May I ask what your project is/was?
What difficulties did you encounter?
Look forward to hearing Luke's answer - as a fellow sysadmin eneterpreneur, he's been a real inspiration (even though I'm in a different line - training).
I like the idea of sort-of serializing the 'post-mortem' parts of the story; going through my diary and emails and writing up buisness-level and technical incident reports; enough time has passed for most of these that assuming I leave off names, it shouldn't be too embarrassing for anyone.
:-)
Also, when I started, most of the competition was using UML or OpenVZ. Xen was unquestionably superior to those technologies for multi tenant systems, so one could argue that this market wasn't as crowded in 2005
Of course, I was big into the idea of a commodity product. Like I said, competing as a commodity requires less marketing skill. Instead of talking someone into trying something new, you start with something they already are using and then just point out the advantages of your implementation, which can be as simple as the blog I posted in the other comment.
Difficulties? Eh, I'm a really bad negotiator. I'm pretty good at picking engineers and technicians (I might reasonably say that I'm really good at doing so... almost everyone who worked for me at retail wages went on to get real jobs that pay real bay area level money.) - but I'm not a good leader. I don't think I got as much out of those excellent technicians and engineers as their next employers did. I really only have very vague ideas of why I'm a bad leader; it's one of those things where I'm bad at it largely because of a lack of wisdom. I actually just wrote another comment on the subject[1] and if that is correct, well, maybe I can become a leader someday, but there's a long journey for me between here and there. I need to become a lot more comfortable with what I refer to as nietzschean self-deception[3], and honestly, I'm not sure that doing so is worth it to me if I can be comfortable as an Engineer for the rest of my life.
It is also a market with a low barrier to entry, and lots of competition. If you can hire one pretty good, experienced Engineer and two smart, juniors you have most of the capital needs met, Of course if you want a good deal on packet and power, you end up buying a lot of that (for me, my power and packet was rather cheaper than a senior level engineer; I mean, it was less than $10K/month. Not a whole lot less. Much less scale than that and you'll have difficulty competing on price) - but the low barrier to entry is important because market opportunities are exploited pretty quickly.
I think I was also bad at strategy. At several points in time, I had overwhelming technology advantages over anyone in the same price range, (or I had dramatic price advantages over everyone with similar technology) and I mostly failed to capitalize. At one point, someone even noticed[2] and publicized this; I had a waiting list longer than my arm.
When you have a waiting list for a pre-paid, sticky, recurring revenue business? Do everything you can to get to the point where you can get capacity up fast enough that people don't need to wait. I'm fairly certain I would have been at least 3x larger at my peak, and I think there was a real chance of 10x, if I didn't run waiting lists for the six months where I had that price/technology advantage and people noticed. If I was 3x larger at my peak, that would be a $1m/year turnover, and I don't think it would have required a lot more power and packet or even labor, just because in this business the biggest problem is just having someone around to answer support often enough. I think that would have taken the business from something that paid me just enough to make rent to something that paid more than I could make as a IT contractor. And, because of me being congenitally bad at marketing, I didn't get another chance.
I think that's one of the key takeaways for me. Know your weaknesses (which I did) but then when something comes along that momentarily boosts that weakness? Jump on it with everything you have. That part was the part I missed. You can create opportunities in areas where you are strong all the time; that's what it means to be strong. But opportunities that negate your weaknesses don't come along very often at all; that's what it means to be weak. They should be treated as the very rare events they are.
I mean, I guess the key thing for OP, who wants something easy is just that running a small business is work - and for the money per effort input, it's really quite difficult to beat even mediocre contracting wages. I mean, certainly, it can be done, but it's not easy, and it's not nearly as certain as getting a consulting check. (Which isn't 100%, either, but it's much more certain)
There's a lot of risk in running a company. There's also a chance of a huge reward, but I think that running a product business is usually not that great of an idea for someone who just wants the minimum money with the minimum work. Running a business makes more sense if you want lottery tickets with better odds where you have some control (and want to feel like you had a lot of control if you win)
[1]https://news.ycombinator.com/item?id=14030580
[2]If you aren't good at marketing (and I'm not, I knew that setting out, and I knew that my values and my corporate values meant that I would always be bad at marketing) you need to jump when someone who is notices you. See https://uggedal.com/journal/vps-comparison-between-slicehost... - that was huge for me.
[3]By which I mean the lies we all must tell ourselves to continue to function as human beings. All of us need to come up with some sort of meaning - as the man points out, you can't stare too long into that abyss. The problem I have with Nietzsche in general is that while he feels right about self-deception and power, I personally find self-deception (well, deception in general) to be more uncomfortable than I find power (or more power than I have now) to be comfortable. In fact, I think I have a pretty comfortable level of power right now; I'm nobody's boss, but I have the power to walk out on my boss at any time, and I make more money than I need. (now, the last decade plus of what should have been my retirement fund was dumped into seeing if I could run a business, so I couldn't walk forever, but I've probably got a good year or so, and I've never had trouble finding work, so while I don't have "fuck you money" I don't need to deal with anything very unpleasant.) Frankly, my feelings on having more power than that are pretty mixed. (having less power than that is certainly unpleasant, of course, but I'm not sure that having more power than that is really a step up from where I am now.) - really, that might be another way I'm a bad leader. I really like being thought well of, and like most people, I do enjoy some parts of power, but I'm super uneasy, in other ways, with having significant power over other people.
