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37

Charlie’s “100 Things Posts About Me”

#37. I’ve been the Chief Technical Officer of a company.

I know, I know; it’s hard to believe. Still, it’s true, and I still have some official business cards to prove it. I was once among the elite, the powerbrokers. A malingering moneymongering muckety-muck. A fat cat. I pressed the flesh, and networked, and wore power ties to power lunches. I ruled the world.

Okay, so it wasn’t really like that. At all. In actual fact, I was the CTO of a twelve-person medical software services company, and wore my shorts and T-shirts (or jeans and rugbys, when I needed to look nice) to a tiny office smaller than the apartment I lived in at the time. I walked to work, ate lunch at my desk — or at the local KFC — and spoke to maybe four people a day. Usually via Instant Messenger. Even though they were sitting approximately twelve feet from me. Such was my life as a CTO.

Eventually, I even changed my own title (hell, I got to make up the first one; why not do it again?) to ‘Lead Systems Architect’, which was closer to what I wanted to do when I grew up. And still is, in fact. (If I ever grow up, I’ll tell you whether I was right about that particular choice.) But I kept the ‘Founding Partner’ part of my title, because it was still true.

So how was I as a CTO? Well, to be honest, I didn’t care much for the ‘business side’ of running a, er, business. If you know what I’m saying. Sure, everything you do in a business is part of ‘the business’. What I mean is, I was much more interested in talking tech specs with clients and testing technology and building systems and coding than in things like managing the books, or setting a budget, or negotiating deals. Or wearing a suit for any length of time, so that eliminated me from quite a lot of the activities that I didn’t care much for, anyway.

So in the end, I handled a lot of the software design and development and in-project client relations, while two of the other founders handled most of the business-related tomfoolery. (Our fourth founder was a bit like me, in that he wanted to stay away from suits, and people in suits, as much as possible, but he was more interested in the medicine than the bits and bytes.) Anyway, the division of labor worked out okay, in my estimation — we were able to function as a software services company for two years without one red cent of venture capital money. On the other hand, the other founders did sink a bit of cash themselves into the business from time to time, and we got paid only when we could afford the luxury, but still, I think we did a pretty fair job.

I left the company to move to Boston around the time that they got sick of being poor and decided to morph the company into a true blue product company. Meaning that they’d fish for VC money to build an honest-to-goodness off-the-shelf product, and sell it for gobs of cash. So how’d that work out? Well, they lasted for about four years, and even got a couple of model systems installed in local hospitals. By all accounts, they were making very good progress.

But VCs are nasty bitches, and the first couple of million dollars in debt repayment came due a couple of months ago. The folks that were left — up to twenty or more at one point, but back to a skeleton crew of just a handful by this spring — had no shot at coming up with that kind of cash, and so there was nothing they could do. The Vulture Capitalists swooped in, took hold of the intellectual capital, sold off all the assets, and shut the doors. Which is their job, I suppose. I don’t really fault them. If someone owed me two million dollars that I’d loaned them four years ago, I think I’d get a medieval on their ass, as well.

Anyway, that seems to be the end of that. I was really hoping they’d make it big, after all. And not because I feel like I had a hand in starting it all, mind you, or that I wanted to be able to say I was once the CTO of a now multi-million dollar cash cow. No. I’m not as egotistical as all that. No, I genuinely wanted them to succeed, because they’re good people — the few left that I know, anyway — and I had some good times there, and I’d like to see them happy.

Okay, okay, just a smidgen might also be because I owned over half a million shares in the company, and if they had ever managed to get the stock listed on a market somewhere, I was going to be insanely, filthy rich. That might be just a bit of why I was rooting for them. But only a bit. Really. I’m sure of it.