Last day for knowledgefest apps + shutting down coworking

A post mortem + free courses + speakers for Ship It

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FHIR 101

Out-Of-Pocket is partnering with Redox to teach healthcare and health tech operators, builders, and business leaders what FHIR actually is, how it works, and what it means for the way healthcare data moves.
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A few updates from moi. I know people love to hear about FAILURES so figured I’d share one of ours. Bloodthirsty mfs.

But first a few things:

Knowledgefest applications due today

It’s the final day to apply to Knowledgefest, our conference focused on healthcare operations.

I feel pretty confident saying we’re one of the best and most practical conferences for people building in healthcare.

If you actually want to jam with people on things like:

  • How are you upskilling your ops team with AI tools? Where is it actually working
  • How money flows are changing. Value-based care shifts, how the new CMS/CMMI models are going to change your ops (how do ops look in the ACCESS model???)
  • What's breaking in credentialing, licensing, eligibility, etc.

You should apply today! It’s not binding to apply + you might actually have fun filling it out.

Convos will look just like this

Ship It Speakers

We’re excited about our new conference for healthcare software engineers, Ship It!

We have some amazing speakers running workshops that I put into Claude to even understand what they’re saying.

But that’s why it’s for the builders and not me 🙂. Conference is 9/17 - 9/18, we’re inviting people off the waitlist soon if you missed your chance.

Ship It 2026 speaker lineup across three tracks

Coworking - some experiments don’t work out

We've made the tough decision to shut down all of our healthcare coworking spaces (except New York, which is doing well and actually has a waitlist).

But for SF, Boston, and Chicago it was a really fun experiment! Our thesis was that there were underutilized coworking spaces and they didn't do a good job getting companies within the space to interact with each other. We could bring people together working in the same industry and create programming that would bring people to the space

It actually mostly did work - we had some awesome people at our spaces (in fact, many are still staying on at the space despite us not being involved anymore)

But the issue is a few fold:

1) People had to churn for lots of reasons outside of our control. For example people getting laid off, company stopped coworking stipend, etc. We were constantly recruiting which ended up being difficult. Especially true in cities where people are more geographically spread out/have space at home to just work there.

2) It only works if spaces were willing to work with us on a good deal. In some cities we'd find out that there's a reason there was a good deal, in other cities deal terms would get changed up on us once things were working.

3) This also became the opportunity cost of other things we're doing at Out-Of-Pocket. We only have so much surface area to tell people what we're up to and it becomes an exercise of prioritization (vs. things like conferences we’re running).

There are still ways to make this idea work but I think we'd have to own our own space. There’s also probably alternative ways of setting this up (e.g. a free space sponsored by a company trying to get in with startups).

Either way I'm glad we experimented and we really did create some great communities and had some awesome community managers and partners. Thanks to all the people that were a part of it! We're running a lot more community experiments bringing magic to our events.

Not all of our experiments will work. But as long as we had fun along the way, felt like we got good people together, and I didn’t go bankrupt...we’ll keep doing them.

Couldn’t have been too bad if the coworkers are sending me unhinged pat leave gifts. Making eye contact with the delivery guy and signing for this was...interesting.

Courses!!! Including free ones (our whole back catalog)

We have a few courses enrolling now:

  • FHIR 101 (8/25 - 8/27) - With the homies at Redox, we’re teaching everyone what FHIR is and how to build with it. If you’re building in healthcare, you should learn how this works even if you’re non-technical. It’s free, sign up here.
  • Value-based care 301 (9/15 - 9/17) - Does hearing the word “care gap closure” send shivers down your spine? Come to our Value-Based care course with Navina, we have an all star cast teaching contracting, ops, and tooling. Sign up here, also free.
  • Healthcare Crash Course 101 (9/21 - 10/2) - Taught by yours truly, Prof K. Learn how healthcare works quickly, get your sales team smarter, your product/eng team smarter, and learn how everyone is incentivized. We do group discounts.

We also have a really deep catalog of free recorded courses you can peruse, some of them might be issues you’re dealing with today.

How to evaluate AI products yourself, Legal Stuff for Telemedicine companies, Interoperability, and more.

Meme tax, enjoy your days

Working on a bunch of cool posts. What happened to the AI diabetic retinopathy companies, why we have pharma patents and where they’re breaking, healthcare as a job program, and way more.

But for now...I’ll leave you with a meme.

Thinkboi out,

Nikhil aka. “the real siren’s song is trying to make any money in real estate thinking it’ll be passive income”

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.

Quick Interlude - NEW COURSE ON FHIR! KNOWLEDGEFEST APPS DUE SOON!

See All Courses →

So...what actually is FHIR? I get this question a lot, but there's never really enough time to explain it and also I would just mumble "technical standard" and walk away.

So we decided to do a standalone free FHIR 101 course in partnership with Redox! Over 3 days in August we'll go over the spec itself, how it differs from other healthcare information standards, and practical tips to build with it.

I wanted to call it FHIR fest but it got nixed. You can sign up for it here, it's FREE and it's 8/25-8/27.

FHIR 101 course

And a reminder that Knowledgefest apps are due this week. If you want to be in a room with the best ops people in healthcare, you should apply like TODAY.

We sell this conference out every year - all workshops, learn how people are building and scaling in healthcare, application based so we only take the best. We have people from Commure, Clarity Pediatrics, Pomelo, and Waymark already coming, join the squad.

KnowledgeFest 2026
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