Inspired by Fred Wilson and Howard Lindzon's recent posts, I'm writing this week about setting off on my own.

The mailroom

My journey started right after finishing undergrad at USC. Dead set on breaking into the entertainment industry, I took a mailroom job at the Endeavor Agency. The talent agency world reveres "paying your dues." Everyone starts in the mail room and works their way up from there. They see it as a rite of passage.

The absurdity of the whole exercise set in a few weeks after I started. I was still waiting to get promoted a desk as an agent's assistant. My assignment one morning was to give orientation to a new mailroom hire. Her name was Julie and she was a recent graduate of Stanford Law School. Meeting her in the modernistic lobby, I took her down a few floors on the elevator to the dingy mailroom. I then explained to Julie how to sort the mail, load the cart, and take it up to the main agency floor to deliver it. Even with a Stanford law degree, I guess you have to start somewhere.

I joined Endeavor as a stepping stone. Some mailroom hires like Julie had ambitions to rise up to a junior agent, then full agent and – with some luck and drive – one day make partner. Others like me saw the job as a foot in the door. I intended to gain industry knowledge and build relationships. At some point I'd leverage those to make the jump to something else. Perhaps a studio job. Or working for a producer or showrunner.

About a month after starting at Endeavor, I got the call up to work a desk. I assisted a young agent who was a good boss and fortunately not a yeller. Her client roster consisted of young TV writers. I remember making lots of calls to pitch clients for a new series launching soon on AMC called 'Mad Men'. I wondered why AMC was pivoting from re-running old movies to producing originals. The premise seemed oddly niche for their first attempt. But what did I know?

Entourage in real life

My existence as an assistant was tolerable, but far from glamorous. It was like 'Entourage', only in the stark tones of real life.  I was Lloyd without the comic relief. The office looked straight out of the show. Turns out they filmed the agency scenes there.  We even had an Ari. Only he wasn't played by Jeremy Piven, he yelled more, and was more intimidating. I worked from eight a.m. to eight p.m. five days a week, always in a pressed suit. The agency paid me and the other assistants around $10 an hour, barely more than minimum wage in California at the time. All for the privilege of connecting phone calls and making coffee.

The whole time I worked at Endeavor, I lived a double life. A few months before I started, some high school friends and I had conceived of Bleacher Report. We worked on it as a side project while we pursued our post-college careers.

I dove headfirst into the Bleacher Report project during my Endeavor days. I needed the escape from the drudgery of being an assistant. When my boss wasn't around, I'd switch over to my personal email to work on the site. During brief breaks, I'd sneak out to the alley behind the building for conference calls with my co-founders. Working on Bleacher Report, I felt a sense of agency that life as an assistant couldn't provide.

Hollywood rediscovers digital

My breaking point arrived when Endeavor took a newfound interest in the digital world. This was 2006. The memory of the early 2000's dot-com bust was still fresh in the minds of Hollywood.

Agencies had written off digital content over the previous few years. But that was starting to change. The recent rise of a new web video site called YouTube fueled this new interest. Google's surprising $1.65 billion acquisition of YouTube blew the door wide open.

In response, Endeavor started a "digital task force." The group would consist of younger internet-savvy agents and assistants. The task force would evaluate new opportunities in digital and make recommendations for how Endeavor could profit from the space. I raised my hand to join. I thought this could be a way to climb another rung of the ladder.

After attending one meeting, I could tell the task force would be a bust. The thinking was limited. The group glossed over the potential of the web for creating new business models and forms of media. Instead, they thought purely through the lens of how to use digital to prop up the traditional film and TV businesses.

Endeavor would eventually merge with William Morris and get its act together in digital. But by then I was long gone. Sitting in that task force meeting, I realized I was better off going my own way. I could slowly climb up the ladder, or I could get off and build an elevator. Bleacher Report felt like my best shot to get to the top floor.

I was young, I had a vision, and – most importantly – I had nothing to lose. If I failed with Bleacher Report, I knew I could find another $25k a year entertainment industry job. But if I didn't give it a shot, I'd be kicking myself for years.

The Los Altos summit

Soon after that task force meeting, the Bleacher Report team had what I refer to as the "Los Altos summit." We took a couple days off work and re-convened at the childhood home of one of my co-founders. The summit focused on sprawling conversations about our goals and ambitions for Bleacher Report. After a year of slow progress building the site and a small audience, I felt like we were at a decision point. Go all in and do it for real, or stay the current path and risk the project losing steam.

So I made an ultimatum. I told my co-founders that I was ready to quit my job, move home, and start focusing on Bleacher Report full time. I implored them to do the same if they believed in the project.

A couple months later, I  said goodbye to Endeavor and L.A., and made the drive up Highway 5 to move back in with my parents in the Bay Area. One by one, my co-founders followed suit. We moved into a small, windowless office a few blocks away from our high school.

Finally, after a year of slowly building momentum, we were out on our own. And we got to work.

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