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Not being web-based is most definitely in favor of Chicago. Here's a story that I think illustrates everything about Chicago: so a group of people decided to f

Not being web-based is most definitely in favor of Chicago. Here's a story that I think illustrates everything about Chicago: so a group of people decided to form a new angel group (http://www.hydeparkangels.com http://www.hydeparkangels.com). Got a lot of people together, associated with U of C, lots of smart, hardworking people. A little younger skewing than other "groups" (I use the term loosely because they're more social clubs since they don't actually invest) in town. What's their first investment? A company that makes automatic fucking card shufflers for home poker games. Yeah, if it's not a manufacturing model - $x input => direct $x+y output, good fucking luck. EDIT: The lawyers, combined, have charged me $60K for stuff that could easily have been done for $10K by an experienced firm in SF (as confirmed by a partner at a representative Palo Alto office of a representative firm). And $10K would have left me another $15K on the loan most good firms will do for a leveragable company targeting VC investment.

mediaman 17y ago
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.
- sachinag 17y ago
  At this point, my costs are sunk. There's no real benefit to moving pre-emptively - unless I can find a full-time developer who wants to jump into Dawdle. Then I'd move anywhere in the lower 49. (Sorry, Alaskans.) Yeah, I've been saying that "Chicago is the next Detroit" to kind of drive home the fact that this region isn't well-equipped to deal with non-linearbusiness models (the "manufacturing mentality"). Instead of trying to really go after a change in environment (like North Carolina did over a 20-30 year period with the Research Triangle), we get World Business Chicago throwing money at firms to establish corporate headquarters here. (I admit the Detroit thing is hyperbole; a better example is St. Louis. If we get the Olympics, it'll be Chicago's last hurrah the way the 1904 Games were for St. Louis.) As for VC, well, I used to work for a VC shop, so I'm not anti-VC at all. I don't blame them for their approach to Chicago; it's up to Chicagoans to get the fuck out. I started here because I wanted to have a big successful startup, give back to Illinois by providing jobs and opportunities here (I went to IMSA), and then become Governor or Senator or something. Ah, the idealism of youth (I was 26 when I started Dawdle). Also, please e-mail me (in profile); I'd love to get beers and compare notes.

mediaman 17y ago

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.

sachinag 17y ago
At this point, my costs are sunk. There's no real benefit to moving pre-emptively - unless I can find a full-time developer who wants to jump into Dawdle. Then I'd move anywhere in the lower 49. (Sorry, Alaskans.) Yeah, I've been saying that "Chicago is the next Detroit" to kind of drive home the fact that this region isn't well-equipped to deal with non-linearbusiness models (the "manufacturing mentality"). Instead of trying to really go after a change in environment (like North Carolina did over a 20-30 year period with the Research Triangle), we get World Business Chicago throwing money at firms to establish corporate headquarters here. (I admit the Detroit thing is hyperbole; a better example is St. Louis. If we get the Olympics, it'll be Chicago's last hurrah the way the 1904 Games were for St. Louis.) As for VC, well, I used to work for a VC shop, so I'm not anti-VC at all. I don't blame them for their approach to Chicago; it's up to Chicagoans to get the fuck out. I started here because I wanted to have a big successful startup, give back to Illinois by providing jobs and opportunities here (I went to IMSA), and then become Governor or Senator or something. Ah, the idealism of youth (I was 26 when I started Dawdle). Also, please e-mail me (in profile); I'd love to get beers and compare notes.