Some changes in Out-of-Pocket Land

Every so often I like to dump my woes of running a content business to you all because you tend to have good ideas.

Today is one of those days! I’ll give you a little peek under the hood, what’s on my mind in content, and how we’re changing things up here at Out-Of-Pocket.

The Big Change

Normally I try to bury the lede so you read the other stuff, but let’s get straight to the big change. This fall will be the last live run for most of our paid courses. So if you’ve been considering taking or sending your team to any of the following courses, you should sign up because it’s probably your last chance to do it live!

• LLMs in Healthcare** (starts 9/8) - We'll dive into core concepts, explore how LLMs are reshaping the healthcare landscape, and guide you through first principles of building and scaling LLM-driven prototypes. 
• How to Contract with Payers (starts 9/15) - The essentials of contracting with payors, including strategy, presentations, negotiations, and deal closure.
• Healthcare 101** (starts 9/22) - I’ll teach you all the main laws, players, money flows, etc. you need to know about US healthcare.
• Selling to Health Systems (starts 10/6) - 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.
• EHR Data 101 (starts 10/14) - Hands on, practical introduction to working with data from electronic health record (EHR) systems. 
• Claims Data 101 (starts 11/10) - Ideal for all healthcare backgrounds, this course covers what claims are, why they exist, and how to most effectively use them.

*(we’ll keep running live versions of these two courses for a bit

Courses have been the largest revenue source for OOP thus far, so this represents a big change. There are a few main reasons we’re doing this:

We’re getting more demand for custom courses and workshops - While the courses do a good job of explaining how things work, companies want to understand how it applies to THEIR problems specifically. 

So we’re leaning into creating custom courses for companies and workshops around our existing courses.

Live courses are getting harder to enroll - This is probably some combination of us not investing in marketing it outside of the newsletter and learning and development budgets being cut. And let me tell you, everyone signing up for a course 5 days before the course starts makes everything incredibly stressful. This is also why we’re focusing on groups - it makes more sense for us to spend time honing the content in for companies than spending time on marketing.

We’re focusing on other parts of the business - Because I only send this newsletter once a week (if I’m REALLY feeling divine intervention with ideas), the surface area of what we can advertise is limited. With limited space, it means we have to pick and choose what we’re selling. As we lean more into events and other things, we can only do so many time-sensitive alerts without annoying all of you.

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Courses are one of the things I’m really proud of at OOP. People have loved taking them - our average course is rated 8+ out of 10 in our post-course feedback surveys. The instructors get texts all the time from people that the course helped.

We paid out instructors nearly $1M over the life of doing it. Instructors were able to quit their full time jobs to explore startup ideas while this gave them some income. And instructors got to show off their skills they’ve learned over many years and fights with their CEOs. But we have to adapt with the times, and we think this next phase will have even more impact. 

‍If you have 10+ at your company who you want to get up to speed on some topic, ping sales@outofpocket.health and we can discuss custom courses, workshops, and more. We’re currently working on some courses for revenue cycle management step-by-step and a deep dive into “how payers work” if either of those are of interest. But we can teach pretty much anything.

‍We’ll also still be doing free courses with sponsor partners on certain topics. These will be in more niche or highly topical areas (we have a few coming out on interoperability, AI evaluations, and VBC operations soon). If you’re a company that might want to run one, we can send you details and pricing, email sales@outofpocket.health.

Thanks again to everyone that’s taken the courses through the years. We’ve had a blast doing them!

A few more things while I have your attention…

Our Podcast Is Back 

First, you may not know this but we do a couple podcasts. I co-host one with my friend Jacob at Redpoint Ventures called Vital Signs. You can see it on Spotify and Apple. 

We recently did an episode with Elliot Cohen, one of the co-founders of PillPack (acquired by Amazon). There's a lot of really interesting lessons from his time at Amazon Health (e.g. how HIPAA makes things very hard), and some of the AI x healthcare bets he’s making at General Medicine today.

We recorded this in person so you can see every pore in my face and my very expressive hands on YouTube. 

In Out-Of-Pocket land, we also have done our own podcast. Danielle and I hosted Ops I Did It Again which had a small but rabid fan base of ops people that would say things like “I feel so seen” and “direct mailers ftw”. We focused on case studies in building healthcare companies, and a lot of you liked it.

Well I’m very excited to announce, we’re doing a new podcast season. This one is called “Product Autopsy” and it’s going to be hosted by my Chief-Of-Staff and healthcare product guy, Alex Dou.

You can see the One-Pager here, but essentially we’re going to do post-mortems of common healthcare things that everyone tries so we can stop making the same mistakes. Our first episode is going to be about building provider directories. I can hear your shudders from here.

WE ARE LOOKING FOR GUESTS WHO WANT TO VENT TO US ABOUT SOMETHING THAT DIDN’T WORK. Please read the document here on what we’re looking for, and then email alex@outofpocket.health with:

• Which product/feature failure you could document
• Intro/overview of the product/feature (who are the users; what problems does it solve for them) 
• What do you think were the main reasons it failed?
• Would you try again? What would you do differently? 
• Availability for a 15-minute intro call for us to dig in 

Coworking!

We’ve been running coworking spaces for healthcare people in NY and SF and it’s been a lot of fun!

• Our NY coworking space is full, but if you want to get notified when a spot opens up fill this form out. And if you have an open space in Manhattan we can turn into a coworking space, let us know :) 
• We’re also going to be doing one in Chicago in September. We’re sending out invites to the first wave of people this week, but if you’re interested in a future spot you can sign up for it here
• We’re moving to a new SF location and opening it up to more people. If you’re interested, you can sign up for it here. 

Final sponsorship stuff for the year!

We have 3 events this fall.

• Healthcare Data Camp
• Our B2B Hackathon
• Our Healthcare Ops Conference

They’re basically all sold out and a highly curated group. We have room for a handful of sponsors for each of them.

If you’re curious what pricing looks like for any of the above, what you get for it, etc. email sales@outofpocket.health. We’re also sold out for basically all of the rest of OOP sponsorship inventory for the rest of the year, so if you want to work with us on something this year, this is your chance!

Some jobs! Engineers in particular

For those of you that don’t know, we do a little headhunting to help growing companies hire the ballers in the Out-Of-Pocket network. 

There are a few roles we’re helping with right now. If any of these seem appealing, fill this out and we’ll hook you up (or any other future roles we help with)

• A payer strategy/operations role at a revenue cycle company
• A senior product role at a different revenue cycle company
• A founding engineer role at like 10 different companies that keep asking me about it

If you’re a company and you need help hiring the best people, (including engineers) come chat with us and we’re happy to tell you more. It’s all contingency, so we only get paid if you actually hire the people.

Conclusion

A lot of stuff is changing in the world of content. People don’t sign up for newsletters anymore, AI slop has permeated the internet, and things that used to work don’t work when everyone needs to worry about their budget.

And yet I’ve never been more excited about what we’re doing. AI tools are opening a whole new area of creativity for us, we have a small and mighty team that can change course quickly, and we’ve stuck to focusing on building a brand that represents quality and fun. 

Thanks for reading along

Thinkboi out,

Nikhil aka. “Oh fuck this is a real business with real business decisions now”

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.