Thriving in Spite of Wisconsin: a founder’s view of the Ecosystem

I’ve been building companies in Wisconsin since 2009. Along the way, I’ve learned something every founder here eventually discovers: if you want to succeed, you’ll do so in spite of Wisconsin, not because of it.

That’s not to say this is a bad place to live or to dream up new ideas. Wisconsin has an innate creativity and a deep culture of hard work. But building here means swimming upstream. We don’t have deep pools of venture capital. We don’t have a steady pipeline of customers who instinctively buy from local startups. And we don’t have an ecosystem that runs on autopilot like the coasts.

What we do have are founders: scrappy, resourceful, stubbornly optimistic people who keep showing up. Since 2020, that’s been the real story: founders thriving regardless of the headwinds.

Community as Survival

When the pandemic shut most aspects of the startup ecosystem down, founders had no choice but to lean on each other. That’s what gave rise to the Midwest Founders Community (MFC), a grassroots network created by and for founders. What started as a series of unpolished and informal gatherings gave way to a place to be honest about the challenges of building here. It hasn’t been fancy or heavily funded. But it is real.

The group has since grown organically to over a thousand founders from the upper midwest. It has tapped into what Wisconsin founders already know: if the system won’t support you, build your own. In a state where institutional infrastructure is thin and public investment is slow, founders created their own lifeline.

But let’s be honest: that reliance on peer-to-peer goodwill is both inspiring and exhausting. Community here exists because founders keep pouring themselves into it, even when they have no time, no money, and no obvious payoff. It’s proof of resilience. It’s also a symptom of what’s missing.

A Patchwork, Not a Fabric

Groups like Startup Wisconsin have made the scene more visible statewide. It’s easier now to see what’s happening in Madison, Milwaukee, or Green Bay. But visibility doesn’t erase fragmentation.

Wisconsin still feels like a patchwork with pockets of energy stitched together, not yet a seamless fabric. A Milwaukee founder may take the Amtrak to Chicago to meet with a capital allocator a day before they’ll drive to Wausau for customers. A Madison biotech startup might spin out of UW only to head straight for Boston. The bridges are better than they were pre-2020, but they don’t yet hold people in place.

Founders who succeed here often do so because they’ve figured out how to straddle multiple ecosystems at once: tapping Wisconsin’s affordability and grit, while reaching outward for funding, talent, and scale.

Infrastructure & Storytelling: Necessary, Not Sufficient

Since the pandemic, Wisconsin has gotten more attention from institutions. The Wisconsin Biohealth Tech Hub brought over $80 million in federal, state, and industry funding. The Wisconsin Investment Fund added $100 million in venture capital capacity. There have been years of advocacy from groups like the Wisconsin Startup Coalition pushing for better conditions for founders like the Qualified New Business Venture (QNBV) tax credit reform. On paper, these are huge.

But here’s the thing: founders don’t live on paper. They live on runways, customer contracts, and cash flow. And for many, the impact of these programs still feels distant. Too much of the capital is locked up in bureaucratic processes or tilted toward later-stage bets. Too much of the hub activity centers on academic research or corporate incumbents.

StartingBlock Madison, Ward 4 and Titletown Tech and Microsoft’s AI Co-Innovation Lab in Milwaukee, Wisconsin Economic Development Corporation - Start In Wisconsin’s statewide directory – all of these make it easier to navigate the scene. And local storytelling, from mkestartup.news to grassroots newsletters, has given more visibility to wins that once went unnoticed.

We’ve built more infrastructure. These things matter. They make founders feel less alone. But let’s not confuse infrastructure with outcomes. A coworking space doesn’t raise your seed round. A news article doesn’t land you your next customer. They are tools, not solutions. And in Wisconsin, too often the tools exist without the bigger systems that make them truly effective.

Milwaukee vs. Madison: Parallel Struggles

The dynamic between Milwaukee and Madison hasn’t gone away, it has simply evolved. Madison has the advantage of Capital Entrepreneurs, UW–Madison, Wisconsin Alumni Research Foundation (WARF), Forward BIOLABS, and a legacy of biotech and software startups. Milwaukee has made strides with the gener8tor, which has long outgrown Milwaukee to become a leading national accelerator & incubator. And we boast the MKE Tech Hub Coalition, FOR-M, and spaces like Wantable Cafe. 

But here’s the uncomfortable truth: both cities are still underperforming. Madison is strong locally but too insular nationally. Milwaukee is trying to carve out an identity but still struggles to retain startups long term. Each city has learned to celebrate incremental wins, but neither has yet built the gravitational pull of Chicago or Minneapolis.

Founders in both places thrive, but again, despite the ecosystem, not because it smooths the way.

What Thriving Really Looks Like

Even in light of all these gaps, founders can still flourish here. They build companies that sell nationally, that raise meaningful capital, that create jobs. But if you ask them how, the answer is almost always the same: by finding a way around Wisconsin’s limitations.

They lean on personal networks instead of institutional pipelines. They recruit talent from elsewhere when local pools run dry. They cobble together grant dollars, angel checks, and side hustles when VC falls short. They endure because they refuse not to, because they believe their companies deserve to exist even if the ecosystem doesn’t make it easy.

That’s the paradox of Wisconsin entrepreneurship: our biggest strength is the tenacity of our founders, and our biggest weakness is how much we require from them.

A Future Worth Fighting For

So where does that leave us?

On one hand, we’re better off than we were even a few years ago. There’s more connectivity, more visibility, and more capital in play. On the other hand, the fundamentals haven’t changed: too little local risk capital, too few customers willing to bet on early-stage companies, too much reliance on unpaid founder labor to prop up the ecosystem.

I’m both an optimist and an opportunist. I believe in the fortitude of Wisconsin founders, and I’ve seen what we can do when we come together. But I also know we can’t keep pretending that grassroots energy alone will fix systemic gaps.

If Wisconsin is serious about being more than a footnote in the national startup story, we need to stop expecting founders to prosper in spite of the state and start building an ecosystem that truly helps them thrive because of it.

Until then, the story of entrepreneurship here will remain what it has been for the past several decades: a story of perseverance and possibility, fueled not by systems, but by the stubborn determination of the people who refuse to give up.

‍Angela Damiani is a serial entrepreneur and community builder based in Milwaukee, Wi. Since 2009, she has co-founded and led multiple ventures, including NEWaukee, and is an active curator of the Midwest Founders Community. She writes about the realities and possibilities of building companies in Wisconsin and the broader Midwest.