Two free courses! New healthcare coworking space! General updates!

We got a lot going on, I’ll keep this brief

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

Healthcare 101 Crash Course

Crash course the basics of US healthcare in a simple to understand and fun way. Understand who the different stakeholders are, how money flows, and trends shaping the industry.
Learn more
Next Cohort:
9/22 - 10/3

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

Here is my court-mandated 6 week update on a few things happening in the OOP universe. I’ll be quick but it’s all fun stuff that will feed your soul (and help ME feed my family).

In the mean time I’m out here in my apartment filled to the brim with stuff for our Healthcare Data conference this week. Your business becomes real once your home becomes a microfulfillment center.

Can’t reveal what’s in the boxes, it’s surprise swag :) But don’t I look excited???

Last run of the courses :(

As a reminder, this will be the final live run of all the Out-Of-Pocket courses (except healthcare 101, which will continue).

If you want to quickly learn all the things needed to build in healthcare or just got a learning stipend you’re itching to blow, these are for you.

  • Healthcare 101 (starts 9/22) - ENROLLMENT ENDS THIS WEEK. If you need to learn US healthcare quickly, I got you. We’ll go through all the major stakeholders, how the money flows, rules you need to know, and trends in the space. Come through.
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  • Payer Contracting 101 (starts 9/22) - ENROLLMENT ENDS THIS WEEK. Trying to figure out how to get insurance to cover your services? How to get in-network or start moving to a value-based care contract? You might be depressed but you’ll learn lol.
  • Selling to Health Systems 101 (starts 10/6) - Maybe you just achieved product-market fit. Or you’ve been selling for a while but just transitioned to healthcare. This course will get you ready to confidently knock on hospital doors and sell to every person who has a seat at the decision table.
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  • EHR Data 101 (starts 10/14) - EHR data has a lot of weirdness when it comes to using it in analyses. Lots of duplicated notes, siloed data, lags in when the data shows up, etc. This course will teach you practical ways to analyze EHR data to help you avoid typical mistakes
  • Claims Data 101 (starts 11/10) - Claims data is one of the most used datasets in healthcare. This course is ideal for all healthcare backgrounds - it covers what claims are, why they exist, and how to most effectively use them.

As always, email sales@outofpocket.health if you want group rates or custom workshops for your company

Two new FREE courses!

We know that you all are sad about some of these courses ending, We know you’re going experiencing course-withdrawal, and we’re here with the Zyns of digital health courses.

Moving past the weird joke, we have two new FREE sponsored courses. 

We’re working with Canvas to teach a course on “AI Product Evaluation 101”. We’ll go through different ways to assess “ground truth”, how different companies approach things like benchmarks, and who should be the graders of the output?

Sign up here, happening 10/28 - 10/30. You’ll get sent the slides and recording even if you can’t make all of the days live.

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Our other free course is with Navina, and it’s on Value-Based Care 202 (aka we forgot how the university numbering system works). It’ll be from 11/18 - 11/20.

We’re going to go through three pillars of VBC - Risk, Quality, and Utilization/Financial Performance. We’ll talk about how they work generally and how data + AI tools are helping there. Sign up to attend, you’ll also get the slides and recording.

Going from high-level to deep in this one, come through 

A secret-ish AI event

Do you work at any of the following companies?

  • Company 1
  • Company 2
  • Company 3
  • Company 4
  • Company 5

We’re planning a fun event with some AI stuff this fall in New York but with very limited space.

Ping Alex (alex@outofpocket.health) if you’re interested. It’s going to be fun 🙂.

We host lots of secretish events, if you’re interested you should sign up here and tell us a bit about yourself so we can invite you in the future.

Healthcare coworking now live in three cities! Boston next?

We now have coworking live in three cities and a few seats have opened up in each. If you’re interested you can fill out the below.

  • New York - $275/person/month for a hot desk. You can find details about the space and form if you’re interested here.
  • San Francisco - $275/person/month for a hot desk ($350 for a dedicated desk). You can find details about the space and form if you’re interested here.
  • Chicago - $200/person/month for a hot desk. You can find details about the space and form if you’re interested here.
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We are entertaining the idea of opening one up in Boston. If you know a space that’s underutilized (either an existing coworking space or an office), hit me up.

Stay tuned on that one.

OOP’s 2026 Calendar

We’re shaping up our 2026 calendar for content, events, sponsorship, and more. 

We’re going to be throwing another:

  • A healthcare data conference
  • A healthcare ops conference
  • Healthcare hackathons (including some exclusive to companies)

And writing/doing sponsored courses about a whole bunch off things.

We’ve already sold the first couple months of newsletter of 2026, so if you’re trying to figure out your marketing or learning budget for next year, let’s chat. Email us sales@outofpocket.health and we’ll tell you all the options.

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Thinkboi out,

Nikhil aka. “Shilliam Fancypants” aka. “moving that product’

Twitter: ​@nikillinit​

IG: ​@outofpockethealth​

Other posts: ​outofpocket.health/posts​

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‎If you’re enjoying the newsletter, do me a solid and shoot this over to a friend or healthcare slack channel and tell them to sign up. The line between unemployment and founder of a startup is traction and whether your parents believe you have a job.

INTERLUDE - FEW COURSES STARTING VERY SOON!!

See All Courses →

A reminder that there’s a few courses STARTING VERY SOON!!

LLMs in healthcare (starts 9/8) - We break down the basics of Large Language Models like chatGPT, talk about what they can and can’t do in healthcare, and go through some real-world examples + prototyping exercises.  

Healthcare 101 (starts 9/22) - I’ll teach you and your team how healthcare works. How everyone makes money, the big laws to know, trends affecting payers/pharma/etc.

Our healthcare 101 end of course survey - that 3 is from my greatest enemy

We’ll do group rates, custom workshops, etc. - email sales@outofpocket.health and we’ll send you details.

INTERLUDE - FEW COURSES STARTING VERY SOON!!

See All Courses →

A reminder that there’s a few courses STARTING VERY SOON!! And it’s the final run for all of them (except healthcare 101).

LLMs in healthcare (starts 9/8) - We break down the basics of Large Language Models like chatGPT, talk about what they can and can’t do in healthcare, and go through some real-world examples + prototyping exercises.  

Healthcare 101 (starts 9/22) - I’ll teach you and your team how healthcare works. How everyone makes money, the big laws to know, trends affecting payers/pharma/etc.

How to contract with Payers (starts 9/22) - We’ll teach you how to get in-network with payers, how to negotiate your rates, figure out your market, etc.

We’ll do group rates, custom workshops, etc. - email sales@outofpocket.health and we’ll send you details.

INTERLUDE - FEW COURSES STARTING VERY SOON!!

See All Courses →

A reminder that there’s a few courses STARTING VERY SOON!! And it’s the final run for all of them (except healthcare 101).

LLMs in healthcare (starts 9/8) - We break down the basics of Large Language Models like chatGPT, talk about what they can and can’t do in healthcare, and go through some real-world examples + prototyping exercises.  

Healthcare 101 (starts 9/22) - I’ll teach you and your team how healthcare works. How everyone makes money, the big laws to know, trends affecting payers/pharma/etc.

How to contract with Payers (starts 9/22) - We’ll teach you how to get in-network with payers, how to negotiate your rates, figure out your market, etc.

Selling to Health Systems (starts 10/6) - Hopefully this post explained the perils of selling point solutions to hospitals. We’ll teach you how to sell to hospitals the right way.

EHR Data 101 (starts 10/14) - Hands on, practical introduction to working with data from electronic health record (EHR) systems, analyzing it, speaking caringly to it, etc.

We’ll do group rates, custom workshops, etc. - email sales@outofpocket.health and we’ll send you details.

INTERLUDE - FEW COURSES STARTING VERY SOON!!

See All Courses →

A reminder that there’s a few courses STARTING VERY SOON!! And it’s the final run for all of them (except healthcare 101).

LLMs in healthcare (starts 9/8) - We break down the basics of Large Language Models like chatGPT, talk about what they can and can’t do in healthcare, and go through some real-world examples + prototyping exercises.  

Healthcare 101 (starts 9/22) - I’ll teach you and your team how healthcare works. How everyone makes money, the big laws to know, trends affecting payers/pharma/etc.

How to contract with Payers (starts 9/22) - We’ll teach you how to get in-network with payers, how to negotiate your rates, figure out your market, etc.

Selling to Health Systems (starts 10/6) - Hopefully this post explained the perils of selling point solutions to hospitals. We’ll teach you how to sell to hospitals the right way.

EHR Data 101 (starts 10/14) - Hands on, practical introduction to working with data from electronic health record (EHR) systems, analyzing it, speaking caringly to it, etc.

We’ll do group rates, custom workshops, etc. - email sales@outofpocket.health and we’ll send you details.

Interlude - Our 3 Events + LLMs in healthcare

See All Courses →

We have 3 events this fall.

Data Camp sponsorships are already sold out! We have room for a handful of sponsors for our B2B Hackathon & for our OPS Conference both of which already have a full house of attendees.

If you want to connect with a packed, engaged healthcare audience, email sales@outofpocket.health for more details.

Let's Keep In Touch

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