Archive for November, 2013

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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A PM opportunity worth leaving Google for

Posted on November 4, 2013. Filed under: startups, wildcard |

At Wildcard we have the mission of replacing every “webview” on your phone with a native card…or a “wildcard.” We believe that webpages are not the way that people will consume and interact with the information of the internet on mobile…and that this new unit, of the card, will eradicate mobile Safari and Chome as you know them. This is a big mission…and our product is a system with multiple parts. We are building product that touches consumers. We are building product that touches developers in the native ecosystem. And we are building product that touches brands/merchants/publishers (or really anyone that has a presence on the “legacy web”). We have made great progress in defining what a card is and how it behaves. We have made awesome progress in building technology that enables scalable card creation and delivery. And we’ve made tremendous progress in defining user experience and performance innovation such that we can say with deep confidence that interacting with cards is better than interacting with webpages on your phone. With that reality in mind, and with the help of our friends at Twitter, Google, Facebook, etc…brands/merchants/publishers are increasingly aware that investing in a “card strategy” is necessary and important.

In fact, the Brand/Merchant/Publisher side of our business is accelerating to a point that it warrants it’s own leader. This leader is a Product Manager who will own the tools that brands/merchants publishers use to effect their card strategy through Wildcard…as well as the relationships that Wildcard maintains with small and large platforms that host card inventory. This Product Manager almost definitely has a background in Computer Science, but gravitates more toward technical product design and product strategy than programming. S/he is the kind of person that is excited about spending time with established internet companies, listening to their feature needs/requirements. S/he understands how product gets built at companies small and large, and wants to create the most frictionless implementation possible for our brand/merchant/publishers user…Thinking in terms of markup, SDKs, APIs is second nature to this person. Experience in the APM or PM programs at Google or the like is relevant…but on the ground hustle at a company like Stripe, Braintree, or Facebook Platform is equally interesting…This is a more senior role, for someone who is confident in their product ability, confident in their outward facing ability, and experienced enough to build and lead a small team of engineers and/or evangelists as we scale our 3rd party facing products to many corners of the internet.

While this effort is discrete and focussed, the PM of our 3rd party tools will be intimately involved in our consumer facing operations. Wildcard is a system that unites around the core unit of “card.” Decisions around this fundamental unit have implications for 1) our users, 2) our developers, and 3) our brands/merchants/publishers. As such, a key responsibility of the PM is to communicate thinking and learning to team members working on all areas of the system.

If you have the experience and product management training from a top tier program, but are ready to make your mark at a young, well funded, and extremely ambitions New York City startup, this is a unique opportunity to become a leader at Wildcard. You will work with best in class engineers and designers to blow out our 3rd party network and product, and you will come to work every day with wonderful people who care about each other and what we’re attempting to contribute to the world.

Here are a few links on who we are and what we do if this is the first time you’re hearing about Wildcard. I would love to tell you more in person:

What Is Wildcard?

10x Improvement

Team Snapshot (a little out of date, we’ve grown…)

P.S. If you would like to come play with some wildcards…email me and we’ll set up a time for you to visit and demo some cool stuff:

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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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