venture capital

Not Every Datapoint Demands an Insight

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

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

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

Happy Tuesday

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Creating Fast Moments

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

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

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

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

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

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When to walk from a deal

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

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

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

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

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

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

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Give it a minute

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

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

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

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Women at Wildcard

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

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

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

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

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

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

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

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

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The Day is Upon Us

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

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

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

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

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

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

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Going Uncomfortably Fast

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

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

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

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

p.s. if you want to come skiing with us…this is where the lift tickets are sold: http://www.trywildcard.com/#jobs

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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 selling..so 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 jordan.cooper@gmail.com…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: http://startupboy.com/2013/11/07/bitcoin-the-internet-of-money/

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 jordan.cooper@gmail.com 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.

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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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    About

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

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