Code Climate, Timber, and NYCode

This coming September, NextView will be hosting NYCode, a half-day conference to recognize and explore the tremendous engineering community in New York City. Below is a brief post to explain why we are doing this. If you’d just like to sign up for early RSVP, click here to do so: NYCode RSVP.

In his recent post about the NYC tech ecosystem, Matt Turck highlighted two developments useful in considering New York’s ability to foster and maintain a local developer community. First, he noted that the talent base here is maturing. For engineering specifically, developers are beginning to leave the New York outposts of tech titans like Google and Facebook to join NY startups or start one here themselves. Second, Matt emphasized ‘Deep Tech’ as an emerging sector in New York. Where once MongoDB stood alone, a cohort of deep tech startups now exists, including growth stage companies like DataDog and Digital Ocean and younger startups like Clarifai and Geometric Intelligence.

To the above evidence of literal tech in New York, I would add the diverse set of schools and courses that now cater to engineering. From Cornell Tech and Flatiron School to the engineering programs at Rutgers and the HackNY Fellows from NYU & Columbia, New York is teeming with avenues to pursue a technical education.These programs and institutions graduate waves of newly minted engineers into the local ecosystems every twelve months, if not every six.

At NextView, we have been bullish on the NYC engineering community for a few years. In the spring of 2014, Dave met Bryan Helmkamp who had founded Code Climate as an automated, static code review product for Ruby. They had a series of conversations about the greater opportunity to build a truly open and extensible platform for a broad set of static analysis, engaging the engineering community to build modules for their language of choice. By that June, NextView was leading the Code Climate seed round. This past winter, I met Zach Sherman and Ben Johnson, two engineers who were leaving SeatGeek to start Timber, a developer tools company focused on user logs. Over a few weeks, we discussed what the two founders saw as an immediate need for a lightweight, real-time logging interface built for application engineers. In February, NextView led a pre-seed investment in Timber, alongside our friends at Notation, Ludlow and Wonder Capital.

What many Deep Tech startups require in a founding location is consistent engineering activity — Meetups to demo their products, other engineering groups or startups to be beta testers, and larger engineering orgs to poach talent from. In short, they need local density. Matt concludes that New York engineering density is finally becoming inevitable and we second that statement wholeheartedly, it is apparent and proving itself to be self-sustaining as the current cycle matures.

As proud advocates of this density development, we want to recognize it. So, NextView is inviting the New York engineering community to NYCode, a half day mini-conference with a couple of panels and fireside chats featuring some of the founders, data scientists, engineers, and investors who are making Deep Tech a reality here. To firmly dispel the rumor that quality, surplus engineering only exists on the west coast, join us for NYCode an afternoon of discussions featuring Eliot Horowitz, Alexis Le-Quoc, Allan Beaufor, Albert Wenger, Bryan Helmkamp, Murat Bicer and more.

Augmented Reality Network Effects?

My friend Jason’s enthusiasm gets me no matter what he’s describing and last night it got me hooked on Pokemon Go. Three quick observations from a relatively late adopter (a crazy statement in and of itself).

Viral Growth — Offline Network Effects:

Rising to 25 million daily active users in its first three weeks in the U.S., the game is the most successful mobile product launch ever. Pure organic viral growth has Pokemon Go breaking app store and OS usage records at the same time. Most remarkable is that the current version of Pokemon Go does not have inherent network effects. That is contrarian compared to the industry-leading consumer products, including games. Snapchat, WhatsApp, Instagram, Draw Something, Farmville, and Words With Friends all benefited from network effects, where new users drove retention. Facebook’s rise is the textbook definition of the same effect. We are in an era where meteoric consumer product growth has often relied on users finding their real-life social networks in-app to drive repeat engagement. Empirically speaking, you play Pokemon Go without any user-to-user interaction. You play the game to find more Pokemon and advance your experience levels; both processes that are born out of and achieved through a virtual world in which you exist largely alone.

Of course, Nintendo can deploy gaming and social features that could achieve a traditional network effect very quickly. It's not hard to imagine what these are. The lures that users can leave to attract Pokemon are an early indication. In-game tips, trading, commerce, battles, and communication — all hallmarks of successful MORPGs — can build network effect moats when given to such a large early user base. I’d like to posit though that there is something else at play with Pokemon Go today that goes beyond buzz. The network effect has already emerged, but it has been achieved offline. Users are communicating, tips are given to one another, real life friends and couples are engaging the game together, commerce is already in place. Its just all happening in the real world. Listen to the conversations you overhear about Pokemon Go, they aren’t all just about the hype. Users are helping each other, recommending what to do, comparing their collections and their avatar designs. Jason literally walked around with me after dinner last night and we played together while he gave me tips. He’s the first person I messaged this morning when I caught a wild Tauros on the train. A product of our first augmented reality network, the social in the Pokemon Go network effect is experienced on the real world side. And its honestly more powerful then if tips and conversation were in-app from the start.

Device Takeover — Single Use:

The Pokemon user interface dominates your device. Certain push notifications can interrupt, but it is by and large a dedicated experience. You have to keep it open in order to keep playing and, even from a pocket, it will run and buzz if there’s something to do nearby. We are clearly demonstrating a desire for this type of UX/UI. Content consumption on Snapchat underscores the same trend. Products that fill up the screen, are easily engaged, and consistently satisfying are winning our attention. We want immersive experiences and may readily sacrifice choice — which app to open, where to read the news — for them.

Nintendo should buy Foursquare:

Just saying…

Authentic Foundation

Last week, I wrote a post referencing Invited Guest, one of the six points that make up our ethos at NextView. Today, I’m calling on another of our ethos points, an adjective that can consistently describe the founders we work with: Authentic. If you’ve had the chance to explore the NextView website recently, you may have found the homepage Easter egg that reveals each ethos point. Authentic is the first one you’ll see:

It may not be surprising then that many of the most successful companies in the NextView portfolio to date were born out of authentic founder experiences.

In the past few months, we’ve invested in three New York-based companies; each hatched by founders whose backgrounds and visions for what they’re building epitomize authenticity. As examples of the types of founding teams that we love to work with and in order to announce some of NextView’s newest investments, I’m thrilled to now shine some light on the founders and founding stories of Dia & Co., Roam, and Timber.

Nadia Boujarwah and Lydia Gilbert met at business school and by the time they graduated were off and running with a startup idea: building a new brand for plus-sized woman’s fashion. And thus Dia & Co. came into being.

The company was not simply the result of a shrewd examination of market opportunities or a spreadsheet-powered analysis of sizing trends in the U.S. Dia exists because their customers have been ignored by the fashion industry. Nadia and Lydia saw a woman forced into the backrooms of brick-and-mortar stores to find her size or resorting to online orders without consideration to her unique fit. They saw a woman with nowhere to shop and no brand she trusted. Nadia and Lydia have since dedicated their waking hours to making life better for this woman.

The Dia mission is to encourage self-confidence and personal agency through ensuring their customers have styles they love in cuts that fit. The whole company values the needs, nuances, delights, and trust of their customer above all else. From profound sizing data that’s collected down to every article of clothing picked and packed for home try-on, Dia is literally built in service to the plus-size woman. Need some proof? Watch this video from Mic.com and then search YouTube for “Dia+Unboxing”. A community is emerging that’s finally getting what it’s deserved. Nadia and Lydia have brought staunch and sincere authenticity to the notion of customer-first. This isn’t a played-out marketing message on a splash page, but the entire reason that their company exists.

Bruno Haid believes that our accepted definition of “the home” is outmoded and restrictive. The 30-year mortgage may not be for everyone and is in fact not viable for many people, yet we’re indoctrinated with the notion that the home we eventually buy as we get older will be both our static, long-term residence and most valuable asset we’ll ever possess. Bruno started Roam as a new living option: a tech-enabled network of communal residences across the globe within which subscribers can move as they so desire.

Who signs up for this? Digital nomads? The freelance workforce? Remote employees? Empty-nesters? Divorced adults? Students taking a gap year? Professors on sabbatical? Regardless of the subscriber demographics, Roam is being built as a conduit for a massive behavioral change. Bruno is the kinetic energy that flows through the conduit, hell-bent on affecting a watershed moment for how we may live. A true nomad, Bruno champions flexible living in practice and conversation; he has opened and resided in communal properties throughout his life. If Roam is a company that exists to offer an alternative to the static homestead, Bruno embodies the early-mover edge to establish this alternative today.   

When founders solve a problem they’ve experienced themselves, they often employ a novel approach that’s so straightforward or simple as to appear an insufficient strategy to outsiders. There is, however, clear authenticity in building a company that you know solves your problem and potentially solves the same problem for many others. For Zach Sherman and Ben Johnson, engineering at SeatGeek meant swimming in a coded sea of user logs all the time. As a major ticketing platform, SeatGeek manages millions of logs every day, and anytime something goes wrong in the code or someone doesn’t get their tickets, those logs have to be called up and poured over.

As a result, Zach and Ben both became intimate with the treasure trove of unique information locked behind the static lists of logged events that were thrown out every seven days or so. For the Timber co-founders, the user log, despite being a huge hassle to access when needed, felt like the lifeblood of the entire company. These logs were the key to everything that was happening on the platform at any given time. It didn’t take long for the duo to unify this notion about user logs into a company focused on unlocking the power of the log.

Timber gives application engineers a lightweight interface for real-time search, filtering, and analysis of clickable, semantic user logs. Born from a painfully sincere toil in accessing logs when there was a problem, Zach and Ben have crafted an original product of which they may well be their own most active beta testers.

—

Starting a company for the sake of starting a company is a doomed endeavor. ‘New founder’ is one of the most challenging job titles anyone can take on. authentic, sincere passion for what you’re building – whether born out of a problem you’ve faced, a wider vision for something you’ve experienced, or a need you’ve felt that’s never been answered – can carry a concept through to becoming a company. Launching a startup from origins of authenticity is a more likely road to entrepreneurial success and a characteristic we seek out in the founders we meet with at NextView. 

Passing: A Great Responsibility In VC

Saying no to someone isn’t comfortable or easy because it’s never what a person waiting for an answer about anything hopes to hear. In our industry, venture investors are responsible for passing on an investment in nine out of 10 companies they meet. Theoretically, passing is what we should be doing most often, second only to meeting new companies.

At NextView, one of our ethos points is Invited Guest. We believe we are guests at the tables of the entrepreneurs we work with, in attendance only because we’ve been lucky enough to be asked. From the first time we meet or speak to founders through our entire relationship with a company, they’ve invited us to be there – especially when such a gracious and fortunate invitation needs to be declined.

We endeavor to be efficient, transparent and helpful in our role as investors during evaluation and diligence of a new company. The phrase I’ve learned from my colleague Lee is: it’s a few days to a no and a few weeks to a yes. When it comes time to pass, we intend to do so with a clear explanation as to why we are. The amount of feedback is generally proportional to the time spent with the founders and how much we’ve been able to learn. One phone call with a founder may mean a shorter pass email; several group meetings and other diligence requests to founders will bring more detail on why we’re passing.

We are, of course, human. While we intend no error in our process as described, we miss or drop things at times as anyone does. This is not a prescription for perfection – to write a thoughtful pass message takes time that isn’t always there. But human error aside, we go into every startup meeting with the intention of conducting ourselves as those founders’ invited guests.

The reason we take passing seriously is because we know something that entrepreneurs know all too well: fundraising sucks.

As a process at the seed stage, it’s fundamentally insane. In meeting multiple times with an entrepreneur, asking them to provide references and jump through various other diligence hoops, we take them away from building the very thing that they are asking us to invest in. Their time is better spent doing that herculean task of building their business then having a sixth partner meeting with a fund that isn’t going to invest. Eliminating the distraction of a drawn-out fundraise is the least we can do.

Personally, I keep the following three facts in mind during any pitch process – a mini reflection on why being an invited guest is humbling:  

What you do is harder than what we do.

What you do is more important than what we do.

Your time is more valuable than ours.

When investors don’t pass appropriately, we are willfully negligent. Unfortunately, there’s less accountability here because our performance is not measured by how effectively we say, “no”. Avoiding these conversations because they might be awkward does a disservice to founders who are already attempting the near impossible by starting a company. If we don’t invest 10 times as often as we do, then we should be passing early and often. It’s the right thing to do and, as a service provider in the startup ecosystem, it’s our job. 

My VC Product Stack

I’ve been spending some time over the past few weeks thinking about time management and the tools I use to facilitate the best use of my time, keep me organized and not let anything slip through the cracks as an investor. 

I’ve mapped out my product stack according to how regularly I use a given product and/or have set time to check/review/reorganize/clear-out the content a particular product holds for me. In reflecting on my stack, I realize that many of the tools of my trade are just containers of information. The essential value then is in getting information out of my head before its forgotten as well as presenting it back to me (and others depending on the product) in a much clearer format in order to process it or collaborate with it. 

A few other thoughts from reflecting on this map: 

Trello has long been a go-to source for company tracking for me as a vc. It is lightweight, has a fantastic mobile experience and each card works well as a unit of summary for a specific startup. The columns are perfect for the stages of meeting, diligence and review. What is lost with Trello as far as a VC-CRM is data - there’s no tagging, filtering, or analysis, even when manually exporting to excel. There may not be a ton of insight from a seed stage venture ‘CRM’ but I would be very interested in what other tools people have used especially those that offer any degree of analysis.

Since the first time I downloaded the desktop version, I’ve never moved off of Tweetdeck as my primary Twitter organization and consumption tool. I wish Twitter would pay more attention to it as far as bugs and simpler UI/UX. It is clunky as hell to get  your initial columns of follower lists set up correctly and, even if that improved, its still only for a power-user. But its amazing once you put the time in and relatively straightforward to shuffle and update. 

If anyone has calendar recommendations as we watch Sunrise ride off into the sunset as a Microsoft product, I would love to know them. The same goes for mobile email client. I’ve begun testing Outlook on my phone for the first time ever as a mobile calendar and email solution and its better then I expected, but I don’t really want to use it as my permanent solution.

The State of NYC Seed

Since joining NextView, we’ve talked often and excitedly about the New York startup ecosystem. With many seed investments locally already, everyone on the team has had a window into how entrepreneurship in the city has evolved over this current cycle.

In the eight years since the housing crisis, NYC tech has been active, to say the least. The community has given birth to tremendous successes and lots of failures, participants have come and gone, round sizes have grown, hot sectors have cooled, reignited, and cooled again, and founders have come from every conceivable background to build here and seek talent, customers, and funding from an increasingly diverse field of investors. Not unlike Gotham itself, the tech ecosystem bobs and weaves to a nebulous beat.

As a further mimic of its host city, New York tech stands tall and stubborn, with a never-say-die presence through flush times and lean. But our conversations at NextView have always ended in excited chatter about the New York opportunity. And it was these conversations that I believe led to the team’s decision to add their own stubborn presence to stand up for seed-stage startups in NYC … me.

Here’s a long story short: We believe firmly that entrepreneurship and startups in New York are alive and well, and we’re here to support them as local seed investors. With conviction in this city, its entrepreneurs, and their ideas — and given that I’m carrying the NextView banner in New York City full-time — I thought I would put some of my analysis and opinion about the state of NYC seed out there to our world. Thanks for taking a look.

The State of NYC Seed:

The State of NYC Seed - NextView from NextView Ventures

- recommend viewing in fullscreen mode -

Will Anyone Care About This?

For creators, I imagine this question must weigh heavy in the moments before their creation passes from intimate and private to public and exposed. There aren’t guidelines along a blank canvas. When a new track, a first novel, a debut film, or a online marketplace are about to be set loose to the world, the only believers are those that made it. 

This is a uniquely insane state that’s not found in many other professions or pursuits. For the majority of the working world, confidence and validation that one is doing something that’s right, meaningful, and productive comes as much, and often times more, from within the workplace as from public reaction. Necks are stuck out for work completed, but not in as drastic or individual a manner as with the artist-creator. 

For the author or painter, there could be some solace in knowing that another canvas awaits to be the filled-in, a new physical outlet for what their minds’ manifest. The sheer lunacy of bringing a creation into the world may fade once its done. Marked on the impact of a completed work, they can begin another. For the entrepreneur, it seems a different lens is applied to answer the title question. A startup founder’s creation will be measured by the impact - utility and/or enjoyment - it delivers over a long period of time. 

Maybe there’s a level of creative mind that doesn’t worry about how their works are received; who are confident in their creations no matter what. But for the founders who launch something into the world with anyone caringmeaning a product or service that’s consistently profound over months and years, the implied commitment in those moments before launch is immense. It may just take insane moments, total devotion and contrarian or eccentric or impossibly creative minds to afford something profound and, hopefully, the answer: YES. 

Startup Employees, Before You Buy Your Options...

A few weeks ago, I wrote a post about a startup’s responsibility to explain equity to new employees. I wanted to go a little bit deeper on equity exercising and tax implications when leaving a startup. 

If you’re leaving a startup after one year or more you likely have some percent of vested equity options available to purchase; the ownership you’ve earned in your time working there. When you were first hired and granted equity options, you probably got a nondescript envelope that looks like this: 

Inside are the Notice of Stock Option Grant and a copy of the most recent Stock Option Plan that’s been approved by the board. There are two types of options offered to new employees, Incentive Stock Options (ISO) and Non-qualified Stock Options (NSO) here are simple definitions and tax implications for each, your envelope should tell you which type you have. 

Incentive Stock Options: Often presented as ‘tax free on exercise’, ISOs are preferable to NSOs but not tax free. While you don’t have to pay an income tax when you purchase these shares, you do have to represent the difference between the strike price of the share at purchase (what you’re paying per share based on the share price when the options were granted to you) and the fair market value (FMV) of the share at purchase (what price the share is valued at today) as a ‘tax preference’ when filing Alternative Minimum Tax documents. The AMT is usually a 28% tax on the difference between the price you paid and the value of those shares today. Better then income tax, but still a large bill.

Example: Purchasing 25,000 ISOs with a $1 per share strike price when they were granted to you that have increased in valued to $10 dollars per share over the three years you’ve worked there would result in a $63,000 tax in addition to the $25,000 you paid to buy them in the first place. 

Non-qualified Stock Options: NSOs are taxed with ordinary income tax rates when you decide to exercise them. So the delta from your strike price when options were granted and the current fair market value of the options is taxed roughly 33% when you file in April. 

Example: Purchasing 25,000 NSOs with a $1 per share strike price and a present value of $10 dollars per share would result in a $74,250 tax in addition to the $25,000 you paid to buy them in the first place.

So, you’ll be out almost $100,000 within a year of leaving just to get and hold the ‘upside’ that you were supposedly a part of building. In theory, a long-term benefit comes after exercise tax when the company becomes liquid and massively more valuable and you sell your shares for a fortune, it is taxed as long-term capital gains, about 15%. 

To Companies:  There’s an immediate issue here that starts with new employee contracts. When you sign your options grant on your first day, you’re agreeing to decide whether or not you’re going to purchase your vested options when you leave within 90 days of your last day. This locks employees into a rushed decision. Those 90 days are rarely aligned with the company’s own growth and are not enough for an employee to assess if their ownership will pay off or not. In many cases, individuals can’t purchase even if they intend to. At a reduced startup salary and in consideration for living and familial expenses, many employees haven’t earned enough money from the company in order to buy their shares of the company. All employers know this very clearly, they can see your earnings and know what general costs of living are.

There’s a simple solution: throw out the 90 day standard and adopt a 5-7 year exercise window. Pinterest is leading the way today in adjusting for the sake of employees and everyone should follow suit. In seven years, most company outcomes will be much more clear and employees can make an informed decision about buying their options. They will also have had time to create a plan to be able to buy them without emptying their savings accounts. Employee options considered over the lifespan of a company as people come and go are never a large cap table burden. There’s no downside for the company or investors to extending the exercise window. Be good people! 

To Employees: Ask for an extended options exercise window when you’re negotiating an offer with a new startup. Its not one of the major levers of immediate compensation but can save you so much when you’re at the other end of your time with a company. Its much harder to ask for an extension when you’re leaving then to have it locked in before you start. 

And then, a word of warning on purchasing options at all. When you do it, you will pay a tax in the year that you exercise and it will be on the company’s paper valuation. Fair market value for private companies is basically made up and is likely to be more inflated then not. Just like any investment, you’re making a bet when you exercise. The advantage you have as a legacy employee is that you know what’s actually happening at the company. So break it down. Do you think the company will IPO? Will it have a huge acquisition? Is it all smoke and mirrors? Are they hemorrhaging talent or revenue or users? Is the leadership superlative or kind of meh? These answers can help you think of a rough percentage likelihood of you making bank on your options versus paying a huge tax on a paper valuation even if the company’s already gone under (yes you’d have to pay it regardless). 

I hope this helps bring some clarity to the equity purchase decision. Its a big one for most people and should be considered thoughtfully. Thank you to Lee, Rob, Sam, and John for their thoughts and feedback on this post. 

Labor Day Resolutions

 For whatever reason, the Summer-Fall changeover feels more like a New Year then New Years this year. Maybe that’s just aging or the nature of my current work. But in lieu of January 1st, I decided on Monday to spend a little time reflecting and write up a few Labor Day resolutions. Just a few things to work on or focus on in hopes that they’ll help me grow and be better heading into the colder months. 

1). Eye Contact - I’ve never been good at eye contact, which I was told seven years ago would keep me from having a successful career. When thinking out loud or vocalizing a new opinion, I find I look anywhere other than the people with whom I’m talking. Maybe its straight awkwardness or its that I lose my train of thought when concentrating on addressing someone directly. Anyways, I’m going to fix this one. I’ve become so accustomed to it that I don’t think about it anymore but it must at times be strange for those on the receiving end. If interacting face to face is in part about discovering true connection, eye contact is one of the few physiological mechanisms at your disposal. Shouldn’t waste it. 

2). On Time - At NextView and with most VCs, 80% of the gig revolves around meeting entrepreneurs. All the time. My bias is to meet in either a neutral setting or, if there is one, that person’s office. I believe it creates a more natural setting to hear a pitch and discuss an idea without putting an entrepreneur into an environment where they either clam up or go into hyper sales mode. (I used to do this for hiring as well). The logistics of this endeavor aren’t ideal and at time I’ve found myself arriving late to a meeting. Its a cliché that VCs are always late but the last thing I want to do is disrespect someone else’s time or reinforce a negative stereotype. While delays in New York transit are inevitable sometimes, I won’t be late on my internal account anymore. 

3). Present in the Present - There seems to me to be unimaginable peace of mind in being able to focus on the immediate here and now without a constant glance over your shoulder or around the next bend into your past or future. I haven’t figured out how to do this yet. Perpetual To Do lists, insecurity about the future, analysis paralysis, thinking about thinking about things, and specters of past misfortune or fumble draw my attention often from any one task, thought or simple moment at hand. I can’t really control outcomes or fix past issues with anything other than the thoughts, relationships, and actions of my present. And its time better spent in a fulfilling present than a present spent stressing about times ahead or behind. 

4). More New, Less Zone Out - Whenever I actually do it, I really love exploring something unknown to me: a new app, a new artist, a new alleyway, a different way home, a different way to take a note, a new author. Its really a requirement for my job. Though often I find myself, in evening hours or quiet moments, slipping into zone out periods where I’m going through the paces of commute or social media black holes without purpose or actual enjoyment. Sometimes distraction and passive consumption are great but not beyond a momentary break. No more of that going forward, I’d like to always be stepping forward into something new. 

City Made

New York City is a tremendous place to be an entrepreneur.  For a pursuit that largely revolves around silent time spent at a computer by one person then, slowly at first, a few more people, a bit more talking, and on and on until, failure, acquisition or IPO, it may seem inconsequential to consider where it all goes down. There are, of course, many necessary considerations, emotions and excursions beyond a laptop and wifi along the path of starting up and so the place does matter.  In the waning days of summer, when we are all either sweating it out or out of it all together until Labor Day, it seems appropriate to reflect on a city that deserves your every consideration to occupy ________ (City) _________(State) on your startup’s mailing address.

“New York, it was an adult portion. It was an adult dose. So it took a couple of trips to get into it. You just go in the first time and you get your ass kicked and you take off. As soon as it heals up, you come back and you try it again. Eventually, you fall right in love with it.”

— Levon Helm

The grit, the grim, and the struggle are all very real. The city is a cold smack in the face when you hop off the Bolt Bus for the first time into a churning sea of people at the 34th Street subway stop who couldn’t care less about you or when your apartment building door clangs shut behind you in the morning and you’re three steps from lanes, lights, horns, and cars that may or may not slow up if you step into the street. The City does not coddle, cuddle, or spoon, with the unsettling exception of morning commutes on the L train. You have to start your day running or get out of the way of thousands of others who will go right over you. As a founder on day one, you are at zero. Your company is an idea that exists in your head and nowhere else unless you’re willing to do anything possible to make it pervade a consciousness beyond your own. My colleague Rob recently wrote about sprinting at the brick wall at a strong pace and at times necessary strategy for a startup at founding or seed stage. What better place to realize the fragility of your state and the need to sprint forward then the city where you have no other option?

Stark reality pervades the streets, avenues, and alleyways here. Entrepreneurship is an endeavor that often requires a suspension of reality to clear mind-space for contrarian ideas, possibilities on the edge of their time, and creation of something that has not yet been. More on NYC’s role in that effort shortly. However, situational reality pairs well with the expected result of a directed vision. Titans of industries, whose buildings dominate the city skyline and whose omnipresence has helped make New York an enduring power, cement the city in reality. Finance ( Exchanges, Services, Banks, Accounting), Media (Publishing, Broadcasting, Digital, Gaming), Fashion & Retail, Advertising, Insurance, Global Governance, Law, Real Estate, Professional Sports, and Telecom all have industry-leading firms headquartered in NYC. At some point in your company’s life, you’ll likely encounter at least one of the above – you’ll be pitching them, competing with them, or being acquired by them. As you travel along that path, these big companies can be your harshest and most valuable critics. They can provide insight into the problems to be solved in their worlds, echo the merit of your concept to a current market, and give product feedback as what you’re building evolves. Should you listen to every word? No, often established industries reject a startup concept exactly when it is most valuable. However, the ability to stroll down the street to Corporate America is unquestionably valuable as a real-world testing ground for Product-Market Fit and answer to the question does or will someone want this thing? Coincidentally, these incumbents will also become your flagship customers and very likely provide a stellar pool of local talent as you begin to staff up.

“I believe in New Yorkers. Whether they’ve ever questioned the dream in which they live, I wouldn’t know, because I won’t ever dare ask that question.”

— Dylan Thomas

Often overlooked in the effort to stay heads down and fully immersed in your company’s existence is the value of a break. Not the vacation kind, although those are important too, but the kind where you direct your mind elsewhere, spend time outside of entrepreneurship, and think and talk and be social about other things. New York is a city that invites escape from whatever it is you do. Statistically the most professionally diverse city in the United States, NYC is home to innumerable people and places that don’t know what an API is, aren’t hosting MeetUps, and will ensure you never feel like you’re in a startup snow globe or coffee shop pitching clusterfcuk. Its good and healthy to have non-tech outlets in your life and in New York City, walk around the block or turn around in your barstool and startup life can disappear for as long as you need.

Perhaps because New York’s startup world is relatively young, condensed and the city itself is breakneck backdrop for a founder, the camaraderie, honesty, and welcome attitudes that the majority of participants display is profound.  Just as there’s an all for one and one for all attitude within a founding team, so New York Tech rallies and supports the entrepreneurs that have created it. Most everyone will find time for coffee with most anyone else, no agenda required. Walk into any startup space – incubator, MeetUp, venture office, company office, co-working space, lab, or school – and you’re more likely to be offered coffee, a desk and a wifi password then shown the door. As an industry, New York Startup may someday live long enough and endure enough scars to reach a point of cynicism with new people with new ideas, most of which won’t work. For the now though, you’ll be met with enthusiasm and encouragement from an incredible group of people who want you to win.

“I still believed in possibilities then, still had the sense, so peculiar to New York, that something extraordinary would happen any minute, any day, any month.”

— Joan Didion

Such universal desire for collective success from all corners of the New York startup community is an outstanding asset for any entrepreneur just starting out. We dream of a future where crazy ideas make life better, solve problems, and then do it all over again. We see potential and unearth possibilities in every train delay, cup of coffee, art gallery, every neighborhood, every borough, every delivery menu, and every frustrating experience at Duane Reade. The chaotic, hardscrabble, overstuffed, raging, romping, intoxicating, alluring, terrifying melting pot that is New York City inspires. There’s a history of creative disruption here that casts a brilliant shadow down Broadway and the Bowery and over more then three centuries. In a place this competitive, innovation is the necessary tool for progress. Those committed to it recognize and root for it - the shear, indelible thrust to make something out of nothing our way - its one part entrepreneurial and one part native New York. If that’s what you see in the mirror, your fellow dreamers are here, in the streets and coffee shops and bars and studios, hard at work on what’s next to come and eager to meet you. 

Explain Equity

When someone goes to work for a larger corporation or public company, the compensation package generally includes an annual salary, a performance bonus or commission plan, 401k, and health insurance. When someone goes to work for an early startup, the compensation package general includes an annual salary, health insurance, and, instead of fixed-cost performance upside, a percentage of unvested options to purchase equity in the company. Of late, I’ve encountered numerous potential startup candidates and newly hired employees who have no idea what their equity means. I’ve noticed this for years – and experienced it myself – but I’m disturbed at the frequency now and so am compelled to write about it.

It falls on the hiring company to thoroughly explain equity options to their new employees. The concept is a nuanced one that, unless they’ve spent a career in startup or studied econ, new hires won’t have a basis of relevant knowledge from which to draw. Often avoided because they take time and could make an offer package seem less attractive, these discussions aught to be mandated so employees aren’t joining a company with a blanket pulled over their faces.

For startup employees who’ve not encountered equity before, there are resources online that will take you through the specific terms and changes in equity value over the lifetime of an early stage company. Check out Fred’s Skillshare class on Employee Equity and Brad’s post on Equity Compensation Terms. What’s frustrating to me is that the true value of equity seems to often be skipped over when a company is presenting a comp package. The common statement I’ve heard from candidates is they told me I’m getting ‘X’ thousands or tens of thousands of options. Full Stop. To the uninformed, 25,000 shares or 150,000 shares or even 5,000 shares can seem like a lot when your only reference is the stock market. And so, questions that should not need to be asked:

1). What’s the total number of issued stock and stock options to date?

2). What’s the strike price ($ value per) of the options I’m being granted?

3). What’s the company valued at today and what’s the total invested capital to date?

With this information an employee or potential employee can understand how much their “X” thousands of shares are actually worth in ownership and, at least on paper, in dollars against the total valuation. When joining a startup, the common refrain from everyone on the team is we’re in this together to create something new, amazing and big. The reasons behind this sentiment are many. A literal one is that everyone sacrifices the security of more money for the opportunity to build a profound idea from scratch and, maybe, share in a potentially tremendous financial outcome. It is either a shady sales tactic or unintended blunder for startups not to explain exactly where each new employee stands in that potential share. This is not an argument for circulating the entire cap table or compensation calendar. Everyone deserves his or her privacy. But in an industry in which early employees (1-20, 20-100) can make a massive difference in a company’s success or failure, startups owe it to those individuals to be sincere, transparent and thorough in discussing equity. Don’t go suckering someone into thinking they’ve already made it on the day they sign their offer letter. 

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. 

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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. 

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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. 

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* 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.