rule of the universe that I could not control…I could almost drop into the rule, or that energy, and ride it….

I believe people “pleasure seek” to areas or arenas where we can fully surrender to a rule or law of the universe that is, again, completely out of our control…and although we don’t realize why, it is the surrender to this rule or law that brings us closer to flow state.  Riding a wave, in fact, when referencing the ocean, is yet another example of flow emanating from surrender.  We paddle and position and work and exert, and then, as the wave takes us, we surrender completely to the force of the sea.  We jump out of planes to drop into the law of gravity…again, surrendering completely to a fundamental state or law where we cannot influence or act upon it, but can become a part of it.

As we walk through day to day life, it feels that we are interacting with many forces, as universal and fundamental as chance or gravity, but perhaps more complex and less visible…we have a choice to either participate in surrender or attempt to control the daily moments of our lives that are tied to these rules or forces…our instincts, or at least my instincts, have always been to control…to exert my will on the way things happen, believing that control to be a path to success and happiness…but as I grow and learn to surrender, I find so much more grace and success and happiness in letting things happen as they will, in “dropping into” the forces that pull me in various directions or situations, more listening and riding waves than paddling or controlling them.

In work, it is so hard to surrender.  The very word “work” seems at odds with surrender. Brute force seems like such a powerful tool to get to where we want to go.  But surrendering to the self, listening to the fundamental rules and forces pulling on you, your company, your team, your market…and simply “dropping in,” participating, instead of pushing…I think is where the flow state lies.  Sometimes the market will ask you to push, to force, because that is the way it expects to interact with you…I haven’t fully resolved how to surrender even in these moments that seem to command an exertion of my will. Sometimes it really feels like controlling for an outcome is necessary…but every time I let go, and surrender without fear, the outcome trumps that of control.  The games that Michael Jordan owned were not the ones he stepped onto the court trying to control…it was when he was “unconscious,” listening to himself and to the forces and rules around him, to the physics of the court… in which he chose to participate, but not control, that he did the greatest damage.

I hear the market asking me to write my future story.  I hear the market asking me to begin exerting my control…but my heart says fuck control…seek surrender…and my story will emerge.

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Keeping it Simple

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

3rd time around, the learning continues.  Today’s observation: as counterintuitive as it might be in the early stages of company development, I am finding myself keeping days pretty simple.  I focus on one or two things in a day, and that’s kind of it.  They are the one or two most important things I can possibly be thinking about, and I punt on just about everything else.  I used to stress about a “to do” list that went unfinished, or an inbox that went uncleared…but not anymore.  If a startup is trying to get to the promised land as fast as humanly possible…nailing the big things can put a nascent project 6 months ahead of what I’ll call the mean trajectory/timeline.  Conversely, knocking down the small things is what prevents a company from derailing or losing it’s way.  I believe the optimal approach, or at least my optimal approach as a founder, is to spend as little time as possible on the small things, but just enough to keep the company out of the redzone, while taking hacks every day at the one or two things that are going to get us our 6 month leaps.

Let’s make it real.  I’ve had paperwork for a new bank account from SVB sitting on my desk for a week.  I would never ask Doug or Eric to deal with this administrative task because our engineering effort is much more important than having a bank account.  The same logic applies to a founder’s time.  In a previous life, I would have stressed that “return SVB paperwork” wasn’t getting crossed off the list…but the reality is…there is no possible way that getting that bank account in place is going to push our company 6 months closer to the promised land…so I will leave that SVB paperwork sitting there until I need to wire a shit ton of venture capital into it, and then I’ll focus on it.  Instead, I dismiss that “small things” voice and spend the mental energy thinking deeply about how to construct our early team.  The impact that the next 3 people we bring on will have on our company is so great…almost nothing else matters at this point…especially not “return SVB paperwork.”

There is a tendency to think that crossing everything that can be done off a list is the same thing as progress…it certainly is a visualization that you are getting shit done…and I guess that can be true, but it is certainly not optimal progress.  Slow down, keep your day simple, find the 6 month levers, and allow yourself the mental space to get those perfect…early days of company creation are no time for optimization and incremental wins…Developing instinct for any given effort to know without stress or deliberation if something is “now” or “later” is so valuable.  Some of it comes with experience, and there aren’t a lot of shortcuts to developing it, but I am consistently amazed at how productive a simple day can be.

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Using the internet on my phone is breaking my heart

Posted on March 6, 2013. Filed under: startups, venture capital |

NOTE: This post took a weird turn and got a little long (but fun).  If you just want to see the job spec for “Founding Designer / Info Architect / UX Specialist” it’s at the bottom. If you want to pick out details of my new company through strange and abstract metaphors…read on

I realized today that I sort of mailed it in on my post about our desire to bring on a “founding Designer” for my new project.  “Founding designer” really tells you nothing except that we are looking for someone with some set of design skills to join our small group attacking the mobile web.  I’d like to get a bit more specific.  In the spectrum from information architecture to graphic design, with UX maybe lying somewhere in the middle, I believe for our specific effort someone who enjoys the IA bleeding into UX side of things would be happy in this environment.  A new friend at lunch today described IA through the example of one who helps a supermarket decide where to shelve what food/products…and I think that analogy is really interesting. One of the inherent constraints of the mobile web is it’s sheer breadth and vastness relative to the real estate available to display it.  How do we take the worlds collective information and knowledge and fit it into a screen that is 4 inches? It’d be like asking the minimart to house every brand and product on earth in a 1000 sq ft space.  Well we could take the aisles out, and fill that space with shelves, but how would people move around? We could leverage the storage in the basement, and store extra skus there, we could only display the products relevant to the people in the store at the time, we could be really smart about dynamically changing product on the shelves based on the customer, we could build underground tunnels for the customers to access a warehouse down the road, we could install ladders in the aisles and double the height of the shelving, we could remove all the products and just install tablets with images of products on the shelves, and drop ship the goods to the customers house, we could rip out the cash registers and replace that space with products, and let the user checkout on their phones, we could change every rule about the way you think a supermarket works, with the one expressed goal of showing the customer every product they want to see (and ideally none of the products they don’t), while still adhering to the core principles and needs of a customer of a supermarket which are to discover the food, pay for it, and consume it wherever they want to eat….

now, that was a bit of a rant, but replace “food/product” with “data/information/urls/apps/actions/content/whatever” and replace “supermarket” with “mobile web/browser/app/operating system/smartphone/whatever” and you see why a designer who gravitates toward IA style challenges might enjoy a problem such as ours.  You might assume that our engineering team is the magic wand that gives you doubleheight ladders, basements and warehouses, dropshipping, etc…and just sit down and help me think about where to put the food, and the aisles, and the ladders, in order to let our customers see every food product in the world without stressing out, or closing applications, or giving up, or accepting defeat, or running for their 13 inch screen (unless we are helicopting them there from our store with white gloves and champaign)….This is an impossible problem that is possible…I know what your thinking…that a search box is seductive, but it’s not the answer. You might think that an infinite vertical scroll of all the food is the answer (especially because that’s the cop out that 85% of native applications have subscribed to)…its not.  And even if you do figure out where to put all the food, and what food to put where, we need to think about how our customers are going to grab the food, and do they have shopping carts, or QR readers? Do we deliver, or do they wheel flatbeds out to minivans? Should products be actual size, or miniatures, or jumbos? Do users want to remember what they saw and order from home, or do they want to act now? Act now, awesome, but what if they can’t reach? Or carry? Go go gadget UX…what if we invert the shelving and have the user pass through the store twice? Second time around the high shelves are low and the low shelves are high?  HOW THE FUCKETY FUCK DO I SHOW A USER…I MEAN CUSTOMER…EVERYTHING EVERYTHING EVERYTHING THEY NEED AND WANT FROM THE WEB..I MEAN SUPERMARKET…NO I MEAN WEB…without frustrating them, or making them feel like my supermarket is tiny and fragile and constrained relative to the mother fucking 1 Billion square foot COTSCO with mile wide aisles that they’ve been going to for years.

Because right now all I see is incremental attempts to jam COTSCO into the footprint of a mini-mart…but you can’t wheel those flatbed pallets around in aisles this small…so some genius platform peeps said “I know, I’ll just put the products outside the store”…it makes so much sense…I’ll just take the stuff that most people buy and I’ll put some shelves up OUTSIDE the store, so a user can just drive up, take what they want, and never have to try to navigate these tiny little aisles…but they didn’t realize…or maybe they did…that I don’t just go to the supermarket for my staples…sometimes I want to try something new…or sometimes I want to try something that I only try once a year…how does Matzoh fit into the outdoor shelving solution?  Do we build a special shelf, just for Matzoh even though people only eat it 10 days out of a year? No…matzoh probably stays inside…and if a user wants to find it, they can deal with the small aisles, and make bad decisions, and not touch and feel it before they buy it…


So these are my problems, and they require ground up solutions from brilliantly creative, patient, flexible, confident, ambitious, and courageous people who either have experience or extreme will to throw at them…. As it happens, I tend to roll with engineers, who want to solve these problems through creative and sound engineering innovation.  I am starting to spend more time with design minded folks who share our ambitions, and more than that I don’t really know…on our small team, I spend a lot of my time thinking through both technical and design solutions to these problems…but the voice and eyes of our user is underrepresented in what amounts to a lot of system design to date…I have strong feelings and desires…and I think every user of the internet is suffering right now on their phone…and the question I have for you who might come lead consumer facing product design at our company…is do you want to internalize this suffering?…and help create the supermarket of the mobile world (understanding that it’s really a chain of supermarkets that share common infrastructure…which makes life harder because not every store is the same)…I’ll support and challenge you, and we’ll all be your family…and our mission is your destiny…and out impact will be the greatest achievement of our collective lives…let’s jam:

The short “job spec” version:

About Newco (sorry I know it’s painful, we’re running the trademark search on a better name/brand, will update shortly): Newco is a technology company with the mission of generating or participating in every mobile web view on the planet.  We pay attention to browser technology, OS level functionality, content delivery, navigation, and any user story that begins, middles, or ends with “user opens the web” (I use “web view” loosely and frankly “mobile” loosely).  We want more of those user stories to happen on people’s phones and we want those stories to end happily.  We are sad that many, if not most, end poorly.  We would like to integrate the web more deeply into every action you take on your phone, and we would like to more deeply integrate every action you take on your phone into the mobile web.

We are three (CEO, VP ENG, CTO): Our last company worked out well, so we decided to work together again.  There is one spot open on this core team through the bootstrap phase and then we will likely become a 15-20 person company over the next 18 months.  You can google around and do your research on “Doug Petkanics” “Eric Tang” and “Jordan Cooper.” (try to do it on your phone…see how fun that is).  Anyway, I think this is a once in a lifetime type opportunity for the right person who is looking to make their mark on the world. See detail below:

Founding Designer / Info Architect / UX Specialist: Half of our challenge and value is in improving the way people move around the internet on their phones.  Banish the concept of the “old web” from your brain and we can begin there.  (The other half is more on the technical/data/architectural side, which you’ll be exposed to, but don’t need to sweat). There are tradeoffs at every turn between the infinite possibility and promise of the web, and the ease of accessing it on this constrained device.  The job is to help lead our thinking at every turn, in every flow, and turn sad user stories into happy, or even better, “mind blown” user stories.

Desired Traits:

–       Belief in yourself and your talent

–       Desire to go big and dedicate your life to this one mission

–       Patience

–       Ambition

–       Work ethic

–       Comfort moving/bridging between abstract and concrete

–       2-15 years product design experience in relevant arenas 

The Package: 1) Supported Autonomy 2) A real stake in the company. Like if things really work out you’ll never have to think about money again stake. And if things go as well as last time, you might have to think about $, but you’ll probably be able to buy a house or something 3) Competitive cash comp to live comfy in NYC 4) 100% healthcare, benefits, etc.


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From Disciple of @cdixon to Selectively Stealth

Posted on February 19, 2013. Filed under: Hyperpublic, startups, venture capital |

Before I started in the venture capital world, an opportunity recognized was an opportunity worth guarding.  Later, after listening to folks who had been around the block, I learned that there was little to no risk in preaching my new ideas to anyone who would listen.  Reading advice such as this post from Chris Dixon only furthered my position that stealth mode was for the naive.

For the last few months I have been working on a new project…and I’d be lying if I said I haven’t reexamined my perspective on what is worth sharing and what is worth holding back. Bijan wrote this post today which crystalized an archetype of founder for whom stealth mode is a reasonable form of operation.  He writes:

“I do appreciate what stealth mode represents to me — namely an idea that takes a long time to build with founders that are wonderfully proud, crazy ambitious with a healthy dose of paranoia.”

A little while ago we incorporated our new company under the name Coopkanics, Inc., not because we had a secret to hide, but simply because we needed to start building “that thing that takes a long time to build”, and while we had a vision for what it was, we didn’t have a brand or a product that was worthy of “market facing” ink.  Our intention was not to be secretive.  Ask me what we’re working on and I’ll tell you.  Out intention is, however, to be straightforward about where we are and where we are not yet.  And right now we’re at “Coopkanicks, Inc.”…3 (arguably) smart guys, who have had some success in the past, working on the biggest thing we could possibly find to work on.  Full of ideas…started to build em, and doing it reasonably efficiently.  Anything more than that would simply be premature, so why sell it?

People always expect you to sell them.  They want you to convince them of your work.  When I meet someone who assumes this position with me, I stare blankly at them.  When I meet someone who wants to engage and contribute, I go as deep as I possibly can.  I guess you could say my position is “selectively stealth.” If you are and idiot, arrogant, or opportunistic “I am working on the mobile internet, and I don’t know much more yet” If you are intelligent, curious, and engaged, “I am working on the mobile internet, and here is everything I know so far.”  Regardless of which conversation I am having, one thing I will not do is sell you.  We are where we are…which is a space that I fear many “stealth founders” can’t live in.

The other side of Bijan’s version of stealth, which I abhor, is the founder who hides behind stealth when they don’t yet know or have confidence in what they are building.  They can’t live with where they are.  It takes a special kind of chicken to mask uncertainty as some sort of strategic decision to stay quiet about one’s work.  If you aren’t confident enough to say “this is what I know, and this is what I don’t know yet” and you’re keeping things under wraps until you have a story to sell, you are doomed.  And if you are hyping your company and brand while playing this game, you are triple doomed.  Unfortunately, I think 1 out of 10 stealth founders are Bijan’s long term thoughtful archetype, and 9 out of 10 are blowing smoke while they try to figure it out behind the curtain.  Those people give stealth a bad name.

I think it’s not about stealth vs. open…I think it’s about sharing what’s worth sharing thoughtfully.

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What Really Happens When You Fail in Startupland

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

This is not going to be an easy topic to talk about, but it needs to be said.  This post is about failure, the way we talk about it in the startup world, and the disparity between the way we talk about it and the way it is.

The party line on failure, if you talk to anybody in the venture world specifically, is that “failure is a badge of honor” or at the very least, “there is nothing wrong with trying and failing.”  This is the line that we tell young founders to encourage them to jump in and take risks.  This is the line that we tell the world so that we appear genteel, respectful of the risks that people take, and admiring of their willingness to risk everything.  It is a pom pom we wave when we are trying to say “we love entrepreneurs and admire their boldness.”

The truth is, and I am speaking from an investor’s standpoint here, we want to believe that we live the reality of this party line.  We want to believe when we lose money with a founder that that loss has no impact on our feelings toward this person…but if I am really honest about it, and I look at empirical data…the party line and the reality don’t always line up.

The truth is, when you fail, your investors tend to have a bad taste in their mouths.  Nobody likes to lose money. Nobody likes to be wrong.  Nobody likes to sit in that space that isn’t so happy…and unfortunately for a founder, his person at the point of failure is an embodiment of many things that nobody likes.  Now sure, an investor doesn’t dislike the founder himself.  If the founder does right and doesn’t succeed, there is no “black ball”, or malevolent desires on behalf of an investor…but I’d be lying if I said there isn’t a slight tinge on that relationship…and unfortunately, in this world, a slight tinge is all the friction necessary to turn momentum into something less.  Note: this tinge is not permanent, and it is not insurmountable…but coming off a failure…you are only as good as your next act…and weather we say it openly or not, clawing your way to the next act, you are starting not at neutral or positive, but with a headwind.

I’ll give the example of my own experience as a founder.  My first company, I raised about $600K.  I operated for a year, failed, and returned about 50% of the capital I raised.  I felt terrible.  Everyone said I did the right thing returning the capital, that I was a standup guy for doing it, but still I lost them money.  Nobody turned their back on me, once the company wound down…but they just weren’t leaning into investing more time and energy on me.  When I went to raise money for my second company, Hyperpublic, weather I asked them or not, not a single investor in my first company invested in my second.  Just gives you a sense of the increased friction you face, coming off a failure.  Sure I was able to raise money from new investors, but I had to answer the question “is so and so from your last company investing?”  and so on.  New investors call old investors and say “What do you think of Jordan?”  Of course, again, investors who lose $ with you don’t “blackball” you, so they say “stand up guy, did the right thing, etc…” but still their signal of not reaching out to put $ into the next thing becomes something a founder has to overcome.

Now, let me show you how powerful the mental impact of a failed venture can be on a relationship.  When I started Hyperpublic, I felt so bad about losing my previous investors’ money, that I cut all of those angels a piece of equity in the cap table of Hyperpublic.  It was free, they didn’t know how much they had, but they signed a piece of paper, that to them was a nice gesture, but still probably worth very little. In their minds they owned a piece of a new thing with an unproven and recently failed person.  Fast forward a few years, I sell Hyperpublic to Groupon, and get to send an email to each of these angels saying “you thought I lost half your money, turns out I doubled your money. Here’s the check.”  Again everyone appreciative.  But now, if I am really honest about it, I only have real relationships with two of the seven or eight investors who lived three years thinking I failed and lost their $.

I listen to the way investors I interact with on a daily basis, from all different funds east and west, talk about their “losers” or the ones that didn’t work out…and it is always the same…a muted expression of disappointment, and slight negative tinge…not a condemnation by any stretch, but we have to be honest about the realities of failure.  It is ok, but it’s a black mark that you have to work your ass off to wash away.  Coming off failure, you are only as good as your present and future.  That’s the reality of the market.  I don’t want it to be this way, but even the most accomplished of people cool off when things go south…which means if you haven’t proved anything, and you fail, you really cool off…only way to heat back up is to earn it back through hard work and new success.

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    I’m a NYC based investor and entrepreneur. I've started a few companies and a venture capital firm. You can email me at (p.s. i don’t use spell check…deal with it)


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