Archive for June, 2012

Rise Strange Thinkers, We Need YOU

Posted on June 25, 2012. Filed under: Uncategorized |

I don’t know how to say this any other way, but things just aren’t awesome.  This isn’t about bubbles, and it’s not about froth, it’s about people in our ecosystem moving at strange frequencies…it’s about healthy naïveté transforming into irrational confidence. It’s about founders not appreciating the risk and commitment of their chosen paths.  It’s about the look in an average founder’s eye, lacking the edge that keeps one’s game tight.  It’s about the fall of the letters CEO.  No longer something to be placed on a pedestal, revered and wondered at…CEO is the new “Analyst.”  It’s about the obvious thinkers…the ones who arrive at logical conclusions, the ones who think the same…getting into a game that used to be dominated by abnormal thinkers…it’s about a lack of soul searching…surface decisions driving surface thinkers into surface startups…it’s about nothing being new…me too…me too….me too…it’s about we’re different because we’re social…or you don’t understand we’re taking a traditional enterprise model and turning it on it’s head with…wait for it…a SAAS model…it’s about a new publishing platform…no a new publishing platform…no a new publishing platform…but this one is  DRAG AND DROP…don’t you see…you can change the font without going into a drop down menu…it’s about what YOUR FRIENDS LIKE…don’t you get it…it’s not just what YOU like…you can actually see what YOUR FRIENDS LIKE…and SHARE what you like with your friends…REALLY REALLY…the big difference is that you can SHARE not just with your FRIENDS…but with your FRIENDS OF FRIENDS…get it…it’s like…people you should probably care about more than strangers…even though you don’t know them…It’s about CURATION…it’s UNDERWEAR commerce but for GUYS…CURATED…get it…Guys wear underwear…call it commerce 2.0….No it’s Socks for GUYS…no it’s BASICS for guys…no it’s GLASSES for GUYS… No COSMETICS for GUYS…don’t you see, it’s been tried before…but this one is really for what GUYS WANT and what GUYS care about…and…it comes in a BOX…are we qualified to build it…HELL YEA we are…you know why? Because we just quit our jobs in professional services…and…WE’RE GUYS…so we know what GUYS want…It’s about increments on increments on increments…it’s about capital markets getting lazy…about capital markets suffering from this biggest clusterfuck of FOMO in the history of FOMO…it’s about “I don’t know if this is going to work or not…but fucking XYZ is investing prelaunch…so it’s now or never…and I don’t see anything better coming down the pipe…because if it’s not this me too, my next meeting is gonna be a me too too…so what am I really choosing between…it’s about the NOISE…frankly…things aren’t hard enough right now. it’s making everyone sloppy….sloppy thinking…sloppy investing…ambition light…image heavy…uninspired entrepreneurship…we are wading through a see of uninspired activity…searching…endlessly for that glimmer of ambition…that crazy look in a crazy founder’s eye…that says I would not last 4 seconds at Bain Consulting and I might have killed a turtle when I was 7 to see if reincarnation was real…where are you strange thinkers?  Where are you weirdo’s? For god’s sake, get weird.  Do different…PLEASE…the fate of our ecosystem rests in your hands…in your mind lives the step function we desperately need…inspire us

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Fuck Pride

Posted on June 13, 2012. Filed under: startups, venture capital |

About a month ago I was having lunch with my friend Michael Dearing at the Creamery in Palo Alto.  If you don’t know him and you are raising seed money…you should, he’s a very good dude and super accomplished.  I don’t remember how it came up (because MY MEMORY IS TERRIBLE), but I remember articulating to him that I was disappointed in myself for no longer “cold emailing” people that I admire.  When I was younger with little or no cred in startupland, I used to email anyone and everyone who I thought was cool.  I’d read an article about Elon Musk, craft a perfect email about why he HAD to meet with me, and then try every email combination known to man until I got through to his inbox.  It was a low percentage game, but I was so inspired by the achievements of others and I just wanted to be as close as possible to the biggest most accomplished entrepreneurs (and more generally people) I could find.  I’d send emails to Bill Clinton, Jay Z, Peter Thiel, it didn’t matter…it was just a game to me…all I wanted to do was sit down in the same room…pitch myself…not my idea…or my company (although sometimes I would)…but just myself…my entire goal was getting those amazing people to believe in me…to care about me…to be open to me the next time I would “need” them….if I’m really honest…I also wanted to see if I could hang…if I could keep up and if they recognized or saw me as a peer. How fast could I get the conversation to even…vs master/apprentice (although, I did appreciate the apprenticeship and was super respectful).  But something changed as I got more mature in this space…I had met enough people and worked with enough people…that even the superduper fancy people became more accessable…no longer was cold emailing the best route to these folks…people were generally one or two hops away, and I guess introductions became a bigger part of how I reached who I wanted to meet…but even still…these types of meetings…and frankly this type of reaching…really slowed down for me.  Maybe I became less wide-eyed as entrepreneurial “stars” revealed themselves as more human, or maybe I got too proud…

So anyway, I was sitting with Michael and I told him I was disappointed in myself for no longer cold-emailing people who inspire me…that maybe I was somehow embarrassed to do it because “I should be able to meet just about anyone now by relying on my friends and colleagues” or because “it’s entirely likely that I will meet the people I haven’t, and god forbid I would have subjugated myself to them via Gmail in advance” or some other stupid fucking reason that I got too proud to keep reaching…Michael sort of agreed with me, and so we both decided to cold email one person who really inspired us and ask for their time.  I had recently watched this Charlie Rose video with Jack Dorsey and was very moved by it…so I opened up my iphone and emailed him right on the spot (I actually had his Gmail from 5 years ago when I talked to him as a young associate at General Catalyst…trying to get into the round USV ended up leading….but for all intents and purposes…this was still a cold email and there’s no way he would remember me I don’t think).  Anyway, the text of my email was simple:

Subject: Hey dude

“I’d love to hang out with you sometime because you inspire me

somewhere along the way i stopped cold emailing people I admire, decided to change that today”

As I reread that right this second, it was actually sort of half assed relative to what I would have written 3 years ago…I should have referenced all our common connections and interests and provided more context for him to connect with…instead I thought my email signature with Hyperpublic and Lerer Ventures and my blog and twitter would suffice (again, maybe a victim of my own pride)…but it really wasn’t as much about getting the meeting as it was about the act of reaching…

Last night I got a note from Michael:

Subject: what ever happened?

From your Jack email. Mine to XXX XXXX went unanswered. 🙂

I sort of smiled to myself, thought for a minute, and wrote back:

“Unanswered as well. But I think we got more out of that rejection than we would have had they responded…that was kind of the point. Put ourselves in a position to be humbled…”

In summary: Fuck pride

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This Desk

Posted on June 11, 2012. Filed under: Hyperpublic, startups, venture capital |

This desk. I am so grateful for this desk. It is glass and large and clean. It lives in a giant loft with beautiful art work, air conditioning, cold filtered water, and a conference room.  It shares space with bright people, motivated to make progress, driven by a need to feel as though they are accomplishing. It represents a home away from home, consistency, structure and purpose.  But more, it represents belief…belief that I am, in fact, the best owner of this desk…it was given to me, first, at a time when that was not clear…not obvious…by a man who had an extra desk…I was living in a tiny apartment in Brooklyn…with no air conditioning…and not a lot of momentum…every morning I would wake up…strap my computer to my back…and head out to a café to claw my way forward…sitting amongst a mix of lackadaisical unemployed web surfers and hardened coffee shop warriors.  Fighting for the corner seat with a plug, or the couch opposite the beautiful girl had it’s moments, but I longed to move beyond a “desk” that existed only in the company of a mandatory coffee or cookie purchase.

Then, one day…I went to interview for a desk at Polaris’ Dogpatch Labs.  I sat down in a group of 6 or so young founders…all struggling to break free of the “coffee shop” stage of entrepreneurship…and explained to the then-reigning Jon Steinberg how I didn’t have a cofounder or a product or any money but regardless was most worthy of a spot that would bring me into a more legitimate phase of my business.  He rejected me. Trips to the coffee shop started to get more frustrating…my back started to hurt from the shitty chairs and hunched over couch computing…regardless my business was making progress…slowly but surely.

Around the same time I visited Kenny in his office in the Meatpacking district…I’m not sure if he could tell how run down I was or not (I had about $1000 left in my bank account and had basically stopped going out to dinner, or movies, or any of the discretionary “luxuries” of life) but he didn’t seem phased by my messy hair and unshaved countenance.  I would have worked for free…just to have a desk…a nice glass desk…in an open loft…with bright people…motivated to make progress…but then it was agreed…I would start investing with him and Benji…and build my company out of his space…and be a real partner…and say goodbye to the pretty girl on the couch….and just in time…I popped into a different sphere of operation…no longer at risk.  I love this desk…while meant for sitting….it gave me something firm to stand on.

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Lessons from my Psychedelic Barber

Posted on June 7, 2012. Filed under: startups, venture capital |

Yesterday I got a haircut from a new barber.  Kenny doesn’t believe me and says I look like an insane professor, but it’s true…I did.  Conversation with the dude who’s cutting my hair typically makes me pretty uncomfortable…I’m always reaching…I’m terrible at small talk…how much eye contact do I need to make?  Is eye contact through the mirror satisfactory or do I need to crank my neck every once in a while? Usually I end up silently nodding my head as the dude riffs on leftist ideals or the importance of the arts over business…but yesterday was a bit different…and weirder.

Somehow in the first 5 minutes of conversation, we arrived (not by my doing) at the merits of psychedelic drugs…for the first few minutes on this topic I thought to myself “great, my barber is a burnout…glad he’s got a straight razor to my neck…” but then he said something that made me pause: he said “it baffles me how most people go through life not even trying to tap into the brain…that’s where everything is happening…and most people don’t even try to explore it.”  Granted…there are many different ways to explore the brain…beyond mind altering drugs (i.e. meditation)…but there was something intriguing about this spirit…it was suggestive of a non-software based incarnation of hacking culture…a culture pervasive in technology and startupland that to date hasn’t really reached the massive processor that is powering human experience…I think about all the experimentation that occurs on machine processors…how we poke at the limits of what a computer can do…experiment on the edges…to unlock previously hidden value or possibilities…and I wonder if my psychedelic barber isn’t just a different type of hacker…his curiosity around the experiences that his brain creates/experiences was very similar to a sentiment that runs through our engineering community…which leads me to wonder…how far am I pushing my brain?  What can it do that I don’t know yet?  How do I really “open up the engine” and experience it’s full potential?  I don’t think I’m scheduling my barber’s recommended voyage to the Mayan jungle for a Shaman guided 7 day psychedelic trip…but I am going to start looking for other forms of experimentation on this “hardware” in my head…in some ways I think the quantified self if a form of measurement/scrutiny of this subject, that when coupled with corrective/transformative actions (my friend Andrew Kortina would call this hacking your brain) is a step in this bio-explorative direction…but generally speaking…we are pretty passively consuming or accepting the “applications” of our minds….perhaps it’s time to be more proactive…what can this thing do beyond what I am using it for is a question I will now ask myself every day.

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How to get out of tight spots

Posted on June 1, 2012. Filed under: startups, venture capital |

Yesterday I caught up with an entrepreneur who is in a pretty tight spot…typically when faced with a problem or issue…I like to cycle through every possible move and then pick the one that has the highest probability of solving the problem at hand.  Usually there are 2 or 3 directions that seem viable and 2 or 3 that we can immediately throw out just by looking forward and playing out how all parties will respond to a decision…In this type of analysis I am rarely looking for a perfect solution or certainty…I don’t need to know for sure that a decision will solve the problem…just that it is the best of the available options…

Occasionally…however…a spot is so tight that none of the 6 options appear to have a high probability of success…it is very difficult to look at 6 alternatives, recognize that the best route is still only 15% likely to solve the problem…and still lean into that decision…but that is EXACTLY what you have to do as an entrepreneur…it is one thing to look for a 7th option…and sure…we can spend a few cycles trying to find it…but usually that which is not immediately apparent does not exist…it’s sort of like holding a crappy set of letters in scrabble…you can stare at the tiles for 10 minutes before you make your move…looking for that 40 point word that is going to get you back in the game on this hand…but the fastest way to a change is to play through the crap letters…make your 10 point word that doesn’t seem to help…but in doing so get yourself to a new context and a new set of letters…that present an option that is more attractive.

Our instinct when faced with 6 alternatives that seem unappealing is to freeze…not choose any because none seem forward moving…and we only want to move forward…but the reality is…something is going to happen if you make a decision…tomorrow or next week is going to look different than today…the tiles will shuffle…new words will appear…today’s decision is not your last decision…just a means to the next decision…when faced with 6 shitty routes…choose the least shitty…actively…lean into it as hard as you would a 95% solution…and wait for new words to emerge…they always do…companies only die when you stop reaching into the bag for new letters

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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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