Midwest Nice Isn’t a Bad Thing. But It’s Also Not Enough.

Although High Alpha is headquartered in Indianapolis, we invest in B2B software companies in the Midwest and across North America. So when we invite a founder from beyond the Midwest to our Indianapolis office, I often greet them with a big smile and my favorite icebreaker: “It’s nice to meet you! Have you been to Indianapolis before, or is this your first time?”

They shoot me back a smile. And respond, “Hah! I have not, this is my first time here.” Or, sometimes, “It’s been a long time, but I actually have visited! Back in 2015…”

I follow up, genuinely interested in either why they’ve been here (Indy 500 is a common response) or how they’re enjoying it so far (highly dependent on the weather and season they visit). 

Where am I going with this? There’s a stereotype that being located between the coasts and embracing a spirit of “Midwest Nice” is a bad thing — especially for venture capitalists. And, at face value, those can feel at odds with one another: the coasts are where ambition and innovation thrive, the Midwest is where you settle down or look for “balance”. 

But, I’d like to offer a different perspective: Midwest Nice, when applied strategically, is actually a differentiator and, dare I say, a strength. And while my perspective is that of someone who works in venture capital, these thoughts can and should be applied to anyone who operates in the Midwest.

The Good, the Bad, and the Ugly: Stereotypes of Midwest Nice

Let’s start with the good: people generally find Midwesterners nice. Or, at least, that is the stereotype of the Midwest, because actual data is hard to come by.

At first, this sounds like a good thing. Who wants to work with mean people? But then comes the explanation of Midwest Nice (what people typically mean when they say it), in publications like The Economist:

“WHAT IS ‘Midwestern nice’? It is apologising involuntarily when scooting past someone, both to warn of your presence and to express regret for any inconvenience your mere existence may have caused. It is greeting people as they step into a lift and wishing them well as they leave. It is a strong preference for avoiding confrontation.”

This stereotype of Midwesterners could be seen, especially in an industry hell-bent on innovation and growth, as negative. In my opinion, it creates the feeling that Midwesterners can’t hang with those on the coasts…no matter how many success stories we actually have. That when faced with the choice to shy away from confrontation or push for what we believe to be true, we default to the former.

So let me offer a more optimistic version of Midwest Nice, one that we consider a strength (for founders AND venture capitalists!): Hospitality.

Hospitality As a Superpower

Hospitality is one of our unspoken core values at High Alpha, and not something typically emphasized at a venture capital firm. But, it’s powerful. When we invite a founder (who, oftentimes, is heading to Indiana for the first time in their life) to our office in Indianapolis, we do both the small things (a warm welcome, snacks and beverages, some High Alpha merch) and the more nuanced, interpersonal parts of hospitality.

In Will Guidara’s book Unreasonable Hospitality, there’s a quote that sums up the interpersonal element well:

“‘Black and white’ means you’re doing your job with competence and efficiency; ‘color’ means you make people feel great about the job you’re doing for them. Getting the right plate to the right person at the right table is service. But genuinely engaging with the person you’re serving, so you can make an authentic connection — that’s hospitality.”

Now let’s go back to venture capital. Firms offer pretty much the same product to all founders: capital. Using the metaphor above, capital is the black and white: merely doing the job with competence and efficiency. But color is what makes the connection authentic. Color is difficult to fake — and it just so happens to be something that Midwesterners have spent decades dialing in.

We recently invited a founder to Indianapolis from elsewhere who was deep in his fundraising process. We were connected to him pretty darn late: he already had multiple term sheets, and the round was going to be competitive. But, when he flew out to Indy and met with our team, the cultural fit was clear — we wanted to work together. (And, I’m happy to share that we did win the competitive process, and led their recent Series A). 

If you assume that Midwest Nice can actually mean an aptitude for hospitality, and hospitality actually means genuine engagement to make authentic connections — genuinely caring for people — then it’s not a stretch to see how Midwest Nice can be quite advantageous — whether you’re a founder building a big business or a venture capitalist nurturing relationships in the Midwest ecosystem and beyond.

Midwest Nice Meets Driving Ambition

Hospitality — the art of serving while building genuine relationships – is not enough. But, when paired with ambition, it’s a recipe for differentiation that can be the Midwest’s cheat code. 

The founder in my previous example didn’t choose our capital over another firm’s capital just because he got along well with our team. We’re talking about building big businesses here! Instead, it was a perfect mix of genuine connection and ambition — the drive to achieve, together. 

The Midwest IS Nice, and That’s Okay

High Alpha was started by a group of operators who have built unicorns. And we’re not alone! There are plenty of examples of innovative companies being built between the coasts — so it’s absurd to write the Midwest off as being too nice to build anything worthwhile.

I do think that some Midwesterners are ashamed of the stereotype. But, let’s be clear: you can be nice, hospitable, and build real relationships and also push the envelope and build big businesses. 

It’s the mixture of both that gets me really, really excited to be operating in the Midwest.