Founder and Creator of Out of Pocket Nikhil Krishnan | Seed To Harvest S2 Ep9

Hello everyone and welcome back to Seed to Harvest. Super excited to have my friend Nikhil on today. Nikhil Krishnan is the founder of Out of Pocket, trying to make healthcare more accessible through memes, shitposts, and humor to explain it. They're building a newsletter crash course, educational novelty products including a game, a children's book, and more to help cut through the noise and explain plainly the business of healthcare and where the industry is headed. Nikhil previously did some stints at CV Insights and TrialSpark. He's also the one that inspired me to write Seed to Harvest, the children's book about VC, and has been super helpful on my journey. So I want to start out with, you write Out of Pocket, which started as a healthcare newsletter rife with memes. Can you share more about your writing and memeing process and how has it changed as your audience has grown?

Yeah, well, I'm excited to be here and chat. Just from the other side of this, it's awesome to see what you've built from shitposting your way to glory also. Yeah, I mean, so, you know, for some context, I was at a company called CB Insights for about 4 and a half years and helped build out the healthcare research team there. And a big part of CB Insights was sort of writing these research reports and newsletters that were kind of snarky, sort of memey there. So that's really where I learned and kind of built the chops of like, essentially, Trying to be informative shitposting, really.

Yeah, like making a good meme.

You know, let me tell you something. It's funny, like people always ask me this. They're like, how do you make your memes?

Tell me your secrets.

Whatever. You just gotta spend a lot of time on the internet. Like, yeah, I sometimes have to like run— I have to run my memes sometimes like past my normie friends to make sure that like I'm not too kind of like brain diseased because my sense of humor is like so degenerate at this point that I like forget what normal people laugh at. But I actually have an entire folder on my phone of just like meme formats that I think are funny.

How many, how many pictures are in the album, if you don't mind me asking?

Like easily 600.

Maybe 600 photos of meme-ready things. And do you just read an article or see something and then go look for like a reaction photo?

Yeah, basically it's like I have a concept in my head. I'm just gonna scroll through.

Where do you find, yeah, where do you find those, like those source photos?

Damn, you're, you're asking for my secret sauce.

I know.

What do people hate me for if they find this out?

This is like more for my personal information cuz I feel like my memes have been subpar recently and I would like to up my game and I respect yours massively.

Listen, I follow like a lot of the meme accounts. You probably know ones that are like very business focused, for example, like Your MBA Mikeys and your consulting humor type stuff. Mm-hmm. But I also follow these like deep niche cut meme accounts that just like post extremely deep fried things that make no sense, like Grape Juice Boys and all that kind of stuff.

Like more like nihilistic ones?

Yes.

Nice. Okay.

And then I'm also on like a lot of subreddits, but yeah.

Yeah. How do you think your approach to being like a creator or writer has changed as your audience has grown? Have you seen any like significant shifts in that? 'Cause for context, how many, how many Twitter followers are you up to now? Let's see. I forgot to check.

I think it's like 42 or 43,000, something like that.

Yeah, 43.

Yeah. You know, it's kind of interesting and it's something that I've talked with some other people who sort of write about. There's sort of like a bifurcation that has happened between, I would say, people that focus on the quality of their audience versus the people that focus on the number of people in their audience. And I think that actually is 2 very different approaches to how you think about building stuff like this.

Mm-hmm.

So even on Twitter, right? Like a lot of it has become way more algorithmic driven just by nature of the feed. And so as a result, you see things like people like doing threads and a lot of stuff that's sort of like algorithmic optimization, which—

I'm shaking in my boots. I've written a lot of threads.

It's just like, I mean, you, you, you've, you've seen it. Like I'm not, I'm, I'm preaching to the choir here. And then it's the same for newsletters, right? Where it's, you can do a lot of things to grow your newsletter pretty fast if you don't really care about the quality of subscribers, right? Like what?

Um, oh yeah, I guess there's It's like, it's not as niche an audience. Well, I guess what I found was like, I did a post like, MasterClass has the ad budget of Shen Yun, and it got like, you know, tens of millions of impressions and a bunch of new followers.

Mm-hmm.

But like, they kind of netted out to like nothing cuz they weren't really in my niche and they were just like, oh, she had like one banger tweet. And then I was like, do I have to keep writing these? Because I don't know how much left I have in my arsenal about like random pop culture things versus like. A lot of people would be very disappointed when they find out I only tweet about venture.

Yeah, I think that's, I think you are running into like the conundrum that a lot of people run into when they start writing stuff online, which is, do I care about branching to a wide audience or do I care about catering really well to a niche audience? And I don't think there's a right answer to this, but it's also 2 very different business models, right? If you are, you know, trying to optimize for your ad load, for example, you're trying to increase the number of impressions. Yeah. Number of things you write, number of impressions, number of eyeballs, all that kind of stuff. If you were trying to do other stuff, then actually you might care about the quality of audience. So like for me, for example, I have very explicitly focused on trying to have a high quality, whatever, like subscriber base, et cetera. And you know, the metric I'm probably most proud of is that the average open rate across all the newsletters is about 53%.

And it's been going for a long time, which means that you have like subscribers that have been following you for like a long time and still opening. I feel like some newsletters that have been around for like shorter periods of time, I feel like your open rate really drops off after a while. So that's really impressive.

Yeah.

So you've been running for 2, at least 2 years.

Yeah.

A little over 2 years now. Yeah.

A little over 2 years now. So it's, yeah.

So wait, I wanna talk about like the way that we originally met through Twitter was I feel like we were mutuals for a while. And then more specifically, you had a niche presentation night at Get Smart, which was really cool. Through the pandemic, you hosted these really interesting conversations. I did a presentation on spatial audio, kind of tied into like my senior thesis around how Shazam works, and it ended up leading to me meeting one of my investors in both Fund 1 and Fund 2, which is super cool. So I'm curious what led you to start that initiative? And then are there any other cool connection stories that you've heard of that have come out of that?

Yeah, so it's interesting. I, you know, originally when I left my job 2 years ago, I was planning to start a very different company, which was not healthcare related at all. The premise was about me helping people meet offline after having like an online sort of whatever rapport. And I had this newsletter that I used to write before, which was sort of, it's called Get Real. I used to ask a question each week. People would respond with their favorite, with their answers. I would post my favorites the next week, et cetera. And the idea was to actually have like these sort of more thoughtful social networks that monetized through events. And the first event that I threw was called Get Smart, and it was these in-person TED Talk style events. And I You know, did about 8 of them in person before the pandemic and, you know, probably like 150 or so people were coming to them. So obviously there was like, there was like touching some nerve for people. And then through pandemic, you know, wanted to like do virtual versions of it and, you know, keep it up. Obviously I ended up not pursuing that company for obvious reasons, but I, you know, the goal of it was really just one, like, how do you make it easier for people to meet in these like semi-structured environments of some kind? And 2, it's just like people have these really niche interests that I just think are cool.

Do you remember some of the examples? I remember the one that I like most remembered was like the origins of alcohol, which was really interesting. It goes into like what different organic materials are like every alcohol made out of and like how they differ across cultures. There's some other really cool ones. Do you have any other topics you remember?

Yeah. I mean, like one of my friends like formerly was in Scientology and do you have a whole talk about what Scientology, about like being in Scientology. You know, one friend did a whole talk on the history of animation. Another person did one on the economics of Chinese restaurants. Like there's like, we were talking like the whole gamut here. It's like very weird stuff.

And it's so fun too. It all, it also like unlocked something in me where I was like, oh, I can talk about my interests that are like super niche and I like know a lot about, like right now I'm reading this crazy, like it's written in 1901, but it's like a, a treatise on like libraries and the architecture of libraries and like all these random manual machines that they used to have for like displaying and reading and doing stuff. But it's really interesting. I was like, oh damn, I like, I wanna do another, gotta do another niche presentation night again.

It's been, it's been so fun. Yeah. I, you know, for a lot of people, I think it's a good way to sort of force themself to like get these like weird amorphous thoughts they have in their head down on paper.

Yeah. You're like, hey Paige, are you ready? And I was like, Yeah. No, no, I'm not.

Not too bad.

And you were like, yeah, it's tomorrow, so like get going. So it's kind of nice to have that forcing function.

And it's like small, you know, the whole point is like you can practice your public speaking in a way that's not like crazy large or like high stakes.

So, so if you're hosting a dinner party, who would be your dream guest? They can be historical or present friends or public figures. And then what would you serve and where would it be?

Oh my God. This is like 3 separate, very difficult questions combined in one.

Yeah.

I'm put on the spot. Um, that's, that's hard. You know, I think the people that I'm most interested in are like, how did people manage to convince large groups of followings to like believe in them? Right. Just like as a broad thematic cover.

Only extremely online Twitter people.

But the, you know, this is like, the thing is like the, the modern whatever person who has managed to build a following has like very different traits and characteristics. Or maybe not. Maybe it's very similar to like people who managed to build followings in the past, right? So like, if you take like the Jesuses of the world or like the, you know, Gandhis of the world, like they managed to rally people underneath something that they were, you know, kind of getting that, that like touched the populace. So, you know, one is just like, how did they manage to do that? And also, I mean, I have like a weird, like, you know, side interest in just religious texts broadly. I just think it's like the— Perfect intersection of like history, sociology, whatever. And it kind of shapes the entire modern world. I think like all the like old school religious figures would be most interesting. And then I guess you gotta pick like a neutral, neutral place to have, to have dinner in that case. So, you know, no meats or anything like that. So maybe Italian. You can go to Lilia. Maybe I could finally get a, a reservation if Jesus came with me. I, Just kidding.

I love that. So I've been really inspired by your playfulness in developing both your content and the merch that goes with it, including a children's book and a game. Actually, like the original idea for Seed to Harvest came because you announced your book and then I quote tweeted and I was like, would anyone be interested in reading a children's book about VC? And then I got like 80 DMs and I was like, I'm writing a children's book about VC. And then you had written all about your process, so I'm, I'm curious. I learned a lot about the process of self-publishing a book, but what was the process like for developing the game? You have a really great blog post that I'll link in the show notes, but if you wanna talk about it a bit, that'd be awesome.

Yeah, so the purpose of me doing the game was actually sort of trying to teach myself like how e-commerce worked very broadly. Mm-hmm. So, you know, as you probably found out for the, for the book, because Amazon has its own self-publishing press, it's very easy to handle the manufacturing side of this thing. But I was actually very curious, like what happens when you add the third party to the mix, which is the manufacturer? And so when I made, so I made a card game that's basically you have to avoid medical bankruptcy and it's a lot of people spend a lot of time on figuring out gameplay mechanics when they figure out board games. I did not do that. I like reskinned some games that are like pretty well known and just like modified them very slightly.

Yeah. 'Cause they've already spent money on like game mechanics design and stuff like that.

Yeah. And also it's like, the point of this is not to like teach people, like, like it's already gonna be complicated enough when they have to read it. Yeah, it's gonna be hard enough when they have to read the like healthcare text on this. Like I don't need to like add, make it more difficult for them. But I was interested in doing, actually, I was examining a few different board game types and the thing that is the constraint point is the more pieces that you have in the game, the more expensive it is, which is like not rocket science to figure out. But now I'm like hyper aware every time I play a board game of like how many unit co— how many units are there? 'Cause I'm like, oh my God, like unit costs for this must be insane.

You gotta do a talk on like the economics of board games.

Now, I did this actually at the last— I did this at the last Get Smart, actually. So the funny thing about, about doing this also was it was during like a lot of the supply chain crisis. So I could actually see in real time how a lot of this was getting impacted because you're making choices between manufacturing domestically versus in China for the most part. And the prices are just like astronomically different depending on how many you're printing, what the shipping costs at the time were, et cetera.

Mm-hmm.

And then you gotta figure out how do I get it to like Amazon warehouses? Learned all about that. You know, being like an Amazon purchaser versus a seller is like drastically—

Totally different worlds. Yeah.

Completely. Now, now I understand how like Amazon gets like squeezes its suppliers like crazy being on the supplier side versus me as a consumer being like, wow, what, like what a fantastic—

This is amazing. Convenient service.

Yeah. Like, oh my God, no, this is like brutal for small businesses.

Yeah. Even with like the print on demand, it's been interesting cuz it's like they just don't ship to certain countries. Like it was like, oh yeah, we don't ship to Australia. And I thought, I was like, okay, like I'll handle that later. And then I went to Australia and I met a bunch of startup people there and they're like, so you wrote this book, but we can't buy it in Australia. Like, can you ship it to us? And I was like, Amazon, like, come on, get it together. Like, ugh.

Yeah, I get this all the time for other countries and I just, I don't know what to do. Am I gonna really like buy, like preprint like 500 copies and just store 'em in a random warehouse in one of these countries? Like, really stupid.

I mean, that's been like the, the best answer for me so far. So hoping Amazon comes up with a different, different one for that. So I'm, I'm curious, like in your research, what is the one problem in healthcare that irritates or confuses you the most?

Oh my God, you're gonna— this is gonna be a whole podcast. No, I'm kidding. I, I think there's lots of stuff, obviously. I think the one that's most frustrating is kind of our— we have like an employer-based health insurance system here.

Mm-hmm.

It's a very uniquely US quirk. You know, it's in post-World War II, it was essentially something the government kind of gave us like a little side benefit to employers. And they were like, look, you have to freeze wages cuz we don't want a crazy amount of inflation. But you can use your tax, these tax-free dollars on other things for employees. And one of those things was health insurance. And so this didn't really matter at the time because health insurance was like such a tiny, tiny cost, but it became a huge problem later down the road as healthcare got more complicated and expensive and all this kind of stuff.

So like tax incentivized because it was tax-free, is that right?

Yeah, basically the, if your employer picks the health insurance plan, they can move tax-free dollars towards it versus if me or you buy a health insurance plan, it is post-tax dollars, right? Because it's coming out of our income. And that just creates like a whole level of warped incentives. You know, everything from your HR manager is suddenly in charge of healthcare benefits, even though they have no expertise evaluating like, like the efficacy of any healthcare company. Benefits in general are tied to your employer. So if you switch employers, you automatically churn from any company that you're using. Any, any service you're using. I'm sure like if you've like switched, anyone listening has switched between employers, it's like a hilarious ritual of like join company, ask HR like what plan should they pick, find a new primary care physician, just kind of like ask your coworkers like, hey, does anyone like see a PCP in network?

And it's like, I was like on, I'm still on my dad's health insurance. Shout out dad. And so I'm like under 26. Yeah. Shout out Obamacare. But he recently switched jobs and Well, okay, not recently, like October, but I haven't been able to like get a new primary care physician because the wait has been so long to switch doctors.

So exactly.

Yeah, very— for that ritual.

Exactly. And it's just so much of this is born out of that one specific problem. And, you know, it gets worse over time, I think, as the government sort of social— like the social safety net erodes a little bit. I mean, you can even, you know, even Looking at things like Roe v. Wade, for example, if employers start leaning into abortion access, it's not good.

Yeah, those benefits are provided by the employers, especially in like a continuously tumultuous market. That seems like very challenging.

Yeah, exactly. It's like you don't wanna get laid off from your job and suddenly not have access to something like abortion care because your employer is the only person that offers it. That's not how we should like be operating as a society, right?

Yeah. Yeah, it's definitely like very disappointing. It's definitely cool to see companies stepping up, but it just, yeah, that one little addition in World War II.

It's, and like the craziest part is actually if you look at other countries in like a post, post-World War II, they went in basically the totally opposite direction. So if you look at like the UK, for example, it was the total opposite. They were like, you know, the war had decimated the economy. The government was basically like, we need to just run this shit ourselves. Yeah. And they, you know, essentially out of that came out with the NHS, which they fund and operate themselves. So, you know, there are other paths that can come out of it. We just chose one specific one and now the ramifications of that are very weird.

Yeah. Yeah. Wow. So on a lighter note, when you were like early days of being an extremely online person, I know I have this, but like you have probably have like extreme ambient knowledge of like random online communities. Who, who did you look up to when you like first started doing Twitter stuff slash being extremely online?

That's a good question. I mean, I think the people who really I thought were so interesting were like the Ben Thompsons and Matt Levines of the world, which is such a, this is probably like a common answer now, but I was just impressed with one, how they were managing to make such interesting, for Matt Levine in particular is just funniest people writing on the internet and writes a finance column for Bloomberg. And takes a topic that like, I don't really give a shit about, to be totally honest. Like, I don't find finance that interesting, but he writes about it so fun, like in such a fun way that it's just entertaining to read. And so that's definitely like one of the, some of the, one of the people who I just was looking up to as a person. Like, wow, he managed to make this very boring subject actually pretty entertaining and easy to read. I actually, you know, it's funny, my like first Online, like being very online experience was actually like pre, pre being on Twitter or anything. I was in high school and I used to be like a frequenter of the Nike SB forums because I used to sell custom sneakers.

Oh yeah, you were a sneakerhead. I didn't know that. That's dope.

I was a sneakerhead. Yes. And so I, not really, honestly. It's just, it's not a good investment anymore.

No.

But I used to like paint sneakers and sell them basically online in these Nike SB forums. And there were all these like, Moderators and like really respected people in these forums that were just very cool. And then I would like DM them sometimes. And so it's actually very funny to see this kind of come full circle again today with DAOs and stuff like that. 'Cause sort of like similar vibes going to similar DAOs.

Similar vibes. Yeah. I think, well, I was like part of, did you, were you part of Eye Mouth Eye? I know you were like, I remember you being extremely online during that point and tweeting about it. Yeah. But I didn't remember a few more.

I'm like, again, like all of this stuff, I'm like the boomer observer from a I remember that was like— But I watched.

Yeah, that was like my first extremely online moment. And I feel like the alumni network that's come out of that is like actually insane. Like everyone is just like so extremely online and it had experienced like this massive like virality and action as an impact of it. Um, so it was interesting to see, like, I was like, oh, online actions can have like really significant impacts or consequences, which was kind of cool to see that in like a very positive way.

I have like a sort of a little bit of like a philosophy around all a lot of the stuff, which is, you know, the first wave of the internet, I think, has sort of been focused on like getting a high volume of like followers or people that you talk with. And this kind of like relates back to the newsletter stuff we were talking about earlier. I am a big believer in like self-selection as a process, which is If you set up enough hoops or like whatever, set up enough roadblocks for people and they come through the other side of it, you get like a very specific type of person that's shaped by the like obstacles that you put in front of them.

Mm-hmm.

So for example, if you look at, if you think, think about like the IMOTHI thing, right? Like the first people who probably started that are probably like just super interested in some weird internet culture stuff and like just Very, it's like a, it's a specific archetype of person, right? That you might vibe with or not. Or for example, you know, for my newsletter, the people who are on my newsletter, like enjoy reading long-form, very unprofessional healthcare content. So if you are like, if you read that and you're responding thoughtfully to that, et cetera, like 99% chance that we'll probably get along. And so I think what's sort of happening now Is you're seeing more of these like self-selection processes get built out so that the people who are like the right vibe for whatever community or audience or whatever you wanna call it, make it through to the end rather than trying to get the largest audience possible. And I think that's sort of changing.

Mm-hmm. Yeah. It's interesting to think about like the hoops that you have to jump through and also like thinking about the different ways that you as a creator, like start to understand and interact with the algorithm in that way where I was like, okay, like you have to kind of have a ratio of like shitposts, like informative things, cuz you have to have a blend of like having a top of funnel and then having your like actual like meaty content that you enjoy writing, but might not have like as vast of an impression impact, but it is like what you're really excited about. And then you have like your random things that you dash off in 5 seconds that like randomly go viral and you're like, oh, hello, new friends.

Yeah, I think like when people think about the funnel, they've always focused on the top of the funnel rather than like, how do you convert the middle at a higher rate? Mm-hmm. If you convert the middle at a higher rate, you don't need a bigger top of funnel, right? So even if your stuff is more niche, if the people go through it at a higher conversion rate, then it works the same, right? If not better, because it's probably like an easier audience to target. So I don't know, same self-selection sort of process, but you get it.

Yeah. Yeah. That's super interesting. Okay. So I know we're wrapping up, but I want to ask you one more question. When you think about your legacy, what are the things that are most important to you?

God. I wonder what my legacy's actually gonna be. Someone's gonna like read my eulogy and it's gonna be like, yo, this dude sucked. Uh, I mean, I think it's a couple things, right? Like, I think one, from like a more specific, like professional output stuff, it's, I want people to like not feel like they need to be professional to get their point across. I want like being casual and having open conversations about What is like probably generally boring or professional, like pseudo-professional topics to be more normalized. And generally I would love to like get people excited about building stuff in healthcare, which is like traditionally just been a very boring and intimidating place for people to start. And then on a personal note, you know, I want people to feel that they don't have to pick like very traditional career trajectories to feel like they are Their voice can be like respected in a specific field. Like I don't have traditional healthcare background at all.

Yeah. I never took a finance class.

Yeah. Like, you know, you just read a lot and talk to people and figure stuff out and play around with new tools or whatever you want to call it. And like, you, you could build your credibility without needing to like go to a master's program or get like the stamp of approval from someone else just to like get your name out there. So my hope is that, you know, the idea of credibility changes and at least in healthcare where this is like a huge issue, like there's a lot of gatekeeping. that happens, like credibility without degrees. You know, I'm trying to change that a little bit, so.

Yeah.

We'll see.

I love that. Well, it was fantastic having you on. I so enjoyed our conversation from shitposting to legacies to dinner parties with religious figures. Where can people find you on the internet if they wanna learn more? I'll link some stuff in the show notes as well, but what's your Twitter handle?

I'm very easy to find on the internet. I am on Twitter on @nikillinit, and you can look at my healthcare stuff on my website, outofpocket.health. Come hang out. I'll teach you about healthcare.

Amazing. Well, thank you so much for taking the time. I really enjoyed our conversation. Yeah, thanks, Paige. Yeah. Thanks so much for tuning in today to Seed to Harvest. If you enjoyed this episode, be sure to subscribe wherever your favorite podcast listening platform is. I'll be releasing new episodes weekly, and if you have any questions or comments, feel free to let me know on Twitter. That's Paige Finn, Paige, and then Finn with 3 N's. Thanks, and see you again next week.