The Secret Founder: Belief isn't the bottleneck, execution is.

I believe our "Midwest ecosystems" are under-optimized; Not under-talented. Not under-ambitious. Under-optimized.

We have founders who can build. Operators who can execute. Universities that crank out technical talent. Corporate buyers who will actually pick up the phone. And yet - too often - our startups either leave, stall, or contort themselves into whatever shape the local capital market will tolerate.

That's not a founder problem. That's a system problem. And yes, I'm including myself in that system. I've played the game. I've learned the scripts. I've smiled through the "let's circle back"s. I've taken meetings I knew were pointless because you never know who knows who. In other words, I've done the Midwest thing.

So I'm taking this opportunity as the StartMidwest Secret Founder this month (check us out, we have t-shirts) to explain what I'd change if I could. These are the kind of things that I'd fix, and that can only happen if all of us in the region - and all the state and local Entrepreneur Service Orgs - are actually serious about building companies that matter here, not just hosting panels.

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Stop pretending you're pre-seed when you're really about proof of success.

One of the most exhausting parts of fundraising here is the semantic gymnastics.

A lot of funds say they invest in "pre-seed" companies. They'll sponsor the 'Founder Happy Hours'. They want to be seen as founder-friendly. They don't want to miss the next breakout deal. All of this is totally rational.

But then the conversation starts around an actual check and suddenly "pre-seed" means meaningful revenue, repeatable customer acquisition, clear retention metrics, a pipeline that looks like it came from a sales org with a budget and enough traction that the round is basically de-risked for everyone but the person sweating to make it work: the founder.

That's not pre-seed. Notable investment platform Carta even took the time to define what pre-seed funding is for, including this gem: "Achieving early milestones to show traction before raising a seed round." In other words, almost everything BUT metrics that show actual performance.

If you want founders to build earlier, you have to fund earlier. If you want venture-style outcomes, you have to accept venture-style uncertainty. You don't get to pitch yourself as 'early-stage' and then only write checks once a company is already behaving like a later-stage business.

My Solution: Midwest funds should publish what they actually underwrite at each stage. This could include:

• The proof points you need
• The risks you are willing to take
• What "too early" means in real terms for your fund
• Where your own funding comes from and what that means for investments: are you a community focused, local-tech initiative or are you an actual venture fund
• The process that is required to get funded: how it starts, what is the process, how will it end - whether you invest or not

And then deliver on all those to match what each means for a founder. Because 'sector-agnostic' or we invest in 'high-growth' founders isn't a thesis. But we should know explicitly what you do and don't invest in because it forces you to get closer to writing a check over just taking meetings. So if the honest answer is "we're not comfortable funding that early," that's fine. If we've reached the end of the process and you don't want to invest, also fine. Just tell us, don't ghost. In general, stop wasting the founder's time with performative enthusiasm or mis-defining yourselves.

The hidden cost isn't just time, it's also our momentum and energy. It's the moment our best engineer decides maybe they'll take that corporate job after all, because our startup is still in your freaking "let's wait and see," whatever tf-phase.

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Take bigger swings, or stop acting surprised when the best founders leave

The pattern I've seen over and over is that the Midwest is great at following.

A company gets a coastal fund to lead. Suddenly, the deal has been "validated." Now it's safe for local funds to participate. Suddenly everyone wants in, They all want to claim the win. Everyone follows so they can say, "we believed early."

But when that same founder was pitching three to six months earlier, when it was still messy and weird and hard to explain? The polite no's came fast. Or worse, the non-no's that drag on forever. (The Secret VC calls them "slow no's" - Ed)

Let me be blunt (and it's annoying that anyone actually needs to be told this): the future often looks dumb at first.

If our capital culture punishes everything "non-obvious," we'll produce a region full of respectable, fundable, medium-sized outcomes - and then we'll keep wondering why we don't produce more category-defining companies. That's one way to look at it, another is… all our local investors just want to get a better valuation for themselves because they think we don't know any better.

My Solution: Ecosystem orgs and VCs should build a shared incentive for originality, not just traction.

That could look like:

• Dedicated capital pools for high-variance bets (clearly labeled as such)
• Investment committees that include operators who have built through uncertainty
• Explicit portfolios that tolerate "weird" (and celebrate it)

And for the love of all that is holy: don't punish founders for building something that doesn't fit last year's (probably five years ago to be fair) template.

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Fix the angel layer, because cap tables are being booby-trapped

This might annoy some people: the angel layer in parts of the Midwest is often well-intentioned, but structurally chaotic.

Founders are more often than not forced to assemble rounds by collecting lots and lots of small checks. That's friction and time. It's administrative overhead. And when angels bring "creative" terms - things like dividend-like economics, royalty-like structures, or other weird side arrangements - it can create cap table landmines that show up later when institutional capital finally takes a look. And we all know it exists, what I'm describing here isn't some outlier possibility.

I've even met founders who didn't even realize what they agreed to. You might say this is self-identifying who will survive or not. You could even be right. But that means the same can be said of those who write the checks under those terms. These things often happen because they don't know the game they're really playing, and when you're trying to survive, you might just sign the thing that just gets you to the next milestone.

The problem with doing so is that if you grow and deliver value for these investors - despite their terms - and then you're in front of the next investor (hopefully a 'proper' one) and they say, "We can't touch this" because of those terms. Or that they can, but the price of doing so is going to hurt the future of your business even further.

My Solution: If the region wants healthier startups, we need healthier early capital norms.

• Standardize terms. Do this from the top with state and local entities offering standards. Boring is good
• Educate angels on what later-stage investors will accept
• Encourage vehicles that reduce complexity (properly managed syndicates, true lead angels who do diligence)
• Stop celebrating the amount raised without caring about how it was raised
• Stop asking for data rooms, to conduct diligence or meet our customers until you've given a solid commitment; most helpfully what terms can you offer?

A messy angel layer doesn't just hurt founders. It hurts the region's whole conversion rate; from idea to investable company and all the way to long-term success or lack thereof.

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Midwest Nice is killing speed, and speed is oxygen

I've heard it said best that we confuse politeness around here with kindness.

A kind ecosystem is one that tells founders the truth. Quickly. Clearly. And with respect.

An unkind ecosystem smiles, nods, asks for "just one more update," schedules another meeting, and then ghosts (that one really gets to me). Or it drags a founder through weeks of quasi-diligence when the answer was always going to be no.

I've watched founders spend months in fundraising purgatory because no one wants to be the bad guy. Meanwhile, their runway is shrinking, their team is anxious, and the business is stuck in neutral.

We don't have infinite capital here. We don't have infinite founder density. Heck, we don't have an infinite amount of time personally either. So wasting our time is not a quirky cultural trait, it's a competitive disadvantage.

My Solution: Normalize fast no's.

VCs and ecosystem orgs should adopt explicit response standards:

• "Yes / No / Not yet" within a defined timeframe
• "If not yet, what specifically would change it?"
• "If no, why", so the founder learns something

And founders: demand clarity. You're not being rude by asking, "Is this real, or are you just being polite?"

Don't get it twisted though: The other side of this is definitely worth protecting. The Midwest can still be a place of super relationships. When people do commit, they often commit in a practical way - introductions to customers, pilots, hiring help, real community support.

The issue here is the consistency.

So let's keep the loyalty. Let's keep the community. But can we please remove the time-wasting ambiguity?

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Build more operator-led credibility: or stop cosplaying "ecosystem leadership"

A couple of months ago, the Secret Founder used the term 'Cosplay' when referring to VCs. Most founders I know loved it. Investors, not so much.

However, too much "ecosystem strategy" is being designed by people who haven't carried the operational weight of building a venture-scale company. They might be smart. They probably even care a lot. They might be great at moderating a panel. But once advice gets abstract, the incentives drift.

At the same time, we prop up programs that keep companies alive without confronting whether they're actually on a path to scale. I'm not anti-grant or anti-program, but I am anti-delusion.

A startup that will never be venture-scale shouldn't be forced to pretend it is. And an ecosystem that wants venture-scale outcomes shouldn't spend all its energy celebrating activity metrics that don't convert into durable companies. Even more annoyingly, we have to endure the meetings I've described above and the slow no's, as well as being questioned why we're staying in the region and not moving out of it when we do head to the coasts… only to find better terms and those who will take a risk on us more easily anyways!

My Solution: Separate paths, and treat both with respect.

• If a company is a great small business: say that, support it, help it thrive.
• If a company is venture-scale: fund it accordingly, challenge it accordingly, and surround it with people who've actually built those kinds of companies, not those who read about it once on Twitter or whatever it's called nowadays.

And here's the real kicker in this: to make this happen we actually need our local, exited founders and real operators to actually show up. Not as keynote speakers, but as participants and mentors who take calls. As angels who lead rounds with clean terms. As board members who help founders make hard decisions.

If the Midwest wants stronger local ecosystems, it needs more people who've actually "been in the room" when something huge was being built.

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Hit 'em where it hurts.

The Midwest doesn't really need more hype, we need more results.

Everybody here knows we have the raw ingredients: talent, work ethic, technical depth, and customers who buy real things. But our system still behaves like it's afraid of risk, allergic to clarity, and maybe even weirdly proud of taking slow decisions.

We need to fix that. Now.

If you're a VC, you don't need to become someone else. You just need to stop pretending you're early if you're not, stop punishing novelty, and stop dragging founders through polite theater.

If you're an ecosystem org, you don't need another initiative. You need fewer vanity metrics, more operator-led accountability, and a willingness to tell the truth about what produces real companies.

And if you're a founder reading this, here's the part that hurts: you can't wait for the ecosystem to improve before you build. But you also shouldn't accept dysfunction as the cost of doing business here.

The Midwest can absolutely produce the next generation of enduring companies. I honestly believe that - I'm still here, aren't I? :)

But belief isn't the bottleneck we seem to think it is.

But execution is.

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