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? 

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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

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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: 

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Before boarding our flight over the Okavango Delta 

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Heading into the Delta via Makoro dugout canoe 

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With our poler Gladys in Botswana 

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Waiting for a ride on the Chobe River, Zambia 

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

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

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Early morning at Kande Beach, Lake Malawi 

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Scuba prep at Nungwi Beach, Zanzibar 

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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…

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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

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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. 

July 29, 2013
We’ve got it Simple

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

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

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

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

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

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

Simple is grand. 

July 24, 2013
Do you want your receipt?

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

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

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

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

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

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