1. It's State National, not sure where you got "Standard" from.
2. Vouch is acting an MGA/Program Administrator, including being involved in underlying insurance product/actuarial design. This is WAY different than being a regular broker/agent. (It's essentially the difference between sales, and sales and operations.)
3.State National doesn't have a reputation for anything--that's what makes them a fronting carrier! Besides providing the paper/AM Best Rating/filing assistance they are not involved in the day to day.
4. Being Surplus Lines Licensed is not a red flag; if they want to offer (possibly in the future) additional options for hard to place risks, then it's being used appropriately. If they are using it just to be able to offer "something" when they know, say, Hiscox would be happy to cover them, then I'm not enthused.
5. Having only a few licensed producers on stuff is not unusual for now; they may be sharing staff with a partner/TPA, plus they may have a large inhouse underwriting team. With so many coverages being offered though, they do need a larger staff than normal to be proficient.
6. It's quite likely that being focused on a narrow class means they can be more responsive/flexible and better able to price risk. I assure you the Hartford does not care at all about the VC funded tech startup market. Program business can be very lucrative AND beneficial to those being covered. Some brokers (large or small) have NO IDEA how to handle tech startups; if Vouch proves itself they may eventually try to place business with Vouch.
7. Some insight in how they will handle claims would be good, I agree--ESPECIALLY for D&O and E&O where legal assistance is critical (and specialized). Being able to offer/get your filings approved for many different coverages is only a piece of the puzzle...you need experienced people on the claims side, irrespective of the bare ability to "pay claims". The fact they don't even discuss claims handling on their site makes me sad :-(
8. Oh, insurance companies get sued all the time for denying claims, not that you want to be in that position...
PS You founded Esurance? Cool!