A Sonic Boom

On Monday, Spotify publicly announced the launch of Discover Weekly, taking out of private beta their signature effort in personalized playlists. After a few days of listening to my playlist, I have to say it’s outstanding. The thirty song playlist, updated every week, is exactly what I most want and stress over in music exploration – artists and tracks that I will like, ideally that I haven’t come across yet, that match a particular moment in my musical taste. 

Spotify drew on a methodical human-machine blend of content and user analysis to achieve what feels like a massive leap in recommendation engine efficacy. The platform’s internal Truffle Pig database and search engine slices and dices every song into each machine-tagged data point or human-input characteristic possible (i.e. ‘1970s Jam Band’ or ‘turns your knees to jelly’). With this degree of specificity, machines and humans then monitor user interaction and listening behavior - from all 75 million users, within groups of users like yourself, and down to your own track by track habits – and creates a playlist not just of music that matches what you’ve listened to but more appropriately what you would want to hear next or more of. The analysis goes as far as eliminating serious outliers to your known tastes (for me: Katy Perry, Dark Horse). Basically the recommendation gets smarter every month. Wired published a great piece exploring Spotify’s perfect playlist here. 

Music may well be the cultural cog and unit of Internet consumption that we are the most picky about. We want what we think we want, although sometimes we don’t know what that is, but we always want it right away. Usage analysis + machine learning = dynamic recommendation has long been the equation in sales pitches and marketing splash pages for streaming services as well as many other online publishing and commerce companies. Until Monday, none of them were sophisticated enough to capture the fine line of accurate individual recommendation consistently. 

With the exception of the person who creates it, everyone discovers anything new from some direct or indirect recommendation. A frustrating state of things online is that as users of every platform on the web, we’ve been putting ourselves – what we like, what we don’t - out there in a clear, measurable way for the better part of a decade. Yet most recommendation engines, which should lead each of us down Internet Interstate ‘Me’, don’t go much further then matching against a set of recurring keywords or purchase history. 

A few services that would benefit from exploring Spotify’s recommendation strategy: 

• Any RSS feed aggregator and just about every major media publisher, old and new. 

• Other streaming media services – despite detailed data, Netflix reccs are too rigid. 

• Retail / Apparel – especially any large marketplace or e-comm. brand with more than 100 SKUs. Granted not as much data exists per customer. Services like Scratch, a NextView portfolio company, are initiating with a 100% human recommendation to jumpstart user interest data in gifts, home goods and apparel. 

• Twitter – the service recommends followers when a new account is created based on user inputs during sign-up but the service should have troves of information on who users elect to follow thereafter, types of accounts they interact with etc. 

• Facebook – the newsfeed could reflect a much more personalized stream of things I genuinely want to know, see or read as opposed to mindless click-bait. 

• Local Places, Events – Songkick, Yelp, Foursquare et al. could have extremely accurate ‘recommended’ lists available to all regular users that push to lock screens when someone is near a recommended place. Past 4Sq attempts at this have been piecemeal and spotty.  

The problem with lookalike recommendations is that we don’t often want the next closest thing to what we’ve just read or recently purchased. With Discover Weekly, Spotify is approaching a sophistication that’s anticipating and encouraging the expansion of one’s taste. One foot out the door of our consumptive comfort zone: similar but not the same.

Joining Nextview

Since I graduated from college, I’ve been drawn to early stage venture investing. I can’t say it was because I studied the asset class or had any financial training whatsoever. I’ve been drawn to two attributes that have always stood as genuine and unique to the field. First, that venture existed at a profound intersection: that of Art & Science, Design & Data, Innovation & its Funding. My mind is an amorphous jumble but this duality is what does shape it. There’s very little more powerful and stimulating than when two of the essential forces for creation and existence - paintbrush and calculator - collide. 

The second is something I’ve learned from Jordan as a measure to live life by: the ability to have an impact. To me, done sincerely, consistently and in earnest, the portfolio model provides a profound opportunity for an individual to have an impact across all of the companies in which they’ve invested. I say sincerely as I believe there is a low bar to actually delivering here. But, done right, venture investing is unmatched in impact potential. 

Today I’m thrilled to say that I’m joining NextView Ventures as their New York-based Principal and first New York investor for the fund. Rob, Lee, Dave, and Jay have built a fantastic fund and presence in Boston as well as SF and NY via the portfolio through focus - leading seed investments - and consistently delivering for the startups they’ve invested in. I’m humbled and thrilled that they’ve asked me to help bring their culture, discipline, and focus to New York. 

I have to thank an entire city, two schools, and incredible ocean of individuals for getting me to this point. I only hope I can repay the kindness, guidance and support you’ve shown by doing venture the right way, which will be a constant work in progress. And by taking everyone who’s had an impact on my career to this point for lunch or coffee or breakfast or dinner, which is what I’ll be spending the next few weeks doing as I ramp up to starting with NextView early this summer. 

A Platinum Age of Radio

In 2007, I started listening to a podcast purely for its utility. I’m terrible at falling asleep so Bill Simmons’ B.S. Report on ESPN was the perfect combination of Simmons’ nasal voice and vaguely interesting sports subjects to lull me to sleep. Seven years later, podcasts are a daily education and entertainment during my waking hours, competing with music when I’m on the move and when I’m not. So are podcasts back? No. Marco is right, podcasts have been around for a decade, their popularity growing very slowly. But they are having a pivotal moment. Progressing from fringe entertainment to established media class, the podcast continues to mature into the modern tech manifestation of radio. 

See: Serial, The Radiotopia collective, ESPN’s network esp. Grantland, This American Life, RadioLab, Gimlet, Earwolf, Welcome To Nightvale and the 6-11% growth since 2006 in percentage of adults in the U.S. who are monthly listeners depending on who you ask.

Aside from popular titles, radio’s straight evolutionary line into podcast can be traced along a path laid by the internet and trod by print and video before it.  A path that reimagines a media’s packaging presentation, delivery, consumption and content. With print publishing, we read what we were delivered every morning: the news that’s fit to print. The fit represented a one-way funnel of information sharing and one-to-many relationship between publishers and their audience. Everyone read the same stuff, controlled and filtered ahead of time. And then… the internet. With cable television, we watched what was shown to us every evening: nightly news, sitcoms. All were media highly programmed by broadcasters and consumed passively and regularly for a few hours every night. Everyone saw basically the same shows within a cable bundle. And then…the internet. Enter the web and humans devoted less time to the printed page, cable TV, and the movie theater as passive consumers become active participants in choosing what, when and how they consume. Today, niché networks abound for every interest, programs and content are all on-demand, wifi and mobile proliferation enable consumption on the go. Thanks to the internet. 

Radio was the unit of media the internet hadn’t given back to us in a shiny new model because the traditional version seemed to work fine on the web. Broadcast radio streams at relatively low cost and it was inherently ‘mobile’ given the ubiquity of in-car stereos. So radio was carbon copied to sections of websites where you could stream from a browser, extending known audience listening power to computers but no true innovation. This industry is inclined to idealize what’s next. We think in fast forward about new mediums and models, staring from the bleeding edge into the unknown where we paint the future. In media, we’ve moved with fervor from text and video into the expansive possibilities of virtual and augmented reality. I’m all for it, but we can be blind to notion that technology can continue to transform traditional media. It may have taken longer, but the internet has developed and begun to mature its version of radio, the podcast: niché, on-demand, high-quality, low-friction.

Below are some thoughts on what’s contributed to the rise: 

Voice as Media - the recent trend of Voice technology as function, efficiency and enjoyment finds a powerful entertainment outlet in the podcast which generally takes one of two vocal formats: conversation or storytelling. For all of human existence, we’ve had a desire hear stories and increasingly we’ve displayed interest in listening to conversations that appeal to us. The podcast is the power of storytelling and conversation in its rawest form.

On-Demand - Touched on earlier, with every episode available across platforms at any time, a power listener can enjoy a new show for hours while the new listener can try out a single episode anytime. Traditional and internet radio didn’t provide this open flexibility and so lost the opportunity for different types of listeners to emerge, growing the overall audience. In certain ways, you can argue that the content of radio hasn’t changed in decades, people listened to detective stories and murder mysterious on AM radio before television. What change was listener preference for a new type of packaging and delivery of radio. We still love compelling narrative, we just want it on our time and in formats that fit our lives. 

Shorter Episodes - Very few podcasts are more then 45 minutes and most successful shows run between 18 and 30 minutes. The content is short enough to fit into a variety of slots during someone’s day, it doesn’t have to wait for a free hour in the evening. Audiences are also left wanting more which leads to binge listening or at the very least a regular, dedicated listener base.

Production Quality - From interview style shows to stylized weave narratives, podcast quality has come along way. While its a more open form of media for creators currently, moving from two guys and mic into a full production staff has meant an inevitable improvement in the content itself. 

And a few more thoughts on what the podcast can become: 

Its Malleable - Chris Dixon wrote that the podcast is in its infancy and so its not clear how to do it 'right’ yet which is exciting. I agree. Successful forms have emerged but I suspect many more to come. Consider what can be done with genres like fiction, documentary, travel, youth, and education as well as forms like surprise endings and surprise participants. As yet undiscovered new voices will emerge as platforms like SoundCloud allow anyone to try. Podcast advertising, which employs traditional media’s separatist model while allowing hosts artistic freedom in ad presentation, underscores how much creative unknown remains for podcast structure and production. 

An Open Media and The Network - A product of its malleability, podcasting wide-open right now. Products like Raur are leveling the playing field to accommodate democratized creation. This is fantastic but likely won’t last forever. The best rise to the top. For podcasts, that will reflect in dedicated listenership and downloads. That may also reflect in the creation of networks of successful shows that cross-promote and can facilitate better revenue opportunities across a collection of podcasts. Gimlet, Midroll, and Radiotopia are early varieties of these networks.  

Listening and the Multi-tasker - The potential listening market for podcasts is not just the commuter. There are without a doubt unrealized listening hours in the commute, but an even larger market exists in the office worker with headphones in. The podcast may be the only media aside from music that can be consumed while doing other things. Mundane tasks at work for example. Many podcasts require less direct concentration then other forms of media. I would be shocked if the listenership for popular podcasts didn't grow significantly during working hours in the coming years. Furthermore, cooking, cleaning and other home tasks now have an entertainment companion that isn’t restricted to a screen or text. This may be where podcasts discover an entirely new audience. 

—-

I’ve not talked about Serial on purpose because I don’t believe its the only reason we should be paying attention to podcasts nor the only model for success. I will say I’m obsessed with the show and the team behind it has broken new ground. Serial demonstrates that with fantastic content and highly stylized editing, there’s a ravenous audience for the medium. The number of times that I’ve heard friends mistakenly say that they watched the last episode of Serial is a testament to its production quality and narrative intrigue. While Serial is not the crowning achievement of podcasting, this type of paradigm shift requires two things: a gradual groundswell of support and a spark that leads to the new form taking a lasting hold. Its entirely possible that Sarah Koenig has lit the fuse.  

**A special thanks to Nick for helping me through all of the above. If you haven’t subscribed to his Hot Pod podcast newsletter, you should!

The World After Apps: 99% Invisible

A few months ago, a notice appeared on the door into our apartment building. Our management company would be replacing our old-fashioned entryway buzz-to-enter system with a video-touchscreen in the entryway and an app for every resident so they can see and buzz-in anyone, directly from their phones. I cried for several months while they installed it and we had no buzzer at all and every day since as the app never works and we have to go down to open the building door. That our archaic apartment manager decided to go all mobile-first on us and failed is the latest example of what’s beginning to feel like app saturation. Over past 3-4 years, every company decided that they needed an app interface in order to remain relevant in a mobile world; fast-forward to today and it’s clear that they do not.

Arriving at an app for everything moment stems from exponential mobile use – the average person checks their phone 150 times per day - and app downloads per smart phone user – 35% annual growth - since 2012. The average smartphone user has 41 apps on their phone. FORTY-ONE!!! That may not seem crazy to our industry’s rabid beta testers but honestly how many television channels and credit cards do you think the average person uses in a given day? That number is nowhere close to 41. Unfortunately, the phone’s layout and ease of access to such a variety of applications on them encourages time management, focus and efficiency to fall prey to mindless, mobile distraction. The application layer has made access to everything we like, do or engage with universal. We’re only human after all, so given a choice between immediately answering an urgent work email when we’re two thumb taps away from a hilarious snapchat story, it’s not even a choice.

With a seamless flow from app to app and the proliferation of apps on our phones, its clear our #homescreen is not sustainable as the default UI and access point to internet services, experiences and communication. New apps will inevitably see a diminishing return as they compete for usage and mindshare. Sensory and focal elements of the human brain do not subscribe to Moore’s Law, the lasting interaction model in mobile remains to be determined.

Here are few types of apps prevalent today that we probably don’t need or use nearly enough to justify downloading: 

Banking-Transaction apps – transactions can be facilitated and recorded by blockchains, confirmed via Apple Pay et al and displayed in a push notification. No need for BOFA and Amex and Citi and TD Ameritrade and Venmo and PayPal apps.

Corporate Apps #1   – airline apps are phenomenal when traveling and useless when not. The same generally goes for live events and ticketing apps. Beacons and/or RFID should be able to confirm flights and check users in when they arrive an airport and boarding passes should be sent through push. Better yet, beacons can again check someone into the gate and you never take your phone out at the airport again.

Corporate Apps #2 – There are many companies who’s core services or products do not translate to the application layer. Coca Cola has over 20 standalone apps in the app store as well as a main Coca Cola app with international versions translated into 15+ languages. There are more effective and direct ways for them to advertise and, judging from their app reviews, these corporations’ app downloads are almost negligible. 

And so, in a world of ghost apps and Instagram holes, where do we go next? Perhaps to keyboards, messaging, push notifications, blockchains and beacons. Messaging, in the traditional SMS flow, as well as in the form of the notifications powered by pushing to locked-out screen, is a potential solution to app overload and an innovative step in how mobile technology transmits information and facilitates communication. One-to-one text messaging caught due to its simplicity, ubiquity, and efficiency. Texting can be both real-time and asynchronous, it carries much less of the emotional and psychological friction of phone calls, and easily expands to group chats. 

Scheduling and commerce are two areas that stand to be improved by the efficiency and comfort of messaging.  As a platform, messaging has built-in engagement, via push, and built-in distribution, via keyboards, that can’t be ignored. If open-sourced, messaging could be the initial interaction for then completing more complex actions faster. Services like Drizzy and the GIF keyboard are sending content directly into text. Stefan’s Head and Text Rexfrom The Infatuation provide real-time commerce and restaurant reccs in your SMS stream. Yo, Hooks, IFTTT, and Sunrise allow push notifications and the locked-out screen to eliminate the need to dive back into your crowded app screens to process an update or facilitate quick communication. 

A mobile experience building towards one-touch interactions that reduces multiple steps and any redundancies is coming. We will interact quickly with our devices, not sinking into them but gaining informational or entertainment benefit and moving back into the physical world. The Apple Watch is a strong step in this direction. 

99% Invisible is a phrase borrowed from a tremendous podcast of the same name, a narrative show about the unseen and overlooked aspects design. The name comes from a quote by renowned design intellect Buckminster Fuller who said that 99% of who we are is invisible and untouchable. The quote has evolved into a notion that some of the very best design is barely noticed by those that experience it. Near perfect design is so seamless, engaging or obvious that its not seen as design at all. The same may eventually be said of some technologies, perhaps the mobile interaction model. If blockchains and beacons, SMS and push notifications can move us past the app, we may approach a period in mobile tech that’s not defined by a new product or service but just a unique experience we have as a mobile user. 

****

I’m aware that many of the ideas for mobile improvement suggested above would still depend on an app as a starting point for data and interaction (most push notifications for example). Hopefully this becomes a post or conversation for another time focused on what could generate notifications or messages on mobile outside of applications. 

Organized To Share

For the first half the 20th century in the U.S., generations of individuals had a singular model for organization, drawn from a seminal structure of their time: the military. From the World War drafts through Vietnam, the military often elicited widespread participation from a significant majority of American men and women. The scope and power of the military machine during those decades and its omnipresence in the lives of those who served and their families made it a natural model for future enterprises. From enlisted soldiers to high-ranking generals, those who cut their teeth in a militaristic system inevitably saw that experience influence the positions, careers, and companies they engaged once discharged.

Some of the defining characteristics of military organization:

Top-down, Authoritative Governance and Dictation

Hierarchy and Seniority

Strict Division of Labor

Separation of Work and Community

Many of our grandparents did not go to college; many more served or were otherwise directly influenced by the above tenets early in their lives. The result - an explosive growth in organizing principles and resulting companies that resembled these tenets: mass industrialization, the working factory with roles defined to the assembled part on a conveyor belt; punching in and punching out; the explosive scale of four tremendous sectors: U.S. Steel, U.S. Auto, and U.S. Advertising, Wall Street. All of these industries, working complexes, and new economies owe at least a hat tip to the military as a blueprint for design and execution.

Today, many younger people in the US have shared the experience of a more recent entity, with a ubiquity akin to that of grandparents’ experience of the military. That entity is the University.  Many more people attend college then enter any arm of the military outright and so the seminal experience of early adulthood shifts dramatically. 

The defining characteristics of University:

Trust and Open Collaboration

Community Encouragement and Building

Flat Organization where Peers are Equals

Free Sharing of Knowledge To Benefit both the Individual and the Group

In the last half-decade, software development and a proliferation of wireless internet access has facilitated an unbundling of the traditional, four-year college. MOOCs are available to anyone, anywhere. Coursera lets me take full semester-long classes from my couch. Codecademy has solved a problem that most schools with decades of a head start still can’t fix. With college tuition at an exorbitant cost that looks like it will keep rising, the Internet and its brilliant denizens have begun to accomplish a truly profound feat in democratizing and distributing education. 

Yet, if certain characteristics of the entrepreneur’s effective platform for building are those of the University, we can point to that four-year experience as a new model for organization. We’ve seen startups, new networks, and economies built for and around a blueprint of trust, sharing, peer-to-peer equality and coordination. While cities have begun embracing the networks that brought these qualities out of them - Uber, SideCar, Handy, DogVacay, AirBnB, KitchenSurfing - campuses have always been ecosystems where those qualities are encouraged. 

Regardless of whether there is a drop in college application and matriculation eventually, maybe this is a moment in time when several generations’ attraction to the University’s socially open and collaborative structure ends up being a most lasting effect of attending. 

—

* Massive thanks to my dad for putting these ideas in my head. 

Closing The Computer

This weekend I intentionally left my computer at my office on Friday afternoon, forcing myself to abandon the temptation to read, send email, or otherwise try to get shit done via the device I use most heavily during weekends full of work. 

It’s probably been three years since I’ve not had access to a laptop from friday to monday morning. While apprehensive at the outset, I achieved a few states of mind that set me free in many ways from the all to welcome shackle of keyboard and screen. Here’s what happened:

• I went outside - and actually stayed outside. Not just to walk the dog and stop at a coffee shop to send some emails and work on a deck or project. 

• I hung out with friends without feeling a need to shape that time spent with people I genuinely enjoy around bookends when I could escape back to my computer. 

• I read! I read like I haven’t in a while because so much of my reading today happens in erratic jumps from blogpost to RSS feed without much substance taken in along the way. I read paper books on the beach and in the grass. It felt amazing and I was completely immersed in each page. 

•  My thoughts wondered not between forgotten to-do list items as they normally would but to the alleyways and corners of my mind I wish to visit as often as I can. I was thinking more, planning and worrying less. 

• I stayed out later, thinking I’d have some more time to ease into mornings, not waking up and opening my computer in bed to begin fretting over items or emails. 

I guess when it comes down to it, I did what you’re supposed to do on the weekends - take a fucking break. For someone who prides themselves on time management, I can be terrible at compartmentalizing and have trouble letting go of the task at hand. Work to me is the basis of everything I enjoy and feel deeply passionate about, so I embody it at all times.

Part of the experience for me this weekend was recognizing that it doesn’t deteriorate from impact or performance to step aside from the literal embodiment of work and see where you mind and body go. I think I went to incredible places this weekend that I wouldn’t have found buried in my immediate responsibilities.

A few people speak often about taking this type of mental and device pause. My friend Tony has the technical sabbath and he’s one of the most productive and thoughtful people I know. I’ll strive to emulate this in my own way more often. My hope is that it becomes a more seamless part of my day-to-day, not always requiring a forced separation over a weekend. 

Time spent in other pursuits and experiences can only enhance and expand the mind and often can solve the problems you’ve been fretting over all day or week. Of course, I was seeing emails come in all weekend on my phone and was stressed enough to wake up before sunrise Monday AM to get back to it.

Maybe I’m not ready for the mobile sabbath, but there’s a balance there somewhere - I hope to find it in the near future.

The Importance of Being Extremely Earnest

Late last night I read a post by Garry Tan on entrepreneurs not drinking their own Kool-Aid. It resonated with me as kind of secret recipe behind all of the pitching a founder must do in order to create, fund and grow their company into a market - look for small wins, focus on the details, don’t spend outside of your budget, don’t be too rigid or stubborn about your original concept. That may seem like the mundane or the assumed for those with a grand vision, but a truly value-additive investor encourages an entrepreneur towards the immediate and focused steps that validate passion and help achieve something that resembles the massive market opportunity or projected user growth that most pitch decks describe. 

But without the passionate vision - the Kool-Aid - all is for naught. In a pitch meeting, at a demo day, during a Monday stand-up or end of the week one-on-one, a twinkle of passion should be the mystic sprite in the room, skipping just out of reach but inching ever closer, a constant inspiration to every audience and assignment. 

Just as the simple tasks, logical burn-rate management, and flexible direction validate the original idea and vision, so that vision propagates the needs of company management and developmental focus. To get caught up in one’s own pitch is to lose sight of why you’re pitching, but without extreme desire at every turn its hard to envision “IT”,whatever one’s idea may be, succeeding. 

How do you break through brick walls without a little help from the Kool-Aid Man? 

Premiere A Movie Online

Some night soon, Netflix will collaborate with Martin Scorsese to premiere a big budget, studio film online only. Everyone who wants to see the movie will be able to buy a ticket in the form of a unique login/password or captcha and see the film from their living rooms. The showing will be at a pre-determined time and will not stream until a certain threshold of individual viewers has logged into the page. There will still be pageantry and aplomb with special messages from the directors and actors and future discount on e-tickets for that first audience. 

Why will this happen? Because this way more people can afford to see a movie, more people will have the time to ‘take’ their whole family to a movie, and the studios stand to make more opening weekend and lifetime gross on movies then in the previous studio-to-theater distribution model. 

Today, going to a movie is an emotional, psychological, financial, and scheduling commitment. You must decide to go, find a theater that’s showing what you want to see and hope its not sold out, potentially find someone(s) to go with you, and pay crazy prices for entrance and snacks. I’m an overwhelming movie-goer and aficionado but this process is a hassle. Unless the theater is a special experience like The Nitehawk Cinema in Williamsburg, it may be hard to justify the expense for many. 

The economics are staggering when you consider the $10.8 billion 2012 total box office in the US and Canada and then multiple the potential audience by at least 3-5X, if not a much higher coefficient. The price per ticket drops in parallel with much lower distribution costs but the volume of purchasers is unlimited (depending on the nature of the premiere). If the movie industry obsesses over opening weekend numbers as a core KPI, the easiest way to insure that number is a good one is to eliminate the barriers for as many eyes as possible seeing their film at the same time. Right now those are the logistics and price concerns discussed above as well as the capacity of physical theaters. The internet solves for each. The word of mouth marketing effect is then amplified and more tickets are sold in the coming weeks. 

I don’t know whether an established channel like Netflix or an independent streaming 'theater’ set up by studios or independent shops is the best medium for online premieres, but at least some in the industry are putting their toes in the water, notably HBO and the Toronto Film Festival. Other startups like VHX are already working on the democratization of distribution and premiere for artists directly, outside of corporate structure. Hopefully, an indie breakout that premieres through VHX or a forward-thinking studio that premieres a major picture online further pushes this dynamic in a more inclusive and profitable direction. 

The Smart Syndicate

Three months ago, my friends Jake, Nick, Lauren and I were discussing syndicated angel investing and how it could work to create a bridge between interested, accredited investors and startups in need of cash and a very particular value-add beyond capital. Then, Angelist syndication went public. Suddenly, everyone was launching a syndicate and the entire blogosphere blew up with news and criticisms of the vehicle. This gave me pause. As an aspiring venture investor, whenever a new idea becomes an apparent touchstone for the future of an industry in every positive and negative direction, I prefer to step back and see where things settle as opposed to joining the frenzy. 

So I stopped trying to figure out how to accredit myself and thought about how syndication can change venture. I came to two major conclusions, one about the potential for syndication and another about how a syndicate would need to behave to achieve that potential. 

Conclusion 1: Syndication can open doors and pull back curtains. 

There are wealthy people - successful corporate executives, serial entrepreneurs, retired athletes, five-star chefs, acclaimed authors - whose unique experience in their fields can lend profound insight and acceleration to entrepreneurs. Those same industry luminaries may have been trying to solve a problem they’ve noted in their field forever and have no idea that someone is working on it, and could really use their support. For example, if Michael Kors was introduced to a startup called Dowery that was trying to solve a seasonal supply-demand problem for wedding jewelry that he had experienced with his brand in the past, that might be an opportunity for true value-add, let alone investment. Doors open for entrepreneurs who can take the elevator up and curtains are pulled back for investors who may find an up-and-comer who’s working on something they’re acutely passionate about solving in their own industry. Where there is passion there is productivity, excitement and involvement from the investor. 

Conclusion 2:  Any syndicate that’s going to be more than just a micro, ad hoc vc fund has to treat each startup-to-investor connection with the craft and devotion of an artist. 

These can’t be fund-and-out firms or spray and pay canvassers. A smart syndicate should exist to ensure that the matches they make and so deals they close are as transparent, mutually valuable, and long-lasting as they need to be. The syndicate researches the startups and industries where interested investors may exist and handpicks the matches that make clear sense for both parties. The investor may not want to deal with a ton of paperwork, the entrepreneur may not want to have to answer to a haranguing investor, the syndicate lives for both of these situations and any other complication that will arise. The smart syndicate is the accountability, sincerity, focus and resolution of the deal and the relationship - for the good of the potential to innovate.  

Maybe ‘bridge’ and 'connector’ aren’t the best terms for the smart syndicate. Its more a dynamic two-way velcro that creates lasting relationships where not just the economics and momentum but true synthesis make sense. 

The Importance of Transparency

I’m a huge fan of the HBO show Boardwalk Empire, a period program about the roaring 20’s and prohibition in Atlantic City, New York, and Chicago. Its an amazing show and I’d encourage everyone to watch it. Among other themes present, the show is a study in sketchy business dealings. Partly because the business done is illegal and partly because everyone is shamelessly out for themselves, no one knows everything and everyone suspects each other. The result? Short-term wealth leads to short-term life expectancy, with many major characters murdered on suspicion or proof of foul play (sorry for the spoiler, but its a mob show, what’d you expect?)

Am I about to draw a parallel to today’s startup culture? Yes I am. I don’t believe anyone’s been snuffed on suspicion of failing to deliver on a product launch date or hitting a revenue expectation, but transparency in all aspects of starting up may be the most important cultural focus for a company going from one person with an idea to two or 500 employees. 

Have you ever been in a relationship and found out that the other person did something that you didn’t know about and after the fact it seems like you should have? That feeling can burn right away and, especially if it was the wrong thing to do, create lasting, toxic resentment. In startup, the exhausted phrase not everyone needs to know everything is often manipulated from its actual meaning - a growing company is complex, things will happen in parallel rapidly - into an umbrella conveying opaque control from unknown direction that inhibits growth because people don’t know what they’re doing or why. 

In my mind, just about everyone should be able to know just about everything at startup, save the board-level financial concerns that aren’t legal to share and anything that encroaches on a colleague’s personal privacy. Not every employee may be interested, but what’s the harm in sharing product road maps, break-even dates, or github repositories? Shouldn’t everyone at least have a chance to learn from other groups at a company and always, always know the grand vision? 

Any founder or executive worth their salt should convey vision for the company and how each team member furthers that vision with ease and detail. Any sincere and passionate founder, executive, or team lead should jump at the opportunity to do so for anyone, especially their teams and especially when things take turns for the unexpected as everyone should expect they will in this industry. 

Confusing? Communication begets transparency begets understanding begets honest motivation begets improved likelihood of cohesive culture and success. It may not have been the way Rothstein or Masseria did it, but neither survived long enough to write their entrepreneurial memoirs. 

The Terminology We Choose To Know

Classroom education begins with the definition of a discipline. What is Biology? Sculpture? Economics? French? From that point forward you enter into a continual rhythm of acquiring new techniques and terms for specific areas of study and, eventually, work. 

In the sciences, you begin this process in undergrad and without it, you may misidentify a new species or lose a life during a surgery because of miscommunication. In other fields, the process of acquiring relevant terminology may begin during a summer internship or the first two years out of school:

Market Cap, P/E Ratio, DCF? Banking. 

Air Sparging, Photovoltaic Electricity, Turbines? Energy Conservation. 

EIRs, APIs, Ruby on Rails, Mongo? Engineering. 

Less certain terminologies you face an uphill battle to break into a new industry or have a meaningful conversation about relevant issues or ideas. Everyone’s had one of those job interviews with some dickhead who drops a question about a term he knows you don’t know. There goes your candidacy and up come the barriers to entry that an unknown terminology can create. 

What’s interesting is how so much of an expertise or career can be boiled down to which sets of terminology we’ve chosen to memorize and understand. Furthermore, those terms create a definitive framework for where we may exist professionally. Can we break out of what becomes an increasingly narrow scope of intelligent professional understanding - particularly with new terms entering our own sets all the time?

Maybe it’s why Einstein studied Dostoevsky and Issac Newton considered Occult Studies as important as the Sciences. Our great thinkers had a genuine interest in and eventually acquired a deep knowledge of terms and concepts outside of their core disciplines. To explore beyond their fields may have meant a deeper, wider understanding of the human condition and surprise expansions or reflections on their own thinking.

So what the hell do we do? 

Read everything, reject hubris, accept knowledge, and always, always be open. That’s all I can think of to do in the face of so many equations and definitions that I don’t even know exist yet.

Bucket List

The other day I saw via Instagram the Patagonia Bowery team on a weekend hike in the Catskills. The gorgeous falls they’d arrived at in the picture were called Fawn’s Leap. I’ve recently been making an effort to get out and about in and out of the city with friends on weekends and I wanted to save this place as somewhere to visit. My first thought: Foursquare. 

What I’m now affectionately calling my Foursquare Bucket List is a new way to use the application, at least for me. Often, people save a place to a list on Foursquare because:

1). They loved it and want to remember it and recommend it to friends.

2). They’ve heard about a place that they want to visit the next time that they’re in a larger place where the former place is located, that place’s neighborhood, town, or city. 

In this new use-case, I’m employing foursquare as a motivational instrument, a wonderful pretext to travel, reminding me of a specific reason I wanted to visit an area or city in the first place. Instead of arriving in San Francisco and looking up my old list of places I loved, I want to use Foursquare as the app of record for thinking about my next trips.

Why do we visit places? Because of reasons we wanted to go beforehand. My foursquare Bucket List lets me capture many of those reasons and store them for when I’m thinking about a big vacation or an early morning hike or anything else in between. Maybe its just a way to listen to that part of my brain that says I’ve always wanted to go there more often. When I can discover something intriguing about a place before I go and then remember it, that may be all the motivation I need to actually go and enjoy it in the future. 

I’m excited about this new use and I hope more people are doing it too and using foursquare in other creative ways. Its an amazing application. 

We've Got It Simple

Simplicity. Sorry, Simple. Its just a very easy word. And tantamount to success for startups trying to build something that didn’t exist before. 

In a recent piece for the LA Review of Books, Tom Streithorst describes a current era of Post Scarcity Economics in the U.S. - the period saturated with myriad supply and nascent or at least confused demand. As an economics piece, Streithorst goes on to analyze what makes people spend and how the government should act. What I found most compelling however was the psychological dynamic between timid demand and over-supply. What does it tell us about usage, purchase and what products are needed?

If people and firms do face a market of over-supply where everyone offers everything or a slice of what all of their competitors offer, then simple will be a distinguishing stripe for companies that win. 

So what is a company with simple? Your idea can be said in two words and your core value is immediately understood: sell shoes, introduce investors, transform insurance. But more than just your mission, simple creates a focus, identity and culture within your company that will allow you to deliver on the simple idea you had. 

Do one thing, do it so fucking well that your brand becomes the metonym for your industry, product field, or concept. 

This is neither rocket science nor profound but in a world in which people have too many choices and instead of supply, demand becomes the economic determinant of the moment - in consumer tech the focus on # of app users or unique views for example - a company stands out because it solves a known problem or improves lives of consumers or firms and its damn simple to understand. 

Simple is grand. 

Do You Want Your Receipt?

I don’t know anyone who says yes to the above question for small, personal purchases.

Do you need the toilet paper roll of barcodes that’s printed every time you go to CVS? How often do you go back to your personal ledger and even up your daily take in coffees from the receipts you're handed?

Paper receipts seem more outmoded because they’re paper - a physical duplicate of a record that exists for any future reference in online banking statements and other, personal financial management tools. 

The two responses I got when I tweeted about why we still have paper receipts for every retail transaction were: to avoid employees stealing from registers and for audits. Both valid and both capable of being monitored automatically online when a transaction is completed.

It feels like the hanging chad issue from the 2000 election, though more an annoyance than determining factor in a presidential electoral review. Maybe Square will make this discussion moot. People will realize that receipts can be emailed and records accessed online. But for the sake of everyone who comes home with crumpled receipts in their pockets and for all the trees wasted printing, how are these tiny squares of economic antiquity still necessary? 

Calypso Walks Into My Life

Calypso, our little lady stray from Tamboo beach, is coming back with us from Puerto Rico.

Wes World x2

So Proud of you today

An EIR on Campus

Last weekend, I went back to Wesleyan, my alma mater, to talk to undergrads interested in startups about internships in New York this summer. These meetings were part of a new initiative from Digital Wesleyan, a group represented by Jim Friedlich, Jake Levine and myself, to fund 10-week internships for Wes undergrads at startups. We’ve noticed a supply-demand paradox that would benefit from an entity funding, matching, and placing students at companies. Interns are smart and eager but not all can afford to work for free; startups are in constant need of body and mind power but few have cash to spare even for 10 weeks of genius. So, if we can find a way to cover the cost of living for a few interns and place them well, everyone stands to benefit, short and long term.

We’ve been thrilled by the response from students and companies alike and hope that the program blossoms in coming years. Yet, there’s another, more systemic reason we felt compelled to seek funding for nyc-based internships: our campus didn’t know about startups.

 As two graduates who happened into entrepreneurship and are now immersed, Jake and I experienced the lack graduating startup knowledge first-hand and continue to see it in current undergrads from many schools. Graduates are not presented startup as a career-path of record or opportunity. Traditional industries still pull the best and brightest because they’re known. Career Resources Centers at schools have specialized employees for these fields: law advisors, finance advisors, science advisors, healthcare advisors, and non-profit advisors. Whither the startup advisor?

Enter: The University Entrepreneur in Residence who would give presence to startups and be an expert in industry trends, alumni introductions and strategy for working as an entrepreneur. In amplifying the liberal arts mission – to have an impact, to go out and change the world – schools need to show their students the field of entrepreneurship, where immediate, essential impact trumps all others. Students want it and the schools want them to want it, so brand it and promote it through an EIR. Opening the gates to a larger and younger talent pool with more awareness does nothing to dilute the startup mystique or lessen the profound passion required to succeed. If anything, this role would touch toe to water for students who I’d bet can already swim, the plunge is up to their vision, intellect, and ambition. 

Backwards TVs and Harmonized Commutes

My roommates and I are reorganizing some stuff in our apartment as some people are moving out. While we moved our TV yesterday, the mass of cords and boxes required to make it all work struck me as absurd. 

Here’s a picture: 

That’s the pre-req for watching Game of Thrones and maybe checking email at home. 

Here’s what it takes to do the same at Konditori, our local coffee shop just around the corner: 

Konditori likely has a router but the point is clear - there’s no technology more antiquated than the TV screen and cable provider as the output and conduit for internet media and televised consumption. As if a 21st century Frankenstein looms large in our living rooms and offices, the TV cannot come alive without foreign modems and chargers plugged-in. 

Might we soon approach a watershed moment for the TV? Its strange to think the flatscreen - so new and shiny a few years ago - is behind the times. It is because standing alone the set carries a fraction of the value of its in-store price point. Apple TV and Boxee offer a better experience than most providers, but they’re still boxes. Lasting innovation should come through the set itself. Custom add-ons should exist as a choice for those that are particular not a necessity for the mainstream. Crazy that it hasn’t happened yet.

While TV strikes a tangled pose of closed system struggling to consolidate, a related breakthrough begins to emerge. On the morning journey from Konditori to my office this week, a crackle of noise came through my headphones between stops on the F Train. Like a CD skipping or a distant radio station, my Songza playlist pushed through the silent subway ride, every 3 or 4 seconds a beat hitting my earbuds.  Could it be? Streaming music and so internet on the subway?

 Wifi is made available at stations every other week it seems but the first hook to reach from my phone to my ears on a moving train was beautiful (Full Disclosure it was Action Bronson - Not Enough Words). Innovation imbues the NY subway and music is the spark. Some comment that internet on the subway will further eliminate human-to-human interaction in public spaces, but when was the last time you struck up a conversation with someone you didn’t know on the train? More access means more connecting with the people you want to, less time warner and superfluous boxes in our apartment, and more music all the time, which is always a good thing.  

What's In A Click?

Today, I gave a class about bitly data at Social Media Week NY called ‘What’s in a Click?' 

Un-Cramping The Kitchen

When you say two heads are better than one and collaboration is key, you   scratch the surface of why a team can be more adept than a single person at hashing out an idea and executing a project. 

But when too many of those key collaborators evolve into cooks in a cramped and musty kitchen, brainstorming becomes a tooth and nail death match for which ingredients in which proportions should be added when. The proverbial cramped cooks converse: 

Cook 1: Two hard boiled eggs 10 seconds after the water’s boiling

Cook 2: its time for the sardines I wrapped them in prosciutto, bacon, and seaweed

Cook 3: I thought we all agreed red velvet cake batter was going to be our secret ingredient? I’m adding it! 

Sounds crazy and disgusting. Even worse imagine a less crowded kitchen that affords each cook space to concoct to their own frankensteinian delight yet still required to combine their offering with their fellow chefs’ - one big, sloppy meal with myriad input and guttural results. 

At a time like the above, someone has to stand back and say: What the hell are we cooking and why? 

Define the core reason for a team and a project to exist. What is your purpose? 

Without defined purpose our three cooks serve up stomach aches and gags for dinner; with it they craft a three-course meal to delight the most sophisticated palette.