Personally, I would be rather peeved to be advertised to in this way. I wouldn't find it clever or cute--I would just find it annoying. I would not end up with a good impression of the company, and I wouldn't want to do business with it.
One reason why I don't find it particularly clever, is that it's really not all that different from all the physical junk mail I receive that tries to visually mimic some sort of important government notice.
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...
Imagine you're an investor, and you drive to "YC demo day", and listen to 30 pitches of small startup companies, go out to your car, and see a flyer in your windshield pitching another startup company...
Are you really going to be pissed at that, or is that just one more pitch (that some on here think shows hustle)? Doubtful investors are going to be pissed at this, and ... so what if they are. A couple of hundred people just visited their web site, most of them with money to invest...
Like handing your CV outside a job fair instead of paying to go in. Those people are there for this very reason and won't be too upset by it. pg and team might be pissed however...
All I can imagine is the sinking feeling I get when I see a ticket on my car. I start fuming about the nice meal I might have eaten for that $50. Maybe if I were a VC, I'd be rolling in so much money that I'd never think twice about $50. On the other hand, I really don't have to worry about $50 either, and yet my stomach still sinks.
If I were a VC, my stomach might sink over the time I'd have to waste writing the check for the ticket and remembering where I put the stamps. Then when I noticed that it was just a "cute prank", I would resent whoever it was who was responsible for causing that sinking feeling.
Why would anyone want to associate their company with that?
It seems gimmicky, which could work, but then throw in the QR code and incorrect usage of "its" and it just seems unprofessional. If you're investing in the person and not the idea, this seems like a very bad first impression to make.
I think under the circumstances it may actually put a smile on peoples faces. They are probably already in a good mood and the right mindset for something like this.
This was a relatively common tactic in Chicago a few years ago, done by restaurants and a band if I remember correctly. Heading to your car on your way to work in the morning and finding a fake ticket that ended up being, as you say, junk mail, really made people angry. I am pretty sure the city got involved people were so mad.
One reason why I don't find it particularly clever, is that it's really not all that different from all the physical junk mail I receive that tries to visually mimic some sort of important government notice.