Your deal almost fell apart because it involved an LLC?
You do an LLC because it has no overhead and pass-through taxes; an S-Corp to issue employee equity and keep pass-through taxes, and a C-corp when you have to. That's not idiotic advice.
Although I've been through the funding process more than once, you really sound like you know it more than I do. But your take seems really biased towards term sheet negotiation. I'm not sure how relevant that is to most entrepreneurs.
No, it was a C-corp. (Again, we were a VC and needed the different classes of stock.) The example is that merely being a C-corp wasn't sufficient.
Again, experienced startup lawyers would have alerted us to this. Mere corporate attorneys would not, and did not, contemplate the edge case I outlined.
Look, if you're happy to bootstrap forever, Chicago's great. But if you even have an eye on VC at any point, GTFO and go to the coasts.
