Where did three months go (AKA where've I been?)
I'm a nobody around these parts, but someone I've emailed back and forth with on here asked me a couple weeks ago where I've been. I'm finally at a point where I can take a breath so I thought I'd post something in the hopes that it helps someone else.

My "day" job is a 1 man IT consulting shop. This started about 8 months ago after a stint at a startup didn't work out. I had been consulting before that startup, but always through firms. I mostly fell back into a job with an old client. It's the proverbial golden goose (easy work, flexible schedule, not a lot of BS, decent rate, pay on time, etc.). Consulting doesn't "fulfill" me, but it pays the bills nicely enough.

About 6 months ago, a friend of mine (we go back 14-15 years now), that I'd done some work for/with in the past, sold his business (a small maid service) and started up another company. He didn't have a great idea. In fact, everyone on here would have poo-poo'ed his idea immediately. He needed software, didn't really have the money to pay for it and asked if I could help. I offered to work with him for sweat equity.

I honestly didn't ask for enough, but I figured the company wouldn't survive anyway (really the idea was something that was a great grand vision but would have been nearly impossible to make a significant amount of money with). I used it as an opportunity to learn Django and Python, and figured, at worst, I just wasted some time. I've got way worse ways to waste time :)

Flash forward 4 months and sales have been slow (surprise, surprise). Then dumb luck struck. A local company, that did something old media like what we were trying to do, new media style, came to us and basically asked what we could do for them since they were having major problems with their current provider (man I wish I'd taken screen shots of what their provider was giving them). We went back and forth a bit over having to refocus the business, but finally came to the conclusion that managing 20-30 large customers is significantly easier to manage than thousands of little ones (which we would require in order to make the business really work). We dove in head first a little over a month ago.

Luckily the choice of Django and Python paid off, because even though we were shifting the direction and purpose of the software, the modifications required to get everything going were not super significant (I say that, but looking back it sure sucked a lot of time, so there must have been some level of difficulty there!). I mean the concept was fundamentally the same. Just how we got our money and information was different.

We now have that one client on board under a long term contract (they've assumed our previous 40-odd clients) and have a very good looking next 10 days (we had a prospect meeting today and a half dozen more next week -- good timing with a conference next week puts them all in the same place :D). It turns out that the client we landed is on the board of one of the associations in their industry and through them we have been able to reach quite a few of their peers.

Decompressing a bit, we stumbled upon a niche market that was ripe for the picking. I sincerely doubt that we could have found this niche on our own. We had to make a few mistakes and then just have some dumb luck and chance to get here. We have some competition (one is within a mile of our office space even), but it is the typical story of poor service, poor offerings and we really do provide a better solution for our customers to sell. Here's what's the funny part: it's boring. Nothing earth shattering, nothing that's going to make use the next Mark Cuban or anything -- just a market that needed exploited. Funny how that works ;).

So finally, I'm coming up for air. By my count, I've been basically working two full time jobs (my consulting practice is paying my bills and I've had the typical deadlines there), raising my kid (not alone, my wife puts up with a lot :)), and still weekend racing my car (work/life balance and all that) for about 45 days now. It's amazing how the human body can survive you putting it through lots of hell and late nights, even in your lower 30's. Of course, I've not "watched" tv in months (sure it's on in the background, but I couldn't tell you what's going on) or played golf since June, so there's quite a bit of time that most people just piss away.

In the next two weeks, if things go as planned, I will likely have to make the tough decision of whether to step off the plank and dive into the business full time (or at least part time in order to maintain my relationship with my client) or to figure something else out.

Of course, my partner and I need to come to terms on a couple things (like more equity for me -- which is a very difficult subject, but considering that we have nothing in writing at the moment I think there's some flexibility there). We also have a bit different styles in that I am more of a "do as needed" type and he likes to be prepared ahead of time. This mostly comes into play when talking about office space (we already have 5 employees including the two of us), equipment, hosting, staffing, etc. I am much more cautious than he is on most fronts. It typically produces a nice balance, but it can cause some bit of conflict.

In any case, I thought I'd post this because I've always enjoyed a bit of voyeurism in reading other peoples' experiences and figured someone might find it interesting. 2009 will definitely be an interesting year for me.

Good luck everyone!