3 ms·

As to a specific city I know well, I've been very vocal - there's no better place on earth to bootstrap an internet/software company than Chicago, but you'd be

As to a specific city I know well, I've been very vocal - there's no better place on earth to bootstrap an internet/software company than Chicago, but you'd be hard-pressed to find a city that's worse to try to raise funds in. I lived in Chicago for 7 years before I moved to the East Coast, and then finally to California. While Chicago does have it's share of great restaurants, a decent music scene and pretty good art scene. It suffers from a chronic second city mentality, which is--It's a pretty good city for being in the Mid-West, but if you're really good at something go to a first rate city liky New York, LA or San Fran. In 7 years, every really talented theater group, actor, artist or musician I knew ended up having to move to either New York or to California. There just wasn't enough going on to sustain those people in Chicago. Chicago also has a huge meathead/jock culture. Just walk within 3 blocks of the bar district along Rush and Division on a weekend night. I'm 6'7" tall, 300 pounds, and I often worried about some drunk meathead picking a fight with me. All that to say, that it's not a really nerd friendly town. If you do move there and you walk around at night, get a black leather jacket preferably with Chicago PD patches sown on it. (The Alley on Belmont and Clark sells them). Walk around with your right hand tucked under your left armpit. You'll look like you're packing heat, and the thugs/meatheads will leave you alone. At least that worked for me for several years. Oh, and the winters really suck. Say what you will, I can think of a half a dozen other cities I'd rather bootstrap in--Austin, Boston, Providence, New York, Portland, Seattle, Vancouver, Toronto, Boulder, San Diego.

sachinag 18y ago
The point isn't whether or not $1 billion in $1 million increments would work in Chicago - it's about where it would work anywhere, including the cities that you name. My argument wouldn't be any different if I said Tampa Bay, New Orleans, Atlanta, or some other city. (New personal rule: stop making throwaway comments, especially w/r/t Chicago. People latch onto them like remoras.)
jackchristopher 18y ago
While not enough to leap the hurdle, what I like about big cities like Chicago is how spread out they are. That helps grow subcultures. And while land mass doesn't create them, it does provide psychological space. A large (but not too large) space matched with good weather and transportation is perfect for cross breeding. You need to carve niches, ask evolution. I realize a small city can grow a larger one, but some are too limited by location, but I'm not hip to which. And you want startup cultures. Every city thinks they have a music scene. In some cities that's arenas, in others, ad-hoc clubs. You want rebels. But you want them in the outskirts not the capital. That comes later; it's demoralizing early on, save coup d'etats. The problem with cities like New York (and Boston) is they have bad habits. Like human habits, they're mini-traditions, they give us expectations, then meet them. The set up is the comfortable feeling. But like candy bars, they taste great in the short run but kill you in the long. And they're addicting. Boston's addiction is college, and New York's finance (and media). Those industries are going into permanent introspection within the next few decades. That's a while off, but it's still a bad play to have the next big thing near the really big thing it's going to outmode. Media is badly wounded, but finance and education are still on their tour of duty. R&D and education are going to split eventually, and finance is just starting to get shaken up. There is vitality to sap, so I think we're too early for official sanction. You set up the pins, we knock them down; That's a political game. We might avoid this with a rich patron. A rebellion can start with a dissatisfied insider. And don't underestimate the second-rate mentality. I felt it as soon as I moved to Boston; And you can tell through the baseball fans. In New York, no one hates the Sox until they come to town. In Boston, they hate the Yanks year round ... and breed children to. It's surprising how far behind the runner up can be. Another thing is that in New York you may have to look around longer to get a sense of everything, but in Boston, it's harder to abstract away the details. The city doesn't have to be that as huge. But we're looking for tightness; muscularity, not fat; Quality not quantity.

sachinag 18y ago

The point isn't whether or not $1 billion in $1 million increments would work in Chicago - it's about where it would work anywhere, including the cities that you name. My argument wouldn't be any different if I said Tampa Bay, New Orleans, Atlanta, or some other city. (New personal rule: stop making throwaway comments, especially w/r/t Chicago. People latch onto them like remoras.)

jackchristopher 18y ago

While not enough to leap the hurdle, what I like about big cities like Chicago is how spread out they are. That helps grow subcultures. And while land mass doesn't create them, it does provide psychological space. A large (but not too large) space matched with good weather and transportation is perfect for cross breeding. You need to carve niches, ask evolution. I realize a small city can grow a larger one, but some are too limited by location, but I'm not hip to which. And you want startup cultures. Every city thinks they have a music scene. In some cities that's arenas, in others, ad-hoc clubs. You want rebels. But you want them in the outskirts not the capital. That comes later; it's demoralizing early on, save coup d'etats. The problem with cities like New York (and Boston) is they have bad habits. Like human habits, they're mini-traditions, they give us expectations, then meet them. The set up is the comfortable feeling. But like candy bars, they taste great in the short run but kill you in the long. And they're addicting. Boston's addiction is college, and New York's finance (and media). Those industries are going into permanent introspection within the next few decades. That's a while off, but it's still a bad play to have the next big thing near the really big thing it's going to outmode. Media is badly wounded, but finance and education are still on their tour of duty. R&D and education are going to split eventually, and finance is just starting to get shaken up. There is vitality to sap, so I think we're too early for official sanction. You set up the pins, we knock them down; That's a political game. We might avoid this with a rich patron. A rebellion can start with a dissatisfied insider. And don't underestimate the second-rate mentality. I felt it as soon as I moved to Boston; And you can tell through the baseball fans. In New York, no one hates the Sox until they come to town. In Boston, they hate the Yanks year round ... and breed children to. It's surprising how far behind the runner up can be. Another thing is that in New York you may have to look around longer to get a sense of everything, but in Boston, it's harder to abstract away the details. The city doesn't have to be that as huge. But we're looking for tightness; muscularity, not fat; Quality not quantity.