You guys are missing the point. AirBnB didn't screw me over - this wa any first deal and I screwed around debating stupid points. I was disappointed they didn't do the deal but this whole post is about lessons learned. And one of the biggest ones was move fast once you have conviction. At the time of this Airbnb event I was just learning. I thought an investor had to worry about all these little details, negotiate tons of clauses, etc. but post Airbnb I realized all that detail was stupid. After that event I learned to move fast.
Example: When I met Peter (Contextlogic now known as Wish) I wrote him a physical check within a day (pretty sure it was his first) as I planned to take whatever terms he ended up negotiating. And then I immediately started brining in other investors, introductions to engineers, etc
So don't take this post as a "Brian screwed me" / the screwing was all self inflicted and a very important lesson
Well, if it did fall apart at the literal last hour and you were going to sign the formal paper work (which only reiterates the terms already negotiated and agreed to at dinner) the next day, but didn't because YC came in overnight and took the entire round...then it does sound like you got screwed.
His general approach does indicate that belief in the product is paramount, his trust in the team second. The takeaway is not to yank the chain too hard negotiating when these two criteria are met. He could have closed a week before.
It also sounds fairly intuitive when you verbalize it: the faster you can update your (presumably sound) strategy to new information, the "better" you are likely to do compared to someone who responds to changing information at a slower rate.
Even if your initial strategy is less sound, if you can (and are willing to) update it faster, you can still win (so long as your initial strategy wasn't too horrible).
I respect you for taking this view cos it's so much easier to be a lesser man and whine about how you missed a great deal. Thanks so much for your candid sharing!
Example: When I met Peter (Contextlogic now known as Wish) I wrote him a physical check within a day (pretty sure it was his first) as I planned to take whatever terms he ended up negotiating. And then I immediately started brining in other investors, introductions to engineers, etc
So don't take this post as a "Brian screwed me" / the screwing was all self inflicted and a very important lesson