Today is my last day at Cintrifuse Capital.
I'm leaving to launch my own fund, Psycho Capital, as a solo GP, which is equal parts exciting and terrifying. It also means I'll be spending more time in Chicago and at Booth, but to be clear: I'm not leaving Cincinnati. I'll just be the Midwestern version of bi-coastal, if you consider Lake Michigan and the Ohio River as my two “coasts.”
When I sat down to write about what I've learned here, my first instinct was to share a highlight reel. I've resisted it, partly because highlight reels aren't useful to anyone and partly because I seem to be developing a habit of mostly talking about the things I've gotten wrong. So this is the messy version, with the screw-ups included.
None of this is just for the VCs either. If you're building something hard in or around the Midwest, inside a startup, a Fortune 500, or even a hospital system, I think most of this will sound familiar.
Nobody has a formula: Build around what you actually know.
The question I get most from folks learning about venture for the first time is some version of: what are investors actually looking for? There's an assumption baked into that question, and I shared it for a long time, well past my first angel check: that somewhere behind the closed door of the partner meeting there's a rubric, and the people who have been doing this for twenty years know what's on it.
Here's what I’ve seen in practice: smart, seasoned people looking at the same deal and landing on opposite conclusions.
I have worked at firms built on completely different theories of the job. Impellent Ventures, where I worked throughout my MBA, is fast, contrarian, and high-action. Cintrifuse Capital is patient, deliberate, mission-driven, and accountable to an entire region. For a while I assumed one of those had to be right and the other had to be the compromise. Now I think one is built to move before consensus forms, and the other is built to steward other people's capital in a place that is counting on it. Both are hard to do well, and neither has a set formula.
So here's where I landed: If nobody has a formula, certainty was never the bar. Conviction is, and so is being willing to change your mind when the facts change. It also means you'd better have an edge you can actually name, because "I have good judgment" is what everyone says. My edge clusters around two things I spent five years on at Mainstay, the startup I helped build: behavioral science, and how companies secure, retain, and empower their customers. That's where most of my diligence time goes now.
It's also the bet I'm making with the new fund. Venture has always claimed to invest in people, and then spent most of its diligence hours on markets and models. I think that's backward, and the gap is widest for the founders I care most about: the ones who have lived a problem so acutely that they can't stop thinking about how to fix it for everyone else. They often don't have the resume that gets you a meeting with the name-brand VCs. What they have is years inside a problem and a customer they understand better than anyone. Until recently, that wasn't enough to start a company. AI coding tools changed that. Someone who knows a problem cold can now build the first version themselves, and the schools-and-logos filter that decides who gets a first meeting is about to matter a lot less. I want to be early to that shift.
So I want to understand who a founder actually is when things get hard, and I want to see the work. How many of those customers have you talked to? What surprised you? What do they pay for today, and why would they pay you instead? A pitch tells me what a founder wants to be true. The customer research tells me what they actually know, and it says more about how they'll run a company than any market slide ever will.
That's also why I stopped waiting to feel ready. I told Cintrifuse from the start that I wanted to start my own fund someday, and for a long time "someday" meant "once I know exactly what I'm doing." If you're waiting for that, you'll be waiting forever. Nobody else knows exactly what they're doing either. The difference is whether you know what you're good at and have built your process around it.
Make your case inarguable
Some of the work I'm proudest of at Cintrifuse was driving things the fund had never done before, including our first time leading a priced seed round and our first biotech investment.
What that took was memos that ran 35-plus pages, plus hours of customer interviews and a clear, written answer to why the deal still fits our risk profile, built around questions I knew our external investment committee would ask before they had the chance to do so.
I won't pretend every one of those pages needed to be there. Some were written to prove I'd done the work, not necessarily to say what I thought. But the rigor underneath them was correct: write for the person most likely to say no, not the one already nodding.
If you're a founder, that discipline applies to you too. When you ask an institution to do something it has never done, your enthusiasm alone will not carry it over the line. Your champion inside the building needs ammunition, and you're the one who has to hand it to them.
I'll keep writing myself the hardcore memo, even when the only person I have to convince is me.
Those memos also hammered home a lesson I'd been avoiding. Underneath all the models, the question that decided every deal was whether the customer would actually pay, and how much proof there was. I spent years in education technology, a sector full of brilliant products and buyers with no budget, and I learned the expensive way to walk away from a great product in a market like that. There's no alpha where people can't or won't pay.
Changing an institution is a skill, and it's slow on purpose
The hardest part of working at Cintrifuse for me was moving a (rightfully) careful organization toward something new.
I was impatient about this at first. I'd spent most of my career in startups, where a decision takes an afternoon, and a bad one on Monday can be undone by Friday. Somewhere in my first year at Cintrifuse, it finally clicked that the care I'd been chafing at wasn't bureaucracy for its own sake. We have a unique LP base anchored by public companies, and we are responsible not just for ourselves but for our region; the caution is, and was, warranted. I'm a better investor for having had to meet that bar.
"Come to the Midwest" isn't a pitch. "You'll build a better company here, and here's exactly why" is.
A lot of that first year went to figuring out which walls were brick and which were squishy. Some constraints are structural: they come from the LPs or the fund documents, and no memo will move them. Others are preferences nobody has revisited in a while, and those give if you bring a good enough case. "We don't do biotech" turned out to be squishy, which is how our first biotech investment happened. Nobody hands you the map. You find out by pushing, politely, and noticing what gives.
The region is the asset: why Cincinnati startups build better here
Builder Fellows was one of the most rewarding things I got to build here. We gave college-age founders ten weeks, a $10,000 grant, a desk, and one rule for customer discovery: try to prove yourself wrong. Most of the founders did, and made a major pivot before the summer was out. One team walked in building drones and walked out selling security-operations software. Another interviewed 63 healthcare providers across ten specialties. Another showed its product at a White House expo. When we asked the fellows at the end how likely they were to recommend the program, the average was 9.8 out of 10. I’d love to take credit for that, but a curriculum doesn’t earn a 9.8. What they were rating was everyone who showed up for them: founders who gave up a lunch hour, CEOs who opened their offices and labs, investors who took their questions over breakfast. A program can’t manufacture that. A region can.
The strongest Cincinnati companies I met weren't here because somebody asked them nicely. They were here because the region made them better. Fortune 500 customers down the street, and the people who used to run those businesses as advisors. Cincinnati Children's and the hospital systems as design partners. Lab space a founder can actually afford over at LifeSciKY. A logistics footprint that puts you a day's drive from most of the country. The data is starting to show it: PitchBook recently ranked Cincinnati the third-fastest-growing venture ecosystem in the world. "Come to the Midwest" isn't a pitch. "You'll build a better company here, and here's exactly why" is. If we can't finish that sentence for a specific founder in this region, we should stop asking them to move.
The last lesson was about the place itself. As I’ve quietly shared that I'm leaving Cintrifuse to start my own fund, the response has floored me. People offered to rip apart my fund deck the way I'd rip apart a founder's (karma, eh?). Folks have raised their hands to make intros to institutional LPs. I'd spent a year and a half making intros, coaching founders, and showing up to things, and I never once thought of it as a deposit. It was. Last year I wrote that the one thing I'd do differently about business school was ask for help sooner. Apparently I needed to learn that twice. Founders: people here want you to win, and most of them are just waiting for you to tell them how.
What’s next for me and Psycho Capital
Thank you to the Cintrifuse team, who handed a whole lot to a Cincy-boomerang with a failed startup on her resume and let her run with it. Thank you to the founders who trusted me with their companies and their worst weeks. Thank you to the Builder Fellows, who taught me at least as much as I taught them, and who I fully expect to be sending me deal flow for years :). And thank you to this ecosystem, which turned out to be a lot bigger, and a lot more generous, than I gave it credit for when I moved home.
Psycho Capital starts from a simple premise: who a founder is matters more than where they’ve been. I’m backing people who have lived a problem long enough to know things about it that outsiders don’t, and using behavioral science to get better at spotting them. And yes, the name is a little brash, but I think it works as a fast filter to identify the folks who are willing to think a little differently about who gets a VC check.
I've written before that I'm not in the arena anymore, that I'm the critic now. That's still mostly true. But I'm about to put my own name on the door and my own judgment on the line, and it's the closest I've felt to the dust and sweat in a while. I'm looking forward to it.
Next time, I'll write about the question I can't stop thinking about, and the inspiration behind my fund: which founder traits actually predict success, and what the evidence says.
Ilana Habib is Principal at Cintrifuse Capital, a venture fund and innovation hub backing early-stage founders and strengthening the Cincinnati startup ecosystem. She’s spent her career in and around the entrepreneurial ecosystem and loves rolling up her sleeves to support founders and operators. She’s also an avid traveller, taking her camera with her to capture some of the most interesting places on earth.
