The same week that I moved back to Chicago from the Bay Area, I opened up 50 slots on my calendar for founders building startups across the Midwest. With the Midwest being my home, I didn’t need to be convinced that smart people were building serious companies here. But after some time away, I wanted a fresh read on what building felt like right now, directly from the people doing it.
Over the next 50 days, I spoke with founders working on very different problems at very different stages. Some companies were still shaping their first product, others were gaining traction, and some were knee-deep in fundraising.
Despite these companies being in different industries and geographies throughout the region, I began to observe a pattern across our conversations. Yes - founders need capital. That’s obvious, particularly in a region that’s historically attracted a small share of the country’s venture funding. But capital wasn’t the constraint that kept coming up. Over and over, founders told me they first needed access to someone who could help them create the evidence that unlocked their next steps.
These were smart, capable people, so I tended to believe them. They shared stories of spending meaningful time trying to get hold of someone who could approve a pilot. Of precious time spent looking for the right, experienced operator to join their team, someone capable of expanding both capacity and capability. Of course, some also mentioned struggling to get time on the calendar with the region’s investors who understand their market well enough to offer an informative thumbs up or thumbs down to their progress.
I try to make relevant connections whenever possible. But the purpose of setting up these 50 conversations in 50 days was to better understand what startup founders are navigating day to day in the Midwest. Their collective answer was clear: progress often depends on reaching a specific person with the authority, expertise, or judgment to move something forward.
The help Midwest startup founders need is already in the region
That intuitively makes sense. I believe the phrase “teamwork makes the dream work” applies here. What makes less sense is how hard it is to get access to the right people here. The Midwest has deep industry knowledge, major employers, significant private wealth, experienced operators, some of the world’s great universities, and a long history of building durable companies. The help that founders need is often already in the region. Yet, much to my disappointment, founders spend too much time figuring out how to reach the right person, while the people I meet with capital and experience often say they wish they had better access to promising companies earlier.
That is an inefficient market. It’s also an opportunity. The Midwest should be the easiest place in America for a great founder to get in front of the person who can change what happens next. As our tech scene stands today, we’re small enough that the flow of resources shouldn’t be the problem.
To be fair, I’d never argue that building a company here should be easy. It never has been. And it still isn’t, even as artificial intelligence changes how we work. However, I’m arguing that the region has an unusual amount of relevant experience sitting close to the problems founders are trying to solve. In many cases, the person who best understands the customer, the industry, or the economics isn't on the other side of the country. Often, they’re just one or two introductions away. That proximity should be a competitive advantage the region’s founders can rely upon. Right now, that’s simply not the case.
We’re almost all to blame. Because, once you’ve spent your career in an industry, you naturally have information someone outside that industry doesn't. You know which problems are painful enough that a customer will pay to solve them. You know how purchasing decisions really get made. You know which claims sound impressive and which ones signal that a founder actually understands the market.
What SOCAP26 in Chicago got right: starting with the problem
I recently attended SOCAP26, one of the largest global events for impact investing and social entrepreneurship. This year, it took place in Chicago, the first time it was held outside of San Francisco in its nearly 20-year history. The conference brings together people from very different institutions, with very different incentives. While speaking with other folks at the event, I couldn’t help but notice how conversations rarely started with the category or the tech. Instead, conversations typically began with defining the desired outcome, and they were some of the most productive conversations I’ve had in a long time.
When the starting point was a shared problem, it became easier to discern where interests overlapped. Investors could openly care about returns, companies could openly care about resolving a very specific operating problem, and foundations and philanthropic organizations could share their opinion from an economic or social point of view. In these rooms, motivations didn’t need to be identical for the solution to create value for all parties involved.
Successful people are busy, their relationships are valuable, their capital is their own. They should be selective. But, selectivity and distance are very different things.
I think the Midwest’s startup ecosystems could benefit from more of that type of thinking.
We spend a lot of time sorting people into categories. Founders talk to founders. Investors talk to investors. Large companies attend their own conferences. Wealthy families often connect with venture capital only through a handful of funds or advisors. Everyone can be active and well connected inside their own circle while still missing the people just outside it who could make a meaningful difference. That’s how a region with plenty of capable people can still feel difficult to navigate.
To be clear, I’m not making a broad call for everyone to support their local startup. There’s no path where that leads to anything but wasted time. Successful people are busy, their relationships are valuable, and their capital is their own. They should be selective. But, we’d do well to keep in mind that selectivity and distance are very different things.
Why getting closer to startups early pays off
People who know these markets best have a strong economic reason to get closer to what’s being built. As the coasts have proven repeatedly, the earlier you’re exposed to a company - whether you’re a customer, an advisor, a connector, or an investor - the more useful your judgment can be. You quite literally are able to shape the future of a technology.
However, if we wait, the opportunity either goes unsupported or the opportunity leaves our sphere of influence. And once a national customer has signed a deal or a well-known venture firm has invested or a company has accumulated enough traction to make their velocity obvious, the opportunity becomes even easier to evaluate. Which means more competition. The company may still win. But the question then becomes: who participated early enough to benefit from seeing it sooner?
The good news is that the Midwest doesn’t need to manufacture relevance. It already has important companies, deep expertise, serious capital, and plenty of founders willing to take real risks. What it needs is a better way for those assets to find one another before the opportunity becomes obvious to everybody else.
That’s good for founders, but it’s not good only for founders. It’s good for the executive who wants a first look at technology that could reshape their industry, the business owner who understands a market well enough to recognize an opportunity others will miss, and the investor who’d rather build conviction from direct knowledge than wait for consensus. Finally, as it may well sound to you reading this, it’s also good for the region. Our innovation is consistently underfunded. Our best and brightest risk takers are saying they need our help, and they’re all willing to share the upside in exchange for a meaningful contribution.
The future won’t be allocated evenly by geography and the market won’t wait for any region to go ahead and organize itself. Great companies in America will be built where founders can find the capital, talent, customers, and conviction they need to keep moving. The coasts aren’t coming to buoy your local tech scene. Fortunately, the Midwest has far more resources than our outcomes suggest, but the people closest to the opportunity should be among the first to recognize it.
Holden Price is the Founder and General Partner of Civic Capital, an early-stage venture firm focused on backing founders modernizing the Midwest economy. Previously, Holden spent nearly five years at M1 Finance, where he helped build the company’s analytics capabilities as it scaled into a fintech unicorn. He later supported mission-driven investing at the Kapor Center. A Midwest native, Holden studied at Miami University (BS), Loyola University Chicago (MS), and the University of California, Berkeley Haas School of Business (MBA).
