Not thinking about it is not the problem. A lack of domain knowledge is. If you don't know how payrolling actually works in practice, no amount of thinking will make you come up with the right solution. The real pitfall here, and the downfall of many startups, is thinking you can understand the domain merely by thinking about it. Engineers can usually think pretty well and can solve many problems in that way. It's crucial to realize not everything can be solved by thinking about it.
"His diplomacy here, as well as with Bethesda, has been stellar"
I don't think his diplomacy regarding Bethesda has been all that great. Openly mocking their claims probably hasn't earned him any goodwill. The quiz was pretty bad, especially the insult at the end. The tweets and encouragement of people ironically getting the two products confused also hurts his case.
His handling of the Bethesda case is only bad if this really isn't a case of an overly-zealous legal department operating on autopilot. So far, there's no reason to suspect that:
All the information that's public indicates that Bethesda's claims are weak or entirely baseless, and they are not interested in reaching a compromise or really any two-way communication prior to going to court.
Any lawyer that starts a tenuous but high-profile suit without considering the PR aspects is simply crazy, but that seems to be what's happening. Notch has been trying to get someone at Bethesda with a human perspective to intervene, but so far, hasn't been successful.
Bethesda is acting rationally and logically. Trademark is easily lost and Bethesda needs to be on top of any potentially infringing marks.
Notch is handling this in the worst way possible. The first thing he should have done is go to his lawyers, have them set up a meeting with Bethesda and their lawyers, then hash out everything quietly. No, the first thing he did was fire up the internet hate machine in response to a Cease & Desist.
Then he challenges them to a Quake match to settle it. Another bad move.
Then he posts a quiz that mocks Bethesda and actually doesn't help him in the way he thought it would as some people actually got some of the questions wrong.
A while later, out of the blue, we got contacted by Bethesda’s lawyers. They wanted to know more about the “Scrolls” trademark we were applying for, and claimed it conflicted with their existing trademark “The Elder Scrolls”. [...] We looked things up and realized they didn’t have much of a case, but we still took it seriously. Nothing about Scrolls is meant to in any way derive from or allude to their games. We suggested a compromise where we’d agree to never put any words in front of “Scrolls”, and instead call sequels and other things something along the lines of “Scrolls - The Banana Expansion”. I’m not sure if they ever got back to us with a reply to this.
Today, I got a 15 page letter from some Swedish lawyer firm, saying they demand us to stop using the name Scrolls, that they will sue us (and have already paid the fee to the Swedish court), and that they demand a pile of money up front before the legal process has even started.
Firing up the internet hate machine wasn't the first thing Notch did. He tried to open up a dialogue, before things got to the cease-and-desist stage. It didn't work. Bethesda's lawyers weren't interested in being reasonable.
Maintaining a trademark doesn't require constantly trying to expand it.
I believe the government's position is that one coin was also stolen property, which they then dealt with in a special way, given the circumstances.
More importantly, the government believes the 10 coins the article is really about were stolen by the family who currently is trying to get them back. A huge difference to the original case of the single coin.
An estimate should always be a range. And it should always cover the "cone of uncertainty".
If you don't know, reflect it in your estimate. Get the client prepared for falling within the range. And comfortable with the cost on the far end. Because while you hope it doesn't happen, it very well could.
In my experience a range of, say, £5000-7000 usually means £5000 to the client and it can take hours/days/weeks to budge that perception no matter how initially prepared they seem. I've also found people who, while comfortable with the upper estimate if it goes there, will then expect freebies on top as recompense for making them pay 'extra'.