The Flakiest Places to Do Business

Austin, TX and the entire state of California.

I think about the geographical and cultural effects places have on their inhabitants a lot.  I have worked with people and businesses from every state for almost a decade, and I love noticing (and exaggerating) the traits.

So why Austin and California?

It’s undeniable that Austin and San Francisco are unique hubs of startups and innovation.  I think that’s part of the problem.  90% of the innovating is done by a tiny fraction of the people there, and everyone else gets the benefit of the reputation.  It’s a moral hazard.  Like how Lonzo Ball can get away with mediocre play because of his dad’s amazing and outsized reputation.  If your entire city is universally acknowledged as innovative, you get a piece of that reputation, whether you earned it or not.  This results in a lot of big talking conference junkies who parrot the innovators, like the kid who shows up to the playground with all the right basketball apparel but can’t be trusted to hit a shot.

The South, where I live now, isn’t flaky, it’s just slow.  No one is in much of a hurry.  They roll with the tides, wait for the weather to clear, have plenty to drink, and enjoy themselves in a unique form of polite hedonism.  It’s a good pace of life for raising kids and gaining a calm mind, but definitely annoying when it comes to getting shit done in a hurry.

The Northeast (From Main down to DC) is pretty decent to do business with.  Yeah, people are a bit rude and full of themselves (sometimes to comical proportions, blissfully unaware that the rest of the world doesn’t really know anything about Boston or care), but they’re not slow, not flaky, and pretty clear and blunt.  They may not be 100% honest all the time, but at least they’re quick and clear.

Everything west of the Mississippi (save Austin and the Pacific coast) is pretty solid too.  Trustworthy and honest.  But overly concerned about doing things slow and right, wary of “move fast and break things” mentality, and a little boring.  But genuine, reliable, and without pretension (except maybe a little pride in knowing their more righteous than the coasts, even if underestimated by them).

Then my favorite, the Midwest (basically, Big Ten conference states).  I’m probably biased because I grew up there.  But Midwesterners are not arrogant or blind to their flaws, they are not flaky in the least.  They do what they say when they say.  They’re not rude.  They’re not slow.  They work hard, take ownership, and move fast.  Their big weakness is small thinking.  This manifests in several ways, from not giving themselves permission to try bold ambitious things, to not giving themselves permission to move away from their boring post-industrial home towns.

My dream combo are people with the wild bold dreaming of Silicon Valley (“Hey, let’s cure aging!”) with the reliable, no BS work ethic of the Midwest (“Why the heck would I pay $200 to go to a conference. I’ve got work to do for real customers”).  I call it “Blue Collar Entrepreneurship” and all the best business people I’ve met have it, regardless of where they’re from.  It’s a combo of pride in the grunt work and willingness to take massive swings.  It’s like Drew Brees on the football field.  Willing to take what you can get play after play just to move the ball, but fearless about chucking a deep ball in the clutch.

These are of course massive, playful simplifications.  I’m not labeling the people in these regions so much as the personality or spirit of the regions themselves as I experience them.