A few weeks into the job I was asked to meet with potential editorial partners. Co-marketing relationships, I was to learn, were a dime a dozen for Web start-ups in the 90s. Non-exclusive, often cashless transactions where you linked back to a partner's Website and vice versa in an attempt to expand your Web traffic. These kinds of deals still exist, but in general I think we as new media professionals have become a lot smarter about when these partnerships actually make sense. I think about some of the deals I did back in '00 and cringe (Online therapy? Really?), but I digress.
What occurs to me now is that these deals didn't need to be particularly sustainable--they just needed to provide a quick burst of traffic, or even just the promise of traffic. The goal was to appear to be growing so that when the time came to exit, the optics were there.
The fellow I met was roughly my age--27 or 28 years old. He'd started his career in San Francisco and seemed much more comfortable with the start-up ethos than I."Is it me, or do people seem not to care as much about work around here?" I said, half-joking. I had a small staff of writers that ambled in and out as convenient, and rather than see this as a management issue on my part, I opted to demonize these people for not having enough drive. I don't think this guy understood.
"We work around the clock," he said. I suppose that was true of many of my co-workers as well, despite my complaints. Staff might have come into work at 10 or 11 in the morning, but they often stayed on call through the night. They just didn't have the intensity I would have preferred. It seemed that they could be doing what they did for any company; ours was just the one that had hired them first. I was used to making my company my cause d'etre.
"It's fine for now," he continued. "Once we sell I'll just chill out."Now here's the part of this story that people don't believe, despite the fact that I knowingly moved across the country to work for a new media start-up, despite the fact that I had a stock option package, I really didn't understand exit strategy. The thought of working your ass off to someday stop working sounded so foreign, even ludicrous, to me that I wasn't sure I understood.
"What do you mean, 'if you sell?'" I asked him. "Is that why you are doing all of this work? To stop working at your company?"
"Of course," he said.
"But what will you DO after that?" I asked.
"If I play my cards right, I'll never work again," he said. A few things went through my head at this point: Fear that perhaps in my haste to secure this job I hadn't paid enough attention to the stock option portion of my compensation. And I felt a more enveloping fear: What if it should ever come to pass that I don't need to work for a paycheck? I had always been validated by work; I would just keep working, would have been my default answer. But this guy felt differently. Who's the chump? Him or me?
"But seriously," I asked again, "what would you DO?"
Now he looked at me like I was nuts. "I'd sleep in, go to the beach, surf more. I don't know; I would just figure it out."
It didn't seem possible to me that he wouldn't want to continue to build on his success at his current company, or maybe even another one. The thought of just stopping didn't make sense to me. Why would someone stop working? I thought of what I would do if I had the option of not working. All of my aspirations were related to work; I couldn't think of anything. I might travel, but then I would have stopped after a few weeks and started working again. Work was my only compass.
This is a rather dramatic example, but I think this encounter gave me an early glimpse into where I needed to be aspirationally before becoming an entrepreneur. We represented two ends of a spectrum of motivation; each on its own could be disastrous to entrepreneurs. Some of us may be more lifestyle-motivated, and some of us more achievement-oriented, but survival as an entrepreneur must borrow from both sides: A life you want, plus a desire to make things happen.
