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Speedrunning every stage of a creator business while in med school

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Today's guest is Jared Dashevsky. He runs Healthcare Huddle, a twice-weekly newsletter for healthcare professionals. In just over four years, he's built an audience of 30,000. He's also built a team of 13, dismantled that team, and been acquired by the media network Workweek.

But, two years after they’d acquired his newsletter, Jared and Workweek parted ways. Today, for the first time since he launched, he is a solo creator.

In this issue, we discuss:

  • 🎓️ The cap on how far Healthcare Huddle can or should scale

  • 😍 Understanding your newsletter’s “true subscribers”

  • ✍️ Creating a sustainable newsletter workflow

  • 🧠 Jared’s four key lessons from four years of newslettering

On the podcast, we also talked about:

  • ↩️ Pivoting from a B2C to B2B audience

  • 🤝 What being part of a media network like Workweek enables

  • 🕊️ Why Jared left Workweek after two years

  • 🧑‍💼 Building a team (and then letting them all go)

— Francis Zierer, Editor

P.S. Don’t feel like reading the newsletter today? Listen to the full interview on our podcast.

“Mainstream healthcare media is so boring. It's so boring. There's no personality behind it. I'm reading the boring stuff so my audience doesn't have to.”

Jared Dashevsky self-identifies as Type A. He's a lifelong athlete who graduated medical school last year. Now, he's in his first year as a resident physician and his fourth year as the creator of Healthcare Huddle, the newsletter he started in his first year of medical school.

Before starting Healthcare Huddle, Jared co-founded Nayroo, which was meant to solve the outdated medical appointment scheduling workflow. He and his co-founder developed a prototype and pitched it to investors the summer after he got his master's degree, but they shut it down because he was starting medical school, and more than founding a company, he wanted to become a doctor.

Type A individual that he is, even with Nayroo off his plate, Jared wasn’t satisfied with academic responsibilities alone. He inevitably found another problem he could solve, with a much lower barrier to entry than his would-be software company:

“Finishing this master's program, starting medical school, I needed to talk to people about healthcare.

I wanted to talk about digital health. I wanted to talk about insurance policy. There are interesting topics, but very few of my medical school peers could actually engage in a deep conversation about how broken the system is. You're not really taught about the healthcare system in undergrad unless you specifically study it.”

In his first months of med school, Jared asked his classmates how they stayed up-to-date on healthcare and found that very few did — they either didn’t know where to go, were too busy, or found existing resources too jargon-filled.

This was late 2019, and Jared had been following Morning Brew for a while, so he saw a clear opportunity to apply their news-summary-for-young-professionals model to healthcare:

“I decided to start breaking down articles every week in a very succinct way and just send the email out to my medical school friends, see if they liked it, what feedback they gave me, and if I should continue it.”

The timing couldn’t have been better — within months of sending the first issue of Healthcare Huddle, the COVID-19 pandemic went global. Suddenly, everyone had more time to read newsletters and, more importantly, an increased need for accessible news about the healthcare system.

Since Jared first launched Healthcare Huddle, the newsletter has evolved quite a bit. He founded it with two other people, his brother and a friend. His brother, Brett, is now Head of Content Creators at Kickstarter and runs a creator economy community in New York. The other co-founder, Harrison Kaplan, is on his way to becoming a surgeon.

A cast of fellow students joined the team in the first year, mostly as part-time content creators and interns. Workweek co-founder (and former The Hustle president) Adam Ryan started advising Jared in the spring of 2021. By that fall, his company acquired Healthcare Huddle and slimmed down the team to just the Dashevsky brothers. Today, there's no team — it's just Jared.

If you want the full story, listen to the podcast — but here’s an abbreviated timeline:

Read on for an excerpt of our conversation and analysis of Jared’s methods.

The following interview excerpt has been edited for length and clarity.

CS: Do you think there’s a cap on how much you can scale Healthcare Huddle in terms of subscriber count, revenue, or output?

JD: I'm very happy you asked that because one of my goals for 2024 is not to grow subscribers but to focus on the "True Huddler" segment and figure out how best to deliver high-value content to them and convert them to the premium membership.

My main goal for 2024 is to figure out how I can build Huddle+ and increase revenue — not to figure out how I can grow an additional, like, 10,000 subscribers. Which is tough, because people will always talk about, oh, how big is your audience?

Your audience can be huge, but if your open rate is 20% and your click rate is 1%, that's not really an engaged audience. I'm trying to ignore subscriber growth and focus on hitting my growth goals for Huddle+.

I quadrupled my Huddle+ subscriber goal for Q1 in Q2. My goal is to get 60 total, which I'm almost at, and we just started the quarter. So I'm underestimating what I want to do, but I hope to convert at least 1% of my entire audience to Huddle+ by the end of the year. And again, 1% is low conversion. Sure. But for me, that's a lot of revenue for writing a newsletter twice per week, delivering content while in medical school or now residency.

Something I'm trying to grapple with is being content with what I have. Like, I don't need to make millions. I don't need to have an audience of a hundred thousand. I just want to be content writing weekly analyses on healthcare, getting feedback from others, educating others, and creating this Huddle+ membership. I just wanna be content with that and hitting my goals, which is tough.

CS: Do you get a different feeling creating content with a premium model as opposed to an ad-supported model?

JD: Yeah. It's much more gratifying knowing I'm being paid to deliver high-quality content to you. It’s totally within my control. I'm using my brain and you're reading my thoughts and analysis and you’re getting value from it.

Ads are great, but I always have this cognitive dissonance that I can't promise the advertiser that this is going to be a successful ad placement. I'm a man of data. Really, we need to talk about averages. If you buy 10 ad placements, I can predict what the open rates will be for each newsletter, what the click rates will be for your ad. But if you just buy one slot, I can't promise you it's going to knock it out of the park. And I don't like that feeling, because I can't promise you I can deliver value.

For Huddle+, I can promise you that I'm delivering high quality content. And that is a much better feeling than having to do ad sales.

Want to hear more from Jared? Listen to our full conversation in his episode of The Creator Spotlight Podcast.

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Understand your “true subscribers”

We wrote about figuring out your ICP (ideal customer profile) two issues ago — you should also be keeping track of your "true subscribers." These are related but different lenses for understanding your audience.

An ICP is more of a hypothesis (even if it's backed by research), whereas "true subscribers" can be easily tracked. How? Couldn't be simpler: determine which tracked behaviors define true fandom for your newsletter and make a segment within your newsletter platform. Done.

(Here's how to make a segment in beehiiv — formerly only available on paid plans, now available to all users.)

Jared tracks what he calls his “True Huddlers.” There are 13,000 subscribers (around 43% of his audience) who fit within this group, defined as:

  • Open rate greater than 85%

  • Click rate greater than 1%

You can apply other metrics, too. Jared has narrowed down versions of this segment for subscribers who also have at least one referral or have upgraded to Huddle+, but there's no need to overcomplicate it. As Jared put it:

“Basically, I just wanna know, who are the people who are reading this consistently, who are engaging with my newsletter, who are paying for the newsletter?”

Once you’ve set up a “true subscribers” segment, you enable yourself to do a few things:

  • Strengthen an already strong creator-audience bond: Send them an email letting them know you appreciate them (maybe include an exclusive new piece of content or a thank-you video).

  • Promote premium offerings: Speak to their fandom and relationship with your content to try and convert them to a premium subscription, buy your merch, etc.

  • Gather audience data: Send your onboarding survey to true subscribers who never filled it out, or a new survey to all of them.

I'd recommend creating sub-segments for things like gathering audience data (add a qualifier for "has not opened X survey"). I'd also recommend making these emails particularly casual and personal in tone — these are your true fans! Email them as you would any of your friends.

Build a repeatable workflow

Jared started Healthcare Huddle while in med school and is now a resident physician. As a resident, he often works 78-hour weeks, but he still finds time to put out two issues of the newsletter every week. That’s an achievement in and of itself — I asked him for advice:

  1. Plan your content in advance.

“I plan my content a quarter in advance. I have all these ideas of what I want to write about and I have a content calendar. I can predict when certain news will drop, like if there's something going on in the Supreme Court, and write about it. Or anniversaries — the Affordable Care Act just celebrated its 14th anniversary at the end of March, so I knew I’d write about it.”

  1. Find clever ways to reuse your content. You might learn something new about a topic you’ve already written about — you can edit that old piece, add some new bits to recontextualize, and send it out again. Your audience will appreciate the continuity!

“Certain content I've written a year ago, maybe I want to resurface and update it, so I can plan that content very far in advance.”

  1. Build a background file for topics you plan to write about later.

“I’m on Twitter, I'm on LinkedIn. When people are posting or commenting on a topic that I plan to write about, I will just skim it, save the link, and put it in my Notion folder for that topic.

When the time comes, I'll then click the links I've saved and actually read through.”

  1. Dedicate specific blocks of time to work on tasks related to your newsletter every week.

“Again, I'm saving content over time. When the time comes to write, I segment my week depending on my residency schedule, so Mondays are like what I call ‘Management Monday.’ That's when I'm just organizing my calendars and replying to emails.”

We’re doing this section a little differently today. I asked Jared to share the three most important things he’s learned in his four years working on the Huddle:

  1. There’s always something to be learned: “Understanding that you're never going to know everything, and being open to what you don't know, is a great attitude to have.”

  2. Consistency is key: “Creating content is like working out. It's a muscle and you need to build muscle memory.”

  3. Create for yourself: “Do it because you want to versus just because the creator space is so hot right now and you wanna get in there. I'm trying to deliver value to others and help them understand the healthcare system. These values and this mission keep me on track, help reduce imposter syndrome, and reduce the need to impress others.”

I also asked Jared to share one piece of advice on the art of newslettering:

“When designing a newsletter — and beehiiv helps with this — making it look good and pleasant on the eyes is truly an art. The content could be great, but a low-quality, unorganized newsletter is so distasteful.

You're capturing your reader's attention. So take advantage of that and don't lose their attention because, you know, the spacing between your first paragraph and second paragraph is too large, or because the colors aren't meshing together, or because you forgot a divider between two key sections.

Part-time effort gets part-time results.”

Further reading on some of the topics we touched on in this issue.

  • I’m a big fan of Simon Owens’s Media Newsletter. I immediately thought of this issue, “Is the Morning Brew model crumbling?” from last year when Jared told me he initially set out to make “Morning Brew for healthcare.”

  • “What journalists and independent creators can learn from each other” — it’s all content! Good article from Neel Dhanesha in Nieman Lab.

Thank you for taking the time to read today's issue. If you liked this one, I highly recommend listening to the podcast version.

On to next week's issue, featuring a creator who spent a decade in traditional internet journalism before venturing out on his own with “A newsletter about having fun online.” Five years in, it’s his primary source of income. He has around 70k subscribers and sends three issues per week (two free, one premium).

Talk soon,
Francis Zierer, Editor

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