This is an exceptionally long rationalization for unethical behavior that well demonstrates why I am so opposed to the focus on "hustle" (or as you put it, "moxie") in some segments of the business world.
If someone leveraged this kind of "moxie" in interpreting a gray area of a contract with our corporation, I'd hesitate to do business with them again -- they couldn't be trusted to ethically consider both sides of a moral/ethical/legal quandary and resolve those gray areas to our mutual benefit.
I think we have different ideas about what the word 'rationalization' means because in my definition what I wrote does not fit that definition.
But to respond to this point: "I'd hesitate to do business with them again -- they couldn't be trusted to ethically consider both sides of a moral/ethical/legal quandary and resolve those gray areas to our mutual benefit."
When evaluating a series of events involving grey areas its always useful to try to understand the principles that are in play. Different sets of principles would lead you down two different paths.
You state your goal is to "resolve those gray areas to our mutual benefit." If you were an investor in Eric's startup you would see that his actions did exactly that, he resolved the grey area to the benefit of the startup which mutually benefits him and the investor. If he had been living for free in AOL's facility so that he could play Diablo III all day on their fast internet connection he would be resolving the grey area to benefit only himself.
So it seems that Eric's guiding principle is 'make the business successful.' And that is a good principle to invest in, but you have to consider 'at what cost.' And that is where people spend thousands of hours in business ethics classes. A typical ethics class might raise the question "Who was harmed?" and how. And the other party here is AOL, so it is up to AOL to determine how they would calculate the harm here. They could use a metric of "What would be different if this hadn't happened?" Would their network bill have changed? Would their food bill? Water bill? Since I've got visibility in to the way these things are costed I can tell you that no, there was probably zero difference in AOL's overall costs with Eric living there and had he not lived there. There was however potential liability on two counts, one the zoning laws don't allow for people to live in buildings zoned for commerce/industrial so AOL has a legal obligation to stop it when they find it, and two there is some injury liability if Eric managed to injure himself while living there. Some of that would be covered by their blanket policy on their facilities with respect to 'guests' and some they could be on the hook for if it could be proven that they knew he was living there and had done nothing about it. Since they clearly acted as soon as they became suspicious he was living there I don't think they incurred any legal liability at all.
Now Eric could use a similar line of reasoning to rationalize his action, I don't know one way or the other. I am just looking at the facts we know and observing what was at stake.
From a business perspective, if you have a potential partner who is focused on making the business successful you can be pretty sure they will resolve questions to your mutual benefit. On the other hand if they tend to resolve those questions to their personal benefit, without regard to the impact on the business then I agree they are not worth doing business with.
I prefer to work with people that resolve ethical questions ethically
So what you really mean is:
"I prefer to work with people that resolve ethical questions according to my personal, subjective ethical standards."
It's not like ethics is some simple, black and white thing, where every question has an obvious "right" and "wrong" (or "good" and "bad" ) answer.
If ethics weren't subject to debate and controversy and analysis, the field would have become completely stagnant centuries ago, with no new philosophical work being produced.
This is a simple 'black and white' ethical case. He didn't have approval for the services and resources he consumed, he knew it was wrong (he purposefully avoided security), and he could have resolved any "gray area" at any time by simply asking permission. QED.
There's quite a bit of debate and philosophy on moral relativism, too. Which is the rhetorical baseball bat you're trying to apply here.
This is far from black and white. The question of to what extent to allow "the ends" (his educational startup) to justify "the means" is one of multi-player game theory and is far from resolved:
E.g. your reasoning would call Robin Hood evil. My conscience would call Robin Hood good. A full game-tree analysis would require investigating whether wealth concentration is good or bad for the tech progress that will cause the Singularity.
If someone leveraged this kind of "moxie" in interpreting a gray area of a contract with our corporation, I'd hesitate to do business with them again -- they couldn't be trusted to ethically consider both sides of a moral/ethical/legal quandary and resolve those gray areas to our mutual benefit.