[keiferski]

At what point does this kind of groveling behavior actually become a negative signal, though?

If you’re willing to fly halfway across the country just to talk to a VC in a diner, it signals a lot of desperation IMO.

I haven’t had a ton of interactions with VCs; however, I have read innumerable books about the VC world, and a recurring theme is that VCs are competitive and don’t like being left out of a deal / losing a deal to another VC.

By willing to fly so far away for nothing, it signals that no other VC is interested.

[iJohnDoe]

You're not really wrong. However, it was a power play by the VC and to make themselves feel important. Hopefully they grew up a bit since then.

No matter how you look at it, if the only question was, "Do you have 100 customers?" then they could have sent and read that e-mail over breakfast.

[lrvick]

Yeah, first "real" startup and we were absolutely desperate for some seed cash. Mistakes were made.

These days I have significantly higher self respect, always have multiple income and funding sources, and a lot more protective of my time.

[keiferski]

For sure, hugely rude move by the VC. But unfortunately I’d just expect that from them.