startups

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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Right Hand Intern/Apprenticeship

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

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

The ideal candidate

-       you were born with your sleeves rolled up

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

-       you are the hardest working person you know

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

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

-       operations, execution and project management excite you

-       you have deep attention to detail

-       you like research and analytical thinking

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

What you’ll get

-       a ground floor seat on our rocket ship

-       I’ll teach you everything I possibly can

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

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

Start Date: ASAP

Send resume / relevant web links to: jordan.cooper@gmail.com (put Intern/Apprenticeship in subject line pls)

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Flow State

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

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

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

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

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

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

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

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Keeping it Simple

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

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

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

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

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Using the internet on my phone is breaking my heart

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

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

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

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

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

NOT IN MY WORLD.  I WILL NOT ALLOW MY DESIRE FOR THE UNUSUAL AND NUANCED TO BE SQUASHED BY THIS APPCENTRIC NIGHTMARE OF OUTDOOR SHELVING DUCKTAPED TOGETHER AS THE COSTCOS DIE AND THE MINI-MARTS RISE.

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

The short “job spec” version:

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

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

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

Desired Traits:

-       Belief in yourself and your talent

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

-       Patience

-       Ambition

-       Work ethic

-       Comfort moving/bridging between abstract and concrete

-       2-15 years product design experience in relevant arenas 

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

Contact: Jordan.cooper@gmail.com

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From Disciple of @cdixon to Selectively Stealth

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

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

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

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

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

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

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

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

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What Really Happens When You Fail in Startupland

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

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

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

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

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

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

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

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

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When the wise thinks himself wise

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

Earlier today Chris Dixon dropped a nice excerpt from “The Principles of Psychology” by William James. The entire excerpt can be read here, but I absolutely loved the following thought :

“As the art of reading after a certain stage in one’s education is the art of skipping, so the art of being wise is the art of knowing what to overlook.”

That is a very powerful concept that I hadn’t fully articulated but have definitely been living as I begin to build the mobile web I want to see in the world.  Said another way, knowing what NOT to focus on at various stages in a company’s development can be as important as knowing what needs focus.  I have actually been pretty dogmatic about focus this time around.  I guess you could say, I’m feeling sort of wise.  I’ve now been through this phase in building a company three times, and I’ve seen this stage in company development at least 5000 times more.

I sat down last week to write a 90 day plan for what we needed to do as a team and as a company…and it took me about 30 minutes to lay out what I’ll call an A- plan.  A few years ago, it would have taken me 6 months to even figure out that I needed to develop a 90 day plan, and the amount of ridiculous crap that would have been in it would have been immense.  So my plan was an A-, and I knew that it would take some more thought and discussion with our team before it got to an A, but I was feeling pretty wise indeed, knowing that there was nothing on that paper that the wise man would or should overlook…but what I learned a few hours later, was that I had gone a little heavy on the “wise whiteout.”

That night I went to a sushi dinner with a dude who I have come to see great wisdom in.  I told him, “this is my 90 day plan, not my big vision of where we’re going, I just want to focus on ops and see if there’s anything you’d be doing differently”  I would have preferred to have my plan at an A, as this dude’s time is scarce, but our meeting ended up being a few days earlier than I had anticipated, so I just dropped in where I was in thought.  I went into the dinner hard pressed to add any major initiatives to the plan (as it was already quite ambitious), but left feeling a gaping weakness in what I had been thinking.  My friend rightly suggested that I had designed a 90 day plan that overlooked one of the hardest parts of our effort.  I wanted to keep the scope of our first build manageable and known.  I didn’t want to commit to a messy challenge, knowing that it might turn my 90 day plan into a 120 or 150 day plan, and so I had “wisely” chosen to overlook it until a time when I either had the resources or gun at my head to address it.

Turns out I thought myself too wise.  Under the guise of wisdom, I gave myself the license to overlook a key element of the company we are trying to build…while maybe not solvable in 90 days, it was certainly attackable…and further…the commitment to attack it will be a key influence in the early DNA and culture of our company….and thus my response to Chris’ post was a retweet with warning: “True but dangerous when the wise thinks himself wise”

 The lesson: wisdom is a spectrum, no matter where you are on it, seek out the wise and they will pull you closer to their end 

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Bad Asses Make Peace with Unanswered Questions

Posted on February 7, 2013. Filed under: startups, venture capital |

As I walked to work this morning, I found myself extremely aware of how wound up I am in moving forward on our new mobile web endeavor.  I found myself hurrying.  Hurrying to shorten my morning routine at home, hurrying to make progress on product design and definition…hurrying to get administrative tasks done…and if I had to take a step back and examine the hurry more holistically…it’s really a hurry to answer all the unanswered questions between today and the future I want to build into the world.  At Hyperpublic I lived hurrying for two years…a founder is never satisfied as long as questions are outstanding…but the question I arrived at today, which I already knew the answer to, I just hadn’t articulated it in my mind, is as follows: “Is hurrying a necessary state of mind for a startup to succeed?”

There is no doubt, when a tone of hurry is introduced into a founder’s mind, and by extension a team’s mind and culture, things get done.  We see founders all the time setting artificial deadlines, things to run at…as though creating a sense of urgency is a necessary catalyst to stretch a team to produce.  Urgency is real, and sometimes a deadline is the difference between getting a deal and not.  Sometimes, when building a startup, you have to be in a hurry or someone else comes along and eats your lunch.  But there is a difference between recognizing moments when we are in a hurry, and creating a culture where the only way to find the finish line is to live and work in a state of perpetual hurry.  It doesn’t take a rocket scientist to know that running a marathon is not simply a consecutive set of strung together sprints…but there is more to this question than just strategic pacing.

Hurrying can be at odds with thoughtfulness, happiness, health, etc…I have seen some repeat-founders, in recognition of this truth, slow down too much.  Having isolated the truth, that hurrying is not the way to win a marathon, they attempt to create a new culture and personal lifestyle that takes urgency out of a startup’s culture…often these repeat founders have had a success in the past, and now in their wisdom, they say “this time, it’s important to be as zen as I was in that lovely 12 month break between gigs, so this is what our new culture looks like.”  Almost invariably, those founders either fail in the new endeavor or realize they swung the pendulum too far, that they lost a full cycle of development and progress, and now it’s time to “get serious and buckle down”…at which point they inject hurry into a culture that isn’t as ready to accept it.

On the other end of the spectrum, I have seen young first time founders hurry the entire way through and either succeed wildly or burn out while running at the finish line.  I think you get to do this once, and only once, in your life.  I have never seen a repeat founder attempt to sprint wire-to-wire the second or third time around.

So where does that leave me?  Sort of retraining myself…My mind and my body recognize this period of deep uncertainty/opportunity as a state where we hurry to answer the unanswered…we’ve been here before…and when we hurried we did well…so I wake up and instinctually I am hurrying…taking deep hacks at the unknown…but as I walk through my day…my experience and rational is talking to my mind and body and saying, “dude, chill the fuck out.  You are not in a hurry right this second.  You are not going to lose this market if you enter a week later.  In fact, you don’t even know yet if your timing is 6 months early or 6 months later than optimal. You haven’t raised capital and you don’t have any burn…time is not running out, it is just beginning.  THESE UNANSWERED QUESTIONS THAT YOU ARE ATTACKING LIKE CANCER WILL GET ANSWERED OVER THE NEXT 5-10 YEARS. STOP TRYING TO ANSWER THEM ALL TODAY.

So the CAPITAL LETTERS in my head are my experience yelling at my founding instincts…saying “you asked to be in this ocean of unknowns…I told you how nice it was to chill on the beach and let the world pat you on the back…and you just couldn’t let us graduate into the life of a non-hurried venture capitalist…waiting for other people to answer the unanswered for you…FINE…we’re back…answering the future ourselves…and making up the answers where no answers exist…I accept this, but remember you are a mother fucking bad ass, don’t act like a fucking kid.”

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What Apple has in Common with Prep School Gangsters

Posted on January 29, 2013. Filed under: startups, venture capital |

My walk to work each morning is substantial.  It is about 20 minutes of uninterrupted time in which I tend to let my mind wander. Some days, I look at the tops of buildings, and notice beautiful lines in the sky.  Other days, I get so wrapped up in a problem or thought I don’t notice my surroundings at all.  Some walks are a mediation, where I try to let thoughts dissipate, and other days I’ll hold on tight to a single question…digging deeper and deeper, pushing to reach the essence of the unknown thing.  It’s interesting to start my walk with a relatively blank slate.  The place where I arrive and focus is often that which is not solved or is somehow causing me stress.

Today, however, was a strange day.  Today I walked to work and for some reason I was replaying in my head a very specific night and moment from my high school experience.  I remembered it very clearly (which is unusual for me with my terrible memory)…allow me to share a formative moment in the life of Jordan Cooper.  On a warm spring night in what I think was my senior year in highschool, I had been hanging out at a friends apartment.  I guess her parents were out of town, and as often the case when parents go out of town, my friend had decided to invite a small number of people over to drink beer and misbehave in the safety of her parents home.  The issue in these “open crib” situations, at least where I grew up, is that word travels fast, and often a small get together would elicit many unwelcome visitors attempting to crash.

So anyway, there was this night in high school where a group of uninvited “prep school gangsters” (see New York Mag article here) showed up at my friends house and were not allowed up to the party.  Angry and adolescent, intoxicated, and rejected, this group of guys decided that they wanted to beat somebody up.  I was never a fighter growing up, and frankly had never even been in a fight, but they knew who I was and didn’t like me I guess, and they called a friend who was upstairs with me and told him to tell me “go downstairs, Jed [Redacted] is down there, and he has beef with you.”  I didn’t want to go, but they said they weren’t leaving and were giving my friend’s doorman a very hard time, harassing and even pushing him I think, and ultimately I decided that if it was my head they wanted, so be it…and I went downstairs.

I remember standing in a circle of about eight guys, and this little shit who I didn’t even know was telling me that he heard I talked shit about one of his friends, and that he had some kind of score to settle with me…I remember another kid in the group who was supposed to be my friend, blowing his nose repeatedly and throwing the used tissues in my face…they kept prodding me and prodding me, telling me we had to settle this with a fight, and I looked at this little kid and said “listen dude, I don’t want to fight, and I’m not going to fight eight people at the same time. If you all want to beat me up right now, do it, and I’ll deal with you through the police…or if you want to walk around the corner with just me, and leave all these guys here, I’ll beat the shit out of you 1-1, which is ridiculous, because I don’t even know you, but I’ll do it if that’s what you want.”  They huffed and puffed, and maybe even pushed me around a little, but I remember them walking off, cursing and calling me a pussy, again unsatisfied not having had the opportunity to beat me up.

I spent all day today baffled as to why this night was the subject of today’s walk to work…and as I reflect further, I now wonder if the underlying issue on my mind was really one of bullying and how to deal with bullies.  I think about where all those kids are today, and I smile at the choices I’ve made…in the long run bullies end up losers by most metrics you’d care about.

As I endeavor to build in the mobile ecosystem, I can’t help but feel a bit bullied by Apple…I view their terms of service and stranglehold on how people use the internet on their phones to be threatening both to me and those like me who seek to build on their platform.  I think my walk today was meant to remind me how we deal with bullies.  Respect the threat, as certainly it is real, but don’t back down.  Don’t antagonize or escalate, simply look at the world, live within the bounds of reason, and act with the maximum strength possible while keeping the threat from turning into adverse action.  Over time, independent thinking, composure, good action, and intelligence win out.

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Vine: Data Compression Applied to the Human Experience

Posted on January 28, 2013. Filed under: startups, venture capital |

Some quickly scribbled thoughts on Vine:

1)   for those who think it’s a flash in the pan, think again, here to stay, and maybe as important to Twitter as Youtube was to Google

2)   the amount of information transmittable in a Vine feels higher than any other unit of shareable data that exists…period.  At it’s core, vine feels like a data compression technology where the human eye/brain can read compressed format…the time that lapses inbetween shots is extraneous and unneeded in the creators story…by editing in the content creation flow, a user can tell an hour long story in six seconds if she chooses the right frames/sign posts to capture

3)   There seem to be two primary applications of this compression technology…one is a horizontal view into a single moment and the second is a linear view through time across moments…the first does not leverage vine’s unique compression capability nearly as well as the second.  Sure, you can fit more of the story about what’s going on in a given moment in your environment if you can stitch together multiple images of every angle and dimension of your surroundings…but the result is maybe a 2/1 compressed view of a 360 degree 6 second video clip…the second, however, is staggering…if a photo answers the question “what were you doing at a point in time” vine answers the question “what were you doing through time?”

4)   I think our minds are wired to make inferences and fill in the blanks of what occurred between frames within vine…and a shared context and brain function between the viewer and creator of the vine enables the creator to tell a full story while skipping the “assumed” details…it’s as though the recipient of a vine has cached a local copy of the human experience in their own brain, and thus only needs to “pull down” and “stream” the dynamic stuff that is changing based on the creator’s individual experience

5)   The aggregations of the vineapp that have been popping up like: justvined.com and http://vinepeek.com/ are fascinating.  They are the window into human experience that I wanted chatroulette to be, and that Youtube bills itself as when highly edited and culled down into fundamental moments…the amount of nuanced human experience consumable per second within these aggregations is so large and dense…I almost believe if I stare long enough I will see the world in it’s entirety from every perspective of the 7 Billion node network of biological sensors (people) using machine sensors (video) to document time and space.

6)   I think the app poses as great or greater a threat to text than it does to photos…this is not an instagram killer…vine’s don’t capture beautiful moments…this is a tumblr/wordpress killer…vine’s tell stories in a way that text/image publishing platforms do…only they are much more efficient and lower commit for the publisher…

7)   I’m not sure how defensible the start/stop mechanic is on the video tool, but what’s lost in defensibility is gained in distribution through twitter…will be interesting to see how Youtube responds…will they make an app that’s focused on the creation side of the video experience…will it use the same mechanic?

8)   If the tweet lowered the commitment to create textual content and created a new sphere of publishers not seen by blogging platfroms, the vine feels like a similar disruption to traditional video capture/publishing

9)   Vine = data compression of human experience into a shareable and consumable unit that vastly increases the volume of transmittable information consumable by a human in a unit of time

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Watching stars fall

Posted on January 26, 2013. Filed under: startups, venture capital |

Oft covered is the guy who ascends through professional rungs, leaping road blocks, defying statistics…he is an outlier, he is romanticized, he is something slightly more than human but not quite divine…the rise of a star is an intoxicating story and object of observation.  A young phenom starts scoring 40 points a game in highschool…fascinating…a hedge fund manager puts up 80% annual returns…fascinating…a little girl starts beating grand masters in chess…fascinating

But like the rise, the fall has always been fascinating to me.  Lance Armstrong drops from world inspiration to nothing overnight.  Steve Cohen from wall st god to alleged cheat…fascinating…  I used to work at a place where the “smartest guy in the room” ran conversations, passed judgment on all, and was respected as the self-appointed “golden boy” of the firm…I remember reading recently of his “departure” from said firm…his wandering around without a home…and ultimate acceptance of a much less prestigious gig than the one he had obviously been pushed out of…I thought to myself…god that is sweet…I’ve watched countless high-flying founders turn their nose up at the world, only to have the rug pulled out from under them 12 months later…the rise is inspirational and the fall is cautionary…the fall is what happens when you lose site of your pre-rise self…when you start to believe you are above the law, or the rules, or other people…personally, I LOVE watching the fall.  If the rise and the fall were on tv at the same time, I’d DVR the rise, and watch the fall live…there is a justice in the fall that is just too good to turn away from…the fall is statistics catching up with you when you forgot that the longer you live, the less likely you are to defy them…there is something so beautiful about the guy who stopped being friend to man…sitting on his living room floor…alone…shamed and shocked…not having a man to call…out of moves…forced to begin again…in a place even lower than where his previous ascent begun.

How a man who has fallen rises again…if he rises again…is much less documented than the initial rise or fall…my guess is because after the fall…a man realizes that the rise and the power and the success meant nothing in and of itself…that the contextual pinnacle that he so proudly and arrogantly sat atop lacked the human foundation that he needed when it all disappeared…so to rise again did not mean bright lights and big bank accounts…but perhaps rather ordinary relationships and ordinary living…which is not a very media worthy resurgence…or maybe after a fall…one who has risen learns to fear the fall…fear the shame of falling again…and thus goes through a second ascent more discretely and tastefully than the prior…I don’t know…but I do love the fall.  It may be that those who do not fear it, acting wrecklessly in their pursuit and preservation of the apex, are in fact more likely to reach said apex…but I will stick with my fear…or perhaps I should say respect…of the fragility behind any state that is comfortable or enjoyed…that which we take for granted or as a given…is not…and while 99% of the days you wake up…things might go as you’ve become accustomed for them to go…keep waking up…and living more days…and the rake will catch up with you…push your whole stack in, (emotional, financial, social, or otherwise), leave it hanging there, in the middle of the table, as you hobnob with the other players and slurp down the “free drinks”…and one of these days your aces will get cracked…OR…maintain the mindset that no matter how big your proverbial stack gets…the rake is the rake, and you are as susceptible to it as the small stack to your left…and you will enjoy a life with small stumbles instead of 1000 ft cliffs…god I love the fall…life’s rake against those who rose without moral fiber, self awareness, and personal character.

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The crumbling network of startupland

Posted on January 23, 2013. Filed under: startups, venture capital |

Lately I’ve been wondering if the startup community is becoming less connected than it once was. It certainly feels like the network is being diluted, and also that the average strength of connection between all nodes in the network is lessening…the primary culprit that is disconnecting us is sheer size…it is not surprising that as a network grows, the strength of connection between nodes dilutes…typically when this happens in an online network, the product and use case of the application which defined a network evolves…twitter isn’t what it used to be (heavier emphasis on content distribution away from multi-person conversation around content), Facebook isn’t what it used to be (pushed downstack to infrastructure layer, pushed experience into 3rd party environments), I never knew exactly what Linkedin was, but you get the idea…

So if the startup ecosystem is a network, and the volume of nodes in the network is pushing the limits of the original “application” which created it (building real technology companies)…it begs the question…must we let the initial application go and accept the new reality of the network?  My guess is yes…where the new reality is a maturing and fragmented market where innovation and creation happens more in vertical silos (industries) than in a horizontal community within one vertical (technology)…or said another way…if technology has largely eaten the world by now…it’s no longer technology that defines starting up…it’s now fashion, or auto, or finance, or foodstuffs, now tech-enabled, spawning industry specific community that is tighter nit and adequately intelligent to support innovation and starting up?

And what happens to the core users, who liked the first application and built relationships and behaviors before the network got too big?  I think they break off and find a new home for their network (see Branch re Twitter, Instagram re: FB), etc…so where do we go, who talked and learned together before a world with infinite content and blog posts and a sea of faceless seed funded founders?  Where do we find ourselves and begin to learn again together?  Someplace smaller?  Someplace with a higher barrier to entry…some place where the technology and challenges are harder… Maybe…it’s as though the infrastructure of coworking spaces, accelerators, public forums, and even capital…all the things that supported us and helped us form community when we were unnetworked…are the very places we can’t go anymore to find what we had…either the network has to contract or shard…wonder which will happen first

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When Founders Melt

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

Between my own experiences, those of my friends, and those of founders who I have invested in, I have seen many startups go through difficult times.  A product flops…a cofounder leaves…the company gets sued…a financing falls apart…an acquisition falls apart…an api gets cut off…the money is running out…the money ran out…

In these times, if you are a founder, shit gets very dark.  More often than not, you start to worry about your team.  You worry about your employees losing faith in the company.  You worry about your investors.  It becomes hard to answer that question from the market and your friends: “how are things going?”  Between the social pressure, self inflicted pressure, investor pressure, and market pressure getting out of bed in the morning is not pleasant.  In my experience, there are two states a founder can exist in when such a situation arises: 1) depressed/stressed/exhausted and 2) melting.

Both blow, but the single greatest predictor of a company’s demise or resurrection is which of these two states a founder is in during the time of duress.  As an investor when I’m asked to bridge through this period, as a friend when I’m asked if it’s worth fighting through, and as myself when I look to calibrate how I’m dealing…the question I always ask is “is the founder melting?”  Once you’re melting, it’s over…there’s no coming back, no bridge will help, no new product effort matters…your going one direction and that’s down the drain.  You know you are melting when you start lying to people…you know you are melting when you lose confidence in your decision making…you know you are melting when you are pretending to execute as opposed to executing…you are a shell of yourself…the outside remains solid, but the inside is soup.

If you are melting, don’t ask for the bridge.  If you are melting don’t ask for your employees’ continued loyalty.  If you are melting don’t tell your family it’s going to be ok.  Be responsible, recognize that you need to exit this situation, and preserve your relationships with your team and investors, do right by them…

More importantly, however, is not to melt.  I know it sounds absurd, to ask someone who is depressed/stressed/exhausted to hold it together…but that’s the job of a founder.  Even when it appears that you have no outs left and no moves to make…the one move that you can always make as a founder is to keep your proverbial cool…to not melt.

There is a reason airline safety demonstrations always instruct parents to place the mask over their own nose and mouth, before helping secure the mask on dependents.  Leader has to stay coherent for anyone to survive. Your first move as a founder is keep yourself alive and functional…if you melt…company is gonzo…Do whatever it takes to keep below melting temperature…don’t just stare at a screen, hoping things will change…go to the movies, go on a date, talk to a shrink, open up to a friend, or advisor, or spouse, go on a week long hike in the mountains if that’s what it takes, whatever it is you need to do to remain in solid form…do it. When founders melt, a small hole forms in the trough of sorrow, and the team and investors and product and company drain out the bottom into oblivion…stay cool

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A Human Foundation

Posted on January 3, 2013. Filed under: startups, venture capital |

Sometimes I write a tweet and immediately realize that there is more to be said on the subject than can fit in said format.  Today, I was sitting in the sun, on the back porch of a rental house on the coast of Uruguay, and I was reflecting on my hopes and ambitions for the year.  Many of them were personal or existential in nature, and of course, some were professional.

I tweeted: “In 2013 my professional goals are all around people I want to work with and not at all around traditional biz metrics. Team is everything.”

It’s strange, because I have been engaged in the same practice of delineating and ruthlessly chasing down annual goals for at least the last 5 years, and usually the professional ones orient around big, visible metrics (i.e. raise $5M, build a product that reaches a million people, become a partner in a venture firm, learn how to code, etc…).  This year was different.  My ambitions were a reflection of maturation in my thinking this time around… 2013 will be strictly foundational for me, in what I feel in my heart to be a coming 5-10 year journey.  I literally do not give a shit about any traditional milestones…when I think about what I want out of this year professionally…my mind visually wanders to the faces of the people who I admire and with whom I have rewarding and rich interactions.  What you come to realize if you’ve built one or two startups is that most business metrics and milestones are simply reflections of a team’s capacity…unless you royally fuck something up, when you assemble thoughtful, ambitious, ethical, humble, deeply intelligent people around a sound yet flexible direction, milestones and metrics follow.

So yea, it’s cool that metrics follow excellent teams, but metrics are not the root of my 2013 goals.  It’s something deeper than that.  Interacting with people takes a tremendous amount of energy…and for me…that is probably more true than for many others.  I spend a lot of time alone, I like thinking through work and life, almost as a mediation, without conversation…so when I do engage people (which at work is often, obviously), I put a lot of myself into those conversations and meetings.  My hope is that what I put in is only a small fraction of what comes out, and for that equation to hold, I absolutely need to work with additive contributors.  Further, I want that equation to hold for any interaction between two members of our team.  If an interaction simply yields the aggregate of what both parties invest, there is no hope for exponential yield…

So people are at the center of my 2013 goals because the people I want to work with will be good for business…no doubt…but it’s even broader than that.  What you come to realize in entrepreneurship is that work is life, and it’s always going to be that way.  Who you spend your life with is on the short list of important decisions that you actually get to make. Spending your life with people you respect and love and with whom you share values trumps any joy that will come from success in business alone.  I see miserable successes everyday and guess what…I’m not gonna be one of them.  2013 will be the year we assemble a group of people who will define my day to day and my future…it’s so important that I get it right…and it is my singular focus

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The Edge

Posted on December 8, 2012. Filed under: Hyperpublic, startups, venture capital |

The edge: the edge is a character trait, type of intelligence, and behavioral style that optimizes for the self irrespective of, but not necessarily at odds with, collective interests.

The edge, or an edge, is not unique to some, but rather present in all…it is a base level intelligence that is responsible for calculating toward optimal outcomes for the individual…what is variable is a higher order function which is an individuals choice of how influential the edge is in how she carries herself in a given setting.  Also variable is the strength of this intelligence…some people are extremely tuned to how their own and others’ actions impact their personal satisfaction…they tend to also be extremely tuned to the presence of edge in those around them…they detect when another is acting from “the edge” and instinctually calculate if the other’s intention is good, bad, or neutral for them…if one chooses to be ruled by the edge, that calculation is immediately followed by the action most likely to minimize adverse impact on one’s self interest.

Ok, sorry for the abstract description, but I wanted to really get across what the edge is.  Some more visible manifestations of the edge, or related real world examples might be seen in, for example, styles of poker.  He who plays extremely tight, with perfect calculation, and optimizes for each individual hand, likely has a strong expression of “the edge.”  He who plays loosely, chats with the table, makes some friends, makes a couple calls for the fun of it, may either not have as developed an edge, or may have made the higher order decision not to be ruled at the action layer by it.  Now, a few things worth pointing out.  The edge player does not necessarily win against a non-edge player…each player has a style that works for them…in the short term, or on a given hand, I’d put my money behind an edge player if I had to bet…but over the life of a game, or many games, the same does not hold…I say this because persistent self optimization is not necessarily the most effective path to overall optimization.

Last night I was talking to a close friend and former Hyperpublic engineer, Eric Tang, about the role of “the edge” in business…and more broadly how to carry yourself in a professional and startup setting.  We talked about a mutual friend who we agreed is incredibly smart and competent.  This friend has ambitions of starting a company one day, and I said “he will be amazing…the only thing that might get in his way is his edge.”  Eric’s response was sort of confused…he viewed the edge to be a powerful tool (which it is) in carving one’s way through startupland…but I explained that in my experience, early startup environments are often to fragile and vulnerable to support a heavy-edged leader (and by translation…culture).  I told him, the edge feels like a sword…that you choose to brandish…and more often than not, I prefer to leave it holstered.  I’d much prefer to lead with love and respect and engender a culture that softens the edges of everyone, than allow for an active “dialog of the edges” to emerge within my organization…

I am not saying that an edge is not important, and there is certainly a time and place for it..in fact, when I do brandish said sword, and act under the influence of the edge…I am fucking ruthless about it…but especially now, a little later in my career…I am very careful and conscious about when I choose to use/listen to it.  I have always had a very tuned edge, and when I was younger, not only was I ruled by it, but I couldn’t fathom why anyone, especially in a professional setting, would choose to mute it.  I viewed those who did not act with the sharpest of edges as less sophisticated of shreud…but I was wrong…I attribute much of my current understanding on this subject to Kenny…who you might have heard…has an edge that will cut glass…but his selection of when that edge gets expressed is masterful and nuanced.  Of course, there are those that get far under persistent influence of the edge…but it is not the only way and not long term optimal approach for many.  If you are playing the long game…and by long game I mean lifelong pursuit of excellence in the professional arena…I believe there is more upside in an optimization strategy that checks the edge’s influence over day to day interaction.

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We Can Do Anything

Posted on December 4, 2012. Filed under: Hyperpublic, startups, venture capital |

I don’t know if surprised is the right word…because I’ve now done this enough times to know that nothing is surprising…but amazed certainly seems a fitting alternative.  Amazed that no matter how much things have changed since the last time I did this, some things…that you would think are contextual…are actually constants…each time I start something new…I think I know where I am as a person, I think I know what I have learned…I think I know what I know, I think I know what I care about and what I don’t, and what moves me, and how I want things to be…and I carry that concept of the way things are, quite confidently and assuredly…right up until the moment where I am standing on the diving board, toes hanging over the edge….visualizing my movement though the air, breaking the plane of the water, propelling myself underneath the surface, and ultimately reemerging again…and then, with  a jump…sure enough…it becomes clear that the view from the edge was distorted…and that there are certain dimensions to starting a company that…for lack of a better term…are simply water activated.

Today I am wet…I realize that sounds disgusting…but in the metaphor of diving into the pool, there is no other way to describe it.  That which laid dormant since we sold Hyperpublic to Groupon on February 17th…all which is water activated, seems to have emerged…for good and for bad…I say for good and for bad…because, which will be no surprise to you or anyone reading this blog, this process has inescapable joys and inescapable struggles…there is no “I sold my last company, so this time it will be ‘struggle light’…and there is no ‘I have done this a few times, so this time it won’t be as special’”…in fact…part of what’s special is interacting with and touching the struggles that are constants…the exhileration of a difficult task, the risk in putting yourself out there…the feeling of your heart leaping up into overdrive…inexplicably…when the calendar reminder tells you “10 minutes to game time.”  These are phenomena that no entrepreneur, independent of their past experiences and successes/failures, can…or even wants to…escape…these are the thrills and anxieties of being in the game…and it is a feeling more alive than I can describe.

I was talking to a friend yesterday who is not part of this world and he asked me to share with him “what is it?” “what is this feeling that has you jumping out of your seat?”…he literally couldn’t understand the speed of my energy and wanted me to articulate and share it with him…I thought for a moment, and really tried to isolate what it was that I was experiencing…and the only words I could find…which I think are the right words, were “We can do anything”

the belief and exploration and testing and celebration of this principle is at the core of my joy and why I love to start companies.

A note on team:  if you want to come on this journey…and explore this principle…if you’ve ever read this blog and thought “that dude would be cool to work with”…you are invited. Jordan.cooper@gmail.com…I speak from experience when I say it will be fulfilling and exciting and so so so hard…senior and junior, all skills…problems will be engineering and design intensive.  The bar is excellence…tough to join, once in, you will enjoy the company of people who share your aptitude, ambition, curiosity, ethics, and general dopeness.  If we do it right, you will not be the best on this team, but you will be on the best team…which is way more fun.

 

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Mobile Distribution Hack

Posted on November 19, 2012. Filed under: startups, venture capital |

So here’s what I was thinking about yesterday.  It is no secret that distribution in the mobile ecosystem is FUCKED.  I complain about it in tweets at least once a month.  No matter which way you slice it, getting people to download your app, even if your app is dope, is really freaking hard.  As was the case 24 months ago, today there are still very few channels by which you can acquire new customers.  The fact that “get featured in the app store” is the number one method for building a native user base is completely absurd. Even if you can get people to “share” in your app, a deep link into the app store just sucks. The drop off is huge. Signing in and installing something before a user gets any value is completely contrary to the way users have become accustomed to acting on the web.  It’s the equivalent of forcing registration in a web app before delivering any value to the user. Imagine if Yelp made you register before you got to read reviews on their site…just doesn’t work.  There is this big step in the funnel from when a user is exposed to a brand to when they commit to it that is simply missing from the native mobile ecosystem.  It’s so bad, that if I had a mobile app that I was trying to spread, I would drive recipients of any share experience to a web based UX where they could interact with my application in a non-native environment…I’d try to win them there…and then attempt to convert my web users to native mobile users down the line…

Anyway, these problems got me thinking…if everyone gets a small install base out of the gate, and then struggles to grow it organically or socially the way they would a web app, that must mean there are A TON of “walking dead” apps.  You’ve heard of “walking dead VC’s” that still exist and have a brand but don’t do anything and don’t die…”walking dead apps” are apps that have install bases of between 10,000 and 100,000 but no growth and declining engagement.  These apps will never be meaningful companies, will never make any money, and at some point I’d imagine they just disappear.  BUT, one thing walking dead apps have is a footprint…small but valuable real estate on a user’s phone.  Granted the user probably doesn’t engage with their app, but they probably haven’t deleted it either…so how much is that footprint worth?  Well…if apps like Groupon or Zynga are willing to pay $5 an install, that would mean a crappy app with 10K downloads is sitting on $50,000 in IOS real estate.  What if…theoretically, there were a way for GRPN to buy “crappy app” for $2 an installed user, replace crappy app client side code with GRPN client side code in an “update”, send an email or push from crappy app to userbase saying “crappy app is now GRPN, check out the app already on your phone”…and then GRPN converts some % of crappy app’s users to GRPN mobile installed users?  I realize the mechanics of this sound ugly…but if someone were to come along and buy lots of crappy apps, put them together in one network, build a large installed footprint, and then sell the real estate plus “services to facilitate and optimize transition/conversion” from crappy apps to “buyer’s apps” …that might be kind of interesting…or better yet, what if someone built a marketplace where crappy apps could list themselves, there install bases, their recent active user base, and there category…and buyers could come along and intead of buying ads inside mobile apps that drive to deep links, they could buy blocks of installed real estate on mobile devices…then crappy apps would have someplace to monetize their now worthless apps, which would lead to more apps being built, which would be good for the ecosystem and Apple actually, and successful apps would have a channel where they could spend $ to effectively acquire IOS real estate.  I realize there are tons of problems with this (Apple’s hissy fit being the primary)…but I’m interested in the idea of fledgling native apps selling installed real estate instead of adspace within their apps.  Give em’ a performance based kicker on successful transition of installed base to “buyer’s app,” unlock more value for those who have been punished by the distribution wall of death…just a rant born out of frustration with the state of the state

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on an inspired day

Posted on November 2, 2012. Filed under: startups, venture capital |

I sat on a stoop beneath a statue in a circle and read a note from a boy about to become founder.

I looked in his eye at the passion and hunger, I remembered the time I dove in myself.

I envied the pain that would come with his journey and listened as he spoke of what was ahead.

I cautioned and warned to make sure he was ready, and embraced his journey as though it was mine.

We sat in the sun and watched life for an hour, then parted to move into the future.

He boarded the subway, wrought with anticipation.

I boarded a treadmill to burn off my laze.

I thought of the question I always come back to, and let it simmer amidst the sea of perfect asses.

I walked into J crew, to replace soiled clothing. A refugee for a moment from minor inconvenience.

I have moved to all black, for it is more simple, and fashion was never my strength anyway.

I sit in the dark, screen glows in my face. The page was once blank, now covered in words

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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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