The Bleeding Edge
How this physician created a career in medical innovation when everyone told him that it couldn’t be done.
April 23, 2025
Are you like Jay Mathur, MD?
Jay never wanted to use his MD to only practice medicine. He wanted to change medicine.
But the pathways to a career in innovation weren’t there for him.
It seemed like there were only two options: practice or go into administration.
But instead of giving up, Jay forged his path in medicine, becoming a hospital innovator at OSF HealthCare, discovering healthcare innovation, supporting the VC in vetting potential investments, and launching an at-home care program during the COVID-19 pandemic.
Jay is now the regional medical director at Contessa Health, leading the innovation strategy to bring hospital-level medical treatment into the comfort of patients’ homes.
We asked Jay how he built his career path and what it takes to make changes—big or small—in a complicated system like medicine.
So, if you naturally think differently in your specialty, read below to find out how Jay kept searching for the right path even when seasoned physicians said to stay in your lane.
What were the decisions that helped shape your career?
I knew that, going into medical school, I didn’t want to be a traditional doctor forever. I didn’t know what that meant or how to talk about it. I knew that there had to be more ways to use an MD than either practicing medicine or going into administration, but I didn’t know what that was or how to find it.
And I mean, a lot of times when I was going through training, I got looked at like I’m crazy, or got told that’s not what medicine is. There is a bravado about working hard every day and helping people, and that’s great. However, there are also ways that you can work smart and still help people and do it differently.
Everyone’s natural response to my goal was, “Oh, so you want to go into administration?” Hospital leadership, clinic leadership, or something like that. I would say, “No, I don’t want to do that.”
So, I started researching cool new things in healthcare and found myself attracted to startups. Looking back at it, it was probably because that was all I had access to.
I had this very narrow view outside traditional medicine. In my residency, I asked if I could be involved in the venture arm of the institution because they were doing new things with different companies, and I just thought it’d be fun.
I was told, “No, no, no, no, just focus on your boards. That’s what you need to focus on. These are distractions.”
"I knew that there have to be more ways to use an MD than either practicing medicine or going into administration, but I didn’t know what that was or how to find it."
After residency, where did you look to feed this hunger for innovation?
During residency, it felt so defeating that I would never be able to figure this out. But, after I finished my residency, I was attracted to an innovation fellowship at OSF Healthcare in Peoria, IL.
I was able to work closely with healthcare startups and technologies, and it helped me understand that innovation is what I like. That’s why I want to be a part of the new stuff that’s going on in healthcare.
But that took forever to figure out because I never had exposure to it. I never had an understanding of it.
I tried to be involved with the healthcare system’s innovation in every way that I possibly could. I was an ankle biter and made my way into any project I could when I had the free time.
I ended up sitting on a venture committee, where I helped figure out how to make new startup solutions fit into the healthcare system. I got very involved with digital health and the different ways you can use healthcare outside of four walls. Ultimately, I think what I learned is that I like challenging the status quo in healthcare, and I like finding new solutions and new territory.
I wish I had known this earlier because that would’ve really helped me figure out how and what the best way to get where you want to be in your career is. Because I don’t just like to be on the cutting edge of innovation. I want to be on the bleeding edge.
I love living in a space where you’re thinking through a problem, and you’re like, “Who’s ever thought of this problem?”
Whatever I think of is something that no one’s ever thought of before. There are not many people in this space, and I love that feeling. But it’s hard to find people who are drawn to it. There isn’t really a good community for it. We know we exist, but we don’t know how to find each other.
“I don’t just like to be on the cutting edge of innovation. I want to be on the bleeding edge.”
Ask yourself:
Biography
Name
Jay Mathur, MD
Residency
Speciality
Medical Director of Implementations
Sub-specialities
Practicing since
2017
Location
Chicago, IL
Current Role
Regional Medical Director, Contessa Health
What kept you motivated to stay in healthcare and create a career path for yourself?
I get this dopamine hit trying to figure this stuff out and challenging the status quo.
Also, I never found what I was looking for, and even now, I’m still not a hundred percent sure I know what I want to do. It’s an ongoing process. I get uncomfortable being comfortable at times. So, I want to keep finding ways to be different.
“I get uncomfortable being comfortable.”
What did you learn early on when you were in these innovator conversations about organizational systems and how to navigate those?
The biggest thing that I learned is that it is challenging to navigate. When you’re starting your career in medicine, it is looked at strangely when you want to explore innovation. It’s much more in vogue now than it used to be. But for a lot of people, it’s still confusing.
If I could go back in time and tell myself something, it would be, “Hey, it’s just going to be hard. There’s no easy way around it. It’s going to be hard.”
So talk to as many people as you can. Throw as many ideas as you can out there. See what sticks. A lot of people are going to look at you and say, “I don’t understand what you’re trying to say. Just go give antibiotics and be happy.”
But you have to keep testing the boundaries of what you think is the right idea. And every now and again, you’re going to have a conversation with someone that puts you in the right direction. When you’re thinking about something in a non-traditional space, it is not going to happen fast. It’s going to happen slowly. It’s going to happen from a series of nudges in the right direction.
You might not find the exact career or the exact calling that you’re looking for, but you are going to find people who nudge you in the right direction. So the more people you talk to, the more conferences you go to, the more you challenge your own assumptions and look at different exposures to things. And the more you can find people like you, the more you’re going to figure it out.
“You might not find the exact career or the exact calling that you’re looking for, but you are going to find people that nudge you in the right direction.”
Was there a moment or a story that really helped guide you in your path?
My dad was talking to a CEO of a health system about me, and he said, “Hey, I’ve got a son who’s really interested in innovation and thinking differently, and he’s really having a hard time trying to figure it out. Is there anything you would tell him that could help?”
The CEO told my Dad, “Medical education is going to ruin him because we beat that out of medical students. We beat that out of residents. We say, ‘Don’t think differently.’ We say, ‘Regurgitate as much information as you can get out of a book, and that makes you a good doctor.”
I remember hearing that secondhand from my Dad and thinking, “Okay, this is gonna be hard. That’s all right.”
It just hit home that no matter what I do, I’m going to feel out of place; I’m going to feel like I don’t belong. But I’ve got to keep doing it.
“No matter what I do, I’m going feel out of place […] But I’ve got to keep doing it.”
Didn’t that response deter you? Why did you keep going?
Part of it is who I am. Part of it was validating in a way that I was onto something.
Sometimes, it feels like the system is put in place to make you just care about things that are in front of you.
But it felt like you were challenging the right things.
Yes, because through med school, all through residency, even when you practice medicine, your worth as a doctor comes from how smart you are and how hard you work. Did you read that latest study? Did you work 14 hours? It’s not necessarily about being a problem solver.
The self-worth of a doctor comes from knowledge, academic accomplishments, and hard work.
It’s not about how smart you work. It’s not about how you make things easier or simpler.
Essentials
Favorites
- Your go to for having a good laugh?
Stand up
- Top 3 things you love to do with your free time?
Go out, run, and binge TV
- What’s one ingredient you put in everything?
Garlic
- Three things you can’t live without?
Coffee, intention, traveling
- Your go-to mentors or supporters?
My Father, Brother, and Best Friend
Leisure & Culture
- If we were visiting your town/city for the weekend, what are your 3 top local tips?
Ride the lakefront, see off-beat museums, do a food tour
- Top 3 travel destinations (and why)?
Italy (lived there and will retire there), Argentina, Panama City
- What’s your current TV obsession?
Severance
- A book that everyone should read?
Supercommunicators
Rituals
- What’s your wakeup ritual?
Wake up later than I thought I would
- What’s your go to bed ritual?
Go to bed later than I thought I would
- What’s your favorite time of day?
9-12, most productive 3 hours of my day
- Go-to snack to power through a long day at work?
Anything with cheese
- Best way to take a rest/decompress?
Music
So far...
- Most adventurous thing you’ve done in your life?
Scuba with sharks, unintentionally
- What’s the biggest surprise you’ve ever had?
Bombing one of many tests
- Best piece of advice you’ve received (and from who)?
It’s all about people. Being successful is all about how you work with people
- Advice you’d give your teenage / residency self?
Whatever you’re thinking about, just get out of your own head and do it imperfectly
- What’s the kindest thing someone’s ever done for you?
My grandma gave me a flask of whiskey my grandpa brought back from the Korean War. He meant to drink it as a celebration when he returned but he never did. She gave it to me for my med school graduation
Essentials
- How would you describe yourself in three words?
Innovative, determined, social
- If your life were a song, what would the title be?
Distracted
- If you made a documentary, what would it be about?
Amari
- What’s your secret talent?
Community organizing
After your time working in innovation at OSF, you joined Contessa Health in the field of at-home medicine. What are some of the big obstacles you’re facing right now in the field, and what are you trying to achieve?
When you work in innovation, the biggest challenge you’re always going to face is change management. Change management is on the individual level, from those putting their hands on patients to those in the C-suite.
Then, there’s going to be change management with large institutions like government, insurance, and finance. It’s just change management all across the board.
And that’s hard because when you are good at what you do or an expert in your field, you see this clearly and vividly.
But it takes these big coordinated efforts to move mountains and make something that’s somewhat acceptable or unacceptable become acceptable.
“When you work in innovation, the biggest challenge you’re always going to face is change management.”
How do you not get frustrated when you can’t make the change as fast as you want to compared to other industries like tech?
I’m a big fan of the saying in the tech world, “Move fast and break things.”
But that is hard to do in healthcare.
Yes, because it’s not like in software where the code is broken; in healthcare, it’s bodies.
Exactly. Centuries of things have been done to create certain outcomes for patients. You can’t break things. You shouldn’t do that. So it’s hard to move fast.
The one thing that I really like about the healthcare space that I don’t see in a lot of other industries is that there is this overlying sense of morality. You have to do the right thing.
That’s what keeps me in healthcare—I love that we are, at the end of the day, trying to figure out the way to do this for the patient. Or figuring out a way to do something for the betterment of society and humanity.
And that sense of morality has to exist, but when you have that sense of morality, you can’t move fast. You can’t move as fast as you want to because you have to question, is this a good thing for patients? Is this a good thing for health systems? Is this a good thing for providers? Is this a good thing for a lot of the different entities?
So when you have all these stakeholders asking, “Are we doing the right thing?” It naturally has to slow it down.
I think that’s probably why, in healthcare, I like being on the bleeding edge of something where maybe I’d be on the cutting edge of something and somewhere else.
Because if you’re gonna move fast in healthcare, that’s the only space you’re going be able to move fast, in my opinion, in that bleeding edge, that super rare air area.
But it’s very challenging. It takes a lot of patience, and a lot of meditation is great, too, to help make that happen.
You also need to be able to communicate your solution or idea to different types of audiences.
One day, you’ll have a conversation with a physician taking care of patients about how to do hospital at home. That same day, you’ll have a similar conversation with a system executive and a staff of 20,000 people reporting to them.
So you need to understand what your messaging is for these two very, very different people about why something is valuable. They should derive the same value from a different conversation.
Everybody has competing interests and priorities because in healthcare, there’s a famous saying in medical school that “half of what you learn here is wrong. The problem is we don’t know which half it is.”
“The one thing that I really like about the healthcare space, that I don’t see in a lot of other industries, is that there is this overlying sense of morality, a sense that you have to do the right thing.”
Quick Q&A
Summer or winter?
Give me Summer!
Morning rounds or night shift?
Night owl
ER or Grey’s Anatomy?
Errr.. ER, obviously
Tea or coffee?
Coffee
Window or aisle seat?
Seat A
Scrubs or white coat?
Scrubs. Simple
Can you share some advice with somebody on a similar path to you or someone who’s in a specialty where they want to innovate?
Find your people. And the only way you’re going to find your people is by talking to people who are probably not your people. So talk to everybody you can about what you want to do. What you would be surprised about is how many people want to meet up with you for coffee to talk about your career and how to get to certain places.
No one’s off the table. Email everybody, text everybody, message someone on LinkedIn to say, “Hey, I really like where you are in your career, and I want talk to you about mine because I’m trying to figure out what to do.”
People are more than willing to talk to you about it, and more often than not, they’re going to give you the wrong answers. They’re going to give you the wrong advice. But every now and again, there’s gonna be a nugget of information. You’ll say, “I didn’t know that. That’s interesting. Tell me more about that.”
So find it out, thank them for their time, and then go find somebody that does that.
“The only way you’re going to find your people is by talking to people who are probably not your people first. So talk to everybody you can about what you want to do.”
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