I've worked for an entrepreneur who seemed to experience manic episodes. There is an incredibly sad quality to working with such people. Most of the time, these people do not do well. And yet, they are full of potential, and ideas, and energy. They can be charming. You want them to do well. But they fail.

The person I'm thinking of, let's call him P, could be persuasive. He generally made a very good first impression. He lacked technical skills but imagined himself a good designer and eventually got to the point where he could design a page in Dreamweaver (the HTML would often be bad, and we'd have to get someone else to clean it up. For instance, divs with fixed height would have to become more fluid). P had inherited several million dollars from grandparents, and spent nearly all of it trying to build the next Google.

P had amazing amounts of energy. He generally worked 16 to 18 hours a day, sometimes for 7 days a week. He would start work at 10 AM or 11 AM and work till almost dawn, the next day. For a few months I lived at the large residential complex he had. Every meal was a business meeting - breakfast, lunch, dinner, late night snacks. It was exciting to be so wholly focused on work, and to let the rest of life just drift away. It is freeing to give up on a normal life and commit to doing just one thing. The long hours matched my own style, and I had a chance to learn a lot of new things.

P would often fantasize about what life would be like after the startup was world famous. He would talk about what kinds of charities he would donate money to, and how the media would approvingly write about the donations he made. Then he would tell us how each of us was going to get rich, we would all get equity and someday it would be worth billions. We would all own our own tropical islands. He really did talk this way. (I find when I describe this era accurately, people assume I am exaggerating.) The talk about equity slowly lost meaning, as all of us slowly lost faith in the project. It all sounded believable in 2002, less so by 2004.

The downsides to this type of personality is that they tend to get frightened by reality. They want to live inside of their lovely dream, where everything works out amazingly well. When we came up against good competitors, he would freak out. His euphoric episodes mixed with episodes of intense anxiety and guilt. Sometimes he would worry that, rather than building the next Google, he was just wasting away all the money he had inherited, and his parents were going to be mad as hell at him. Which is exactly what happened.

In his fantasies, the startup was suppose to sail smoothly to big success. Building the company was not suppose to involve tough decisions, rather, it was suppose to involve moments of brilliant insight, one after the other, as his company easily leaped in front of any potential competitor. When the years went by and nothing successful devolved, he began smoking a lot of pot, to try to control the anxiety.

I worked with this person, on and off, from 2002 to 2008. We first came up with a CMS to compete with TypePad. But then TypePad got way ahead of us so he switched our focus RSS feeds and podcasting. We started work on something like Odeo, about 6 months before Odeo showed up. When Odeo showed up, P quit working on podcasts. Then we worked on the CMS some more, we were going to sell it and compete with Expression Engine. That would only make sense if we were way better than Expression Engine, which was a moving target. WordPress was also a moving target, and by the end of 2005 it was becoming clear that WordPress was going to be really good. We went back to working with RSS and music and we came up with something very much like Hype Machine. This was early 2006, a few months before Hype Machine started. We gave up on that project for no obvious reason. Then I wanted to work on something like Google Pages, and this was about 6 months before Google Pages came out. I worked on this for a month. I couldn't interest P, so he killed the project after a month or two. Then we did some client work and then we did some web sites devoted to mp3s and videos, but none of these projects were developed enough to be taken seriously. In short, we tended to drift from idea to idea, as P would lose interest in one thing and then get manic and over-excited about the next thing. Then we went back to working with RSS, but the next project was embarrassingly stupid, it didn't amount to much more than grabbing Yahoo Pipes and running it through a PHP script to strip out any mention of Yahoo Pipes. That is about when I left.

On the one hand, working with someone who likes to daydream can be exciting - work becomes a brainstorming session that lasts for several years. On the other hand, as they say, who can live for long in an euphoric dream? There comes a point where you want to get to work. There comes a point where you want to stick it out with something, to try really hard, to take some setbacks but still keep going. Every startup needs to change the plan a few times, but to change the plan every 2 months, year after year, is a good way to burn through several million dollars and accomplish nothing. Which is exactly what happened.

For my part, I mostly had a good time, though the whole thing was like a minor tragic epic. It is rare that you see someone burn through so much money, with such an odd mix of manic intensity and crushing anxiety.