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Great thread.
I think my decision was based on the convergence of two entirely unrelated reasons, a professional and a personal.
First the professional. I moved to NYC in 1999 to work in advertising, specifically media planning. My first job was at one of the oldest most prestigious agencies, but the salary was only $24K. Even though I was able to partially subsidize my existence with a savings account, it was tough to get by so I left within a year for a more senior position with a $36K salary and hiring bonus at a smaller agency focused on tech/financial clients. That's also right around when the dot com bubble burst so they ended up laying off many employees including myself within 6 months. I quickly found a freelancing spot at another big, well known agency, but the job focused solely on print media. They kept offering me a permanent position and I put them off for as long as possible, but it was difficult to find a job doing exactly what I wanted b/c I was already typecast as a 'job hopper'. Combine that with the fact that I liked the people, plenty of room for growth, and the ability to walk to work from my West Village apt, I ultimately caved in, took the job, and was there for the better part of 9-10 years even though I never really liked what I was doing. During the last few years, I would even only work during 'contract season'. It was actually kind of sweet b/c I did real estate, traveled, and did other random shit during the six or so months per year that I had off before coming in as like a hired gun to negotiate contracts and manage three or so dozen employees, which is something that I actually did enjoy. Well, it didn't last because during my last contract season, I came up with the strategy that we should no longer negotiate contracts. That we should just tell the newspapers what our rates would be, that we would not sign contracts, and that if they didn't approve of our proposal, we would just move the money to another local medium or outside the dma. Reasons being that our client had grown and print media had been struggling. The strategy was so brilliant and worked so well that my contract negotiating skills were no longer needed the following year!
They did call me in for another freelance assignment, though. It was for a process mapping project where we as a team discovered and documented the beginning to end processes for each medium, mapped them, looked for similarities between each, and came up with suggestions as to how the processes of each could be made so as to be more in sync with parallel processes used in other departments. The goal was to come up with process maps which enabled employees to be more interchangeable (i.e., expendable). It was fun, challenging, and high level stuff, but during the discovery phase, I realized how little I knew about the online aspect of the business and that I needed to somehow learn more about it. Even though I knew I didn't want to work at that company or at a similar company ever again.
Now the personal. At around the same time that last project was ending (April 2010), some type of glitch caused my 'babe list' on FreeOnes to be deleted. There were a ton of girls on there too! I'm a bit of a spreadsheet dork, so when I began to repopulate the list on Freeones, I also put the info into an excel spreadsheet. Then after reading some article about information sales and affiliate marketing (which I had not even heard of beforehand), I started brainstorming ideas and came up with the idea of pimping out the porn star spreadsheet, bundling it with discounted memberships, selling it, and loading it with affiliate coded links so as I would also make money on the back end. I was able to sell a few hundred of them but my lack of experience led to so many tactical errors and things didn't exactly work out as planned. So I just shifted the site to be straight up affiliate marketing and voila!
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