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In my late twenties, I had the misfortune of attempting a dot-com start-up right as the bubble collapsed. The experience did not go well. As we were in the midst of our most painful death throes, I penned a missive to a site called Open Letters, which they published on January 3, 2001 - two days before Open Letters itself would stop publishing new content. In the years since that debacle, my life has righted myself, but I'm curiously glad that this letter exists - if only to remind me of how far I've managed to come since then. That was a grim time, and it's made me immensely thankful to have come out the other side relatively intact – certainly with a lot less money in the bank, but obviously money's not the only metric in life. The writing has been on the wall for about six weeks now. In about two more weeks, the writing on the wall will come to an end. My company has about $2500 in the bank now, and unless some miracle happens in the next two weeks, that last $2500 will provide one more paycheck to our only remaining paid employee, one last check to the lawyers, and then we collapse in a heap. We will have probably $20-30,000 worth of unpaid bills staring us in the face at that point, give or take some insane amount. I wish I could say that it wasn't my fault, that I could believe in some "it's the market's fault!" excuse, but it ain't the market's fault. I have become coldly analytical about my mistakes, to the point where I don't particularly feel as though I did much of anything right, including starting the company in the first place. Mind you, self-pity is a loathsome endeavor; what I'm experiencing now is not self-pity at all. It's more like abject terror in the face of what comes next. My financial life is a complete ruins, with three months worth of bills facing me and no idea when I'll be able to concentrate on getting a new job. Most of those bills are the outrageous credit card debt I rang up while trying to start the company in the first place. I don't yet know what the ramifications of my company's pending bankruptcy will be, whether I'm going to get personally nailed for some of the unpaid bills - I'm afraid to ask my lawyer at this point because every time I talk to him he charges me $200. I will find out the hard way I'm sure. Our President, a friend I hired earlier this year, is working the phones, and getting nowhere. Last week an old radio buddy of his told him he was considering investing, but we'd have to give him a brand new Harley Davidson if we ever went IPO or got acquired. Naturally we promised him two fucking Harleys if we ever went IPO. He hasn't called us this week. Last week our President talked to a guy who runs a company in LA that seemed like they wanted to give us money. He hasn't returned our calls in a while. This is an old story this year; every time someone wants to give us money, their stock in some other company slides 53,000 points and suddenly they're not interested. The irritating thing is, things looked good for a while, and I think I pretty much blew the opportunity. I got started too late; I spent money unwisely, although to my credit, we never spent $5000 on a goddamn office chair, and I think anyone who ever did should be taken out and brutally maimed. My spending mistakes were strategy mistakes, which is a much more painful category than just "stupid profligate spending." I thought it'd be "cool" if we did X, thought it would "eventually work" if we just kept doing Y, gambled on getting another round of investment before the money ran out and neglected to budget money for promotion, etc. etc. until I just wish I'd never had this idea in the first place. The only things I did right were getting us a quarter million in the first place, and then hiring some extremely talented people; but even those things are bitter, because I raised the money from friends and family, and those talented people are good friends of mine. I can't imagine what it will feel like to tell each one of them, it's over. I know it's going to happen, and it's like some sad recurring nightmare in my head - rehearsing for it means it keeps happening over and over again. Tomorrow we have a pretty important presentation of the software we've developed for a much bigger, more impressive local company. They have our fate in their hands, to some extent. When I met with their CEO, he casually mentioned he could finance us if he liked what we had to offer, but the minute you start believing what successful people tell you, you're always in for a rude surprise; they hold cards you don't, and you're not particularly even playing the game until you have eleventy billion in capital from Pompous Venture Fund Incorporated. Goodness, maybe this is self-pity. I profusely apologize. I started my career as a temp in Chicago, for the Director of Marketing for a huge global company with 30,000 employees. When she got promoted, she hired me on to be her full-time "executive assistant." After a while, a friend convinced me I had more skills than that and got me hired as an "associate consultant" for another giant company, and then eventually I got promoted to "consultant", and then I eventually became a "content manager" and then an "associate producer" for multimedia-based training products, and then I wound up working as a "project manager" for web application development & web projects. Time elapsed: about five years, give or take, and somewhere along the way, I got the idea to start my own company, and so I became "CEO & Artistic Director." For a while, I used to walk down the street giggling at the idea that I was a CEO. Tee-fucking-hee! The idea for the company came to me in the middle of a heavy experience involving homemade ayahuasca, but that's probably another story altogether. I convinced my uncle to chip in, and later convinced my old boss to chip in a big hunk, and then convinced our future President to chip in, and invited him to join our rising star. Just in time, as it turns out, for all kinds of things to go wrong: I had made some bad decisions early on concerning the viability of video on the net; I had burned up development time on a project that we would eventually replace with something smarter, but not before wasting months of effort; leads kept drying up for future financing; the sneaking suspicion began to overwhelm me that if I was an actual CEO, I'd know what to do, but instead I grew paralyzed as we slowly ran out of money. I had known all along this was the likelihood; most companies fail in their first year, and when dot-coms started collapsing all around us, my fight or flee instincts started selling me out. I'm 28 years old. I don't belong at the helm of a company, and it's clear to me now that that's one of the major reasons our business plan met with such little success. I'm young enough to try this again someday, but I swear to god, this has been an overwhelming, exhausting, overly emotional experience. There is a personal side that the sneering commentators overlook, but then again, my experience is a common experience. Everyone knows what failure feels like, so is there any need for me to ruminate out loud about the subject? Try to come to some conclusion about the experience that offers insight or inspiration beyond the vivid shame that accompanies failure of this magnitude? When I got my degree in theatre, I had no clue that I would someday burn through mountains of credit cards, all of my savings, and $250,000 of other people's money in the reckless pursuit of my own creative freedom. The technical people who work for us have been slaving away. Our director of software development said to me a week and a half ago, "I don't want to look back on this and realize there was something more I could have done." I don't have any such way to focus; the things I think I know how to do at this point require money I don't have to accomplish. I am at a complete loss, and I spend my days waiting for something to happen. My own personal network has been tapped out; the developers can keep developing, our President can keep making phone calls. This meeting tomorrow could go well; chances are, it will go just fine but they won't commit to anything and we will shut down before the end of the month, go our separate ways, and look back on this however we choose. I'm the only one who has to answer to those investors, of course, and god knows my old boss is going to kick my ass for losing his money. I'm going to go back to consulting, make enough money to pay off my debt, try to get on with my life without such enormous ambitions. I haven't been able to write anything for months, because of the stress; maybe I'll get back to being artistic again when this is all over. It's just a company, just a callous attempt at making money, it doesn't deserve this level of mourning. And it certainly isn't the first time I've poured enormous amounts of energy into something that ultimately failed to meet its mark. There's plenty of time for me to figure out a calm, meaningful path. I think it's easiest if I just blame computers. I fucking hate computers.
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