Midwest Mentality
What Exactly is the Midwest Mentality?
Midwest Mentality sounds vague until you leave the Midwest and enter a room where people move faster, write shorter emails, and treat directness as normal instead of rude.
My friend Adam ran into this when he was applying to startups in San Francisco. He felt thrown off by these subtle but crucial cultural differences. He wasn't sure how to pitch himself, write emails, or even introduce himself without coming across as rude or overly confident.
The clearest way I can show you what Midwest Mentality looks like in real life is through a conversation Adam and I had while he was trying to figure it out:
Adam: Your knowledge on talking to these startups and fast-paced business people is valuable, especially for people from the Midwest, because it goes against how they were raised.
Me: Interesting, say more.
Adam: In the Midwest, even though it's never explicitly said, pitching yourself and speaking confidently often feels like cockiness. Doing an introduction without a dozen “thank yous” or “nice to meet yous” feels socially taboo. If you don’t write a long message, the other person thinks you don't care. And phrases like “I think” get added everywhere, even if you’re 100% sure, just because it’s expected.
He summed it up perfectly:
“The classic Midwest stereotype is someone getting bumped into, then apologizing to the person who bumped into them.”
Adam is right.
Midwest Email vs. Direct Email
Midwest version:
“Hi, sorry to bother you. I know you’re probably super busy, and I totally understand if this isn’t possible, but I was wondering if maybe you might have time to talk sometime?”
Silicon Valley version:
“Hi [Name], I’m building [thing]. I think your work on [specific thing] is relevant. Could I ask you one question or send a two-sentence summary?”
The first email apologizes for existing.
The second one respects everyone’s time.
Growing up in the Midwest means you learn to soften your words, show constant humility, and avoid anything that might come across as overly confident or rude.
But startup culture, especially the SF startup culture, is almost the exact opposite:
- Confidence and brevity are expected and required.
- No filler words or long intros. Get to the point.
- Saying “I think” when you're actually sure makes people doubt you instantly.
Me: These startup and SF people expect you to talk humbly but at the same time with extreme confidence. Humble means casual language, no pointless formalities, rejecting social norms. Confident means you're as specific as possible, clearly provide value, talk fast, and never say “I think.”
He admitted he was still getting the hang of it:
Adam: Definitely a new type of crowd for me.
I reassured him right away:
Me: That's fine. It’s good you’re learning with these people now. Ultimately, if you're good, you're good. That’s all that matters. And you’re good, so don’t worry about it.
Adam joked, but it led somewhere more interesting:
Adam: Ever done motivational speaking? You’d be a natural.
Me: What would you actually want to hear or learn? Also, it’s not a compliment, just an observation.
That’s when he pushed it further:
Adam: I think someone who can tell Midwesterners that brevity is okay, not rude, not careless, just culturally different, would be super valuable. There's also this Midwest tradition where cold emailing or skipping the formal job-interview process feels rude or arrogant, so people don’t even try.
This was an important insight, and I agreed:
Me: Fair point, but better to get rejected than never try at all. If you email the founder or CEO, they want clarity, brevity, and no bullshit. All these formalities are just virtue signaling by startup people anyway.
Adam got it immediately:
Adam: I agree completely, just fascinated by the regional differences.
I laughed, adding:
Me: Just wait until you experience the East Coast.
By the way, shortly after we had this conversation, Adam received a job offer from a Silicon Valley startup. Moving to San Francisco and working in tech had long been his dream. He probably would've gotten the offer regardless, but realizing that directness isn't rude, brevity isn't careless, and confidence isn't arrogance helped him stop second-guessing himself.
You don’t have to change who you are. But once you realize not everyone’s playing by the same unwritten rules, and you start to notice the assumptions behind how people speak and act, you stop wasting energy trying to follow invisible scripts.
Midwest Mentality as a Hidden Advantage
Interestingly, Marc Andreessen, one of the most famous tech entrepreneurs and investors, had a similar realization. When he left the Midwest for Silicon Valley, he thought he was weird, a total outsider:
COWEN: In what sense are you still a thinker of the rural Midwest?
ANDREESSEN: I thought I was a fluke. I thought I was strange. It’s like, you leave the Midwest, you go to the coast, you get involved in tech. You’re on a very different path than the people I knew. I just assumed that I was weird and different.
I got out here to Silicon Valley, and then I started to get oriented. Then I read this profile that I recommend to everybody, which is, Tom Wolfe, the great novelist, journalist, wrote a profile of Bob Noyce, who was the original founder of Intel and basically the father of the chip industry. I read this profile. I don’t mean to compare myself with Bob Noyce, but basically, Tom Wolfe describes an archetype.
The archetype is the Midwestern tinkerer who basically comes out of a very practical, farming-oriented, mechanical, dirt under the fingernails, working with machines, with your hands, culture and background — literally for farming, for light mechanical work — and then basically ends up in advanced technology. So, I went in one shot, after reading that profile, from thinking of myself as a fluke to thinking of myself as a cliché. I think the cliché definitely applies.
—Marc Andreessen and Tyler Cowen, Marc Andreessen on Learning to Love the Humanities (Ep. 152), Conversations with Tyler
The Midwest Mentality can feel limiting when you’re dropped into a high-speed, hyper-confident environment like startups or tech.
But once you recognize it, it can become your biggest hidden advantage.
The humility, practicality, and genuine care for people that the Midwest instills actually make you stand out, even if you have to learn how to balance it with the confidence, brevity, and directness expected elsewhere.
And that’s the secret.
Stop using politeness as a disguise for fear. Keep moving.
The appendix keeps the examples, guides, profiles, and source trails close. The book gives them sequence, context, and a way to turn curiosity into action.