To me, this would work beautifully if the startup were actually involved in solving traffic or transportation problems. Ridejoy, for instance. If Ridejoy had pulled this stunt, it would have been very cute.
That said, I'll give the man his props. This is ingenuity. Perhaps it's misdirected, to an extent. Perhaps it'll backfire. But it's something different. It is clever, regardless of whether we find it enjoyable or annoying.
EDIT: Minor nitpick, but I wouldn't have made so many grammatical errors in the fake ticket. They're pretty glaring. Especially for a first impression.
I would find this pretty annoying personally. Not only that but this is how the pizza joint around the corner advertises(literally). Is that really the feel you want?
I think the key difference is that it's unexpected, given the context. Investors have just finished hearing a bunch of pitches, so they're primed to be receptive to clever "roadblocks" like this one -- whereas people who park next to a pizza joint are going to be annoyed when they find flyers stuck to their windshield wipers.
Funny, we considered flyering the entire auditorium during Startup School last year, but decided that was too annoying and ended up flyering just the bathrooms instead. No one got the fake grimlock references, sadly...
That said, I'll give the man his props. This is ingenuity. Perhaps it's misdirected, to an extent. Perhaps it'll backfire. But it's something different. It is clever, regardless of whether we find it enjoyable or annoying.
EDIT: Minor nitpick, but I wouldn't have made so many grammatical errors in the fake ticket. They're pretty glaring. Especially for a first impression.