September 17, 2014
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. 


July 22, 2014
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.

April 9, 2014
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 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? 


January 14, 2014
Premiere A Movie Online

Some friday night in the not so distant future, Netflix will collaborate with the Weinstein Bros to premiere a studio film online only. Everyone who wants to see the movie will be able to buy a ticket in the form of a unique log-in/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. 

January 7, 2014
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. 

November 30, 2013
There and Back Again


It was a place devoid of excess. Where the soil echoed the mystic, true beginnings of humanity, where the nature of things became wondrous discoveries to visitors from the outside. A place brought to our eyes by Livingstone, Grzimek, and Mandela. A place that blossomed long before these men and will continue to flower long beyond our existence. 6,000 year old trees map everlasting roots holding fast to magical red soil and animals, fierce and Jurassic, roam free. 

Calamitous crags form the major roads in this world as endless, unnamed villages pass by the windows of our truck. Transient parleys from our eyes to the eyes attached to bodies seated in half-built shops and half-harvested fields convey an array of intention: joyous greeting, passing jealousy, desperation and a chance at a quick dollar, a shared smile at the tacit knowledge that we’ve arrived in perhaps the most wild place on earth. 

I’ve just returned from Africa and can say that the continent where man first walked is profound and without equal. What we were afforded the opportunity to experience in 28 short days I imagine I’ll spend years fully realizing: the  fauna bonanza behind a nearly inaccessible marsh curtain in Botswana’s Okavango Delta, the mind melting heat of two days in the Kalahari Desert and what we’d do if the truck broke down (probably die), the Chobe River and Serengeti Plain as flush with marvelous great migration herds and trailing predators as every wildlife show always made them out to be; gorgeous people, less suffering and more living the way everyone should wish to: simply, with contentment and pleasure in their daily existence; Zanzibar! and the aura of arabic-caribbean influence and speed, exquisite coffee, and the birthplace of Freddie Mercury!

I can’t really start writing about these experiences in depth here because I know no one would read it. I’d go on for too long and delve too deep. There are a lot of people I have to thank for encouraging and enabling this voyage, none more than Jules Davies and the amazing people at Topo Designs. Without their enthusiasm for the trip we were about to take, their generosity with their awesome gear, and their desire to be a part of this experience, I doubt we would have engaged it with the fervor that we did. Like a Where’s Waldo book, Topo became a core part of our experience and so our photographs throughout the trip, below a selection of the best from a month with Topo in Africa: 


Before boarding our flight over the Okavango Delta 


Heading into the Delta via Makoro dugout canoe 


With our poler Gladys in Botswana 


Waiting for a ride on the Chobe River, Zambia 


Outside our tent on a particularly cold night on the Zambezi River, Zambia 


Post bungee jump, straddling the natural border between Zambia and Zimbabwe


Early morning at Kande Beach, Lake Malawi 


Scuba prep at Nungwi Beach, Zanzibar 


Packing the safari vehicle for our last game drive in the Ngorongoro Crater, Tanzania 


With more gratitude then I can possibly express on my blog for my sister, our guides, and the Topo team, I return ready for more adventure and forever humbled by an experience in Africa I don’t expect ever to replicate outside of dreams in reflection and breathtaking memory. 

October 24, 2013
28 Days Later…


Over the past few weeks, a bunch of people have asked me what I’m up to next. While I should have a cool update about my NY-based pursuits soon, for the next four weeks I’ll be trekking from Johannesburg, South Africa to Nairobi, Kenya with my older sister Lizzie. After booking our safari, I reached out to Jules and the team at Topo Designs about anything I could do for them while in Africa. As a result of some great email conversations, I’m excited to say that I’ll be repping Topo throughout our six country journey. They were nice enough to send the gear in the layout above and in exchange I’ll be writing Topo focused blogposts and publishing images of Topo apparel and gear in places like Victoria Falls and the Ngorongoro Crater to various social media platforms. 

I’m so thrilled about this opportunity to help amplify a brand that I love in a place I’ve been wanting to visit since I was five years old. There will likely be a few posts here during the trip as well as on the tumblr Lizzie and I are sharing: We Had A Blog In Africa. If anyone’s interested, please check them out. We’re off tomorrow and return from this adventure on November 22nd, perhaps wilder and wiser than before. 

Here goes nothing. 

October 22, 2013
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. 

October 1, 2013
The Terminology We Choose To Know

Classroom education begins with definition of 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 mis-communication. 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? Tech. 

Less certain terminologies you face an uphill battle to break into a new industry or have 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 thirst for and eventual 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.

August 29, 2013
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. 

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