As a Minnesota native and Silicon Valley transplant, I can say one thing with absolute authority: the cultures of Minneapolis and San Francisco have very little in common.

In SF, it would be weird to strike up a conversation with a total stranger; in MN, it would be weird not to. In SF, folks find meaning in novelty; in MN, folks find meaning in tradition. And, most notably for this newsletter, folks in SF are disproportionately likely to work in new and fast-growing tech companies, rather than MN’s industry stalwarts like 3M and Target.

Many people ask whether there’s something about Silicon Valley culture that makes it such a fertile ground for startups. But few ask the inverse: is there something about the Midwest that is incompatible with successful entrepreneurship?

It’s a downer of a question, but one that merits a thoughtful answer — especially because at face value, “good Midwesterner” and “successful entrepreneur” seem to contradict in a number of ways.

🤴 Contradiction #1: Self-promotion

As a native Midwesterner, self-promotion is against my very nature. I cringe every time I promote this newsletter online — every tweet and LinkedIn post is sent while my inner Minnesotan yells “don’t toot your own horn!”

The Midwest strongly discourages acts of self-promotion — or “bragging,” as we call it — but entrepreneurship requires such behavior. As a founder, you need to be irrationally self-assured and you spend most of your time pitching yourself to investors, recruits, customers, and more. This is so widespread that there are entire Twitter accounts dedicated to memorializing self-promotion from startup founders (click the tweet below for an epic thread).

Founders congratulating themselves 🙌🙌🙌 @founderbrags

(0/x) 🙌THE FOUNDER BRAG COMPENDIUM 🙌 A non-exhaustive list of brag phenotypes (humble or otherwise) that founders deploy on Twitter. Sometimes through instinct, other times through wit and cunning. Spread the word. A Thread 🧵->

February 23rd 2020

81 Retweets403 Likes

If I was featured on such an account, I might shrivel up and die — as would most folks from the Midwest. I struggle weekly with pushing off the secure shores of obscurity to wade in the potentially-lucrative, but certainly-scary oceans of the great online game. Are Midwesterners too afraid of sticking their necks out there to succeed in entrepreneurship?

😊 Contradiction #2: Agreeableness

One time in Chicago, I jaywalked across (what I thought was) an empty street, and stepped directly in front of an oncoming car. The driver screeched to a halt, rolled down his window, and I prepared for an earful. But the guy just asked, “Hey buddy, you alright?” I said that I was, and he replied, in all sincerity, “Okay, good! Have a great rest of your day, sorry about that!” If you’ve spent any amount of time in the Midwest, you probably have a similar story: Midwesterners are just so damn nice!

Science agrees. According to a psychology study that assessed people from all 50 states, Minnesota is the second-most agreeable state, just behind North Dakotans and ahead of Wisconsans.

But great startup founders are disagreeable, aren’t they? Katherine Boyle, a venture capitalist at General Catalyst, certainly thinks so:

Katherine Boyle @KTmBoyle

Disagreeableness is an under-appreciated trait in work and life, and it’s concerning that disagreeable people are less likely to succeed in tracked professions like medicine or academia. Disagreeableness is essential for good leadership and decision-making. We need more of it.

June 11th 2021

220 Retweets1,884 Likes

Pop culture supports this version of events as well. The trope of the asshole founder, as exemplified in The Social Network and corroborated by the popular accounts of tech CEOs like Steve Jobs, Jeff Bezos, and Bill Gates, is widespread. Could Minnesotans just be too nice to be successful entrepreneurs?

🙅‍♀️ Contradiction #3: Openness

Although I consider myself a native Minnesotan, I was born in Kansas and moved north when I was about five years old. And although my fear that my kindergarten teacher wouldn’t speak English proved to be unfounded, my family did find one speed bump that made our move more challenging: the highly insular nature of Midwestern culture.

For whatever reason, most Midwestern states are among the ten least open states in the union — where open is defined as “curious, creative, imaginative, unconventional, and insightful.” (Same study as above.) Sounds pretty terrible to rank low in that category, but it’s understandable when you think of the alternative to openness as tradition.

Midwesterners love the “tried and true.” As David Foster Wallace said an essay about Bloomington, Indiana:

Like many Midwest towns, B-N is lousy with churches: four full pages in the phone book. Everything from Unitarian to bug-eyed Pentecostal. There’s even a church for agnostics. Except for church – plus I suppose your basic parades, fireworks and a couple corn festivals – there isn’t much public community. Everybody pretty much has his family and neighbors and tight little circle of friends. By New York standards folks keep to themselves.

In contrast, California is the fifth most open state in the US. It’s a beacon of diversity, home to immigrants from all sorts of countries, and world-famous for its celebration of creativity, imagination, and alternative lifestyles. Said more simply, Burning Man could never have been created in Minnesota. It would be hard to believe that the West Coast’s openness wasn’t a factor in the disparate rate of innovation between California and the Midwest.

The conflicts listed above are admittedly caricatures, but they tell a real story that many have internalized — that innate differences that separate Midwestern traditionalism and entrepreneurial success. I have even done some of that internalization myself: it is true that growing up in Minnesota encouraged me to avoid self-promotion, to be nice to everyone, and to fear venturing into the unknown.

But it’s also true that I became an entrepreneur anyways, and that my Midwest upbringing helped me along the way.

First, there’s something to be said for the perspective of living for a while in “flyover country.”

The startup culture of Silicon Valley is amazing, a historical anomaly, and I’ve talked before about how this culture has spawned a curriculum that defines a “right” way to start a startup. It’s very easy to fall into the trap of believing that the Silicon Valley way is the only way, that every founder should start a software-as-a-service company that sells primarily to other startups, and that what works here is likely to work everywhere else in the world.

Having lived in an area of the world that is far more average than Silicon Valley, I have some perspective that native San Franciscans might lack.

Amanda Goetz @AmandaMGoetz

Coastal investors: your life is different than life in the Midwest. Product adoption is on a different timeline. Tastes are different. Be careful your experience bias isn’t missing out on massive opportunities for a cohort you just don’t understand.

July 9th 2020

8 Retweets146 Likes

But perhaps even more importantly than that perspective, I also have the experience of living in a more traditional culture, rebelling, and ending up somewhere new. Silicon Valley prides itself on being contrarian — and there’s nothing more contrarian than breaking from the culture in which you grew up.

As a teenager, I found more community on the internet than in my hometown. In the words of Marc Andreessen (Wisconsin native and legendary founder/investor):

We have this theory of nerd nation, of forty or fifty million people all over the world who believe that other nerds have more in common with them than the people in their own country. So you get to choose what tribe or band or group you’re a part of.

Everyone has to choose their tribe, and living in a world that predisposed not to start startups might ironically have the effect of weeding out folks who aren’t actually fit for the grueling, counter-cultural, energetic role that is a founder at a high-potential startup. If startups are in the water, everyone — whether founder-material or not — will start a company. But if startups are uncommon, perhaps only the folks who really, desperately want to start companies will do so.

My takeaway here isn’t all that simple: yes, the cultural odds are stacked against Midwestern entrepreneurship, but no, this doesn’t mean the Midwest will fail to produce any great entrepreneurs.

(I’m not even personally convinced by my first two “contradictions” above, for what it’s worth. Some of the best founders I know are not self-promotional; some of the best founders I know are extremely nice, thoughtful people.)

The “closed” disposition of the Midwest is particularly worrisome. I have never met a founder who was anti-change, and if the Midwest does indeed select against such behavior, it’s surely at a disadvantage in the startup race.

If I still lived in the Midwest, I can imagine getting angry reading the conclusion that the odds are stacked against me: “Who is this guy to tell me you I can and can’t do?!”

Responding to my hypothetical self here, I’d say first to stay angry! Nothing would make me happier than you printing this article, putting it on your fridge, and having that righteous anger drive you to achieve startup success and prove me wrong. I mean that in all sincerity.

More practically, though, I’d just advise keeping culture in mind as you embark on your startup journey. Even if these stereotypes don’t apply to you personally, they might apply to the people you know. Be careful to not let your friends and family push you into a closed mindset. Your goal is to be curious, creative, imaginative, unconventional, and insightful, but the gravity of the Midwest may pull you towards familiarity, safety, security, convention, and tradition.

If you want to be an entrepreneur — no matter where you are in the world — don’t let that gravity win.

Thanks for reading!

My name is Christian, I’m the Chief of Staff at Astranis, and I’m a native Midwesterner. If you enjoyed this piece and want to join 370 folks in getting an email from me every Monday, I’ll help you understand Silicon Valley using normal-human words.