How Dr. Jared Dashevsky Built a Profitable Newsletter Business During Residency

You may be familiar with Healthcare Huddle, a popular newsletter read by over 30,000 healthcare professionals including physicians, administrators and medical students.

But you may not know that Dr. Jared Dashevsky, a resident physician at the Mt. Sinai Hospital in New York City, launched it in 2020 as a medical student.

Four years in, Healthcare Huddle continues to cover the biggest trends in healthcare, as well as what many would consider mundane and complex aspects of healthcare policy. However, when shared through Jared's accessible analysis and welcoming voice, these topics become a joy to read about and engage with. Just ask his community!

Jared has expanded the brand to include a premium subscription tier, courses, partnerships and community forums. He has navigated his business through an acquisition and continues to evolve his model — all while working as a resident.

So, how does he do it?

In this episode of How I Doctor, Offcall co-founder and emergency medicine physician Dr. Graham Walker sits down with Jared to unpack his journey within medicine, share key learnings from building a profitable business, and bring us into the life of a physician-entrepreneur.

And even if you're not a writer, there's plenty to learn from Jared's journey. His lessons apply to anyone interested in pursuing an entrepreneurial endeavor alongside their clinical work. We break down three key lessons below.

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1. Lean into your clinical skills as a competitive advantage

Having this clinical background, this real-time clinical experience helps me be a better writer … and also gives me leverage when people who have not set foot in a New York City emergency department. It gives me leverage to be like, you are wrong.

While maintaining clinical hours may seem like a distraction from pursuing a successful side venture, both Jared and Graham highlight how their clinical experience has provided them with an advantage.

In Jared's case, hands-on experience enables him to develop the unique authority to critique and analyze broader healthcare inefficiencies. Similarly, Graham's ongoing clinical practice helps him sharpen his views on topics like AI in medicine, healthcare policy, and physician workplace dynamics — all of which are integral to Offcall.

If you are pursuing a side job of your own, both Jared and Graham advise you to lean into your clinical skills because this credibility sets you apart.

2. Pursue partnerships that complement your skills and solve for your weaknesses

Workweek - you could think of them as a record label, where they pay the creator to just create content. And they'll take care of the sales, the partnerships, advertising, whatever. That's exactly what we need[ed].

Jared shares the importance of pursuing strategic partnerships from the earliest days of Healthcare Huddle. He believes the right partners can complement you where you are less skilled, and as a result, can accelerate the path to getting your business off the ground.

Jared partnered with Workweek, a media company that supported the sponsorship and operations of Healthcare Huddle. This partnership enabled him to focus on content creation, his superpower within the business. This led to not only an increase in subscription numbers, but also enabled him to launch new content formats like trend reports and op-eds.

3. Think deeply about your audience and what you can uniquely build for them

When I started medical school at Mount Sinai, I really wanted to talk to people about these problems - about digital health, about insurance, about the drug supply chain. And even though these were some of the brightest people that I've ever met, they didn't know anything about these topics.

Jared started Healthcare Huddle to educate medical students and professionals about healthcare system inefficiencies, the same inefficiencies he discovered while studying social policy as an undergraduate.

He initially built a fan base of other medical school students, but over time, Jared learned how to broaden his audience to other medical professionals through deliberate trial and error.

For example, he added a section to his newsletter called "Dashevsky's Dissection" to share his perspective as a doctor on the front lines. "I do that because not everyone can just be at the frontlines of healthcare and be a doctor. There's a huge bar. So that's a very unique take that I provide, but also other physicians reading it would understand what I'm talking about. They would be able to empathize with what I'm seeing," he said.

The message to other physician entrepreneurs is clear: Think deeply about the audience you are appealing to and what you can uniquely build or say to connect directly with them.

You can subscribe to Healthcare Huddle here and connect with Jared on LinkedIn

Make sure you don’t miss an episode of How I Doctor by subscribing to the show wherever you listen to podcasts. Read the full transcript of the episode below.

Full Transcript

Dr. Jared Dashevsky:

The healthcare economy doesn't function as other industries' economies. There's really no such thing as economies of scale when it comes to hospitals and physician practices. Because economically speaking, as you consolidate practices, you become more efficient and that should correlate into more savings and increase physician pay. But what we're seeing is that private equity firms, hospitals, they acquire these physician practices, give them a lump sum of money, which is nice, but then may not be a good deal afterwards where pay is tied to too many factors.

Dr. Graham Walker:

Welcome to How I Doctor, where we're bringing joy back to medicine. So I'm extremely excited to talk to Jared Dashevsky today. He's the founder of Healthcare Huddle. He's somehow doing this during medical school and now in residency, writing content frequently about the business of healthcare, how the systems of healthcare really impact the day-to-day work of a doctor and impact our patients as well. Jared, I am a huge fan of Healthcare Huddle, and I was super excited to talk with you today. So thank you for joining me.

JD:

Thank you for having me. Very excited to meet you because I've seen all your content behind LinkedIn. I use one of your platforms every single day, MDCalc, so it's really cool to meet you and chat with you.

GW:

Jared, can you just tell me a little bit about Healthcare Huddle, maybe for listeners that don't subscribe yet, and what was the inspiration?

JD:

Sure. I send out a newsletter breaking down Healthcare Trends and trying to simplify it for medical students, physicians and residents who really don't have time to do their own research and stay up to date. And the impetus was when I started medical school, I had just graduated from a master's in healthcare systems engineering, where I learned about how complex and inefficient this healthcare system is.

I was very naive before that program. I literally thought this healthcare system was wonderful, streamlined the best in the world. So it was an eye-opening experience. And so when I started medical school at Mount Sinai, I really wanted to talk to people about these problems, about digital health, about insurance, about the drug supply chain. And even though these were some of the brightest people that I've ever met, they didn't know anything about these topics. So in between classes, my first semester of medical school, I was trying to figure out what the problem is. When I asked my peers, why aren't you on top of everything in healthcare? They don't have time. I knew about the Morning Brew at the time, which is a business newsletter. So I thought, let me just create the Morning Brew for healthcare.

GW:

So it sounds like you tried to solve healthcare during med school. Did you fix healthcare for us yet?

JD:

I did not fix healthcare, but maybe I moved the needle just a little exposing med students, residents and physicians to problems they may have not have noticed before and maybe have educated them and inspired them to solve more problems.

GW:

It's a different way to also think about healthcare challenges, not just I'm a doctor, I'm seeing one patient with X problem, but thinking of it from a systems perspective that are impacting the individual encounter and what's making that challenge as well. I was a social policy healthcare policy major in college, and so I still to this day really think that impacts the way I think about anything I post about on LinkedIn or any policy I'm going to recommend. I'm always thinking about what are the implications. I'd love to ask you a little nitty-gritty about healthcare huddle and how you managed to maintain it. I mean, you are still putting out newsletters, frequently posting on LinkedIn. Is it still just you? Do you have other people that help support it?

JD:

Just me. So if we get into the backstory, when Healthcare Huddle started, it was me, my medical school friend, Harrison Kaplan, shout out to Harrison, and my brother Brett, he was going to work at Capital One, and then Harrison went to MIT and he's just the most brilliant person I know. Can code all that stuff. And so I brought them on because we all complimented each other. My brother Brett basically made the branding of Healthcare Huddle look like as if we've been around for years. So it didn't look like we just started. It looks like, oh, they've been around. I basically spent the first months just completely iterating how I produced content, what my process was for writing content, very, very stressful at first, especially as a new medical student. And then COVID hit, so everything went virtual. So technically I did have more time. I just made better use of my time because I could be in class and then as soon as it ends, I just shift focus. It's like, okay, what's happening in the news?

And over the first couple months, people started to reach out to me and asked, hey, Jared, love what you're doing with Healthcare Huddle. Would love to join your team. And I'm like, oh. And so we started making some ad revenue, not a lot, very little, but it was cool. That's my first time coming up with an idea and making money, and I'm like, whoa. So over the first year, more people added to the team. We really got started in social media making succinct, fun, not boring content, really to educate the, I guess the Gen Z, millennial users on what was happening in healthcare, especially with COVID.

And then heading into year two, things were stable and we wanted to add more products. We launched an educational platform called Concepts, which basically broke down healthcare concepts. What is a copay? What is the ACA? What is an RVU? These are just common terms in healthcare that if you took an first year medical student and asked them what they mean, they couldn't tell you exactly. And then since everything was online, college students were really bored. So we launched an ambassador program, a college ambassador program, and I basically said, I will teach you about healthcare and give you an inside scoop on Healthcare Huddle if you share Healthcare Huddle.

GW:

Cool.

JD:

And again, these college students were super bored being virtual. They weren't out partying. It's like Healthcare Huddle just grew, grew, grew, grew, grew, grew, and it was awesome. And then in year two over the summer, this media company called Workweek reached out to us and said, "Hey, love what you're doing. Would love to talk about ways that we could basically acquire Healthcare Huddle." And I was like, huh.

GW:

That's another step up of seriousness too, of this thing you've got. Yeah.

JD:

So then I'm like, "Whoa, whoa, guys, guys, what do you think?" And throughout the second part of building Healthcare Huddle, we knew someone would have to drop out to focus on actually building a full-time team. I knew I wanted to be a physician. I did not want to drop out, plus my parents would kill me. Harrison wants to be a surgeon, and he's like, "I'm not dropping out." And my brother, Brett, who was at Capital One was like, "I just got here. I am getting my retirement fund matched. I have great benefits. I don't want to leave to take this risk."

GW:

Yeah, there's a lot of risk for all three of you.

JD:

Exactly. And so we discuss back and forth with Workweek. You could think them as a record label where they pay the creator to just create content and they'll take care of the sales, the partnerships, advertising, whatever. I'm like, "That's exactly what we need." And so we went through with the acquisition in November of 2021, and part of the deal was that I would be the sole writer of Healthcare Huddle, but part of the deal was that I switched to more like a business-minded newsletter, which looking back was the perfect decision. And then also my brother Brett would join Workweek, not part of Healthcare Huddle, but to be an employee there.

And then once I started residency, things got a bit chaotic with time management. And so [inaudible 00:07:53] ended up leaving Workweek with Healthcare Huddle in November of 2023. So basically two years career with Workweek where they helped me grow. I grew as a writer, as a content creator, but I think overall it was a good decision because one thing I don't like is people relying on me for work that I'm doing for myself. So now it's just me and it's just me against me.

GW:

I mean, you cover everything. I mean, how do you decide, oh, this week, let's talk about antibiotics versus CT scans versus Medi-Cal versus Obamacare?

JD:

Residency is very busy, but I have such a robust process that it truly allows me to do both. But I created a content calendar where I plan two quarters ahead roughly of what I'm going to write about each week. So every Sunday I send out a general newsletter on the healthcare industry. Every Thursday I send out something, a newsletter called Inefficiency Insights, which is part of my premium membership where I just basically complain and analyze the inefficiencies I come across in healthcare. And then every month is a Huddle trends report, which is a very dense deep dive on a key healthcare trend. And I plan all these out. And so if I plan something out two quarters in advance, then I have two quarters to basically build a repository of articles. And so by the time it gets to November, I just look at the articles I've saved and I remember what my thinking was at the time, and I'm just able to write. And of course, if important news, trending news, pops up in the meantime, I can pivot and do that.

GW:

You definitely write right at the intersection of the healthcare professional audience. What have you learned or do you have tactics on how you think the best way to target or write to that audience?

JD:

That's a perfect question, and that's something I've continued to iterate with. The last section of each article is something called Dashevsky's dissection. And then there I started incorporating my medical perspective and what I'm seeing on the front lines. And I do that because A, not everyone can just be at the front lines of healthcare and be a doctor. There's a huge bar. So that's a very unique take that I provide, but also other physicians reading it would understand what I'm talking about. They would be able to empathize with what I'm seeing. So since November 2022, I've been adding that final section, the Dashevsky dissection, which takes the physician perspective, but also mixes it in with the business perspective. And after that, then I started seeing more physicians subscribing, more NPs, advanced practitioners. And I think the best way to approach it is to speak as if you are a physician and really try to get your audience to empathize with you.

GW:

Jared, thinking for other entrepreneurial physicians, what were your financial considerations when you decided to partner with Workweek? When you decided to leave Workweek? Were there things that you thought were particularly important in what your agreement looked like?

JD:

The number one priority was making sure Healthcare Huddle lives on. Even if they decided, Jared, thanks for writing it, you could step aside and we're going to find someone else to write Healthcare Huddle, which at the time was the plan. But once Workweek took care of all the things that were occupying me, I was like, I actually love writing and I want to keep doing it. So I stayed. And then we had, I think at the time maybe 6,000, 7,000 subscribers and we had the Instagram, so we had a valuable audience, and so we wanted to be compensated for at least growing that audience. The only issue is that, again, because it was very consumer, a consumer audience, it was a lot of medical students and college students, medical students and college students notoriously have no money-

GW:

And residents.

JD:

Yeah, they would be valuable. This audience would be valuable five-

GW:

Eventually.

JD:

Yeah, eventually, but not then. So the audience really wasn't super valuable, but we can make it valuable.

GW:

Well, I think that's a really good point, and that really resonated with me. The idea of, hey, if I can find a partner that allows me to keep doing the stuff that I actually really enjoy about this work and have somebody else handle the stuff that is just not where I'm strong, not an area that I particularly am excited by, that's what I would consider a really good partnership.

JD:

Exactly.

GW:

Like, oh, if you can help me, let me keep doing the stuff I love. And if you love or will manage the rest, that's great. Then there's probably a really good corollary of allowing the doctor to do the stuff the doctor really likes and finding partners that can help the clinical physician do the stuff that they like that they're really good at, that they're paid for, and have other people help with the other pieces too. You've written a lot about physician pay. Is there stuff that you're surprised by in your research about physician pay?

JD:

Before answering that, important to note some macro trends. It's just like the physician's now becoming an employed physician versus the independent practice provider.

GW:

Yeah, I think, 80% of us are now employees, and a decade ago, I literally was in residency a decade ago, or maybe a little longer than a decade now, but not that long ago, it was 20%. In a decade, that shift of our profession is profound. I think it's one of the reasons there's so much change in medicine right now.

JD:

Yeah. And then since then, over that decade, physician reimbursement has decreased and consolidation of these independent practices have increased by private equity firms and hospitals. And one thing that you realize over time doing a research is that the healthcare economy doesn't function as other industries' economies. There's really no such thing as economies of scale when it comes to hospitals and physician practices because economically speaking, as you consolidate practices, you become more efficient and that should correlate into more savings and increased physician pay. But what we're seeing is that the private equity firms, hospitals, they acquire these physician practices, give them a lump sum of money, which is nice, but then it may not be a good deal afterwards where pay is tied to too many factors.

And I think with the FTC and these non-competes, I think could be a glimmer of hope for physician pay and increasing the competitiveness of the market. I think what the Achilles' heel for physicians is, again, we are not taught anything about business and negotiations. I would be scared to be like, give me more. It would give me too much anxiety, and I think PE firms know that, hospitals know that, and so physicians are taken advantage of. Hospitals take advantage of physicians, even though we are so needed, there's a shortage of us. Nothing makes sense. So one of my goals with Healthcare Huddle is to really educate physicians, medical students, residents on these trends. And-

GW:

This is great. This is totally resonating with me about why I made Offcall. All the challenges that we are seeing. You are literally, you're reading my mind.

JD:

There's this EM physician who's now executive, who you should probably have on the podcast. His name's Adam Brown. When I chatted with him, he said something very interesting to me. He said, being a physician is the only career where you basically spend hundreds of thousands of dollars to get into and you have no idea how you make money once you're out of medical school.

GW:

That's fascinating. Yeah.

JD:

Right? You don't know. I'm still trying to wrap my head around RVUs and value-based care. If you're a lawyer, you know win cases, you get money. In medicine, you have fee-for-service, sure. You do XYZ, you get paid, but now that you're employed, you're salaried. It's like where's everything going? And I think it's so important for physicians to understand this because the more you know... Knowledge is power. Physicians are brilliant people. If it were easy to be a physician, everyone would freaking do it.

GW:

Tell me if this resonates with you. We're paid well relative to other Americans and other countries, but I don't know that any physician is trying to get rich quick being a doctor. I think we want to be paid fairly compared to what the hospital's getting, what the health insurers are getting, the entire system as well. I don't think any of us are like, oh, I want to do no work and just make a lot of money. I just don't think... Physicians would not go through taking the MCATs and organic chemistry and med school and residency and boards and all these things just to sit back and not do anything. I think it weeds out people that are unwilling to work hard or who aren't dedicated to the art, the profession. You mentioned that you're interested in maybe a pulmonary critical care fellowship. Do you think about the future of, in five years you would be done with that in fellowship? Do you think about the future of 5 or 10 years in Healthcare Huddle? Is that your full-time job? Is it allowing you to work less clinically?

JD:

I don't see myself being a hundred percent clinical. I just know I need to have the weeks where I'm being creative doing my own thing. It's difficult to do with residency right now with Healthcare Huddle. I basically treat my short call days as my weekends, my short call day's 07:30 until 03:00, so 03:00 until 07:00, I'm treating like a weekend and just doing Healthcare Huddle. So ideally 5, 10 years from now, once I'm practicing, there would be some percentage of clinical work and a percentage of fun work, which could be Healthcare Huddle. I truly love medicine, and so I definitely need to have that clinical experience still. And I will note that having this clinical background, this real-time clinical experience helps me be a better writer for Healthcare Huddle and also gives me leverage when people who have not stepped foot in a New York City emergency department, it gives me leverage to be like, you are wrong. You can't just expand an ED and expect all your problems to go away. So yeah, I love clinical medicine. I love Healthcare Huddle.

GW:

I totally agree. If I didn't continue to still practice clinically, I don't think my opinions would be as formed and as strong when I talk about AI in medicine-

JD:

A hundred percent.

GW:

Or anything else. It's informed by the fact that I see patients and I'm trying to advocate for my colleagues and my patients when I'm talking about this. And if I was not still doing that, I don't think I wouldn't be as strong. People also wouldn't like my opinions as much.

Jared, in our last few minutes, these are rapid-fire questions. They're for Off-Call and we're calling it On The Clock, but what's something you didn't learn in med school but is crucial to your daily practice as a physician?

JD:

How to prioritize and be efficient. You are not taught that in medical school. You have to learn that through real-world experience. Healthcare Huddle and my masters in healthcare systems engineering taught me that. It's such a good skill to be able to prioritize triage and be efficient.

GW:

Jared, what's the best financial advice you've ever received?

JD:

I think live below your means is something everyone should follow, especially in residency when all of a sudden you're making tens of thousands of dollars you weren't making before. But also whenever you get a raise, save or put 25% of that raise for one year into an investment account like a retirement fund, and then that way that forces you to live below your means because you already take a chunk out, but it's growing at the same time.

GW:

What is the most ridiculous thing you've gotten dinged for?

JD:

I think I actually got dinged for a standardized patient, like OSCEs.

GW:

Sure. Yeah.

JD:

I think it was one my first ones and for some reason they're so nerve-wracking. I think I walked in and I was so nervous I didn't ask the patient what their name was. I just, what brings you in today? I have a cough. I'm like, "Okay, great." So when they did feedback after, they're like, "You didn't ask me my name." And I'm like, "I'm so sorry." And my face turned red.

GW:

And they're so high stakes that you can't even focus on being a human. You would normally introduce yourself to another human.

JD:

Exactly. You have seven minutes to take a thorough history.

GW:

Jared, I think you'll like this one as a policy guy. If you could design a new medical specialty, what would it focus on and why?

JD:

I guess it would be like a mix, like a physician executive specialty where you are practicing medicine, but also you're an expert in the system, which will make the physician better equipped to run hospitals instead of people with MBAs who've never treated a patient.

GW:

Love it. Jared, what's a lesson from an attending, a mentor in medicine that you think of frequently?

JD:

So my mentor is my father-in-law, who's a critical care doctor, and he has the most sage advice. One thing he said, he's like, "Take an hour per week to read about medicine. Go through the New England Journal of Medicine, JAMA, see what the top articles are. Find an interesting case you saw in the hospital. Read Harrison's." And he said, if you do an hour per week, that's 52 hours per year, and that's 52 hours per year more than someone else who wasn't doing that.

GW:

Dr. Dashevsky, where can listeners find you and how can they support the work that you're doing?

JD:

Yeah, so you could find me on, I'm much more active on LinkedIn now, so just Jared Dashevsky on LinkedIn. If you want to subscribe to my newsletter healthcarehuddle.com. Or just type Healthcare Huddle into Google. And you know I've been working on that SEO and we have the number one position, so you'll find it there.

GW:

Love it. Love it. Jared, thank you so much for taking the time to talk with us. This was really fantastic. It's great to finally get to meet you and talk and learn so much about you.

JD:

Likewise. Thanks for having me.