Makers: Olivia Webb Kosloff

For Olivia Webb Kosloff, questions aren’t barriers. They’re catalysts. And her comfort with them may be what makes her original work must-read. 

Olivia is the founder and writer of the newsletter Acute Condition. She is also a policy analyst turned comms leader turned creator-consultant. That breadth of experience has infused into her work qualities that are largely absent in today’s often styrofoam-light content: in-depth and responsible reporting and analysis, humility that actually widens her editorial lens and prowess, and a True Detective-like curiosity in connections previously unseen. Together, these attributes and a tireless commitment to clarity and concision make Acute Condition not a short-shelf-life newsletter with hot takes but a legitimate, substantive publication for some of the sharpest minds in healthcare. 

Over email, Olivia and I chatted about her work on Acute Condition, the influence her career in policy, in-house comms, and VC has had on her role now as a creator, and the future (or peril) of healthcare policy. 

How would you describe what you create, and what is its value proposition?

My newsletter is about the intersection of healthcare, tech, and policy. I want to write in a way that's both valuable and interesting for those people who are healthcare experts but don't have time to delve deep into a specific policy area or aspect of the healthcare industry. I’m also a senior fellow at the American Economic Liberties Project, where I focus on healthcare and access to markets.

Who is your ideal audience, and what is their pain point you’re helping them solve?

In general, I'm writing for healthcare nerds who love the field as much as I do. I'm trying to help them understand an area that might be adjacent to their area of expertise, or to spark an idea for how one thing can lead to another thing. 

One of my favorite examples is with user-friendly design. I wrote about it in the context of the Covid vaccine rollout websites (which weren't designed in a user-friendly way), which ties into state capacity (another issue I'm really interested in). Someone who's working in healthcare day to day might not have time to research and think about that as a coherent narrative, so I'm trying to bring that to them. And then maybe they'll remember the example of how planes after World War I started to be designed with pilots' ease in mind, and it'll change the way they're building a healthcare interface.

I discovered Acute Condition during the pandemic. It was one of the most recommended newsletters I'd heard about, and there's no surprise why. You took a brief pause writing for it, but it's back. Why now?  

I started my career in health policy, then I did stints at a startup and a VC firm, and now I'm doing more policy work. The major difference is that (a) I have a better sense of what each sector within healthcare is thinking about, and (b) I'm interested in bringing this experience together. I think there is a big problem with state capacity, or the ability of our country to provide (or enable) essential goods and services like healthcare. We're struggling with provider shortages, bed capacity issues, and supply chain – there's a common thread here, and I want to write about it.

You have a versatile background as a creator: you're a policy analyst, you've published as a journalist at the American Prospect and American Affairs, you managed comms at Thirty Madison, and you led content at Andreesen, in addition to running your Substack. That's quite a run. What have you learned about creating over the last few years that surprised you? 

I mean this seriously — no one knows what the answer is. That's not to denigrate anyone – I've worked with some really smart and talented people. But no single group has "the answer," and that was a valuable insight for me.

When you're going deep into policy or some facet of supply chain, do you have an editorial strategy or a voice in mind to keep the reading experience clear and engaging? Is it tough to "code switch" from deep policy analysis to your creator or journalistic voice? 

I start by explaining the topic to myself on paper. If I can't do it, that means I haven't done enough research myself. Then I have a really intensive editing process, where I review what I've written and cut away at it, usually over the course of a few days. Sometimes I cut half of what I've written. The goal is to explain the issue as I would want it explained myself, in as few words as possible. 

Which brands or creators inspire your work?

There are a bunch of great healthcare newsletter writers out there right now. 

I particularly look to Brendon Keeler as a model of writing about a complicated topic with expertise and humor. I'm a member of Nikhil Krishnan's Out of Pocket community, and I've gotten so much value from that. Chrissy Farr does a great job at being smart on social media, and Deb Perelman (not healthcare, she writes the Smitten Kitchen blog!) is particularly good at Instagram.

I'm generally just a fan of writers and content creators, and I love to talk to people about how they set up their model for their specific audience.

When you’re working on content, are there first principles you lean on consistently? 

My first principle is that the topic has to be something I'm interested in, and I have to be able to go one layer deeper than a journalist would. Journalists are usually reporting on the topic, and I try to go one layer deeper with analysis. 

My other must is that I have to be sure I'm accurate. That often takes much more research than shows up in the piece. I still get things wrong, and I wish I had an easier way to fact check, but I can't send a piece unless I know I did everything I could to verify it.

What’s been your best content, and how do you measure that? 

There are two types of articles that I've really loved writing and that I'm proud of. One type is where I made an educated prediction and then it ended up being correct; these articles get quoted back to me frequently. An example is the article that I wrote in March 2021 about telehealth becoming a commodity. 

Another type is where I get to go really deep into an obscure area of healthcare (usually logistics or supply chains-related). Two examples are the article I did about veterinary drugs, and a piece I wrote for American Affairs on pharmaceutical supply chains. 

I measure success in an ad hoc way, but getting pieces quoted back to me or hearing from a start-up that I helped inspire their work is the highest form of praise.

What’s in your tech stack for creating? 

This might be a holdover from my time in policy (a notoriously Microsoft Office-heavy sector) but I just use a Word doc and Google. I read 50-75 books a year and often those will help inspire content. I used to use a stock images website for my cover images, but now I generate with the free version of ChatGPT. I keep track of potential ideas on scraps of paper on my desk. I think I've hinted at this before in my newsletter, but I'm kind of a Luddite in my personal life, and that bleeds over into how I write and manage my content.

Your work is wide ranging. It can cover vaccine technology and distribution, pharmacy financial chains, the Camden coalition, and more. How do you choose a topic and plan your content? 

I read a lot. If you read enough, you start to see repeating themes, and those tend to become articles. I'm a little more chaotic with my own newsletter than I am when planning others' editorial content as part of a consulting gig (for that, I plan weeks or months in advance and track in an editorial calendar), but that's the benefit of being independent.

What’s your optimistic contrarian take on healthcare or health tech this year? 

Healthcare policy is dead; long live healthcare policy. By that, I mean that both political parties have tested some far-reaching health policy ideas (from the right: shutting down Obamacare and now cutting Medicaid; from the left: Medicare for All) and voters don't seem to be responding positively to any of it. 

Healthcare has kind of fallen out of the political discourse. I think that will long-term be a good thing, because the slate is being wiped clean. What will the next set of healthcare policies be? I think a lot of it will have to do with corporate consolidation of power, state capacity, and national security — making sure Americans have enough care and the right care — but it remains to be seen.

Last question, and on a lighter note: If your content had a theme song, what would it be? 

“For What It's Worth” by Buffalo Springfield. That famous lyric “There's something happening here...what it is ain't exactly clear" is something I find myself thinking all the time.

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Olivia Webb Kosloff is the founder and writer of Acute Condition, an in-depth newsletter covering the intersection of healthcare, technology, and policy. In addition to managing Acute Condition, Olivia is also a senior fellow at the American Economic Liberties Project, and a consultant available for select communications and policy projects. You can connect with her on LinkedIn.

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