Archive for May, 2012

7 things I’m thinking about now and an invitation for computer scientists

Posted on May 30, 2012. Filed under: Uncategorized |

This has been an interesting few months…after we sold Hyperpublic to Groupon, my calendar freed up pretty quickly…I had more time than I knew what to do with…I think I invested in 4 or 5 companies through Lerer Ventures, and spent a few months in San Francisco hanging out with our west coast portfolio companies and friends that we don’t get to see as much…but for the most part I just recovered…when people asked me what I was doing, my typical answer was “healing”…which is true…you don’t realize how much physical and mental damage you endure as a startup founder until you are abruptly pulled out of the fray…

Last week I moved back to New York City.  I did enjoy the hiking and biking and reading and general calm of SF…but “relaxation” is not a comfortable state for me…during that time I kicked my lens out really far…read about things that won’t have an actionable application for 10-30 years, and generally looked at the world from afar (which is not something you get to do operating a company and living in “execution mode”)…I am done looking far out for a while…and am starting to reign it back in to some sort of actionable focal length…actually, to this day…focal length of vision is an area that is hard to get my arms around…with Hyperpublic, while we had really interesting thoughts about what we could grow into, we built something that had a pretty short time to maturity and market value…as I think about new projects, I am pushing to extend that vision and time to maturity by 3-5 years…but timing markets/trend/consumer curves is always a bit of a moving target…

Anyway, now is a pretty creative period for me…most of my thinking has been pretty insular and self-directed…but I’m ready to start thinking collectively again…and bouncing some things off other people…one thing I learned over the past two years at Hyperpublic is that I get the most value out of thinking and ideating with engineers…we were a 10 person company with 9 engineers and although I didn’t write a line of code at HP, our lead engineer, Eric Tang, recently described me as “conceptually technical”…which is a phrase that I definitely identify with…when I think about products, I don’t have a visual mind…I have a reasonable intuition around experience but not good enough to drive product/ux of a consumer application…when I think about product in my head I tend to see the plumbing…I visualize the back end…the api connections…the data structures…the algorithmic logic…etc…and it just happens that most frictionless conversation around these topics happens with engineers…

I am fortunate to have a lot of really creative engineers in my life, but sadly…many of them are now 3000 miles away from me in Palo Alto…so I’d like to build a new “study group” if you will…no agenda…come with your ideas, whatever you’ve been thinking about…happy to riff on it, help define it…talk about market potential…steps from here to there…I’m not looking for investment pitches…just creative thinking and some new people to think with.  For ease, I have cleared my entire schedule next week in New York.  If you are a computer scientist or data scientist and want to shoot the shit or just say hi…I have  open office hours in Soho from 10:00AM – 6:00PM every day.  Just mail with “day and time request” in the subject line…if you want to include a sentence about your background/interests/side projects etc…that’d be cool. Word

**Some themes I’ve been thinking about**

1)   the interface layer between hardware/software and users

2)   new applications of personal data exhaust

3)   creative input mechanisms for non-sensor based information

4)   wearable technology

5)   intracorporeal (in body) hardware/software/sensor solutions

6)   non-healthcare applications of physiological information

7)   interfaceless software applications

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the bizarre social currency behind “hearts” and “likes”

Posted on May 10, 2012. Filed under: Uncategorized |

Why do I “heart” some photos and not others? Why am i sparing? I know it will make the photographer feel good. it subtly strengthens my relationship with them. it doesn’t cost me anything…but why when I scroll through 10 photos on Instagram will i only “give out” one heart? Am I worried about being perceived as “loose” or “easy” with my hearts? Do I think they’ll have less positive impact or perceived value by my graph if I “heart” too much? Does what I heart say something about me to my graph? Do i want the publisher/content creator to appreciate my taste, think of me as discerning, or maybe I just want to have power and be judgmental…and dole out accolades only as I please…only when I feel like a piece of content or a photo is worthy…maybe it’s just about me and holding even the slightest modicum of authority over my friends and acquaintences…I spend my “likes” and my “hearts” like a spend money…only where i see fit, only when I see value…and what I spend it on says something about me and also says something to the recipient of that value…but if i spent money on everything I would be wasteful…and I don’t want to be wasteful with my social accolades…because they will lose their value from every dimension…so no…that awesome puppy you just published to instagram??? i’m not gonna heart it…because I hearted your sunset yesterday…and i’m not that easy

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Fix your own fucking printer (a non-tech founder’s guide to starting up)

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

I’ve spent 4 years going from non-technical founder/CEO to reasonably technical founder/CEO…along the way I learned a ton of “business guy don’ts” that are common mistakes non-technical founders make that hurt engineering culture.  Here are some of the biggies to avoid:

1)   Don’t ask how long something is going to take to build. Just because you don’t understand the scope of the feature or build for which you are advocating doesn’t mean you are exonerated for your ignorance.  You have to make an effort to get better at understanding the scope and challenges of software development even if you’re not programming yourself.  Instead of asking how long something will take (which teaches you almost nothing), ask how hard something is to build and where the challenges are.  Listen to the answer, understand which components are unknowns and which are easy plugins.  It’s so disrespectful not to invest the minimal energy required to start answering your own questions…and you will suck as a CEO or founder if you can’t get a grip on the pace and predictability of your product cycles.

2)   Don’t ask your engineering team to help you set up email on your iphone.  Just because you don’t want to put the effort into googling “how do I set up exchange on my iphone” doesn’t mean it’s ok to ask your engineers to do it for you.  Again, totally disrepsectful…these people on your team are Stanford educated computer scientists, not IT guys…one, it’s disrespectful of their time and two (and more importantly) it shows a lack of willingness to make yourself (even slightly) more technically competent than you are…just because you didn’t study C.S. doesn’t mean you get a “freebe” when it comes to anything with an on/off switch.

3)   Don’t spit out every single product idea or feature idea you had on the walk to work during your morning standup. It’s great that you’re creative and thinking toward the future, but you’re engineering team has a very full plate all the time…each cool idea you have represents serious time and effort from the team…there can be a feeling of “we are already overwhelmed, you’re not appreciating the challenges of what we’re working on right now.”  Very important to communicate what we’re building toward and to have an open dialogue about new ideas and directions, but how and when you present that information as well as how clearly you indicate importance and where in the roadmap these new ideas lie is super important to be mindful of.

4)   Recognize and celebrate the wins (even if they aren’t customer facing).  This can’t be bullshit…it’s not just “oh, today we say good job because you’ve been working so hard)….actually understand what the hell people are grinding on day in and day out…if someone has been working on deduplication for the past month…what are the metrics that we’re measuring progress based on…how are we doing, what’s good and what’s great? What are the approaches that others have used? Where’s our innovation? Did we do something smarter than state of the art?  Understanding the build with this level of intimacy allows you to know where special things happen on the engineering side.  When they do, we stop and show appreciation and respect.  The sales guy who brings in $100K gets celebrated all the time because everyone at the company can comprehend his contribution…it is essential that everyone at the company understand the contributions of our engineers.

5)   Minimize interruptions.  Control yourself when you have ideas or questions that you want to discuss with your engineering team…just because you just thought of something cool, doesn’t mean it’s the right time to tap an engineer on the shoulder…not every engineer is the same, but many appreciate uninterrupted time to get through a challenge or problem…wait until the headphones are off or you are walking to lunch to discuss whatever you wanted to…tap an engineer on the shoulder every 30 minutes while their editor is open and you will officially be the worst person in the world

6)   Don’t fake the funk.  Pretending you understand things that you don’t is the worst.  Don’t sit down with a new recruit and talk about the awesome technical challenges associated with your product if you have no fucking idea what they are and why they are interesting…just saying “obviously was have some awesome big data challenges” rings incredibly hollow if you don’t even know your own stack and what challenges your engineering team is actually tackling…let your engineers speak about what’s interesting technically. “I’ll let our VP Engineering tell you about all the interesting work we are doing” rings a lot more true than your BS attempt to check the recruiting box of “engineers are attracted to hard problems, show them your product presents interesting challenges.”  Further, the quality of your engineering team will sell itself…know where your competencies begin and end and be ready and wiling to defer where appropriate.  That demonstrates a healthy working relationship between tech and non-tech as well.  That chemistry is perceptible and a positive to outsiders if you can show you have developed it.

7)   Fix your own fucking printer

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Why Facebook really bought Instagram

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

NOTE: this is pure speculation, but I haven’t really heard this angle or read it anywhere, so I thought I’d take a crack (Fbook employees feel free to crush any/all of these assumptions):

A few weeks ago, I had a long talk with a smart investor and blogger about Facebook.  He expressed a concern that Facebook was losing it’s intimacy, that the user no longer had the emotional connection to Facebook’s product that was once so central to it’s experience.  He contrasted the current Fbook user experience to some smaller apps that he loved, and for sure he was right…my response, however, was that I don’t think this loss of intimacy is a problem…rather I think it is quite intentional…the reason?  Because Facebook is a piece of infrastructure, and no longer a consumer application at it’s core.  Facebook Connect and the graph have pushed the company downstack to a much more valuable and defensible position on the web…one where they are the broker of basically the entire online population’s personal and social information.  They are plumbing, a point of connection for 3rd party applications and publishers to better understand users and customize experience as well as optimize revenue outside of the Facebook application.  In Facebook’s push to this layer, they executed flawlessly…they became not just the platform, but the operating system for the social web…you cannot build a product today without connecting it to “the graph” and Facebook has the most comprehensive graph in the market.  It seemed that this infrastructural path was the future of the company, which I believe it is for sure, but then something weird happened…about a year ago, Facebook and Spotify unveiled an INCREDIBLY deep integration…all of these “connected publishers” were doing well on the platform, but then…somehow…Spotify secured this unprecedented real estate inside the Facebook application…It was the first  attempt to push back up stack to relevancy at the consumer application layer that I had seen in a very long time…why?  Why did it all of the sudden matter if users were interacting heavily inside Facebook as opposed to inside 3rd party environments?  Was it the ad revenue?  Doubt it…I think Facebook may have realized that their “graph data” was getting stale…that it didn’t matter to me anymore if my Facebook graph/friend group was current, because the consumer app was declining in value relative to individual vertical Fbook connected applications…but if only 70% of my real graph was represented in my Facebook graph than their value at the more interesting “infrastructure layer” would decline…So Spotify gave me a new reason to keep my Facebook graph current…for the first time in a long time…I started friending people again…because I wanted to listen to their music…

BUT…why did it take music to reengage me with the Facebook app…what had gone away that used to be so fulfilling?  I’ll tell you what…PHOTOS…where were all the photos in my stream…yes mixed in with an increasing amount of noise from 3rd party apps publishing to my stream (facebook, afterall, had to promise distribution to connected apps…and where better to offer hope than the stream)…but I have a theory that the avg number of photos per user was on steady decline…what’s the change?  Why did people upload less photos than before?  The answer lies in the death of the point and shoot camera.  It used to be when I took digital photos, I would do it on a Sony Cybershot or something like that, then use the desktop software that came with the camera to get the photos off the camera and onto my PC.  Once there, I could upload from my PC to the web easily, and that’s how photos got into Facebook.  But as Facebook grew, so did smartphone penetration…all of the sudden, people were taking photos on their phones and not on their point and shoots…and guess what?  They stopped downloading those photos to PC…so volume of photos going into the top of the FBook photo funnel starts to decline, and at the same time, not only are these smartphone photographers not uploading to PC…but because they were on connected devices…they started to upload directly to the cloud from their phone…and Facebook did not have a mobile UX that was oriented around photo capture and publishing…it was primarily a consumptive experience…Enter Instragram…all those photos taken with the native device, now pushed directly to the cloud, via mobile first experience optimized to steal users photos away from Fbook…and those photos never reached Facebook…So why did Facebook buy instragram…graph freshness…they need the consumer app to matter again because they can’t afford a stale graph…my guess is that we will see a Spotify-esque integration and INstagram will start repopulating Facebook’s consumer application with the the photos it was missing…Instagram = supply of photos = reengaged facebook app user = freshest most comprehensive graph on the web = MSFT like infrastructural position in the web ecosystem…and this @cdixon, is why I think MSFT is better comp that LNKD for public market in valuing Fbook…cc @om

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In Pursuit of “Brain Doppelgangers”

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

Every once in a while I run into someone in this business who’s brain works exactly the same way as mine.  It’s not the norm, or even close to it, but when it happens, it is an incredibly refreshing experience.  I tend to think in abstractions and rules.  999 out of 1000 times when I meet someone I need to hold back on speaking the way that I think.  Most people don’t like to digest information in that format, so I end up translating my thoughts into whatever framework the other person is speaking in.  Some people see the world through consumer experience, or user’s feelings.  Others see the math and the numbers, others the simplicity or essence of an opportunity…I learn from those people, and we make progress as a pair or group…it’s become so common that I almost forget that the framework we are pushing forward in is really a second language to me…

But then, one in a thousand times, I sit down with someone who speaks in principles and rules.  I like it when people string together conclusions as opposed to descriptions…state the inputs, agree on the conclusion based on known business/economic principles, and string conclusion into conclusion until we arrive at some place deep in the future that seems pretty sound.  Back into the 1 or 2 unknown assumptions we made and then say “if this one thing is correct, we’re pretty sure things are going to land here.”

Yesterday I went up to Dartmouth for the day and met with a founder who’s brain worked the same way as mine.  Every sentence that he said followed the exact order in which I would have structured my thinking around his space, and the conversation was basically a bunch of half finished sentences where he’d start, I’d say “yup” and we’d move on to the next thought…I don’t know exactly what type of relationship I want with this guy…I don’t love what he is working on…the single major assumption in his analysis I believe is false…but there must be some efficiency to working with a guy with whom we can both speak in our first language with absolutely no translation.  The rate of progress and information flow was way faster than most discussions…

I don’t think surrounding yourself with like-minds is necessarily the right approach to making progress, but I am definitely going to try to allocate a distinct portion of my time to finding more “brain doppelgangers.”  Truly a weird and awesome connection when you can find it.

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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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