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Substack Podcast #014: Healthcare with Nikhil Krishnan

Substack Podcast #014: Healthcare with Nikhil Krishnan


We spoke with Nikhil Krishnan of Out of Pocket, a newsletter that’s tackling healthcare with an entertaining and approachable voice.

While working on the healthcare research team at CB Insights, Nikhil started an industry newsletter that grew to 90,000 people. He then worked at a clinical trial company and now writes about healthcare full-time on his own newsletter, which he started earlier this year.

We spoke to Nikhil about why he’s trying to make healthcare more interesting, his early paid experiments, and how to grow a thoughtful reader community, one person at a time.



  • (04:31) On making healthcare feel accessible to more readers and how to value expertise

  • (10:39) Being a writer vs. being a practitioner

  • (19:15) How he grew his list on Instagram, Twitter, Slack, and LinkedIn

  • (29:56) Experimenting with different paid offerings for readers

  • (37:27) Building a community that maintains high-quality conversations

  • (43:03) Subscription tiers and price differentiation

On figuring out which experts to trust:

I think the key is really finding people who are flexible experts. Like people who have studied their field for a long time, but also still remain default skeptical of their field. And once you find those people, really attaching yourself to them, I think is really important. I try to use those people to spitball thoughts off of pretty frequently.

On writing about healthcare:

[Matt Levine’s] newsletter is literally one of the funniest things I've ever read. He's so masterful and I don't care about finance, just to be clear, but he makes me care about finance, because it's so good, funny, and well written. And I'm thinking to myself like, "If finance can do this, healthcare can do this."


Nadia: (00:23)

You write Out of Pocket, which has one of my favorite one-line descriptions, which is “healthcare, but funny.” And you have this sort of elaboration that US healthcare is a joke, and it may as well get funny.

Nikhil: (00:35)

Yeah, exactly. I think people in the US probably empathize with that. I try to keep it as short and punchy as possible.

Nadia: (00:44)

Yeah, I was thinking maybe people outside of the US don't find healthcare funny, but if you're in the US, you immediately understand the appeal of this newsletter.

Nikhil: (00:51)

I think it's one of those things where in the US, it's gotten so absurd that it's now funny. You know how when movies are so bad that they're good? But if you're watching from the outside, you're like, "What is going on?"

Nadia: (01:05)

Exactly. Or from the inside.

Nikhil: (01:06)


Nadia: (01:06)

So you started this pretty recently, just this year and it seems like the response has been great so far. I know you have a long history of doing healthcare research previously. So we'd love to hear a little bit about how you got here and why you ended up starting a newsletter about healthcare.

Nikhil: (01:21)

Yeah, definitely. So for some background, after college, I went to a company called CB Insights for about four and a half years. For those people who don't know, CB Insights basically tracks tech trends, just generally starting with private markets and kind of data happening in the startup universe and then expanded into kind of just tech in general.

Nikhil: (01:42)

One part of the CB Insights kind of business is the research team, which I was a part of and helped to build out and more specifically helped build out our healthcare research team. So I was doing that specifically for about three years or so. Part of I guess our growth strategy at CB Insights sites was to create these newsletters using the data that we had and put interesting things together. And so when we were building out the healthcare research side of things, one of the things I had to do was basically create our healthcare specific newsletter. And I was trying to think how I could make the newsletter different.

Nikhil: (02:20)

We had some data, which was interesting, but there were a lot of healthcare newsletters that had data in it. So I figured what I could do better than other people in the kind of health care newsletter landscape was be funny, which is pretty low bar and health care. So I was like, "I could definitely be funnier than these people." I started to kind of inject humor into the newsletter and that was pretty on brand for the rest of the CB Insights newsletter. It was kind of this snarky, humor-filled kind of content.

Nikhil: (02:52)

And we realized pretty quickly that it filled I think a really big niche for people. I think generally people are looking for tools and content, etc in the business world the same way they consume it in their regular lives and having a funny industry-specific newsletter sort of filled into that.

Nikhil: (03:10)

So anyway, I wrote that newsletter and I got to about 90,000 people by the time I had left. And after that, went to a company called TrialSpark where I was on the partnerships and business development team, basically creating new business lines and types of partnerships. And it's a clinical trial startup for anyone who's curious. And then yeah, about two and a half months ago or so, decided to leave to pursue Out of Pocket full-time.

Nikhil: (03:39)

I'm actually doing two newsletters, funny enough. One is sort of a side project called Get Real, which I'm happy to talk about later, but the main one I'm working on is Out of Pocket. So I saw the need for kind of funny, approachable, digestible healthcare research. I think a lot of people... I think it's really exacerbated now during kind of the COVID endemic that there really aren't that many good approachable sources of information for people and we're really seeing the divide of "healthcare experts" and then "healthcare novices".

Nikhil: (04:13)

And I think there isn't a good way to bridge people from knowing nothing about healthcare to learning about healthcare, it's a very uphill battle and I want Out of Pocket to kind of be an easier way for people to get involved in healthcare and then level themselves out. That's the long spiel of my life.

Nadia: (04:31)

I love it. It's funny. It feels like we've seen on the Substack, there are all these sort of drier industries like... Well, I think they're dry. Like finance and trading, healthcare in your case, venture capital. And so they're sort of attracting these meme makers. It's always just sort of something dry but then also made funny and entertaining and approachable.

Nadia: (04:59)

For me, coming from the world of open-source software, there were people that were developers on the ground and then there were also people like Tim O'Reilly, who were sort of translating what was happening there to a broader audience. Do you feel like your audience attracts mostly healthcare nerds and insiders, or is it people that are interested in understanding healthcare? Do you have to be a healthcare nerd to get the jokes?

Nikhil: (05:22)

What I try to do with the newsletters is make it understandable for average people regardless of their healthcare knowledge or experience, but I do like to insert some deep-cut references for the people who are pros. I tried to kind of bridge both worlds. I think the other reality is, most people in healthcare are usually experts in their own domain within healthcare. Healthcare is a lot of different industries: it's pharma, it's hospitals, it's insurance, etc. I think for a lot of people, they might know their own specific domain really well but are still novices when it comes to the rest of healthcare.

Nikhil: (06:02)

The goal for me is to make sure that I was approachable as possible for anybody. And I try to do as best of a job as I can for giving all the context you need within kind of the realm of one given newsletter. So, try to explain all the acronyms that are relevant, provide one-mind contextual sentences that are helpful about other parts of the industry. But the idea is that every newsletter should theoretically stand on its own and you should be able to read it as kind of a lay person. What I'll probably end up doing as the newsletter develops is having more backlinking to sort of primer style posts. So if you're confused about something, you can kind of backlink your way into the stuff to give you context.

Nadia: (06:48)

Can you talk a little bit more about this expertise issue of... I think this is especially true in healthcare where there's this fear, especially for people that aren't necessarily familiar with healthcare, they're not exactly sure who to trust, and I think there's maybe some especially tension with this and the cross over to tech where at least my experience of tech being that a lot of people emphasize an amateur point of view and saying, "You don't have to be this credential expert in order to speak authoritatively about what's happening." But I think there's a fear for people that are consuming that information of like, "What if I'm trusting the wrong person?" And like, "I don't have the context to necessarily understand which thing is good and which thing is not." From your position, how would you counsel I guess, a reader to think about that? And then also from your position, how do you balance the things that you know about versus the things you don't know about?

Nikhil: (07:43)

Yeah, totally. I think healthcare field is probably more acutely than any other field because it's very heavily kind of credentialed as a whole. I get it. Most physicians are spending decades of their lives to become experts in their field and to have someone who's kind of armchair epidemiology stating things when they've learned it for two weeks, you can probably understand why someone who studied this for 10 years might be a little peeved or kind of like skeptical. At the same time, I think some of the most interesting observations have come from people who are outside of the healthcare industry, even if there's like a higher noise-to-signal ratio.

Nikhil: (08:29)

I think the problem is that the two sides have acted very antagonistic towards each other as opposed to hearing each other's arguments and kind of finding interesting middle ground. I think there's still a lot of room there. So to answer your question a little bit more specifically about if you're a reader and you're thinking about healthcare, what in healthcare information to consume and digest, I think for one, there are obviously credible and less credible sources. And I think part of what I've been trying to do is follow people where networks of people I find credible also find those people credible.

Nikhil: (09:10)

If there are people who I've seen consistently seem to have really interesting thoughts historically and have trended towards correct, and then they endorse other people or their work, then I view it with a higher level of credibility. So it's a little bit more about focusing on the people specifically.

Nikhil: (09:32)

And then, for me, personally, in terms of things I know and don't know, I really try to try my best to build my own base knowledge first and then consult with people who I think are experts in their given field on where they think improvements can be made. I try and poke around the edges a little bit based on what I know is kind of like a novice in a lot of these areas and see how they respond. But I think the key is really finding people who are flexible experts. Like people who have studied their field for a long time, but also still remain default skeptical of their field. And once you find those people, really attaching yourself to them, I think is really important. I try to use those people to spitball thoughts off of pretty frequently.

Nadia: (10:19)

I really like that. It sounds like there's one aspect of it that's about using people you trust almost as credentials. And then, how to find those people sounds like part of it is just looking for people who are inherently skeptical, but also well-read and understand what they're doing.

Nikhil: (10:37)

Yeah, exactly.

Nadia: (10:39)

Do you find that you're in a different position to understand this kind of stuff? Because you're sort of looking more broadly at research and overall trends as opposed to being a specific practitioner, for better or for worse?

Nikhil: (10:51)

Yeah. I think there are pros and cons to the place where I sit. I think for one, I think I understand the worlds of healthcare and tech, a little bit better than anyone who sort of siloed in each of their specific domains. And then two, one thing that I really appreciated about my time at CB Insights is that actually when I started, I was covering healthcare but I was also covering consumer packaged goods, construction, agriculture and autonomous vehicles, which is mile wide, half an inch view on any of these. What was really, I guess nice about that is that you can actually see interesting trends across industries and do better compare and contrast of why different things happened when they did.

Nikhil: (11:40)

So for example, if you look at autonomous cars and you see the relationship between kind of like OEMs, manufacturers, etc, and you look at Pharma and try to understand what the difference is between the manufacturers and supply chains, you can see really super different dynamics at play, because of how patents work, of how consolidated the supply chain is, how specialized it is, etc. So it was nice actually seeing a lot of industries concurrently because it became easier, it became more interesting to kind of view them in parallel with each other.

Nikhil: (12:16)

I don't view that as very differently than when I'm viewing different parts of healthcare itself. So even looking within healthcare to see how health insurance works, versus how maybe auto insurance works, for example. They're very different dynamics. Health insurance is way more proactive in terms of trying to deliver care to patients versus auto truly access, catastrophe insurance.

Nikhil: (12:46)

I think being able to kind of sit at a bird's eye view makes that really fun and interesting, but simultaneously, there's going to be a lot of frontline really nitty gritty stuff that I'm going to miss out on. One piece of advice a mentor sort of gave me which I think was really useful was to try and alternate your career between really macro and then really micro viewpoints. And so at CB insights I was obviously sitting in a more macro stage, and then at that TrialSpark, it was working on really nitty gritty problems and really being on the front lines of things. And now I'm kind of oscillating back to the macro side. And so both gives you kind of like a industry lens on how your industry is changing, but then you can see on the ground, how does that actually impact the day to day operations or something. That's-

Nadia: (13:36)

I really love that. There's sort of a parallel there to the blogging versus building thing that I've also heard of. Sometimes it's really good to be zooming out and thinking about stuff and sometimes it's really good to be on the ground and they inform each other. I found this for people doing any sort of independent research or writing really deeply about a topic. It's so important to get both those things and a lot of people don't necessarily get the luxury of being able to do both.

Nikhil: (14:00)

Yeah. A hundred percent. I think being forced to write for a long time really made me realize actually how difficult the process of crystallizing your thoughts really is. And then, also feeling confident enough in the stuff you write to put it out in the public sphere, knowing that there's a high chance you'll probably get roasted over something you got wrong, which is just like reality of putting stuff in public but being confident enough in yourself to put that stuff out is really important.

Nadia: (14:29)

How does writing a newsletter at CB Insights compared to writing one on your own now? Are there tradeoffs here with editorial independence versus reach?

Nikhil: (14:40)

Yeah. I mean, there's definitely a lot of differences. One, when I was at CB Insights, my only job was to create the analysis. Now, we're doing my own. Writing is one portion of it, but other portions are like, how do I market this properly? How do I come up with the drip campaigns for people who are... There's a lot of logistics stuff in the back end. And then also, thinking about product roadmap is very different. Because obviously at CB Insights, we had an entire product team and the CEO is obviously very... Had his own vision for the product and the target customer was Fortune 500 and the goal was to sell more of the CB Insights data product. So, obviously very different motivations.

Nikhil: (15:26)

On being on my own, one had to think about different monetization channels. And then therefore, what does the product roadmap look like for a different channel? That's definitely different. And then editorial independence wise, there's obviously writing on your own, you definitely can write as much as you want. One thing I will say that I miss is... When I was at CB Insights, two things that were really helpful were one having really good editors. I can't stress enough how much having good editors really leveled me up as a writer and an analyst, because it forced me to basically distill my thoughts into things that people who are not healthcare people could understand. And that was really important.

Nikhil: (16:13)

Obviously, there's also the copy editing stuff, which I'm awful at, which, as anyone who's on these newsletters has probably seen at this point. And then the second thing was having co-workers to balance ideas off of was really useful. And obviously, being a solo writer, that poses its own challenges. And it's important, I think to create your own networks to bounce ideas off of other people as you're writing them. That was another I guess, struggle of going solo.

Nadia: (16:43)

Can you talk a little more about that? Just about how... Does having the newsletter now, has it led to you finding people that you can talk to about this kind of stuff?

Nikhil: (16:54)

Oh, yeah. Definitely. I mean, not only will I say that... I think I've built a network in healthcare people that I feel like I can balance ideas off of pretty regularly to fact check myself as well as come up with new ideas, but the newsletter itself is actually drawn an interesting kind of cross-section of people in health care who are masters of domains in their own area and are very willing and happy to chat about any topic that they feel like they're experts in which is awesome, because one thing about healthcare especially and I'm sure this is the case in a lot of other "legacy industries" is there's all these just like layers to it, that I still to this day I'm learning exist.

Nikhil: (17:40)

You'll discover there's some random industry that sits between two healthcare players and actually, billions of dollars pass through it. I'm like, "Wow! I just never knew these people existed." Once they... A lot of people will reach out and be like, "Hey, I work at this company. We do X, Y, Z thing. We're the wholesaler to wholesalers." I'm like, "What? How is that even an industry?" And then, will kind of like lead me to the rabbit hole of either chatting with them pretty quickly or looking into it myself and just learning way more just because they made their presence known as part of the industry, a part of the chain that exists.

Nikhil: (18:23)

It's been great to kind of riff with these people who are kind of masters of their domain. The other thing I will say is also people who at least for now, opt into reading out of pocket are typically the kind of people who wants to be kind of flexible experts. And so the nice thing is that it sort of creates this self selection mechanism of people who sign up for the newsletter and then also are motivated enough to actually reach out and say, "Hey, I really like this. Here's a quick paragraph on things I'm interested in and we're building here. I think you might be interested." There's a higher likelihood that those people are the flexible experts I was talking about before. And so I'm always very happy to chat with them and understand how they're thinking about their field.

Nadia: (19:15)

How did you grow your list for Out of Pocket? How did these people find you initially?

Nikhil: (19:20)

Yeah. I mean, I will say that I think I sort of built a following on Twitter to begin with by again, sort of shitposting my way to glory on the healthcare side of things. Definitely the initial cohort was people who were following me on Twitter or LinkedIn or something like that. And then since then, I've basically been reaching out either cold to people in different industries. I started an Instagram. My first ever Instagram, I'm not on Instagram personally so this is a journey and a half for me, I really truly feel like a total Luddite when I'm trying to use Instagram, but trying my best there.

Nikhil: (20:02)

But yeah, a lot of cold outreach. I think I'm going to be doing a lot of interviews with some people who have their own followings too. And well, I have been also asking people to post it in different kind of healthcare specific Slack channels, etc. So, really just trying to find any area where there seems to be healthcare interested people who kind of want to level themselves up or are interested in following trends in healthcare, etc. The pandemic has obviously proven to be an interesting kind of environment to do this in, because I think there are a lot more people who are now interested in learning how healthcare works. And so I've been trying to ride that trend a little bit.

Nadia: (20:45)

Are there a lot of pockets that already have, since... I don't know anything about the world health care of people that already sort of clustering and talking about this in different forums, if you're sort of I guess, looking to borrow or siphon off parts of other people's audiences?

Nikhil: (20:58)

Yeah. I mean, there's definitely a lot of people... There are definitely a lot of healthcare channels where people are talking about things. Lots of healthcare Slack groups, lots of other newsletters that are just generally about health care. Lots of, just I guess, different audiences. I think I'm the only person who's specifically trying to use humor and memes and stuff as their differentiating factor.

Nikhil: (21:25)

Those definitely exist. I think that a lot of this is for... I don't know how many of these communication channels are specifically targeting people who are not healthcare experts who want to learn about healthcare. I think a lot of these channels target people who are already in the industry and the whole point of Out of Pocket is sort of to make it more accessible for people. I usually have to find some other channels or partner with people who are also just attracting people who want to learn more generally and maybe it's not healthcare specific, it's just, "Hey." These are ambitious autodidactic folks who want to learn more about how the world works, not necessarily about healthcare, but those are I think, also good audiences to kind of show my wares basically.

Nadia: (22:23)

Can you talk a little bit about writing about healthcare on Twitter versus Instagram, which sounds like it's a new format for you and then also on Substack of just... how do the means transfer on Instagram versus on newsletters? Do you prefer one over the other?

Nikhil: (22:38)

It's so fascinating to see how... I mean, this is more of my anecdotal experience. I don't know if this was true for everything or not, but the audiences are so different, I will say. I think part of it is just... And it makes sense. People are going to these different avenues for different reasons. If you've opted in to sign up for an email newsletter, there's way more flexibility into the amount that you can write for the newsletter, obviously.

Nikhil: (23:08)

I take liberty with that and I try to create emails that are long and kind of in-depth. Because the format sort of allows for that. And I want people also to forward it and share it with other people because they thought it was informative. Twitter, I think people want to just bite size pippy anecdotes or stories. They want just the interesting part of the entire newsletter, they don't necessarily want all the context that's associated with it. And then for Instagram, it's almost entirely visual. There just aren't... There's no text.

Nikhil: (23:45)

Even trying to use Instagram for the first time, it's so funny because I'm like, "Man, why can't I link my newsletter in this?" And then my friends are like, "Dude, you only get one link." I'm like, "Oh, okay. This is very different." I'm trying to figure out... I think it's funny because I think memes are the great lowest common denominator across all of them. People just like memes. And I also think that if you can have basically a meme summarize whatever your main point is, and it helps I think solidify the takeaways for a lot of people, but they work well across different platforms.

Nikhil: (24:23)

And then the last thing I will say is that my whole shtick in life is trying to blend my personal and professional worlds very closely together. I think I'd like to reduce the delta as much as possible from who I am as a professional to who I am as a person where I think a lot of people try to keep those worlds separate. And so I think me posting on LinkedIn as if I'm a individual who's again making trash memes on the internet makes me seem a little bit more humanizing and I am not kind of writing this LinkedIn poetry about things. I'm trying to just be who I am as a person on LinkedIn, which I think maybe is not normal for a lot of people. But yeah. Anyway, I think there's a lot of medium differences but I'd like my style and tonality and personality to kind of show up no matter where it is.

Nadia: (25:18)

I didn't realize you're also on LinkedIn. You've really hit every channel possible.

Nikhil: (25:22)

I'm trying. I'm trying out here.

Nadia: (25:26)

There are actually a number of Substack writers that have built their audiences on LinkedIn. And then are also building on Substack. And I guess for me, I didn't realize there was so much going on but it sounds like it's become more attractive as a platform for sharing things in the past couple of years. Am I crazy? Where did this come from?

Nikhil: (25:43)

I think a lot of industry people still use... I think a lot of people who are, who are deep in their industries still use LinkedIn a lot. I was talking to a friend once and we were talking... The conversation of default social networks came up and he said LinkedIn and he to this day still gets roasted over it. I don't think people would ever out word me in the middle out of this and I also think, candidly I think anecdotally there seems to be a bit of also an age gap and difference or also a role difference and gap.

Nikhil: (26:12)

If you're... I think primarily, in a lot of sales marketing roles, LinkedIn is really important. I think it really just depends on the channel you care about. I will say that, I found that LinkedIn is a... So two things. I think one, LinkedIn is a great place to shill your wares to coworkers that you used to work with who maybe you're not... You don't have personal... You're not connected with on personal social networks. And then the second thing is, I think LinkedIn has a way higher noise to signal ratio or quality of readers just generally. So it really depends on what your goal is as a writer.

Nikhil: (26:54)

I think if you just want to get eyeballs on your stuff, then LinkedIn is great for that. I think if you're trying to do more interesting things with your readership specifically, then I think it's a bit of a crapshoot to get people from LinkedIn.

Nadia: (27:13)

Actually, I wonder about something related, which is, did you feel like when you had a newsletter, you're writing at CB Insights that it could be, I guess, as much of a calling card for lack of a better term versus Out of Pocket in that both are technically these branded newsletters that are... It's not like it's your personal newsletter or anything, that you're just kind of writing about whatever you're thinking about. Like they have a very specific focus. But in one case, it feels like you're, I guess writing for a company versus something that you've spun up yourself. Do you feel like one attracts more people to you than the other?

Nikhil: (27:48)

Yeah. I mean, I think the CB Insights brand was really strong. And so that definitely helped open a lot of doors both in terms of getting new readership because it was very it easy to sort of be like, "Hey, you've seen the CB Insights newsletter? We're doing the same thing with healthcare." People understood then what they're kind of getting into versus Out of Pocket, which is sort of a new approach to it that I have to sell a little bit more. And then the other thing is there's a lot more cross posting on the CB Insights newsletters too.

Nikhil: (28:23)

If you're interested again, in general corporate strategy, and you're a healthcare person, then you're probably signed up for the main CB Insights newsletter, and we'll tell you about the healthcare one, and you're probably interested in that. So there are definitely benefits to that. I think writing as a person has, I really have to focus a little bit more on selling me the person as opposed to any brand that I'm associated with. And that's definitely harder, but it's also something that I've tried to do a little bit more deliberately through the course of my life, especially just writing on my own personal blog and trying to build up my Twitter followers and posting on LinkedIn and all that kind of stuff.

Nikhil: (29:08)

I want people to know that I do know what I'm talking about a little bit as an individual and so, there hopefully is some merit to me writing as a solo person. I'll also say I've also leaned very heavily on people who I think like deeply believe in the stuff that I'm doing and writing about and working on as an individual to be a lot of the early evangelists of stuff. Having that support from people is really helpful especially in the early days. That's one of the benefits of also writing as a person as opposed to a brand is, I'm really leveraging my relationships to kind of help with distribution.

Nadia: (29:56)

Makes sense. I'd love to talk about the paid Slack experiment that you announced recently, which I thought seemed cool. It sounds like it's available only to people that subscribed out of pocket and sort of building upon this list that you're creating. Why did you decide to go with a paid Slack as your first paid product experiment?

Nikhil: (30:14)

Yeah. For some context, I'm doing a paid private Slack for Out of Pocket members where you have to fill out a form, I'm vetting the people who are coming in, then charging per month and also having a very heavy hand in sort of helping a moderate both in terms of... Mostly in terms of discussion starters and kind of curating events and some homework for people to do, etc.

Nikhil: (30:41)

So, that's the first product. I think there's a few reasons why I went down this route. I think a lot of people on Substack, probably their default monetization path is, "Hey, let me monetize the Substack." And I totally get it. But for me, like I said, the goal here is to help people are healthcare curious, get more involved in healthcare. And I think by forcing people to pay for the Substack, that kind of goes against the general principle of trying to get newcomers into healthcare. I wanted to try some other monetization experiments before I went down that route.

Nikhil: (31:19)

The reason I decided to do a kind of paid Slack channel is one, I think there's still a gap to having... There's still a gap right now of a really small group of healthcare operators specifically, who are building things, want to share tactics and advice and also are really, really interested in not just kind of asking for favors from a Slack channel, but more building a real community and kind of actually being somewhat friends with each other. If you were to go to a city and someone in that Slack channel, actually lived there, would you hit them up? And trying to actually get that happening. So stuff like that.

Nikhil: (32:04)

I also think that having a curated group of people, and understanding their thoughts about the industry is really important for me to understand for in terms of future things I'd like to write. And also in the future, I'd hope to use this kind of vetted group of people to, I don't know, either put out surveys and get their general sentiment on things and really get a true understanding of what I think they're happening in the ground. I think there's still a lot of room to build good healthcare communities. And I think this Slack is sort of one step to that.

Nikhil: (32:43)

It's probably worth also just explaining a little bit about what I hope Out of Pocket is in the future and how the Slack kind of fits into that. I really would like Out of Pocket to essentially be the onboarding mechanism for people who are interested in getting involved in healthcare. And so understanding trends and what's going on in the industry is one part and that's where the newsletter fits in. But I'd like to actually help people learn from nothing to being an expert. And that can start with basically crash courses. Eventually going to a three day intensive to help understand exactly how this part of healthcare works, maybe it's clinical trials or how does health insurance reimbursement work.

Nikhil: (33:27)

So that's where you learn about a really specific slice of healthcare, the newsletters to help understand trends in the industry broadly. And then once you're sort of in the weeds of healthcare itself, how do you connect with other people who are also in the weeds of healthcare, and that's where the Slack channel fits in. That's kind of the overarching product thought process.

Nadia: (33:48)

You refer to sort of this being a way for people to... Out of Pocket, in general being a way for people to familiarize themselves with the world of healthcare. There's still some self selection, I guess, or is there, around... It's not just necessarily someone who has zero... It's just sort of a casual, like I would love to learn a bunch more. Are there people that are coming at it from maybe like an investor perspective or an analyst perspective where they kind of need to get up to speed with healthcare? Or are you aiming for an even more general audience than that?

Nikhil: (34:23)

I think it's a little both. I think it's... Even when I think especially for a lot of startups, and I've seen this across a lot of friends who have joined startups, a lot of them join these companies maybe from... They go from tech to a digital health startup or something. And there isn't a great onboarding process in a lot of cases to understand how their industry works normally, and then how the startup works differently and what pain points they're trying to address.

Nikhil: (34:48)

So I kind of think of this actually as like almost external bootcamp to understand how your industry works also. So it could be from an analyst side of things, it could be from an actual operator side of things. It's funny because I went to... I did a Wall Street financial modeling boot camp just kind of for shits and giggles, maybe six months ago or so. And it was funny because people went around the room to introduce themselves and basically every single person who was there because their company paid for them to be there as part of their onboarding process, whether that was onboarding into a new team, or onboarding into like an investment bank or etc. And then they got to me and it was like, "Hey. Yeah, I'm just here just because..." And it made me realize that like, "Oh, there's a lot of people here," just because their company doesn't do their training internally. They do their training largely externally.

Nikhil: (35:44)

When I was at TrialSpark, and I joined, I really wanted to understand the nitty gritty parts of the process of how clinical trials worked. And there are a lot of courses that are either really cheap online and $50, but no real accountability into like, learning in and they're really dry and boring, or there's these two-week fully immersive $10,000 courses and it's like, that's also not what I needed. I sort of taught myself and asked a lot of questions with people at the company internally, but I think it would have been really useful if even before I had started working to do like a three day intensive to learn the process. I'd like Out of Pocket to eventually move there.

Nadia: (36:31)

Had you thought about doing video courses or some sort of educational content? It's just interesting. A discussion group is so different from that.

Nikhil: (36:40)

Yeah. I think that's eventually where I'll move. But the discussion group is more just because... And frankly, it's one because I think corporate budgets for education are just way lower now, given it's a pandemic. And two, I think the audience was self selected into the Out of Pocket's Slack/my general I guess friends and followers are usually more deep in healthcare. And so this seems like actually just an easier to lift to start with. But eventually I would like to go into this educational component to get people leveled up either through video courses, or maybe it is in person boot camps or something. But yeah, basically moving into that area.

Nadia: (37:27)

And so you had this like... You touched us a little bit, but you had an application process. It's capped at max 15 people, there's homework. It's like, the bar is high. And you make that really clear to people that are I guess, thinking about applying it. Like, this is something that they should take seriously. Is there's maybe some crossover here with Get Real, which you mentioned early on about your experiment to create more authentic connections? I'm assuming all this is sort of done to keep Slack conversations interesting because they sort of die, they often die after the initial launch and everyone being sort of excited. I think that fear keeps a lot of people including myself from starting to Slack. What are some of the things that you've learned either from Get Real or from doing this, of just how to keep conversations interesting and at a high bar?

Nikhil: (38:18)

Yeah, totally. And you sort of have, I think, seen the connection here, but get real has been my community building experiment on the side. And again, for context, if anyone's interested, I was going through my quarter life crisis three years ago, so I started this newsletter where I ask a question each week, I answer it and then I get other people's thoughts and post my three favorite answers the next week. And that's sort of the gist.

Nikhil: (38:46)

What I've learned about good communities, I guess it's they hinge on a few things. One, you need really active key members/moderators. There's always a few people that you need to be constantly kind of keeping the conversation up and engaging people, other people in the group. And it usually has to be more than one person. I would say it's one, two, maybe three people who are really, really active participants and group members to kind of normalize the idea of participating regularly. That's one thing.

Nikhil: (39:21)

Two, is you can't scale it very fast. I think this is a trap that most people fall into, especially when you're monetizing directly off the people who are in the community or whatever is you start a community, a few people join and you seem to have a really high-quality group, then you raise a seed round or a series A round and then you just put all that money into paid marketing or whatever, and just dramatically increase the size, but then the quality drops inevitably.

Nikhil: (39:53)

You have to be, I think, really deliberate about how you grow the community and I think it's very tempting to just grow very fast. But I've never once seen a community that grows fast that managed to keep the community feel. And then the third thing is, I think by requiring work from the members, people are more invested in the community itself. I think generally, the internet community is at least in V1, and maybe this is changing a little bit, but most internet communities, they try to lower the friction joining as much as possible to get as many members as they can, usually because they're volume-based communities.

Nikhil: (40:38)

I'm trying to actually increase the friction so that the people who join the community really are serious about it. And if you... It's a lot... It's going to be work. Like you said, there's some homework, there's as an application. If you are willing to jump through all of those hoops, then you're someone who probably cares enough about this and you will find other people who care enough about this that I think that will select for people that are wanting to be a part of a good community and then therefore will be better members of the community. I'm trying to increase friction and make it harder to be a part of this community, but make the reward, I guess more worthwhile.

Nadia: (41:19)

I like that. It makes sense with all the different places that you're writing about this stuff that... It's sort of like there's this drip filter of someone might just casually follow you on Twitter, and then they might be like, "Oh. I'll sign up for this newsletter." And they're like, "Oh, maybe I'll try out the Slack." And it's like... It's sort of cultish in a way of thinking something like level zero, level one, level two or something, of getting all the way up to like that, paying money to talk to you.

Nikhil: (41:48)

Yeah. For one, I promise it was not as engineered as you make it seem. It was just very random. And two, I'm totally cool with being friends with people for free. You don't have to pay to be my friend, but I think of it a little bit more. I think the tiering thing is right. I think the sense of... I want people to opt into whatever level they feel like they want to give the commitment to, which is why this is... There are different products that are targeted towards different levels of like, I don't know, healthcare experience and commitment.

Nikhil: (42:30)

So, if you're someone who is just healthcare curious, I don't want you to have to do a lot of work to be a part of... To get something out of this, out of Out of Pocket. There's a level that works for you too. But if you're someone who is really trying to meet people who are just as ambitious as they are in terms of stuff they're trying to build in healthcare or just as deeply knowledgeable, then there's something for you too. So I'm really trying to like create products for those different tiers of kind of expertise and interest.

Nadia: (43:03)

It feels like that's one of the most important shifts from, for lack of better terms, “volume-based” monetization versus “context-based” monetization, where I guess just think about advertising or this sort of core belief that you have to make money off everybody that's looking at your stuff. Whereas, I think one of the cool things that you can do by having these more filtered places is... It's fine if 90%, or 95, or whatever, most of your people are just completely reading all the free stuff and you make nothing off of them. And that's fine, because there's some smaller group that's willing to pay a lot more that sort of subsidizes it for everyone else.

Nikhil: (43:45)

Yeah. I think that's totally right. I think one interesting thing, for Get Real, I don't really treat that as much as a business right now. It's more of a side project, but I started a Patreon for it because obviously there are some costs associated with just even running it. But I went with a tipping based business model because I think one of the interesting things is people get different levels of utility out of any product or any, I think even any newsletter.

Nikhil: (44:15)

When you create... When you don't have tiers of subscription, I actually think that you kind of have a cut, like a loss. You either have a... listen man, I'm blanking on-

Nadia: (44:30)

Deadweight loss kind of-

Nikhil: (44:31)

Yeah, yeah. Deadweight loss. Thank you. I'm getting PTSD from Econ 101.

Nadia: (44:36)

Me too.

Nikhil: (44:37)

You have like a deadweight loss basically. People who actually probably would have been willing to pay more because they got more utility. And then you also lose a lot of people who probably were willing to pay less, but still get some value out of it. And the price point you picked is just a little bit outside of their range. And so I think that... I think having the tiering is really important because you want people to sort of stay in your universe, per se. And then pay the level that they care about or the level they get utility from to minimize that deadweight loss.

Nikhil: (45:09)

And I think if you just pick, one specific price point for one product, etc, then you're... I think you're doing yourself a disservice. So, yeah. I'm interested to hear how other writers have thought about different product tiering if they have, but that's sort of the way I've thought about it.

Nadia: (45:28)

It seems especially relevant for people where's someone who's paying might be paying... I guess they have access to a corporate sponsor or whatever. They could charge it to some sort of corporate expense account. And then you also probably have people that are just sort of casually interested and want to do it for themselves. So you're sort of catering to a lot of different budgets as well.

Nikhil: (45:51)

Yeah. I also think... One thing I've noticed, at least one thing I've noticed is that there are some people who are just like voyeurs for the most part who are just consuming content and maybe don't necessarily want to be a part of a community, etc, but when you start talking about topics that those people are specifically experts in, it's awesome to have them as part of the newsletter so that they can chime in.

Nikhil: (46:14)

And so the problem is when you, I don't know, maybe do like a weekly... When you do like a monthly recurring revenue business, there's some people that are not going to get as much value every month that they do, but you don't want to lose them because in the months where they are specifically experts in that area, then it's awesome to have them there. And they can chime in when they feel like it. And so I really like those people really on the edge who are on the fence about getting involved or not because I think when they do... When it is something relevant to them, their contributions are awesome. I wouldn't want to exclude them, if that makes sense?

Nadia: (46:57)

Yeah. How did you decide on your pricing for the Slack group? It's a good price. $20 a month?

Nikhil: (47:06)

I got to tell you, there is no science to this one. I have some people that are like, "Man, that's like really high. I spend this much per month on Netflix and this is double that." And then I have people on the other end being like, "Dude, you're charging too low. People are looking for this. Their willingness to spend is probably way higher." And I'm like, "Wow. I really, really don't know what the answer is." And so, I'm being totally honest with you, it's random. It's very random. It's what I feel like I would have paid if I wanted to join Slack that was valuable. And the pricing is probably going to change over time.

Nikhil: (47:48)

There's going to be probably different... Some people may be grandfathered in until this pricing, maybe they'll have to drop it or increase it. It's weird because it's kind of like the in between of what an individual willingness to pay would be like, which is a little higher than that and then it's probably way lower than what a corporation would pay. And so I'm curious to see what this kind of middle of the lane pricing looks like. It's an experiment. We'll see. We'll see how it goes.

Nadia: (48:20)

Yeah, I love that. I love that you're just sort of taking this very experimental approach to absolutely everything that you're doing. It feels like you're building this sort of mini media empire, but you're testing out all the different waters and seeing which things resonate, which is really cool.

Nikhil: (48:35)

My third or fourth newsletter was about experiments with too many confounding variables. And the irony is that I think... I don't know if I'm going to do that, but we'll see.

Nadia: (48:48)

If you had to point to like, I guess to get philosophical as we're wrapping up here, what would you say is sort of the center of that whole brand or empire, all the things you're trying like? Is it you as an individual and your reputation? Is it like a certain content format that you're sort of the bread and butter of everything?

Nikhil: (49:06)

I think it's a combination of the two. I think it's really just about me as a entity that sort of informalizes healthcare, using humor, using very everyday language, etc. I think that just the world of non-healthcare and healthcare has gotten so divergent that there have to be more channels to bring them together and make people who are not in healthcare understand how healthcare works, people in healthcare to be better about explaining what they're doing.

Nikhil: (49:38)

And I guess one of like one of the people who are doing that, and so this may be right now at least centers on a lot of the stuff I'm doing but I'd like you to expand past just me. I'd want more people to kind of get involved to be. Maybe it's people within the Out of Pocket community who are teaching other people about areas that they're experts in but doing it in a way that is sort of on the same kind of brand of accessible funny, informal like this is me teaching you as an individual if we were at a bar or getting a drink, rather than, "Hey, I'm giving you like a corporate pitch presentation about what we do."

Nikhil: (50:20)

So, yeah. The goal for Out of Pocket generally is just in formalizing healthcare a little bit, and I hope more people are interested in doing that.

Nadia: (50:33)

Great. It reminds me of talking to folks in the finance Twitter kind of world who say that there was a time when not many people were doing that and now it feels like a lot of people are doing it. So it seems like you are sort of at the beginning of that with healthcare.

Nikhil: (50:46)

I think it's really funny you mentioned that because finance in particular, I think, has this amazing army of this pseudo anonymous, hilarious, but very highly analytical and technical group of people. Even just whether it's on Instagram or Twitter, a lot of the fintech anonymous accounts, they're really smart and they're very funny. And actually, the inspiration for Out of Pocket came from Matt Levine.

Nikhil: (51:14)

And I think his newsletter is literally one of the funniest things I've ever read. And he's so masterful and I don't care about finance, just to be clear, but he makes me care about finance, because it's so good, funny, and well written. And I'm thinking to myself like, "If finance can do this, healthcare can do this." And so yeah, it's funny you mentioned finance, because that's exactly the trajectory I hope this takes.

Nadia: (51:40)

Me too. It's been really fun to watch so far.

Nikhil: (51:43)


Nadia: (51:44)

Thanks for joining in chatting. Where should people find you if they want to check out your work?

Nikhil: (51:49)

Yeah. You can come to the Out of Pocket Substack which is https://outofpocket.substack.com. I write about the things on my personal blog. It's https://nikhilkrishnan.com. And if you're interested in joining Get Real, it's https://getreal.club because you can do cool things with URLs now. And also on Twitter @nikillinit. That's basically where my most half-baked thoughts are. So happy to chat with anyone who's interested in learning more about healthcare.

Nadia: (52:21)

Awesome, thanks.

Nikhil: (52:22)

Thanks so much.