I'm not sure, and furthermore, I'm not sure I agree with being overly 'fuck-it' about legal matters. But I can tell you what it's like having been where you were with the "endless lawyering," and why it sucked so badly.

I worked for a startup once in which our CEO was a really smart guy, but the kind of smart guy that got overly worked up over tiny details and edge cases. We'd spend months working through "what-ifs" in Powerpoint, Excel, or Visio, instead of building and testing features. Anytime we wanted to make a strategic decision, we'd need to run it by our extremely expensive law firm. Picking the name (!) for our company took over $50,000 in legal bills and at least 3 weeks of everyone's time. In retrospect, I'm amazed anything got built at all.

The lesson I personally took from that experience was that entrepreneurs need to make decisions, and often, they need to make them more quickly than they feel comfortable doing. They might fuck up here or there. And one day, when they're successful enough actually to need to run everything by lawyers, they can afford to do so. The ROI on legal fees and time is much more positive when the nature of the threat is being measured in the millions or billions of dollars. In the beginning, though, the biggest threat isn't a lawsuit; it's running out of time and cash.

Lawyers still have their place, though. You need them in certain situations. But they can't wear your balls for you. When you feel the need to run every key decision through a third party, you're basically stripping the "E" out of your "CEO" title.

Here's where I'll risk sounding contradictory: contracts are a crazy beast. Given your circumstances, the "fucking sue me" approach probably made sense. But you also got really lucky.

It's not a terrible idea to consult a lawyer if you're entering into an agreement of a nature you've never taken on before (i.e., with a Fortune 500, with a scope of work you're not used to handling, etc.). I say "consult with," though, not "tie up." Most Fortune 500s have a take-it-or-leave-it policy w/r/t their contractors and their RFPs. They know they've got the bigger guns, so you're kind of playing on their terms. No amount of lawyering on your end is ever truly going to overcome that home-court advantage of theirs. So it's often a wasted and self-defeating effort to fight too hard on any terms -- with the possible exceptions of payment structure and timing (the ones that affect your ability to keep the lights on), provided they seem overly wonky as written. Fight to get paid on time, to get paid fairly, and so forth. Don't fight over nice-to-haves, because you won't get them.