Makers: Nikhil Krishnan
David McCarthy
Nikhil Krishnan’s content deserves a thesis.
Its format, its voice, its memes and references, and even its humility defy the grammar of traditional healthcare content. In a stiff, old-guard industry like healthcare, his approach is genre busting.
It’s genre forming, too. In many ways, the founder of Out-of-Pocket, as well as other creators, is defining a new standard. Today, Substacks and LinkedIn posts about health tech echo the aesthetic Nikhil has leaned on since starting his newsletter back in 2016, using memes to punctuate key insights and communicating the way friends do on a group chat.
Plenty of signals validate that Nikhil’s work is gaining traction among up-and-coming leaders and getting bookmarked next to the usual industry-insights suspects. For one, nearly 35,000 read his newsletter. But even anecdotally, his peers say as much. When I ask other creators who I should also interview or who they read, Nikhil is one of the first names that come up.
(Google, it turns out, also sees him as a credible source: as of April 2025, Out-of-Pocket outranked Healthcare.gov for the keyword “out of pocket healthcare.”)
His ambitions for Out-of-Pocket’s future, which he outlined in one of his most recent newsletters, will only further deepen his role as a go-to figure among emerging leaders in healthcare.
The Out-of-Pocket “thinkboi” and I chatted over email about his (unsurprisingly) refreshing approach to creating, the difference in brands building trust and creators building trust, the futility of labeling his work, and the audience growth he gained by ignoring the marketing funnel and the data that comes with it.
(And yes, his responses are as entertaining and as smart as his newsletter.)
Deep cuts from Nikhil
If you’re new to Nikhil’s work at Out-of-Pocket, you may want to start here.
The New Out–of-Pocket 10 Year Plan
How would you describe your content? What is its value prop?
It's supposed to be funny and easy to understand. Healthcare is a boring and dry topic that intimidates people trying to learn about it. Making it funny makes it easier to learn too. If you don't find it funny, don't tell me that.
It crosses a lot of different themes in healthcare and outside of healthcare. When we're in healthcare, it's a full time job to know what's going on in your role. My full time job is understanding what's happening across everywhere, and I try to bring that in.
It self-selects for a group of people that are curious about learning. When we do events, etc., people know other people coming are in that camp which makes it easier to gather people.
Who is your content for, and what is their pain point or desired outcome?
Anyone that wants to understand how healthcare works – whether they're already in the system or not. The only way we'll make it better is by trying to understand how it works currently and the tradeoffs we're making with different decisions.
You’re one of the most-referenced creators that people say I should chat with. But sometimes I wonder: is “content creator” even the right category for you? You run events, offer courses, co-host a podcast, run hackathons, and sell healthcare-related board games.
Honest answer is...I've never understood why the designation even matters lol. I think people really box themselves in when they try to compare themselves to other business/models. They look up "creator playbooks" and try to rinse and repeat stuff. This is how you decay, commoditize, and become boring.
I just do things that I think are fun. I don't think about what kind of "business" this is or if I'm a "creator.” Plus there's only one creator *looks up to the sky*.
You don’t create content that’s like most in the industry. You use memes. You reference pop culture. You’re funny and self-deprecating, neither of which is common in healthcare. Was it intentional to subvert that, or did you just decide to use your usual communication style?
When I got started writing a newsletter in 2016, I didn't know much about healthcare so I wasn't sure how I could stand out. I tried being funny/personable since everybody in healthcare has the personality of a cardboard cutout. It was partially deliberate, but I kept it going also because I just have way more fun writing like that. It's the same as how I speak, I don't have to edit it down.
An interesting byproduct though is that people are much more casual and informal when they talk to me or come to our events. I think that allows people to let their guard down more easily, talk about what's actually working and not working, and make friends with other people in the OOP network because they view them as more human.
A follow-up: do you think brands in healthcare and health tech will adopt a similar aesthetic, especially as our generation starts to move into decision-making roles?
I don't think brands will, and frankly I don't really think brands should. I’m tired of this "yassification" of brands and all of them pretending they're humans. It's annoying, and in healthcare, I also want companies to take me seriously. I write a newsletter – that kind of business is very different.
But I think people in healthcare should start talking more like people and not like brands. It's really one of the only ways to build trust – feel like the person you're talking to is a real human.
This is even more true in the age of AI where everything sounds like a bot wrote a script, even the things real people say online.
In some ways, you compete with healthcare and health tech brands for the attention of decision-makers and those in the industry. But a ton of research shows that people trust people, like creators, more than brands.
If you were advising brands, what would you recommend they do differently to keep the interest of their audience?
Do things that your audience/customers actually find valuable and interesting, not the things that optimize for your funnel. It's amazing how many companies I talk to that just cannot operate without thinking about their funnel and require every single action/communication to be data-driven.
Data-driven marketing and communications are inherently going to be extremely boring simply because most people are looking at the same data.
I use almost no data in my business. It's partially because I'm a lazy f***. But it's also because I don't want data to be telling me what I should be writing, saying, or doing. We should be close enough to our audience to figure that out ourselves otherwise there's a problem.
Figure out what's fun and interesting. Do novel things. Don't just optimize for your funnel.
There are likely more publishing brands and creators in our industry than ever before. Do you think that the up-and-coming healthcare professionals will be the most informed generation in the industry because of the work you and others are doing?
I don't think so. I think the issue is that we're now inundated with content because everyone has tried to turn it into a business. On top of that, everyone on social media optimizes their content, which now puts the onus on people to sort through the mountains of content to figure out what's real/good, etc.
Even though all the information is out there, you now need to put a ton of effort to distill it into something that's useful for you.
Are there brands or creators whose content inspires your work?
Ben Thompson really created the newsletter industry and was inspirational in showing that you can make it work by yourself.
Matt Levine is really the GOAT and showed how it was possible to take a relatively boring industry like finance and make it interesting and understandable for people outside of the industry
I'm always really impressed with all of the stuff mschf puts out -- they're just incredibly creative and always thinking of weird stuff.
When it comes to creating content, what are your first principles?
I try to avoid writing about any "topical" things or current events because so many smarter people are usually covering those things.
Instead I try to write things that answer questions that have always nagged at me or explore concepts I haven't seen many other people write about.
What’s been your best performing content?
The one that gets most mentioned is Six Stages of Health Tech Grief – and even though I don't really do any analytics, I would guess that's probably the best performing over a long period of time.
All the ideas in it are so common that people keep sending it to friends who are thinking about one of these ideas. There is a seemingly never-ending supply of people that want to build a new electronic medical record, so the staying power of it is massive.
With your volume of subscribers and your engagement rates, you’ve attracted some notable sponsors, like Abridge, Turquoise, and Particle.
The variety of your sponsorship products is impressive: courses, podcasts, events, and, of course, the newsletter. Why do brands partner with Out-of-Pocket?
Three things, really:
We are creative partners — we co-develop everything with our sponsors so they feel native to our events, newsletter, courses, etc. They should feel like a value-add to our audience, not a thing they have to sit through.
We're fun! People actually listen to us and our sponsors, which is why we have a really high engagement rate on everything that we do.
There's no better place to get in front of the health tech community.
Also, if you're an enterprise that needs to train your people quickly on how healthcare works, how to do claims analyses, learn value-based-care ops, etc., we can help with that, too. Let's chat.
What’s in your tech stack for creating?
I have an insane Google folder of half-written posts. I have about 50-plus drafts of different topics at any given time at different rates of completion. I keep adding to them over time as I read more things or have related ideas. Eventually a piece starts forming, and then I actually finish and write it out.
Virtually everything is in those Google Docs, and then I use ConvertKit and Webflow for emails and hosting the blog. I try not to overcomplicate this process.
to say Your work is wide-ranging is probably an understatement. you’ve covered value-based care, EMRs, and also the strange world of dental benefits. How do you choose a topic and plan your content?
You might be sensing a theme here...I don't have a plan, lol. I really just keep reading about a wide range of stuff, and then when I feel like I have an interesting opinion or POV, then I finally start jotting things down on paper and doing deeper research.
I don't like gassing myself up, but my edge is that I read extremely fast and synthesize things quickly. So most of the planning just comes from consuming way more information than any sane person should about healthcare. I'm slowly becoming the Joker, but until then it'll come out in newsletters.
What’s your optimistic contrarian take on healthcare or health tech this year?
We're going to see leverage swing back to patients, who have historically been the least empowered stakeholder in the entire industry.
AI tools are putting experts in the pockets of everyday people and and given them the tools to wade through the admin morass that tries to bury people.
Data interoperability is actually becoming a real thing slowly but surely.
This administration has a high priority for making things more patient friendly.
People have written off consumer healthcare companies for a long time, but I think the window is opening to build totally new workflows for patients.
If your content had a theme song, what would it be?
Nikhil Krishnan is the founder of Out-of-Pocket, a company making healthcare accessible, entertaining, and understandable for anyone that wants to learn how it works. He publishes at OutOfPocket.Health and on LinkedIn and X. Subscribe to his newsletter or reach out to him about sponsorship opportunities.
