An update about Out-Of-Pocket

lemme sell some of your attention plz

Looking to hire the best talent in healthcare? Check out the OOP Talent Collective - where vetted candidates are looking for their next gig. Learn more here or check it out yourself.

Hire from the Out-Of-Pocket talent collective

AI Agents in Healthcare Ops 101

Out-Of-Pocket is partnering with Champ to teach a hands-on course on what AI agents can actually do for healthcare operations today, taught through real revenue-cycle and network workflows: eligibility, denials, credentialing, referrals, and prior auth.
Learn more
Next Cohort:
10/27 - 10/29

Featured Jobs

Finance Associate - Spark Advisors

  • Spark Advisors helps seniors enroll in Medicare and understand their benefits by monitoring coverage, figuring out the right benefits, and deal with insurance issues. They're hiring a finance associate.

Data Engineer - firsthand

  • firsthand is building technology and services to dramatically change the lives of those with serious mental illness who have fallen through the gaps in the safety net. They are hiring a data engineer to build first of its kind infrastructure to empower their peer-led care team.

Data Scientist - J2 Health

  • J2 Health brings together best in class data and purpose built software to enable healthcare organizations to optimize provider network performance. They're hiring a data scientist.

‍Looking for a job in health tech? Check out the other awesome healthcare jobs on the job board + give your preferences to get alerted to new postings.

Check Out The Job Board

Hello there! I appreciate everyone that’s been reading, sharing, and sending feedback about Out-Of-Pocket. It’s crazy to think there are now nearly 6,000 of you on this newsletter - I really didn’t think this was going to resonate with so many people.

One of the main reasons I started Out-Of-Pocket was to make it more accessible for people to understand how healthcare worked in a more fun way, even if they aren’t in healthcare currently. To that end, my goal is to have a free tier of the newsletter forever. Hopefully by the time I die, GPT-69 can just train itself on my old posts and keep spitting them out.

I’m thinking through some different monetization strategies - and one of them will be advertising.

Before you skewer me and call me a sellout, I’m going to try advertising slightly differently though. I think the main problem with ads is that the ads themselves are terrible, intrusive, and generally not relevant to the audience they’re actually sent to.

I plan to actually make interesting ads that are fun to read as sponsored posts. They’ll look a bit more like analyses - clear cut and understandable about what the product is and even include pros/cons of the product and company.

My rules for ads are going to be:

  • I’m not going to do any ads for products I don’t personally believe in
  • I’m not going to do any ads that wouldn’t be relevant for this audience
  • You will understand exactly what the company does by the end of the ad
  • I’m going to paint as objective of a picture as I can about the company (e.g. how it compares to alternatives, tradeoffs picking this specific solution, bring any reviews of the product/service that would be relevant, etc.)

I’m in the camp that good products are worth giving attention to, and unfortunately these good products now have to compete for attention with a bunch of bad products (who usually have more $ to deploy for attention).

I also think publishers should actually care about the ads that get displayed with their brand instead of outsourcing that to third-party ad network.

So hopefully you won’t freak out when you see sponsored posts going forward! It’ll help me keep the free tier available to everyone and I think you might actually like some of these ads. I’ll give a disclaimer for all of the sponsored posts.

If you’re interested in advertising on Out-Of-Pocket and you’re willing to play by the rules above, let me know! You can email me at nikhil@outofpocket.health.

Thinkboi out,

Nikhil aka. “my landlord does not accept ‘social capital' as rent payment'“

Twitter: @nikillinit

IG: @outofpockethealth

Quick Interlude - Announcing Build @ Deerfield, powered by Out-Of-Pocket

See All Courses →

One of the goals of Out-Of-Pocket is to make it easier for people to start healthcare companies. For the last few months, we have been working behind the scenes to cook up something awesome for people who want to start something.

We’re excited to announce Build @ Deerfield, powered by Out-Of-Pocket. This is a five-week hackathon for early-stage healthcare teams with $250K+ of non-dilutive capital in grants and prizes.

Build @ Deerfield, powered by Out-Of-Pocket. January 20-21, 2027, New York City

You can see more details here, but in general Deerfield and Out-Of-Pocket are joining forces to do something big for the New York healthcare community. We’ll select 12-15 teams that will:

  • Receive cash to start building
  • Access to mentors during the program
  • Get a chance to present what they’ve built to the broader New York healthcare community at a showcase and reception on January 20-21 at Cure in NYC.
  • Judges will select a handful of teams for additional non-dilutive grants and prizes.

If you have an idea you’ve been meaning to build, or your team has just started out, this is your sign. We had such an awesome time doing this last year, you can see some of the projects here.

Now we’re doing it bigger and better.

Participants at a previous Out-Of-Pocket hackathon

Apply by November 19, 2026, there’s nothing to lose and a ton to gain. You can find more details and apply here: https://www.outofpocket.health/build-at-deerfield

This is going to be a lot of fun and we’re really excited to be doing this. A personal joy of mine is seeing someone take the plunge just before they build something great, and we’re happy to be a small part of that journey.

Email back if you have any questions. But look at the FAQ first cause we know half of you are about to ask “am I a good fit” or “what are you looking for in an application”.

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