How To Write Killer Healthcare Content

I agree. Sure, your content needs to be high value. But consistency is a key part of growth too. Everyone debates this — say you write a newsletter. Healthcare Huddle goes out every week; I haven't missed a week in years. Some people say, "I only write high-value content whenever I feel like it." You're not going to grow if you post every now and then versus every week.

And my content — I think it's high value, but it's the depth I go into. It's not that deep, because I'm producing every week and I don't have time to dive deep. So I like that percentage. About 70% goes into high-value content, and 30% I'm trying to write something on Twitter or LinkedIn, or create an Instagram post, that brings people to the newsletter and acts like a funnel. That's where I get all my readership — on these social platforms — so I need to dedicate time there too.

I remember writing Healthcare Huddle back in 2020, and it was really starting to pick up — to the point where if I stopped writing today, people would notice. That's how I knew we'd reached a point of no return. And I remember sitting in a coffee shop thinking, am I going to be writing this newsletter every single week for X amount of years? It scared the hell out of me, because I didn't have a robust system in place where I felt confident and not stressed about finding content. Finding content is stressful, and it freaked me out.

But over time, as I developed my system and started planning content weeks and months in advance, it became much easier to produce every week, because I was not freaking out about "what am I going to write about this week?" I had content planned. I knew what I was going to write about. I had backup content plans. This didn't happen until about two years in.

That's how I balance residency and content creation — I know what I'm writing about this week, and next week. If big news in healthcare pops up, I'll pivot to that, but I always have some idea. And throughout all this, I'm curating content. For example, when Neko Health announced their business back in January 2023, I thought, this will be something to write about. So I saved the article, and I started saving Twitter responses to it. Then they announced a funding round in July, and I saved more articles. In July, I wrote a whole piece on it — I'd been saving content for six months, because I knew I'd write about it someday. That whole backlog is less stressful, and it lets me be persistent. If I'm totally burnt out from residency or not in the mood to write, I don't force it. I'll just reuse content — literally copy and paste previous content and add some more thoughts to it. And that's it.

I'm a big fan of "don't work harder, work smarter." So I always try to connect new content to old content — I can just reuse pieces. When I talk about drug pricing, I copy and paste previous content I've written and add updated thoughts. But before each quarter, I've been trying to plan when healthcare news will drop. If new policy is going to be published at the end of December, I'll note it — "here's a piece of content I'm going to write." Once I have all my content filled for the quarter ahead, then as people talk about things on Twitter, as news comes up, as I get inbox news from the other newsletters I subscribe to, I literally just add it to my Reminders on my iPhone. I have a "Healthcare Huddle content" reminders list.

So throughout the week, I just add it to my Reminders. I don't read it. I see, oh, this is on GoodRx and someone has an opinion on it — save it to Reminders. I don't look at it. The next Monday, I call it "management Monday," and I go through all my reminders and start adding them to my repositories of content I plan to write about in the future. I still won't read the article. It just goes from Twitter, to my Reminders app, to the content folder where I'm writing the piece for, say, December.

Notion. It's beautiful. I can add tags, I love it, it's very user-friendly. I was using Google Docs before, but it's too much — I just need everything connected. So when December comes, I click and read all the articles I've saved, and then I create my piece. At this point I have a whole framework for writing content, so it's relatively easy to put stuff out there. Researching and curating is honestly 80% of my work; 20% is just writing.

Yeah. I pride myself — or Healthcare Huddle — on the ability to write in a very succinct, understandable way. Healthcare industry news is beyond complex, and my audience is the physician who doesn't have much time to know everything about what I'm talking about. So I really try to stay high-level. I use something called the McKinsey inverted-pyramid principle. I forget exactly what it means, but this is literally how I started writing Healthcare Huddle, and the framework I've used for almost four years. Basically you start with the main point in the first sentence, then your sub-points — the first sentence should be the most important line of each paragraph.

So when I write, I do my intro and stick to three points. The details are usually the first section, some further analysis is the second, and the third is my "Dash's Dissection" thoughts — how I'm bringing together the clinical, the healthcare-systems-engineering, and the business perspective. It's always three sections, always in the same format. You could read the first sentence of every paragraph without reading the rest, and you'd understand 100% what the article is about.

A thousand percent. People who create content don't use Twitter enough. You need to be on Twitter. All of my controversial takes, I test on Twitter. And I store controversial takes through my process — just throw them in my Reminders and add them to my content folder. I'll see people talk about Prenuvo and I'll store it, putting it in my back pocket to address in a future newsletter. I've had some really hot takes on Twitter regarding continuous glucose monitoring and whole-body imaging — spicy takes I know people will love to see in a newsletter.

You need to be provocative. My brother, when we were creating it, told me to stop saying "I think" in these newsletters — just say something with conviction. Don't say "I think Prenuvo will do X, Y, Z." Say "Prenuvo will be a successful business, but the evidence behind it sucks." Just say it. And that makes people on the other side of the argument get a little flustered and angry, and they'll respond back.

In my last newsletter on Sunday, I wrote about how new legislation will reduce drug prices for people on Medicare — 65 and older in the US. Someone way more informed about drug pricing than I am — he started a huge company that got acquired by Amazon, it's called PillPack — reached out with one sentence: "How do you really think this is going to affect consumers?" I wrote back, and he responded with paragraphs breaking down why I'm wrong. And I said, "Hey, thank you for writing this — you informed me." So it's very important to throw a spicy take into every piece, because it engages the audience way more than just regurgitating news.

For sure. And I'll respond to that — people look at you like you're one up. Publishing content is fucking scary. Sorry — am I allowed to curse?

It's scary. It's not easy — if it were easy, everyone would be publishing content. There's definitely a fear component, and once you've overcome the fear, you're a new type of person. In the early days of Healthcare Huddle, I'd have such anxiety pressing send. What if I made an error? What if I said something too controversial? Now I schedule-send on Friday and don't even think about it. If I made a mistake, great — they'll know it's a human writing it, not ChatGPT.

But in regards to networks — Healthcare Huddle was acquired by Workweek through Twitter. The co-founder of Workweek DM'd me in March 2021, a year and a couple of months after Healthcare Huddle started, saying, "Hey Jared, I love what you're doing, can we chat?" I already followed him, because he'd worked for The Hustle, another newsletter. He'd tweeted the day before, "all the magic happens in the DMs." So I thought, maybe I should answer this.

We had a chat. He said, "I want to come on as your advisor — I know you guys aren't familiar with the media space, I can help with growth." And I said sure, we're building the plane as we're flying it, we have no idea what we're doing. So he came on. Then in summer 2021 he reached out: "I'm building this media company called Workweek. Think of it like a record label — we acquire the creator, all they have to do is write content, create the music, and we plan the marketing, partnerships, and operations." And I said, that is great, because I'm drowning in medical school while balancing content creation. I need a lifeline. We went through the acquisition in November 2021. And all of that happened because I answered a freaking DM on Twitter.

Creating content, you connect with so many people. You had Morgan Cheatham on, you had Patrick Malone on — I know those people because they're in my healthcare network on Twitter, in Slack groups I'm in. Your network expands exponentially. And before residency started, when my time would be limited, I made an effort to meet the people who follow me — a 15-minute Zoom just to get to know them, see how I could help them or they could help me. The network is amazing.

Interesting. I'm very big on being lean — I pride myself on being efficient and effective. But it requires a mix of both: good packaging, and being efficient and effective. When we first started Healthcare Huddle, we were totally on the lean-startup side — iterate, throw stuff out, go back to the drawing board, publish, keep doing it. That's how we perfected the Instagram very quickly. And because we perfected it quickly, we could then focus on packaging.

Now that I have my system in place, I'm all for packaging — to the point where before I send any email, I send a test to my phone and read it as if I'm a reader. If my thumb is doing too much scrolling, I need to cut stuff out. There's thumb fatigue with reading a newsletter. In this very ADHD world, people want things to look good and to be stimulated, so you need visually appealing, provocative content. But there's a time and place for being lean — perhaps in the early days, when you're figuring out what works and finding your process. Once you do that, you can pivot the majority of your time to creating this beautiful, packaged content.

I'll add something. My brother — again, a co-founder with me — pays such close attention to detail that it annoyed me. Healthcare Huddle used to be extremely active on Instagram with educational posts, and he'd stay fixated on where a bubble in the background was placed on the first slide. "Does it look good there? Nah, move it over." It was attention to detail, focus on the package that you wouldn't notice unless I pointed it out. Focusing on perfection isn't scalable, but when you do it over 50, 100 posts, it starts scaling, and people say, "this content always looks beautiful."

For writing, I have a different take, but for podcasts and audio and video — by doing your own editing, watching and listening to yourself, you start to realize the little twitches you do, your stutters, where you go off topic. Editing yourself is a great way to reflect on how you can improve. If you outsource all that, you're never going to improve how you produce content. It's also a great skill — you start realizing what looks good and what doesn't, where audio or a song should or shouldn't be. So for audio and video, a hundred percent, do your own — until you reach a point where you've done enough that you know your own style and you're past the learning phase, on the plateau of the learning curve.

For writing content, though — especially when it's you, not a brand, it's Jared Dashevsky writing for Healthcare Huddle — I spend a lot of time making sure the packaging is right, making sure it looks good with no thumb fatigue. But content-wise, the actual written word, I don't do much editing.

At first I was very anxious and fixated about having a spelling error or typo. Early in the pandemic, I was reporting on the number of COVID deaths, and I accidentally put three extra zeros after "million" — so I said a billion. Someone reached out, so angry: "You are just like all the other people on the left, blowing this out of proportion." And I thought, this is obviously a typo. After that — about six months into Healthcare Huddle — I was so nervous about making errors.

But once we got acquired by Workweek, the co-founder said, "Don't worry about making mistakes in grammar and writing. It just shows a human is writing it. It doesn't need to be perfect. Fix stuff, make it look good, but don't pull your hair out over a typo." Sure, I use Grammarly for last-minute checks, but I breeze through it. If it says "you could try restructuring this sentence," I say, no, I'm keeping it. For video and audio, I think you should edit, especially because people expect more perfection there. But as a sole creator writing, I think you can get away with not editing — though you should still make it presentable.

Healthcare news is boring. Who wants to read about drug prices? You make it fun by adding your own voice, perspective, humor — and sometimes small errors. You might even revisit those errors in the next email: "Hey, if you caught this, good for you — you read my content to a T." My dad, after every newsletter, will screenshot and circle stuff and send it to me: "What's this? You misspelled this." I say, "It's okay, you don't need to do this to me."

Here's an error I made two days ago. I schedule-send my newsletters on Friday so I don't have to worry over the weekend. It goes out Sunday morning at 8:15 AM, based on your time zone. When I scheduled it, I accidentally selected PM. So instead of 8:15 AM, it went out the night before — everyone got it at whatever time, two in the afternoon or four in the morning if you're on the West Coast. But I just left it. It says "good morning" in the newsletter, but people know I meant to send it earlier. Not going to worry about it.

Fantastic question. When Healthcare Huddle first started, I was so against being myself, because I thought physicians are conservative, they just want the information. So for the first year and a half, there was no personality to it — very succinct and well-written, but no personality. I had a whole team helping me write, maybe three people on one newsletter, which at the time I thought I needed.

But when Workweek reached out for the acquisition, the co-founder said, "One thing I need you to do — I need you, Jared, to write the entire newsletter. No one else. It needs way more personality. Like you said, people come for information, but they want to stay to learn more about Jared." So in August 2021, I told my team, I'm going to write all my content and experiment with this. I was in the middle of rotations, drowning in work and struggling. But if this is what's needed for acquisition, I needed to try it.

Writing Healthcare Huddle became way more fun with a personality behind it — me. I added a new section called "Dash's Dissection" — a play on my last name, my analysis of the content. Now people come up to me: "Yo, Dash's Dissection, loved it." In the intro I say something about myself — what I did over the weekend, what rotation I'm on. "Just finished my week of nights, well rested now to get this huddle out." As a sole creator, you need personality. Blake Madden, another Workweek healthcare writer, just talks about golf at the end of each newsletter — people love hearing his golf score. I'm big on fitness, so I started adding what my big workout was for the week. Someone in New York City who reads it emailed back saying, "Let's go for a run together." I ran with him in Central Park three times.

Think about what that does for your content. Not only was this person reading my content — now he knows who I am. He ran with me, heard me huffing and puffing, grunting in pain. That's a deeper bond with my audience.

A lot of times they oppose. Are you talking about being a generalist versus focusing on a niche?

This is so interesting — you're asking the questions we had to ask ourselves building Healthcare Huddle. We started out totally in that consumery news. Some flashy report hit CNN, NBC, BBC, and we'd write about it. It was entertaining. But no one's going to give me money to put their brand in front of consumer news. Up until a year and a half in, it was all consumer news — what's trendy, what's the flashing lights in healthcare right now.

Then, once Workweek was testing acquisition potential, they said, "Jared, you need to make it more B2B. Write for the physician, for the healthcare executive. Give them news and takes they want to hear." So I had to shift from hot, flashy consumer news to — I won't say boring — higher-impact news that affects business and decision-makers. Which was tough, because writing about consumer stuff is so easy.

Take the Prenuvo, whole-body imaging stuff. There's a consumer part, but also a huge business component. I state the evidence: there's no evidence to support whole-body imaging scans unless you have something like Lynch syndrome. But this is going to make money, because you have people like Kim Kardashian advertising it, unprompted, unsolicited. So these rich people are going to spend money, and Prenuvo is going to make a ton. You can make money on consumer news — you'll just be like CNN. They make a lot of money, but you don't want to be the next CNN. It's the B2B that separates you, that executives and key decision-makers read. Blake Madden writes about UnitedHealthcare's earnings, the largest insurer in America — sure, it's information, but he adds spicy, sassy takes and gets people riled up. So I agree: you need to go the B2B route to be a successful content creator.

Fantastic question. First, I have an ideal reader in mind when I write — the physician who has their own independent practice and is interested in the business of healthcare. That's who I write for. Funny enough, early on we tried to capture a wide net. Then, about a year in, we realized we actually had no idea who our audience was. We assumed it was a bunch of students. So we started asking people who they are when they subscribe — "what do you do, what industry are you in?" It's annoying, but we get great data. Now I know who's reading my articles.

So I helped create it, but Workweek are the people running it. I think you're actually subscribed before you fill that out — so it's like an empty threat to fill it in. And the money question is: if you work for company XYZ, how much revenue are they bringing in? Basically to see if we can contact you and put us in touch with your company for a partnership. If your company makes hundreds of millions annually, maybe you have ad spend you could give us.

I'm all about a streamlined subscribe process, and this is a little friction — pros and cons. But we get such valuable information. When it comes time for partnerships, my team can easily present to partners: this is who's reading Healthcare Huddle, this is how much money they have, this is where they're located. A lot are in New York City — oh, I want to host an event in NYC and sponsor it, so I can host a happy hour. That's very valuable.

For sure. So at first we were targeting medical students, and we started a college ambassador program — this is what Morning Brew did, very successfully. We had 10,000 Instagram subscribers, and we recruited college students where I'd give classes on healthcare 101, teach them, give them Healthcare Huddle apparel, and in return they'd refer people. It was during COVID — these students weren't out drinking and partying, they were bored, so they did Healthcare Huddle stuff, and it helped us grow so much.

Then when it came time for the Workweek acquisition, they said, "Focus on the physician, the resident, the decision-makers. Stop focusing on college students — they have no money, no purchasing power." And I thought, damn, we put in so much time to build this audience, but they can't buy what we're trying to sell now. They've all grown with me — they must be in medical school or working by now. But it was very interesting when Workweek said, "You need to focus on the people who have money, and we need to know who they are." That's why they started asking these questions at sign-up.

30,000 subscribers, 55–60% open rate every week — that's great. But who's opening and reading? It goes to something Workweek likes to say: we've captured all this attention, but how do we turn attention into intention? How do we get them to buy the products we're selling, or register for a virtual event? Intention is tough — that's the metric of who's listening to you, trusts you, and wants to learn more about the product you're offering.

Not religiously, but I've seen videos. "Jerry! Jerry!"

I think you're right, but it's so tough. If you're a sole content creator, you're very controlling of your brand and content — taking feedback is tough. I write what I think my audience wants to hear. I know if I'm right based on how provocative it was and whether people respond. Some Sundays no one replies, and that's when I think, I'm never writing on this again — I guess it was boring, but I thought it was interesting. I thought people needed to know about it to take better care of patients. It's very tough. I feel like I know at this point what my audience wants, and for the most part I do — but of course there are weeks where I write a shitty topic I put so much work into, and it just flops.

When I pitched a previous startup, before medical school, my co-founder and I pitched to this very stoic, asshole professor. The first thing he said was, "Who have you talked to about this startup?" We said, "Our friends and family." He said, "What did they say?" We said, "They said it's a great idea." He said, "Your friends and family will tell you what you want to hear. You need to talk to strangers. Cold-email people, go to Starbucks, randomly pitch your idea to someone — because strangers won't tell you what you want to hear, they'll be honest."

So for creating content, I don't text my dad and ask, "Was that a good huddle?" I value his opinion, but he's not going to tell me "this newsletter was shit today, I didn't read it." It's the random people in my newsletter whose feedback I really value. And honestly, if I don't get any replies, I take that as it being a poor email, or not provocative enough.

At first I was obsessed — I'm in medicine, I'm big on data, I don't like doing things without data. So I was very big on subscriber growth and open rate — what percentage of people are opening, not reading, your email. Then I got fixated on click rate — how many people are not just opening but clicking the links, because clicking is a surrogate for engagement. Obviously click rate is substantially lower than open rate. There are passive readers, engaged readers, and then people with intention, where I say "this is a product I like, I think you'd like it too," and they click and convert to a purchase on the partner's end.

Nowadays, I don't give a shit about open rate. It could be 40% one week, 60% the next — great. I care about click rate. Who's clicking through the links? How can I optimize to get people to click previous content? And if I have an ad, I want to see from the partner's perspective how many people I got to their website and who purchased. My job for the ads is just to get people to the website — then it's on their website design and copy to convert. Because that's intention, and that's the highest value. Especially with these virtual events — I advertise them in the newsletter, I see people click, but how many actually go through with registration? That's intention. So now I'm very focused on intention: who's listening to what I'm saying and following what I recommend. That's the highest value I can look at.

One thing you wrote down was "doing things that don't scale." This goes against the lean-startup idea, because the whole point of being lean is doing things that will scale and be efficient. But for content creation, doing things that don't scale can add more value than doing things that do.

For example, when you subscribe to my email, you get a welcome email from me. I say, "Tell me about yourself, here's a bit about me — who are you, where are you, what do you do in healthcare? What do you love and hate about the US healthcare system?" — I should actually open that up given my global audience. People respond, and I respond back, just to engage. This does not scale at all. If I get 10 emails a day from new subscribers and I respond to them all, that's 30 minutes. But those are 30 minutes I'm putting into creating an engaged audience.

If someone who's the CEO of a hospital system in Montana subscribes and takes 15 minutes to respond, I need to reply: "Thank you for writing this, great to see you're working at this hospital, you'll enjoy this newsletter." Sometimes they reply back and it becomes a conversation where they ask me questions. That's an engaged person who's going to 100% open my email next Sunday. This does not scale, but I think it's essential to creating a very engaged audience.

Wow, he's making a lot.

For sure. In the early days of Healthcare Huddle, each time someone followed us on Instagram, I'd message them: "Here's who I am, we'd love to learn more about you, I have this newsletter — please subscribe. You can just give me your email and I'll subscribe for you." So that's even more inefficient — I'm not sending a link, I'm saying, give me your email and I'll put you into my system. We must have done that with 2,000 people, and we converted a lot of them. It didn't scale, it took work, but I have a more engaged audience in return. Like I said, I value engagement and intention way more than just subscriber number and open rate.