The New Out-Of-Pocket 10 year plan
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How To Contract With Payors
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Before we get into my diatribe which will inevitably make a few MBA and MPHs tell me I don't know what I'm talking about...
Course Enrollments Are Ending Soon!
A few courses are ending enrollment very soon.
1) Claims Data 101 ends enrollment TODAY. Claims data is one of the most used datasets in healthcare to analyze things like market share, how patients are using the healthcare system, understand risk, etc.
But what’s in a claim? What happens when the claims clearinghouse goes down and leaves a big ol’ hole in claims? Enroll for the course starting Monday here and we’ll talk about it.

2) How to Contract with Payers ends enrollment next week. I’m tired of saying this nicely, if you’ve never tried to get payer reimbursement then you need to sign up for this course. You’re embarrassing the rest of us when we need to pitch them.
This course goes over the process of getting in-network, how to negotiate your rates, and even the important parts of value-based care contracts and how to get into them.

3) Healthcare 101 starts 4/22 - taught by yours truly, i’ll go over all the major stakeholders in healthcare and how the money flows and many case studies to explain things.
People keep saying “PBM” and you’re confused how they make money? You don’t really know the difference between Medicare/Medicaid? What do brokers have to do with anything? Come through and I’ll explain it all.

Out-Of-Pocket’s 5 year Anniversary
Out-Of-Pocket recently celebrated its 5 year anniversary this month.
It’s been a surreal time and a blur. I have proven that you can make a business out of anything if you’re funny and slightly overshare about your personal life.
In the first year, I laid out the Out-Of-Pocket game plan in a post. The idea was to create an onboarding system for healthcare - and we’d do it through content first, then courses, then meetups, and finally a venture studio
For the first time ever in my life…I absolutely f***ing called it. I’ve never called my shot and had it hit in my life (WORST horse player you’ll ever meet). But I actually did it this time, with the exception of starting a venture studio which I think we can all agree was a collective fever dream of 2020-2021.
Today we’re doing all of these things, and they all reinforce and feed into each other.
- The OOP slack group gives me ideas for the newsletter
- Events we do create content for the newsletter
- The newsletter lets me demonstrate expertise to sell courses
- The courses get people interested in being part of other OOP things

Now as per usual, the haters wont let me bask for even one second and are asking me things like “what’s the end goal?”. So I decided that it’s time to call a new shot for the future and see if I can go 2 for 2.
The Problem of Higher Education
I’d like to first explain the problem I’m trying to solve. There’s clearly a crisis happening in higher education.
The masters programs are getting insanely expensive. Wharton’s own estimate for its Healthcare Management program is $250K+. More people are taking out loans and coming out of school more in debt (which alters life/career choices, makes them more risk averse). And yet the share of people finding jobs post-MBA and more “generalist” masters programs has been decreasing. What employers want + willing to pay extra for in employees seems increasingly divorced from the things people are getting from their grad programs.
There’s a very real question on whether there’s still a worthwhile return-on-investment for getting these degrees, especially if the whole point was looking more attractive in the job market. Most of these programs are not tied to the outcomes of their students.
A parallel shift is also happening. Knowledge work is changing much faster than these universities can keep up with thanks to tools like ChatGPT/Deep Research. You can prototype and build things faster than ever. The expectations of what a knowledge worker and white collar professional needs to be successful is changing rapidly.

And finally, if you’re a person whose goal is to BUILD a company there isn’t really a healthcare program that’s a good fit. There are tracks within certain healthcare programs that try to do this + biodesign programs that get very close. But I don’t think there are enough or they each have their own tilt to them (e.g. focused on medical devices).
So how do I think that can be solved? I’ll tell you what I’d eventually like to build toward. But first…
An OOP Dinner and Healthcare Coworking Space
Events are becoming a much bigger part of OOP. The internet is a hellscape we all are tired of being on, checking it out of habit like an empty refrigerator.
So we’re here to provide an escape. We are hosting a dinner on 05/14 in SF for folks debating whether to build their call center operations in-house or outsource. If you are:
- VP+ in an operations or customer success role
- At a digital health company ($50M+ revenue, not hospital/payer side)
- Grappling w/ this existential question
You best believe the menu is delish. If you want to join email us events@outofpocket.health and tell anyone you think is cool who wants to come.
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Another in-person thing we’re experimenting with…are coworking spaces. We asked if people wanted to do a healthcare coworking space in NY, got 100+ responses, and got it set up in three weeks. You can just do stuff.

So we’re testing out to see if anyone wants to join us for a healthcare coworking space in SF. If this is something you’d be into, please fill out the form.
It's been particularly good for individuals that work at remote companies who want to come in 2-3 times a week to be around other healthcare people. This isn’t for people that want to sell their wares, but rather learn from each other.

The…Out-Of-Pocket University?
So what’s my new 10 year goal? To create a new “school” for people who want to build things in healthcare.

At its core, I think 2 year higher ed programs that act as sabbaticals where you pay a lump sum are a relic of the past. My hunch is that education as an adult needs to be shorter, more regular, grounded in real-world application, and use different funding models.
I actually think the principle of continuing medical education credits is a good model, though execution is a whole separate discussion. In order to keep their license, doctors have to do things in the pursuit of keeping their skills sharp and learning new things via courses, conferences, etc.
I haven’t fully thought through this, but here’s my current thinking of what a new “higher ed for healthcare builders” might look like:
- A 1 year or less program. It’s a co-op program where you’re essentially learning and working in some kind of healthcare company (large company, startup, private practice, etc.) based on the track you’re interested in.
- Curriculum that’s almost entirely technical and focused on real-world applications which you can apply at the company you’re working with during this time. Building patient intake flows, attribution methodologies, prototyping with Claude, how to use claims in risk adjustment, hackathons to test ideas, etc.

- Capstone is building a company or product and getting 1 pilot or paying customer. Everyone needs to learn sales, I’m still shocked this isn’t a core skillset you learn when it’s 70% of running a business.
- Yearly one week bootcamps after you graduate where you train on new skills based on the new tools available or learn from other industries (e.g. how a restaurant operates) which you can bring to healthcare.
- This also likely needs new financing models. A portion paid upfront and a subscription for the regular meetups/bootcamps feels traditional. But you can get weirder like income share agreements based on their future salary, or headhunting fees from the employers for placing people, or a venture fund tied to the school for people that spin out? Or maybe one of you is secretly really rich and will cut me a check.
Why do I want to create this?
I want to teach people things they’ll face in the real-world and make continuing education a core part of careers. Creating valuable networks can be done in shorter periods of time and are richer IMO if you’re building things together vs. 6 trips to Medellin. People need to learn how to be high agency - you can just DO things you want to see in the world. It doesn’t all have to be a setup so you can recruit into finance/consulting. And I don’t think this needs to be as expensive as current options.
Currently at Out-Of-Pocket we’re building the component pieces to this vision.
- We already teach courses, and are looking to do more in-person workshops
- We run an ongoing community based in a subscription model with a yearly retreat where we learn new things for a weekend
- We run events and spaces that are conducive to building like hackathons and coworking
- We do early-stage investing in healthcare companies.
But there are still many missing pieces like structuring a clear curriculum, figuring out an economic model that works, and finding partners that would want to enable a co-op style model. Plus the OOP brand and offering has to be attractive enough that people would actually want to come and employers actually feel like a person coming out has credibility.
So we have our work cut out for us, but figured I’d put it out into the universe. Let’s see what the 15 year OOP anniversary looks like 🙂

Thinkboi out,
Nikhil aka. “Headmaster Thinkboi”
Twitter: @nikillinit
IG: @outofpockethealth
Other posts: outofpocket.health/posts
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Interlude - Courses!!!
See All Courses →We have many courses currently enrolling. As always, hit us up for group deals or custom stuff or just to talk cause we’re all lonely on this big blue planet.