The Secret Founder: Hey Midwest VCs, please stop cosplaying Silicon Valley

The Secret Founder is our way of sharing stories from the frontline of entrepreneurship: the reality of building in the Midwest. It will be a different founder each month to ensure we find all perspectives. This is the first in the series.

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I’m going to say the quiet part out loud: the Midwest venture ecosystem doesn’t have a “capital” problem as much as it has a behavior problem.

And yes, I know how that sounds. It’s easier to blame macro conditions, interest rates, or “the market.” But a lot of what founders experience day to day isn’t macro. It’s the way investors show up, the way they don’t, and the way everyone pretends this is normal because Midwesterners are polite and we don’t want that next rooftop mixer to be awkward.

I’ve spent a lot of time fundraising across regions. The contrast is… not subtle. Coastal investors can be exhausting. They’ll act intensely interested, then ghost you like your email address has committed a crime. But they’re curious. They dig in. They seek you out. They travel. They are on the hunt. They move.

In the Midwest - in my opinion - too many venture firms don’t do enough of those things.

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Curiosity is a muscle, and ours is under-trained.

One of the biggest differences I’ve seen is curiosity. Midwest investors are often less curious than coastal investors because they’re less willing to go elsewhere, literally. On the coasts, I’ve watched venture folks fly all over to learn what they don’t know. In the Midwest, a lot of investors seem to force themselves to only be “Midwest.” I believe this does more harm than they realize, with missed opportunities to bring more outside perspective, ideas and modern best practice from the outside that could help elevate what we build and create in the region.

We only become a hub if the outside world is coming to us. We only get the outside world coming to us by reaching for more and pulling in.

If you never leave your own lane, you only ever invest in what you already recognize. That means founders have to do the heavy lifting of educating investors on new industries, new approaches, and new models - before they even get to the pitch. They seem to just hope talent and ideas come to them. Half the time I feel like I’m explaining the basics of a category just so someone can get remotely close to understanding what we’re doing.

That’s not venture. That’s tutoring.

If Midwest investors want the ecosystem to improve, they have to rebuild their curiosity. Go outside the box. Go outside your friend group. Go outside your calendar of the same three recurring events thinking that will shepherd talent to you. Curate rooms where people actually engage in innovation, not rooms where founders perform for investors as a means to get out of the house.

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Our “process” feels like it time-traveled from the 80s.

Here’s another blunt truth: the way too many Midwest firms run deal flow feels OLD school. I’m talking late 80s, early 90s old school. It’s rigid, it’s on their turf, and it’s designed for investor convenience, not founder reality. Some even enforce a requirement for in-person meetings. Talk about a way to only get very local ideas.

Founders are asked to travel hours, wait hours, then present in a cattle-call lineup while a bunch of other startups go before them. You don’t get real time. You don’t get a real conversation. And more concerningly from my perspective, as someone who has raised before, we’re not building trust or adding necessary context. We all mostly just learn who has the most patience and the best, most obvious pitch…or who is the most desperate.

The annoying thing is that everyone in the Midwest then acts surprised when “the pipeline” isn’t producing the innovative companies that define their category or industry like it once did.

If you’re a Midwest investor reading this and feeling defensive, ask yourself a simple question: do your structures actually help you understand teams and ideas in a personal, high-signal way? Are they built around you or to encourage finding the most innovative ideas? Or do they just keep you insulated while founders audition like it’s a high school play?

Because in my experiences outside the region - even if you quickly get ghosted - investors at least find ways to dig in quickly and understand the core idea or impact on the industry. Here, we’ve got a lot of theatre and not enough traction.

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“Relationship-first” is useless when it turns disingenuous.

Midwest investors love to say they’re about relationships. Great. As I’ve said above, relationships matter because trust matters. But here’s where it breaks: when it’s time to be transactional - when it’s time to lead, follow through, commit, and send a signal - too many firms don’t know how to do it.

They’ll tell you they believe. They’ll tell you they’re supportive. They’ll say all the right things. Then their actions don’t match the words, and you’re left trying to interpret the gap like it’s a personality test. It becomes disingenuous, and for founders like myself, that’s worse than a clean, concise “No.”

If your fund changes direction, just say it. If you don’t believe anymore, say it. If you can’t invest, say it. Don’t beat around the bush. Founders can handle direct feedback. What we shouldn’t have to handle is spending months in a fog of polite ambiguity while the clock keeps ticking.

This may not even strictly be a venture problem, it may indeed be a Midwest cultural reflex. But the fragility of the investment stage is where that reflex can kill companies.

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Small checks, big entitlement.

Now let’s talk about one of the most quietly toxic dynamics: boundaries after the check clears.

If an investor is truly strategic - meaning they can bring something real to the table - then yes, deeper engagement can make sense. But that’s rare. What’s more common is a long tail of smaller investors who want major investor access without paying major investor prices.

They want detailed insights. They want frequent updates. They want individualized time. And sometimes they’ll pressure you for things they don’t even have rights to in the contract and then make it personal, like: Why wouldn’t you share that? Are you hiding something?

No. I’m not hiding something. I’m running a company and your terms don’t give you this access. It’s there in black and white.

Founders, hear me clearly: time is your most valuable asset. A cap table full of people who each want a slice of your attention will drain you faster than any competitor. You can’t do ten, twenty regular separate investor relationships at full intensity. It will become all-consuming.

If Midwest investors want to help the ecosystem, they should stop crossing boundaries to get unreasonable access. If you want major rights, write a major check. If you want board-level transparency, take board-level responsibility. Otherwise, let founders build. 

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Leads, signals, and the self-inflicted wound.

This is the one that still makes my blood pressure spike: lead investors who aren’t equipped to lead.

I’m aware of situations where investors have nearly torpedoed a raise because they were positioned as a “signal” for the round but didn’t have the guts - or the capability - to act like a real lead. When it came time to follow through and send the signal that unlocks more capital, the partnership talks vanish. The relationship talks vanish. And suddenly founders are stuck trying to solve a problem that never should’ve existed.

Sometimes it just takes a little follow-on to change the story of a company. A lead choosing not to invest in the next round sends a message, whether it’s fair or not. When that happens everyone asks, “Why didn’t they invest?” And then the herd follows the implication.

Personally, I don’t think our region has enough true leads. Everybody wants to follow, but fewer people are willing to actually lead. And when no one leads, founders are forced to take their best ideas elsewhere - not because they love coastal arrogance, but because they need competitive demand and reliable support.

That’s the tragedy: I want the reward to stay in the region. I want Midwest firms to win. But if we can’t trust that the very people who helped set a company up won’t also become a failure point, what are we supposed to do? Bet the company on vibes?

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Risk aversion isn’t “Midwest grit.” It’s just a confused venture.

Yes, Midwest investment culture tends to be risk averse. It prefers proven concepts and personal connections. It likes “skin in the game” to the point where I’ve heard of founders being asked how much of their own money they're investing.

The answer we should all be thinking, if nothing else: Our skin is our time.

Committing years of our lives with no guarantee of reward. Carrying the stress home every night. That’s not “skin”? Let’s get serious.

Here’s the bigger issue: if investors need everything de-risked before they invest, then they’re not doing early stage investing. They’re doing something else while calling it “venture” because that sounds way cooler at a dinner party.

If you want measurable proof first, fine. But then don’t pretend you’re funding the messy early part. Because that mismatch - “we invest early” with “prove it first” - is exactly how you starve companies before they have a chance to become inevitable.

I believe the Midwest can absolutely produce generational companies. It has done so before, and continues to do so. But we won’t do so anywhere near as frequently or as easily as other parts of the country while local investors cosplay Silicon Valley, while founders are wasting time performing for outdated systems, and while everyone stays too polite to call out what’s clearly broken.

If you want the best entrepreneurs and ideas, start with the behaviors that quietly shape who gets funded, how companies survive, and whether the best founders decide to stay… or whether they decide to leave the Midwest.

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