Every weekday morning, around 6:58 a.m.,
I bolt awake, zombie-walk to the living room of my New York City
apartment, turn on CNBC, then trudge downstairs to fetch
The Wall Street Journal from my stoop. It’s a fairly mundane
routine, and one that I was doing several years ago when I was a
financial analyst for a handful of hedge funds. But now I do it
for different reasons.
Sometime in 2000, on behalf of a client, I was researching technologies that help businesses maintain online content when I came across a company called Pyra Labs that had recently developed a piece of software under the name Blogger.com. It looked interesting, so I created a blog called "Capital Influx" and did a few posts about technology and finance.
I forgot about the blog for a few months, but in 2001, increasingly bored at work and looking for a creative outlet for things that were on my mind, I picked it back up. And when people began responding to what I was writing, it quickly became addictive. There was a small but growing community of people who were doing the same thing— many of them working in technology — and it became more than just an outlet for my opinions, rather a forum for discussion.
In spring of the next year,a friend, British Internet entrepreneur Nick Denton, took me to lunch to talk about an idea he had for a commercial website that would be an insider guide to New York. I had analyzed several startups for my clients and was under the impression that Nick was asking me for business advice.
"I like the pitch," I said, while picking at an overpriced tuna salad, "but how is it going to make money?"
"Advertising," he said.
New York ’s Silicon Alley was littered with the corpses of failed online advertising models, but if it didn’t cost much to produce, and you could hire a writer cheaply,why not?
As it turns out,Nick did find a writer to hire cheaply: me. The pitch over lunch was actually a very subtle job offer. So subtle, in fact, that I didn’t realize it until several mutual friends asked me if was going to accept it.
Six months later, our city guide, which we called Gawker.com, had morphed into a gossipy, mischief-making, pop culture blog about New York,Manhattan-centric celebrities and industries that were particularly indigenous to the city – media, in particular. I had stopped doing financial analysis and was writing Gawker full-time. I didn ’t know much about celebrities or media so I approached both subjects the same way I approached new industries and products in my finance job: I researched, talked to people, mapped out the industries competitively and tried to determine who the major players were. And while my commentary on Gawker bore little semblance to the fairly technical reports I issued for investors, it was remarkably similar in tone and form to the acerbic, off-the-cuff emails I sent my clients when pressed about a sub-par company and its sub-par management.
And people were reading it. The editors about whom I was writing were reading it; Howard Stern was reading it; and as I discovered when we got a cease-and-desist letter for linking to some unsavory paparazzi photos, Catherine Zeta-Jones’ lawyers were reading it. The traffic on the site ballooned to over 50,000 readers a day in less than nine months.
And we were having a great time. I was getting paid (albeit not much) to basically write jokes,and hadn’t opened a spreadsheet in ages. But I wanted to write longer pieces, which I had done only intermittently while writing Gawker—mostly to pay the bills—and was interested in doing magazine work. So I left in September of 2003 to go to New York magazine (and back to dead tree),where I edited their gossip column and wrote pieces about entertainment and media.
After a year and a half I was getting restless again, missing the business aspects of my previous jobs. I was accustomed to looking at businesses from management ’s perspective and being so far removed from high-level decision-making processes made me feel like a professional skill I enjoyed using had been turned off until further notice. A media industry website called MediaBistro.com approached me about taking over as their editor-in-chief and revamping the editorial department. I had some reservations about returning to online media because I didn’t intend to simply repeat my Gawker experience and was sure it would be perceived that way, but also thought MediaBistro would be a good place to combine my business and editorial skills.
A month before my year-long
contract with MediaBistro was set to expire, I sold a novel to Simon
&Schuster and resigned.
Blogging, my original work avoidance strategy, had now twice become
work, so my new strategy was fiction writing. The book was about
Wall Street and the business world, and was perhaps indicative of
what I subconsciously wanted to be doing.
I had toyed with the idea of writing a Wall Street gossip blog when I was still writing Gawker — Wall Street being more familiar and interesting to me than Gawker’s editorial twin pillars of Paris Hilton and Vogue Editors You May Or May Not Recognize — and after a couple of months of full-time fiction writing, I was getting restless again. I’m too social to spend all day by myself, too "Type A " to be content with one creative project (Plus, I have irrepressible mischief-making tendencies that need to be indulged.) So I mentioned the Wall Street blog idea to a friend of mine and he offered investment capital. It was the ideal situation: I would have full control over both the creative and business sides of the site, something increasingly important to me because I have skill sets relevant to both that I enjoy utilizing and which keep me balanced personally and professionally.
DealBreaker.com is, at the moment, less than a month old. The traffic is over 200%of what we projected for the first month and I’m slowly assembling a staff and business infrastructure that will allow the company to expand into a network of similar websites. When I drag myself out of bed in the morning — which is always hard, because I ’m constitutionally incapable of being a "morning person"— it’s to work on something that is both a labor of love and a real business.
DealBreaker is something that I like to think is interesting to a certain type of reader: the young financial analyst with a range of other interests, sitting in her office and avoiding an open spreadsheet.
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