Detroit Healthcare Startup Ollivate Wins $425,000 at PitchMI

There is something funny about preparing to convince a room full of judges that your company is taking off while your company is, quite literally, taking off.

In the weeks before PitchMI, Ollivate was having the biggest month in our history. Revenue hit a record. University partnerships kept growing. And nearly 4,000 nurse anesthesia residents from 150 schools were in the middle of our September School Showdown, on their way to answering more than one million questions.

Meanwhile, Josh and I were trying to fit the whole story of Ollivate into seven minutes. What matters most? Which numbers actually tell the story? How do you explain what makes the product different without spending five minutes explaining healthcare education first? How do you describe the size of what you're building when you deliberately started in a very specific corner of a very large market?

On October 1, we walked onto the PitchMI stage at Hudson's Detroit and gave it our best shot. About 30 minutes later we were sitting in the audience with Tyler Mays, our founding engineer, surrounded by investors, advisors, friends, and a lot of the people who had helped us get there, when they called Ollivate's name. We had won $425,000 at PitchMI, one of the largest founder-focused startup competitions in the country.

The room erupted, and that is the part I keep thinking about. We are very excited about the check, to be clear. But the people around us had invested in us, challenged us, made introductions, taken our calls, torn apart earlier versions of that pitch, and carried pieces of the company while we prepared. They believed in Ollivate long before anyone knew we'd win, and suddenly they were all on their feet screaming. Josh and I were the two people holding the microphones. There were a lot of fingerprints on those seven minutes, and even more on the company we were up there talking about.

There are a lot of fingerprints on this win

Pitch competitions have a way of putting two people on a stage and making a company look much smaller than it really is. Josh and I delivered the pitch. A much larger group of people made it possible.

Our investors and advisors did the heavy lifting on the pitch itself. They read draft after draft, sat through practice runs, pushed on our numbers, caught the places where we were being too modest or too vague, and told us plainly when something wasn't landing. The version of the pitch that won on October 1 looked very different from the version we started with, and that is mostly their doing.

The MSU Research Foundation, which runs PitchMI, put us on noon Zoom calls with experts every day for weeks leading up to the competition. The AANA is both a partner and an investor in Ollivate, and their early belief in what we're building has mattered enormously, not only as capital but as validation from the professional association representing the very community where we began.

And then there is our Ollivate team. While Josh and I disappeared into pitch practice and rewrote slides for what felt like the hundredth time, they ran the actual company. They pulled data, rebuilt slides, supported customers, shipped product, solved problems, handled details we normally would have handled ourselves, and somehow tolerated our increasingly ridiculous schedules during Ollivate's busiest month ever. None of that work shows up in the pictures from PitchMI, but it's in every one of them.

The companies beside us were solving hard healthcare problems too

Ollivate was one of five companies selected for the PitchMI Healthcare & Life Sciences semifinal in Detroit, alongside Authsnap, PathwaysGI, Signal Bioscience, and TruVue. What struck me about that group was the caliber of the work. These were founders tackling difficult, consequential problems in healthcare, from insurance denials and inflammatory bowel disease to diagnostic testing and cardiovascular care.

One of those founders was Dr. Khaldoon Alaswad of TruVue. Josh and Dr. Alaswad have worked together on a lot of cases here in Detroit, and they are two of each other's biggest fans. They are also both the kind of people who ride their bikes to the hospital, which tells you something about how they're wired. They knew each other first through patient care, standing on opposite sides of the same operating table. Years later they ended up in the same startup competition, each building a company around a problem they had lived with through their own work in healthcare. Sitting in that room while Khaldoon pitched, and knowing he was in the room while Josh did, is one of my favorite memories from the day.

People tend to talk about startup ecosystems in terms of capital raised or companies launched. Sitting in that room, the more interesting story was the depth of expertise behind what's being built here. For investors looking at Michigan startups, Detroit healthcare companies, health tech, or emerging Midwest companies, that's worth paying attention to.

Why we're building Ollivate in Detroit

We chose to build Ollivate in Detroit. We live here, we're raising our four kids here, and the company is headquartered here. But building in Detroit has become more than a line in our company bio.

Over the last couple of years we've watched a network form around Ollivate: founders willing to share what they've learned, investors willing to make introductions, advisors willing to take a call, and organizations like the MSU Research Foundation and Michigan Rise willing to put actual resources behind early companies. The capital matters, obviously. So do the introductions, the honest feedback, the relationships, and the expectation that companies built in Michigan can compete on a national scale. We've been the beneficiaries of all of it.

So there was something fitting about walking onto the PitchMI stage at Hudson's Detroit, telling the story of a company we're building here, and winning in our own city. There was nowhere I would rather have done it.

What we're actually building at Ollivate

If you're discovering Ollivate because of PitchMI, here's the simplest explanation. Ollivate is a healthcare education technology company using gamification and learning science to make learning more engaging and effective for healthcare professionals.

We started in nurse anesthesia for a reason. Josh is a CRNA, professor, and exam writer. He knew the education problem from the inside. Healthcare professionals are expected to master enormous amounts of information, pass high-stakes exams, and then keep learning for the rest of their careers, and a lot of the tools available to them still look remarkably like the tools we used decades ago. Question banks. PDFs. Recorded lectures. Courses people buy with every intention of finishing and then avoid opening until they absolutely have to.

Today, CRNAs use Ollivate to earn accredited continuing education. Nurse anesthesia residents use it to study, prepare for boards, and build mastery through daily practice. Universities license Ollivate across their cohorts. Inside the product are many of the mechanics people already know from the best consumer learning products: levels, streaks, leaderboards, challenges, immediate feedback, spaced repetition, progress, and a reason to come back tomorrow. And people do come back.

That matters because gamification isn't the goal. Better learning is. A beautifully written question bank that nobody wants to open isn't particularly useful. Engagement creates repetition, repetition builds mastery, and in healthcare what someone retains eventually matters far beyond an exam score. There is a real person on the other side of what a healthcare professional knows. That's the larger idea behind Game Your Brain®.

Nurse anesthesia is the beginning, not the market

One of the questions we've had to get much better at answering for investors is why we started in such a specific market when our ambition is much larger. The answer is that we think specificity is an advantage.

Nurse anesthesia gave us a community we understood deeply, a high-stakes education problem, a clear board preparation use case, a continuing education market, universities that could purchase Ollivate for entire cohorts, and healthcare professionals whose learning needs continue long after graduation. It gave us a place to prove the model.

But the underlying problem is much bigger. Nurses, nurse practitioners, physician assistants, and other healthcare professionals all move through versions of the same journey: school, boards, clinical practice, credentialing, and lifelong continuing education. The education market serving them is still remarkably fragmented. We don't think healthcare professionals should need one product to study in school, another to prepare for boards, another for continuing education, and another every time they move into a new specialty. We're building Ollivate to move through that journey with them. That's a much bigger company than a nurse anesthesia study app, and increasingly, that's the company we're getting to build.

Why the timing matters

The $425,000 is meaningful to us not simply because it's more capital. It arrived at an interesting point in the company's trajectory. Universities are adopting Ollivate across cohorts. Healthcare professionals are building learning habits inside the product. We're learning what drives engagement and what doesn't, and we're starting to take what worked in our first market and apply it to the next ones.

What happens next

In April 2027 we'll return to PitchMI, and this time $1 million is on the line. Between now and then, the work is the same work it was last week: more university partnerships, more learners building a daily habit, the Educator Portal getting into the hands of program faculty, and the first real steps into the healthcare professions beyond nurse anesthesia. Ollivate is at the point where something is clearly working but almost nothing is guaranteed, where the numbers are getting bigger and the decisions are getting harder. That's a good place to be, and we plan to make the most of the next six months.

For today, though, I'm going to enjoy this one.

To the people who challenged us, invested in us, advised us, made an introduction, carried something for us, or screamed when our name was called: your fingerprints are all over this win. Thank you.

Now, back to building.

healthcare startup, Ollivate, won the PitchMi Semifinals in Detroit, MI