Digital Hustlers: Living Large and Falling Hard in Silicon Alley by Casey Kait and Stephen Weiss

Tara Taghizadeh

Serves as a diary of the main players involved in the heyday of New York's Alley.

Digital Hustlers

Publisher: Regan Books
Subtitle: Living Large and Falling Hard in Silicon Alley
Author: Stephen Weiss
Price: $26 (U.S.)
Display Artist: Casey Kait and Stephen Weiss
Length: 256
Formats: Paperback
US publication date: 2002-07
"The aphorism 'content is king' was so common in New York that its validity was
-- estioned . . . if content would be king, New York would be its throne."
— Casey Kait and Stephen Weiss

In 1996, right at the beginning of the Internet boom, I landed a writing position at America Online, where as a freelance contractor, I was deprived of the lavish stock options that had been heaped on staffers. A casual atmosphere populated by 20- and 30- something bright young visionaries had established the company (back then) as a hotbed for digitally-inclined talent who worked hard and played even harder.

The consistent slew of perks, parties, happy hours, and work-from-home policies had created what appeared to be the ideal environment for those eager to extend their collegiate lifestyles into the "real world", if you will. And after a few years of a jolly good time, the long-anticipated prize AOL offered was the main incentive: cashing in stock options and retiring -- which many did. By 1998, a couple of friends had already turned in their notices, called their financial advisors, and eventually walked away with a cool million, all before turning 30.

California's Silicon Valley is indisputably the home of the Internet, where Mosaic (which eventually became Netscape) was born. However, the rising surge of the world wide web had also swept the East Coast by the mid-90s, and its headquarters was in New York City, a.k.a. "Silicon Alley," which is the basis for Kait and Weiss's book, Digital Hustlers: Living Large and Falling Hard in Silicon Alley.

Live large? They sure did. Fall hard? Absolutely. By mid-2000, the death knell for the great Internet hope had been rung, as one company after another laid off staff, downsized, or completely shut their digital doors. But for a few years in between, the "digerati" ruled the roost and astonished the corporate world with their multi-million-dollar digital revolution.

Digital Hustlers serves as a diary of the main players involved in the heydays of New York's Alley, and chronicles their thoughts, insights, and hindsights in interview format. Kait and Weiss, both Silicon Alley veterans, interviewed a slew of digerati, and provide a step-by-step analysis of the rise and fall of several Alley companies and their larger-than-life entrepreneurs.

The story of the digital revolution is, after all, the great American success story: young, intelligent, enterprising youths with dreams of changing the world and raking in mega- bucks. As the authors explain: "By the year 2000, Silicon Alley was employing 250,000 workers and producing nearly 17 billion dollars in revenue." Whereas California was more focused on the technology aspect, New York concentrated on "content," thereby luring employees whose backgrounds were more ingrained in the arts and media. As Kait and Weiss write: "Geek chic quickly became the new gold standard," and personalities such as Josh Harris, founder of Jupiter Communications and, Scott Kurnit, founder of, Nicholas Butterworth, CEO of MTVi group who helped build, and Craig Kanarick, cofounder of Razorfish, were the toasts of the town.

Most entrepreneurs initially started their companies at home or in a shoddy office with "literally one little desk, two broken chairs, and a computer (which is how founder Steven Johnson describes the magazine's original settings). However, by 1996, the revolution was gaining momentum, as the media and the rest of the world tuned in to the hype surrounding the Internet, and money started pouring in as one investor after another smelled the lucrative potentials of investment in online ventures.

Kait and Weiss explain the initial hype over Silicon Valley (which had already enjoyed a notable history), while its counterpart, New York's Alley was ignored, since the "get- rich-quick tales" were largely based in California. But the savvy New Yorkers quickly learned to court the press and generate the necessary buzz, frequently with a lot of help from their all-night raucous parties, invincible demeanors, and relentless promotion of their start-ups. As Razorfish cofounder Craig Kanarick explains: "We were all a pain in the ass, and we were all brash. It was all about being brash and being different and being new and being independent . . . and being, Fuck you, Mr. Big Company, you don't know what you're doing."

The greatest threat the Internet ventures posed was in disrupting the old boys' network of the old economy. Media companies were predominantly affected, as talented employees realized that there was serious money to be made online, so why settle for a measly entry- level publishing salary? Just learn HTML, and pour your creative juices into dot-coms. On the flip side, though, the arrival of start-ups fueled the economy greatly, and resulted in the creation of thousands of employment opportunities.

During this time, the cyber cafes were in full swing, and the lax work atmospheres of online companies had found their way into media coverage. Showing up late, smoking pot and snorting coke were often the norm. According to's former executive producer Robert Galinsky, "In the first few months [the company] was a clubhouse. . . . Smoking marijuana? Could be half the company within the first year, on the job."

The bubble soon began to burst, however, when many Internet ventures realized that advertising was the driving force behind successful content, and a lack thereof, would lead to depleted funds. Which is exactly what happened in many instances. Previously successful companies such as Echo and had folded by 2000, followed by a slew of others. In addition, the brash young entrepreneurs were now being replaced by the same "Mr. Big Company" types whose motto -- according to Kyle Shannon, founder of UrbanDesires and -- was: "Get in a manager. The wacky kid with a vision? Get him out of here."

Despite the tremendous successes of a few Alley ventures, such as Razorfish (Kanarick was worth $200 million at the age of 33), DoubleClick, and, "the vast majority of the new millionaires were rich only on paper." Reality had stared to set in. By March 2000, CDNow and a number of other corporations were in trouble financially, and the news of their shaky status served as a sort of domino effect, as company after company began to fire staff, or in most cases, totally collapse. A popular site called served as a grim reaper as it listed the impending failure awaiting online corporations. As the authors explain:

"Perhaps even harder hit than the public companies were the thousands of start-ups that had yet to go public, which were often suffocated when angel investors, many of whom had made their fortunes on the tech bull market, could no longer provide new investment money."

The end was near and within a few months, thousands of former dot-com employees, spoiled by high salaries and promises of cyber celebrity dreams, were back on the streets searching for employment. The fallout also affected Silicon Valley, which is still the lifeblood of the Internet industry, and thousands of San Francisco Bay Area companies suffered -– and are still suffering -– from the crash.

Digital Hustlers serves as homage to all those brash young things who had a digital dream, and for a few years, rocked the world. The book offers unusually interesting insights into the lives of the industry's stars and their influences on the dot- com phenomenon. It's important to note that this is very much a New York story, and the book's wider audiences will inevitably be readers who are fascinated by the inside story. (As an aside, Kait and Weiss should also plan a similar project, this time focusing on the equally gripping legend of Silicon Valley.)

Having walked away with billions of dollars, a few of the dot-com stars can rest assured that their efforts and visions have proved effective: practically every nation in the world, after all, is in some fashion, connected to the Internet, and if there really is a "global village," it exists online. This revolution has been won, and despite its current shakiness, its future should prove even more interesting.

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"Now I am just more tired and poor. So no, I haven't changed. I'm just older and more tired," says French radio journalist and documentarian Sonia Kronlund, as she looks back on the experience of making The Prince of Nothingwood (2017).

Joining Salim Shaheen, the most popular and prolific actor-director-producer in Afghanistan on his 111th no budget feature, Kronlund documents the week-long shoot and the events surrounding it. She crafts an insight into a larger than life persona, yet amidst the comedy and theatricality of Shaheen and his troupe of collaborators, she uncovers the heavier tones of the everyday reality of war and patriarchal oppression. If The Prince of Nothingwood will popularly be remembered for celebrating the creative spirit of its star, it is equally an important communication on Afghanistan, it's culture and its people. Alongside the awareness of the country cultivated by mainstream media news outlets, Kronlund's film offers an insight into a country that can humanise the prejudice and xenophobic tendencies of a western perspective towards Afghanistan.

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Why filmmaking as a means of expression? Was there an inspirational or defining moment?

Not really, no. I have always done documentary. I used to write scripts and TV series but I only make documentaries myself for radio and television. For this story, I figured out after a while that it deserved a bigger ambition and a bigger screen and that's why I don't very much believe in inspiration. To be honest, I made this film because I had to do something. I didn't have a big project where I thought: I want to make this. I went there and I found a little money and at the end the ambition and the inspiration came along the way. But there was not an urgent necessity to make this film. It fits with a lot of things that I'm interested in, like popular culture -- What does art stand for and why do we go to the cinema? What is the purpose? This is a question I'm interested in, but inspiration, not so much.

Has The Prince of Nothingwood provided you with the answers to those questions?

It has, and I hope it helps people to think about this question. It tells you that there is an urgent need to make images, to make films, even during war,and even if you don't have the money. And even if the films are not very good, they will find somebody who will like them. So something is going to happen, and I think that's very touching. I don't like Shaheen's films, I hardly watched them -- I paid somebody to watch them. But I'm very moved by all these people that do like his films, and it makes you think about the value of art and the purpose of why we make cinema. I used to study aesthetics in London, so it was one of the questions I had and while the film is lighter than this, that's what was in mind.

The film uses Shaheen as a doorway, beginning as a story about one man which becomes a story about Afghanistan, its people and culture.

Yeah, but it's not so much about Afghanistan and it's not my purpose is to say things about the country. There's one guy like him in Iran who makes cowboy movies in the Iranian desert and there's also a guy like that in Tunisia. I mean you have this person with an urgent need to film whatever they have under their hand and since it's war, then it tells you something about the war. But it's not so much interested in him.

There was a lot of editing, 148 hours that you haven't seen [laughs]. Making a documentary is really telling a story and I don't have any idea of objectivity -- it is my point of view on Shaheen. Some people say to me that they would like to show his films, that they really want to see his films, and I say: "You don't see how much I have edited. I show you the very nice parts of his films." People think he's a great filmmaker and that's the story I wanted to tell -- but I could have told another story.

To my mind, objectivity is a human construct, a falsity that does not exist.

Except mathematics maybe, and sometimes physics.

The purist opinion of documentary as objective is therein built on a faulty premise. From the subjective choices of the filmmakers that bleed into the film to the subjectivity of the subjects, it's not purely objective. Hence, it calls into question the traditional dividing line of the objectivity of documentary and the subjectivity of narrative fiction.

Totally! It's the editing, and why you chose this guy, how you film it and what you show, or what you don't show. It's not only subjectivity, it's storytelling. Not many people ask me about this, they take it for granted that it's the real Shaheen. But I'm not lying, I'm not saying things that aren't true, but I am telling a story, a fictional story out of what I filmed. I took scenes that happened one day and I put them with another story that happened three months later and that's why we had seven months of editing with three editors. So it was a lot of work.

One of the striking aspects of the film are the light and comedic moments offset by a darker and heavier sensibility, which include moments when, for example, Shaheen talks about arranged marriages.

We made 70rough cuts and there was one version we tested and you couldn't believe you were in Afghanistan. People would say: "Oh this is too funny. You don't see Afghanistan, it's just a bunch of crazy guys." I then said: "Let's put in a little more darkness." You then have to strike a balance and to me, if it's not perfect, I'm happy.

Shooting the film in a dangerous and volatile part of the world, was the approach that once you had enough footage you then looked to shaping the film in the edit?

It's not when you feel you have enough, it's finding a balance between security and artistic concerns. That's it. You have a plan and you have an agenda. There are things you want to do, but it has to be balanced with security concerns. The real story I was going to tell about Shaheen I found in the editing room and in the end, I only kept five days of the shoot. The whole film takes place in Bamyan (Province), nothing in Kabul, although I had weeks and weeks of footage there that I had to take away.

There's a moment when Shaheen asks if you are scared, which sees him verbalise our silent recognition of your boldness and courage to bring this story to the screen.

It's very difficult and it's not like you are walking in the street and there's a bomb. This is not what's difficult. The difficulty is to cope with your fear and to have rules and to follow or to not follow those rules. There are many foreign people that never go out at all in Kabul -- it is forbidden. You have British diplomats who do not even drive their car from the airport to the embassy -- they will take an helicopter that costs £2,000 each way. Then you have foreign people who walk in the street without a scarf -- these girls get kidnapped.

In between these you have Shaheen, who is telling me all the time that I'm too scared, because it's a man's value to be brave and he's a brave guy, there's no question about that. He was in an attack two weeks ago. There was a bomb in a Shia Mosque and he helped to carry out the bodies. So there's no kidding about the fact that he's a brave guy and he has to be because he's been fighting to make his films. But you are in the middle of this and I'm not a brave person at all and I don't think being brave is a very important question. It is, but I'm not brave, I'm very scared and so in the middle of all of this stress it's enough just to manage to not go crazy, or to not drink too much [laughs].

Salim Shaheen and Sonia Kronlund (courtesy of Pyramide Films)

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