The Boomerang VC: Ilana Habib on Midwest Grit, Patient Capital, and Building Bigger in Ohio

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Ilana Habib is a venture capitalist at Cintrifuse Capital, where she brings a rare mix of lived experience as a founder, operator, angel investor, and early-stage VC, shaped by years spent building and investing in coastal and large-city startup ecosystems before returning home to Ohio.

Before Cintrifuse, Ilana was an MBA Associate at Impellent Ventures, a pre-seed and seed fund, and spent five years at Mainstay (formerly AdmitHub), where she helped scale AI-powered tools that supported more than 15 million students on their college journeys. She’s also taken a swing at building her own company, supporting early-career professionals and earning a finalist spot in Booth’s Social New Venture Challenge. She’s quick to note that her failures as a founder were just as formative as her wins, skinned knees included.

In this interview, Ilana breaks down what truly differentiates the Ohio and Midwest startup landscape, where patient capital creates strength and where it can slow progress, and why founders here need to get more comfortable thinking bigger and asking louder. Clear-eyed, candid, and optimistic, she makes the case for a Midwest ecosystem that’s confident, ambitious, and ready to scale.

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Landscape Differences

You’ve worked and studied across several major innovation hubs, including Massachusetts and Illinois, and now Ohio. From your vantage point, how does Ohio’s VC and startup landscape differ from places like Boston and Chicago? What advantages or tradeoffs stand out most to you?

One of the things that I’ve enjoyed the most about entering the Cincinnati/NorthernKentucky (I lovingly refer to it as Cincitucky) ecosystem is the collaborative ways in which we support local founders, whether through capital or through other means. It can be so hard for companies to get honest feedback from VCs, but because of Cincinnati’s patient and community focused approach, I find conversations to be much more open here between founders and funders. People lean in to help companies they aren’t investing in. There’s a mentality of extending support without any expectation of receiving something in return.

We also often see different types of founders here than I engaged with on the coasts. Our founders skew older and more experienced. They build their companies with more patience and attention to fundamentals. This can be both an advantage and a disadvantage for our founders. By building companies that are cash efficient and steady, they are able to make a lot out of a little, but I think that focus on making do can sometimes prevent them from considering what could be possible if they had access to “more”. I want to see Midwest founders actively show both local and coastal VCs a vision of what they could do with “more”, as I think that’s how we ultimately create an ecosystem where we actually grow “more”. The vision and the ask have to come first. In hub cities, it’s considered more socially acceptable to create audacious plans and make audacious asks. We shouldn’t stop ourselves from doing the same. 

Why Boomerang?

You’re a Midwest boomerang. What ultimately drew you back to Ohio, and how has that decision shaped how you think about investing and ecosystem building?

I never thought that I would move back to Cincinnati. I have spent nearly my whole career in the early startup ecosystem and just didn’t see the region as somewhere I could do that kind of work. When I learned about Cintrifuse Capital and what activity was happening in Cincinnati’s venture scene, in the final quarter of my MBA, my post-graduation plans changed rapidly. Suddenly I had an opportunity to not only relocate to the city my family still calls home, but also to build a stronger community of innovators and investors in my own backyard.

It’s been amazing. On the personal side, I now get to attend family dinner every Sunday. I can join in on an impromptu Skyline or Graeter’s run with my niece. It allows me to show up to work a more grounded version of myself. On the professional side, it’s allowed me to bring together learnings from across my different experiences and return to my love of engaging hard at the ground floor. The entrepreneurial ecosystem here in Cincinnati is present and thriving, but also ever-evolving, and it feels like a place where effort actually can change outcomes. I’m excited to shape norms here rather than just participate in them.

Founder/Company Trends in Ohio vs. Elsewhere

As an early-stage investor, what types of founders or company characteristics are you most drawn to in Ohio right now? How do they compare to what you’ve seen in more established coastal or large-city ecosystems?

The type of founder and company I’m looking for is geographically agnostic. Part of why I was comfortable switching to a firm with a geographic mandate outside of a hub city is that my entire venture career has been focused on founders in “under-served” geographies.

If you’re investing in SF and surrounding regions, it’s easy to come up with an ideal profile or resume for founders: folks who attended certain schools or worked at certain companies, etc. Investors can let those organizations serve as a filter for them. I’ve never invested with that mentality, and I think we lose out on incredible founders and companies when the industry operates in that way.

I get excited by investing in non-hub founders because I think making the decision to become a founder in non-hub geographies requires a different type of grit. The activation energy required feels higher when it’s less socially permissible to go start a company (and likely fail). And from a deal perspective, because those giant funds on the coasts are less aware of these founders and are nervous to invest without the traditional markers, there’s more opportunity for finding alpha.

Sector/Building Trends in Ohio

Looking specifically at 2025, what are you seeing emerge among Ohio startups, whether in sectors, founder profiles, or how companies are building and scaling? 

I’ve been really delighted by how many hard tech and robotics companies have been coming across my desk. It’s a sector I did not expect to work with as heavily in my role at Cintrifuse, but it has consistently been one of our most active and exciting areas. My working theory is that when you combine targeted funding through programs like TVSF, deep technical talent at places like Wright-Patterson Air Force Base, and academic innovation at institutions such as the University of Cincinnati, you start to see a real spark for getting these kinds of companies off the ground. I think we’re beginning to see a similar dynamic emerge in healthcare, particularly with the collision of anchors like Cincinnati Children’s and new innovation spaces like the OneNKY building.

Zooming in on the human angle—and ultimately I believe we are investing in people more than companies—I have been especially excited by the number of founders I’m meeting who bring “earned secrets” from the industries they are building in. My dream founder is someone who has experienced a problem so acutely that they can’t stop thinking about how to fix it for others. I’m finding those founders here. 

One example is Alex Boyd, who started a land-clearing business and became deeply frustrated by his inability to track and maintain hours-based equipment. That frustration led him to build FieldFix, a software platform designed to solve his own problem. He demoed the product at one of our events last night, and seeing the excitement from other builders in the room was a great reminder of how powerful that kind of founder-led insight can be.

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Landscape Differences

You’ve only been back in Ohio for a short time, but you bring perspective from investing and operating in other markets. Based on what you’re seeing so far, how does today’s Midwest capital environment compare to what founders are navigating in larger or more established ecosystems?

From a capital perspective, the Midwest benefits from patient, long-term oriented investors who are deeply committed to the region. That patience is a real strength. At the same time, it can sometimes show up as slower decision-making, smaller initial checks, and more consensus-driven processes. We see fewer clear leads and more party rounds, which can leave founders without a single investor who feels true ownership and accountability. The result is not a lack of support, but support that can feel fragmented.

What gives me optimism is that local capital providers are actively working to solve this problem. When I think about what’s happening at Cintrifuse Capital and beyond, the building blocks are already here. Our ability to lean in with marketing support, connections to talent, and downstream capital connections positions us to be true value-add investors, and we’re working everyday to strengthen that muscle. I’ve historically been skeptical of fund of fund structures, but in blending both direct investment and fund of fund investing, it’s created a super interesting flywheel where we’re able to create outsized impact when our portfolio goes out to raise. I’m excited to see how other Midwest firms can continue to get creative about how we leverage the resources at our fingertips.

You’ve been a founder, operator, angel investor, and now a VC. How does that multi-angle experience influence the way you support founders today?

It colors everything I do. My experiences as both a founder and an operator give me deep, lived empathy for the day-to-day reality of building a company. I’ve had to fire people. I’ve slogged through sales. I’ve lived through a co-founder breakup. I know firsthand that building and running a business is hard, personal, and emotional. I have enormous respect for founders who are willing to put themselves, and often their families, on the line in pursuit of their vision.

Because of that, I try to show up for founders with as much directness and transparency as possible. I share feedback where I hope it is useful, I’m clear about timelines, and I explain how we are thinking about an investment and where our concerns are. For me, clarity is a form of respect and kindness. Nailing the dance between direct and polite is tricky as someone who spent over a decade in the Boston area, so I don’t always get it right, but I am constantly pushing myself to do better. 

As we look ahead to 2026, what are you most excited about in the Ohio and broader Midwest startup ecosystem? 

Like many investors, I’m hopeful that we start to see some relief from the liquidity lockup that has defined the past few years in venture. The market has gone through a huge contraction, with roughly 35% fewer dollars flowing into VC per the Wall Street Journal in 2025 than in 2024 (and our own data and story backed this up as well - Ed). While some of that was likely a continuation of the appropriate re-adjustment after the overheated COVID-era years, my hope is that as some long privately held companies begin to explore public markets this year, capital can start flowing back to LPs and the system can loosen up again.

What excites me about this moment, especially for Ohio and the broader Midwest, is the opportunity it creates for regionally focused investors to step up. We are seeing a high concentration of LP dollars in mega-funds, but those funds are not always well positioned to support companies building outside of traditional hub cities. That creates real opportunity here to show up with conviction, context, and long-term partnership for founders who may not fit the coastal archetype. I’m excited to be part of that work, to keep learning alongside the founders we support, and to help build an ecosystem that is increasingly confident, resilient, and ambitious as the broader venture landscape continues to evolve. 

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Cintrifuse is a non-profit organization accelerating startup growth in Greater Cincinnati by leveraging its three branches: Cintrifuse, Cintrifuse Capital, and StartupCincy. Together, these branches create an ecosystem which aims to amplify Cincinnati’s reputation as one of the best places in the Midwest to launch and scale a business.