I'm familiar with Hyde Park Angels and talked with them for a while. Never got any traction with them and kept getting pushed off for a pitch, for vague reasons

I'm familiar with Hyde Park Angels and talked with them for a while. Never got any traction with them and kept getting pushed off for a pitch, for vague reasons. This was after we had reached >$1mm in annual sales. Now I know it was because of the card shuffler. I see what you're saying. Although my business isn't web-based, it is a media company that relies on advertising as a sole source of revenue. There were a lot of misconceptions and distrust about anything related to advertising. I've gotten the most absurd questions during pitch sessions. To the extent anyone invested, it was because there was personal trust. My challenge has been that most rich people here have, by and large, not made their money in "startups" (even more loosely defined than on HN). Many of them have made their coin in big corporate management, finance, or from family. That kills the investment ecosystem because they largely turn it over to their financial advisers, who have no reason to consider risky startups. Angel groups here are a joke. Our money came from getting to know people individually. Have you considered pulling up stakes and moving? Edit: on VC -- I have turned quite anti-VC since being here. I think it is because most of the VCs, when asked why they are in Chicago, tell you it is because they can get "great deals" on "desperate" companies. Even on the angel side, I've had to explain to people why EBITDA multiples are not an appropriate valuation mechanism for early stage ventures. And then they act like I'm trying to con them.