A Stage Set for Unstoppable Change
How Rob Moskowitz, MD, MBA, pivoted his childhood dream of acting into a career in emergency medicine and startup business.
Entrepreneurship
April 9, 2025
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Rob Moskowitz, MD, MBA
Rob Moskowitz, MD, MBA, is the President and Chief Medical Officer at Contessa Health, a subsidiary of Amedisys. He is also a practicing emergency room physician with over 20 years of experience, including 16 years as a healthcare administrator.
Rob grew up in New York and completed medical school at The University of Rochester School of Medicine, residency at The Ohio State University, and business school at Vanderbilt University. He is coming up on his 25th wedding anniversary and has two teenage sons. Rob and his family have lived all over the country - Nashville, Miami, and, most recently, Massachusetts.
When did the world of medicine first catch your attention?
Growing up, I wanted to be an actor and a writer. I had headshots, an agent, and my family would take me into Manhattan for auditions.
So that's the life I leaned into. I just happened to really enjoy school as well. Academics always came easy for me, and I was always interested in what I was missing while on auditions. I loved reading. I loved math. I loved science. But if you ask me what I wanted to do, it was to become an actor.
However, I did not come from the most stable financial background.
So, in college, I had to decide whether I should follow, for lack of a better phrase, something whimsical and passionate but not very stable - or hunker down and go after something more pragmatic. And there's probably a part of me that—when I pivoted towards medicine—was trying to figure out what sort of field my personality fit best.
I enjoyed theater's chaos, shooting from the hip, and sometimes having to go off script.
The same thing that fed me a passion for theater, being in the moment, probably took me towards emergency medicine and into the startup business world.
Funny enough, there’s a tradition at the University of Rochester where the graduating medical school class puts on a show for the rest of the school. I got to flex my theater background in the writer's room with Eric Mann (Lucens founder and CEO) and other friends, and we put on a show with others in our med school class. It’s still a fond memory during a challenging time as a med student where I got to use my passion as a writer and performer in the context of my chosen career in medicine.
Ask yourself:
Biography
Name
Rob Moskowitz, MD, MBA
Residency
Speciality
Emergency Medicine
Sub-specialities
Practicing since
2004
Location
Massachusetts
Current Role
Advisor | Chief Medical Officer, Contessa Health
What made you shift into the startup world?
Hospitals aren't chaotic enough for me. That’s why I joined the startup of the business world!
But in all seriousness, when I was an ER doctor and administrator, my role was to control the chaos of the emergency rooms from an operations standpoint, and the role was interesting and challenging to me.
So much so that I decided to do an executive MBA program, rather than a healthcare MBA.
Out of 50 students, only four were doctors, and I enjoyed that I was not going through business school with only physicians. After getting my MBA, I returned to hospitals and but realized that I was assigned accountability to solve problems, but not given the appropriate authority or autonomy.
It becomes tremendously frustrating if you've ever been in an organization where you’re charged to fix problems but not given the authority or autonomy to do it.
And I think that's where I started looking outside the walls of medicine and saying, “Hey, if I want to fix things within healthcare or whatnot, I need fewer constraints and more opportunities to tinker.”
That led me into the startup world. I wanted to be outside a fixed construct and improve the healthcare system with more flexibility.
Essentials
Favorites
- Your go to for having a good laugh?
My close friends
- Top 3 things you love to do with your free time?
Watch my kids play hockey, hang out with my wife, watch the Yankees
- What’s one ingredient you put in everything?
Hmmm. Not sure. But I like mayonnaise with my fries
- Favorite piece of clothing you own?
Old T-shirts that are worn in
- Three things you can’t live without?
Wife, kids, dog
Leisure & Culture
- If we were visiting your town/city for the weekend, what are your 3 top local tips?
Let’s grab lobster rolls, watch hockey, and walk to get ice cream
- Top 3 travel destinations (and why)?
Caribbean (love the beaches), Iceland (coolest country ever), Italy (nuff said)
- What’s your current TV obsession?
Not a big binger, but back in the day - Entourage, Scrubs, Ballers
- A book that everyone should read?
Stamped From the Beginning - Ibram X. Kendi
Rituals
- What’s your wakeup ritual?
Crossword puzzle and the gym
- What’s your go to bed ritual?
Falling asleep to mindless TV
- What’s your favorite time of day?
5:00am
- Go-to snack to power through a long day at work?
Snickers
- Best way to take a rest/decompress?
Napping with our dog
So far...
- Most adventurous thing you’ve done in your life?
Flown in a small airplane with a friend who built the plane and then dropped to zero G for a bit.
- What’s the biggest surprise you’ve ever had?
Being a parent (you can’t ever be prepared)
- Best gift you’ve ever received (or given)?
Being a parent (I think I’m being redundant).
- Best piece of advice you’ve received (and from who)?
Ignore criticism and praise from someone who you wouldn’t seek advice from in the first place. (Multiple people)
- Advice you’d give your teenage / residency self?
Your only competition is yourself
Essentials
- How would you describe yourself in three words?
Curious, Family-oriented, Outgoing
- If your life were a song, what would the title be?
I Did It My Way
- If you made a documentary, what would it be about?
Adoption
- What’s your secret talent?
Tap Dancing (It’s been a few decades though)
What steps did you take to transition into the business world?
My wife knew that I was less and less happy working as an ER administrator, and she said, “Listen, this isn't where you wanted to be, but this doesn't have to be the end of your story.”
I couldn't figure out my next step, and she said, “Just stop.”
I said, “What do you mean stop?”
She said, “Stop. You're an ER physician. You want to stop, so take a few months break. You happen to have a career where you can pick up shifts. We’ll be fine.”
We had just adopted our boys, who were about three months old. So I stopped working, spent more time at home, and mentally recharged.
But it wasn't the moment of clarity when I figured out what I wanted to do next. I wish I had listened to my instincts then, but I was good at hospital administration. And it's hard to leave something you're good at, even if you're not enjoying it. So, I went back to emergency room administration, but with a different organization thinking that would be enough.
Seven years later, we were living in Miami, Florida, I was by definition “succeeding” and moving up the ladder. But I reached the same point, and my wife recognized again that I wasn’t happy.
She said, “You did this once before. I'll tell you the same thing. Stop and figure it out. You've always had your irons in so many fires, and you've been doing hospital administration and ER shifts for as long as I can remember. But why don't you stop doing administration? Just do shifts for a year. You'll have more free time to figure it out.”
So, I resigned from my admin position.
The day I resigned, I went to one of my closest confidants and said, “Hey, I think I want to be more in the business world.”
He was a physician colleague who had entered the business world about a year before and told me to start networking because it could take a while to find what I wanted to do.
So, I emailed about 10 or 15 colleagues I had gathered over the years and said, “Hey, I'm not going to do hospital administration anymore. I'm going to be out of that. I would love to get into the business world and have a conversation over a cup of coffee.”
And I got an email that afternoon that said, “Are you free next week?”
Within two weeks after resigning, I sent one email, had coffee with a friend, and was in line to interview for a chief medical officer job with a startup company.
My wife got mad at me because I told her I would take a break for a year.
I said, “You’re right. Two weeks isn’t much of a break, but I'm much happier.”
Did you face imposter syndrome shifting from medicine to business?
I learned over the years running emergency departments that I never hired people solely based on their resumes.
I would hire somebody with a less impressive resume who showed the earnestness, willingness to work hard and learn, and be able to adapt than I would for somebody who simply had a better resume. I had to flip that switch and say, “Well, that's what they’ve got be looking for on the other side. I need the introduction. I’ve got the willingness, I have the drive, and I'm going to learn.”
For example, you don't want to give a cliched answer when somebody asks, “Do you know this?”
Instead, you should answer authentically, “No, but I'll tell you how by tomorrow, or I'm going to go find you the answer and figure it out.”
You get over imposter syndrome by having that innate willingness to learn and be humble about it. That combination is unstoppable.
That was the curve I needed to adapt to because that’s how I hired people; I just wasn't giving myself the same grace.
Quick Q&A
Summer or winter?
Give me Summer!
Morning rounds or night shift?
Bright and early
ER or Grey’s Anatomy?
Errr.. ER, obviously
Tea or coffee?
Coffee
Window or aisle seat?
A? No way!
Scrubs or white coat?
Scrubs. Simple
Did you experience any surprises or misconceptions entering the business world?
It was one hundred percent what I expected, and I was certainly nervous to navigate this world because I'd never done it before.
My first foray into business was an early-stage seed startup. I was hire number four or five, and they couldn’t pay me a physician’s salary, so I was still working full-time shifts as an ER doctor. And in doing that, it was a quick indoctrination to why most startups fail, even though nobody's going into this ecosystem to fail.
I went into business with the mentality that it wasn't win or lose. I was a winner if I learned.
And if you go through your mistakes and internalize them as losses rather than as learning opportunities, you'd be quickly failing. So, at our first company, there were moments where I thought, “Oh, okay, learning mode. I should not do that again.”
The first company I worked for eventually dissolved, but I wouldn't be who I am now as a leader, and my business acumen wouldn't be as strong as it is without those mistakes.
Now, I can see those previous errors in judgement coming a mile away. So, don't get me wrong; nobody says, “I wish to be a part of a startup that doesn't work.” It's win or learn. Do not go into this as a win or lose. Because everything that we did right, I held onto. And I held onto everything that we did wrong. You can talk to anyone successful, and they’ll admit that they've made more wrong decisions than right ones.
The company I'm with right now is the second startup I've worked for, and we've done very well. But I've not taken credit or blame for either one; companies don't sink or swim because of one person.
What one thing do you think the medical community should know about?
You can break down current constructs. There are many things built into our healthcare system in the US that are counterproductive to actual patient care for various reasons.
It's easy to be disillusioned with how the US healthcare system works. Many young physicians (including myself) enter medicine with this idealistic construct and then feel like, “Wait a second, where did this go wrong?”
That’s why I think some doctors should look to be outside traditional healthcare systems; there are just countless ways that you can impact people. The overarching healthcare landscape can be quite demoralizing. So, discover those opportunities to serve and help people beyond the current status quo.
You have the power to make a difference. If you want to, it's possible. So go do it.
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