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. Links Out of Pocket, Nikhil’s newsletter Get Real, Nikhil’s online community experiment Matt Levine’s daily finance newsletter, Money Stuff Nikhil on Twitter: @nikillinit Highlights (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." Transcript 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) Right. 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. An